Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) oleanonic acid derivatives, holding some cyclic amines, linear polyamines and benzylaminocarboxamides at C28, has been synthesized and screened for antiviral activity against influenza A/PuertoRico/8/34 (H1N1) and Dengue virus serotype...

Full description

Saved in:
Bibliographic Details
Published inMolecules (Basel, Switzerland) Vol. 27; no. 23; p. 8499
Main Authors Smirnova, Irina, Petrova, Anastasiya, Giniyatullina, Gul'nara, Smirnova, Anna, Volobueva, Alexandrina, Pavlyukova, Julia, Zarubaev, Vladimir, Loc, Tran Van, Tran Thi Phoung, Thao, Hau, Vu Thi Bich, Thuy, Nguyen Thi Thu, Khine, Myint Myint, Kazakova, Oxana
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 01.12.2022
MDPI
Subjects
Amides
Amides - therapeutic use
Amines
Antimicrobial agents
Antiviral activity
Antiviral agents
Antiviral Agents - therapeutic use
benzylidene
Cancer
Cell cycle
Cytotoxicity
Dengue
Dengue fever
E coli
Herbal medicine
Humans
indole
Influenza
Influenza A
Influenza A Virus, H1N1 Subtype
Influenza, Human - drug therapy
Methicillin
oleanolic acid
polyamine
Polyamines
Polyamines - pharmacology
Polyamines - therapeutic use
Selectivity
Serotypes
Severe acute respiratory syndrome coronavirus 2
Triterpenes - therapeutic use
triterpenoids
Ugi derivatives
Vector-borne diseases
Viruses
China
polyamine
influenza A (H1N1)
indole
Ugi derivatives
oleanolic acid
triterpenoids
antiviral activity
Dengue virus
benzylidene
Online AccessGet full text

Cover

Abstract A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) oleanonic acid derivatives, holding some cyclic amines, linear polyamines and benzylaminocarboxamides at C28, has been synthesized and screened for antiviral activity against influenza A/PuertoRico/8/34 (H1N1) and Dengue virus serotypes of DENV-1, -2, -3, -4. It was found that 28-homopiperazine and 3- -phthalyl amides of oleanonic acid demonstrated high potency with selectivity index SI 27 (IC 21 μM) and 42 (IC 12 μM). Oleanonic acid aminoethylpiperazine amide and C-azepano-erythrodiol appeared to be the most effective compounds against DENV-1 (IC s 67 and 107 μM) and -2 (IC s 86 and 68 μM correspondingly) serotypes.
AbstractList A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) oleanonic acid derivatives, holding some cyclic amines, linear polyamines and benzylaminocarboxamides at C28, has been synthesized and screened for antiviral activity against influenza A/PuertoRico/8/34 (H1N1) and Dengue virus serotypes of DENV-1, -2, -3, -4. It was found that 28-homopiperazine 2 and 3-N-phthalyl 22 amides of oleanonic acid demonstrated high potency with selectivity index SI 27 (IC50 21 μM) and 42 (IC50 12 μM). Oleanonic acid aminoethylpiperazine amide 6 and C-azepano-erythrodiol 23 appeared to be the most effective compounds against DENV-1 (IC50′s 67 and 107 μM) and -2 (IC50′s 86 and 68 μM correspondingly) serotypes.
A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) oleanonic acid derivatives, holding some cyclic amines, linear polyamines and benzylaminocarboxamides at C28, has been synthesized and screened for antiviral activity against influenza A/PuertoRico/8/34 (H1N1) and Dengue virus serotypes of DENV-1, -2, -3, -4. It was found that 28-homopiperazine 2 and 3-N-phthalyl 22 amides of oleanonic acid demonstrated high potency with selectivity index SI 27 (IC[sub.50] 21 μM) and 42 (IC[sub.50] 12 μM). Oleanonic acid aminoethylpiperazine amide 6 and C-azepano-erythrodiol 23 appeared to be the most effective compounds against DENV-1 (IC[sub.50′]s 67 and 107 μM) and -2 (IC[sub.50′]s 86 and 68 μM correspondingly) serotypes.
A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) oleanonic acid derivatives, holding some cyclic amines, linear polyamines and benzylaminocarboxamides at C28, has been synthesized and screened for antiviral activity against influenza A/PuertoRico/8/34 (H1N1) and Dengue virus serotypes of DENV-1, -2, -3, -4. It was found that 28-homopiperazine 2 and 3- N -phthalyl 22 amides of oleanonic acid demonstrated high potency with selectivity index SI 27 (IC 50 21 μM) and 42 (IC 50 12 μM). Oleanonic acid aminoethylpiperazine amide 6 and C-azepano-erythrodiol 23 appeared to be the most effective compounds against DENV-1 (IC 50′ s 67 and 107 μM) and -2 (IC 50′ s 86 and 68 μM correspondingly) serotypes.
A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) oleanonic acid derivatives, holding some cyclic amines, linear polyamines and benzylaminocarboxamides at C28, has been synthesized and screened for antiviral activity against influenza A/PuertoRico/8/34 (H1N1) and Dengue virus serotypes of DENV-1, -2, -3, -4. It was found that 28-homopiperazine and 3- -phthalyl amides of oleanonic acid demonstrated high potency with selectivity index SI 27 (IC 21 μM) and 42 (IC 12 μM). Oleanonic acid aminoethylpiperazine amide and C-azepano-erythrodiol appeared to be the most effective compounds against DENV-1 (IC s 67 and 107 μM) and -2 (IC s 86 and 68 μM correspondingly) serotypes.
Audience Academic
Author Petrova, Anastasiya
Khine, Myint Myint
Hau, Vu Thi Bich
Zarubaev, Vladimir
Tran Thi Phoung, Thao
Giniyatullina, Gul'nara
Thuy, Nguyen Thi Thu
Kazakova, Oxana
Loc, Tran Van
Volobueva, Alexandrina
Smirnova, Anna
Pavlyukova, Julia
Smirnova, Irina
AuthorAffiliation 2 Department of Virology, St. Petersburg Pasteur Institute of Epidemiology and Microbiology, Experimental Virology Laboratory, 14 Mira St., St. Petersburg 197001, Russia
5 National Institute of Hygiene and Epidemiology, 1 Yersin Street, Hai Ba Trung, Hanoi 10000, Vietnam
3 St. Petersburg State Institute of Technology, 26 Moskovsky Av, St. Petersburg 190013, Russia
4 Institute of Chemistry, Vietnamese Academy of Science and Technology, 18-Hoang Quoc Viet Street, Cau Giay District, Hanoi 1000, Vietnam
1 Ufa Institute of Chemistry, The Ufa Federal Research Centre, The Russian Academy of Sciences, 71 Prospect Oktyabrya, Ufa 450054, Russia
6 Department of Chemistry, University of Yangon, University Avenue Road, Kamayut Township, Yangon 11041, Myanmar
AuthorAffiliation_xml – name: 4 Institute of Chemistry, Vietnamese Academy of Science and Technology, 18-Hoang Quoc Viet Street, Cau Giay District, Hanoi 1000, Vietnam
– name: 5 National Institute of Hygiene and Epidemiology, 1 Yersin Street, Hai Ba Trung, Hanoi 10000, Vietnam
– name: 1 Ufa Institute of Chemistry, The Ufa Federal Research Centre, The Russian Academy of Sciences, 71 Prospect Oktyabrya, Ufa 450054, Russia
– name: 3 St. Petersburg State Institute of Technology, 26 Moskovsky Av, St. Petersburg 190013, Russia
– name: 2 Department of Virology, St. Petersburg Pasteur Institute of Epidemiology and Microbiology, Experimental Virology Laboratory, 14 Mira St., St. Petersburg 197001, Russia
– name: 6 Department of Chemistry, University of Yangon, University Avenue Road, Kamayut Township, Yangon 11041, Myanmar
Author_xml – sequence: 1
  givenname: Irina
  surname: Smirnova
  fullname: Smirnova, Irina
  organization: Ufa Institute of Chemistry, The Ufa Federal Research Centre, The Russian Academy of Sciences, 71 Prospect Oktyabrya, Ufa 450054, Russia
– sequence: 2
  givenname: Anastasiya
  orcidid: 0000-0003-2910-6805
  surname: Petrova
  fullname: Petrova, Anastasiya
  organization: Ufa Institute of Chemistry, The Ufa Federal Research Centre, The Russian Academy of Sciences, 71 Prospect Oktyabrya, Ufa 450054, Russia
– sequence: 3
  givenname: Gul'nara
  surname: Giniyatullina
  fullname: Giniyatullina, Gul'nara
  organization: Ufa Institute of Chemistry, The Ufa Federal Research Centre, The Russian Academy of Sciences, 71 Prospect Oktyabrya, Ufa 450054, Russia
– sequence: 4
  givenname: Anna
  surname: Smirnova
  fullname: Smirnova, Anna
  organization: Ufa Institute of Chemistry, The Ufa Federal Research Centre, The Russian Academy of Sciences, 71 Prospect Oktyabrya, Ufa 450054, Russia
– sequence: 5
  givenname: Alexandrina
  surname: Volobueva
  fullname: Volobueva, Alexandrina
  organization: Department of Virology, St. Petersburg Pasteur Institute of Epidemiology and Microbiology, Experimental Virology Laboratory, 14 Mira St., St. Petersburg 197001, Russia
– sequence: 6
  givenname: Julia
  surname: Pavlyukova
  fullname: Pavlyukova, Julia
  organization: St. Petersburg State Institute of Technology, 26 Moskovsky Av, St. Petersburg 190013, Russia
– sequence: 7
  givenname: Vladimir
  orcidid: 0000-0002-5224-3771
  surname: Zarubaev
  fullname: Zarubaev, Vladimir
  organization: Institute of Chemistry, Vietnamese Academy of Science and Technology, 18-Hoang Quoc Viet Street, Cau Giay District, Hanoi 1000, Vietnam
– sequence: 8
  givenname: Tran Van
  surname: Loc
  fullname: Loc, Tran Van
  organization: Institute of Chemistry, Vietnamese Academy of Science and Technology, 18-Hoang Quoc Viet Street, Cau Giay District, Hanoi 1000, Vietnam
– sequence: 9
  givenname: Thao
  orcidid: 0000-0002-1107-7332
  surname: Tran Thi Phoung
  fullname: Tran Thi Phoung, Thao
  organization: Institute of Chemistry, Vietnamese Academy of Science and Technology, 18-Hoang Quoc Viet Street, Cau Giay District, Hanoi 1000, Vietnam
– sequence: 10
  givenname: Vu Thi Bich
  surname: Hau
  fullname: Hau, Vu Thi Bich
  organization: National Institute of Hygiene and Epidemiology, 1 Yersin Street, Hai Ba Trung, Hanoi 10000, Vietnam
– sequence: 11
  givenname: Nguyen Thi Thu
  surname: Thuy
  fullname: Thuy, Nguyen Thi Thu
  organization: National Institute of Hygiene and Epidemiology, 1 Yersin Street, Hai Ba Trung, Hanoi 10000, Vietnam
– sequence: 12
  givenname: Myint Myint
  surname: Khine
  fullname: Khine, Myint Myint
  organization: Department of Chemistry, University of Yangon, University Avenue Road, Kamayut Township, Yangon 11041, Myanmar
– sequence: 13
  givenname: Oxana
  orcidid: 0000-0002-5606-1588
  surname: Kazakova
  fullname: Kazakova, Oxana
  organization: Ufa Institute of Chemistry, The Ufa Federal Research Centre, The Russian Academy of Sciences, 71 Prospect Oktyabrya, Ufa 450054, Russia
BackLink https://www.ncbi.nlm.nih.gov/pubmed/36500593$$D View this record in MEDLINE/PubMed
BookMark eNptkktv1DAUhSNURB_wA9igSGxYkGLHj9gbpKgFOlKhiMfacuzrqUeJXeJkpOHX4-mU0gHkha3rcz77Xp3j4iDEAEXxHKNTQiR6M8QezNxDqpuaCCrlo-II0xpVBFF58OB8WByntEKoxhSzJ8Uh4QwhJslREb9uwnQNyafXZRsmXy2C62cIP3V5gT_hUge7q59DWM5Qtmbyaz9tyujKtvriw7L8GK13Hmx51YPOP_Qmq7wtP8d-owcfoDyH0a91NkJ6Wjx2uk_w7G4_Kb6_f_ft7KK6vPqwOGsvK8M4mirTCRDGNtI5MEw4YQFxQJZzLTnCwvIOUdF0BCPrJMIWc9I1zmEE0tmOkpNisePaqFfqZvSDHjcqaq9uC3FcKj1O3vSgOG_oFqEZsZTVIHnNHRVdJzgG2TWZ9XbHupm7AayBMI2634Pu3wR_rZZxrWRDBCd1Bry6A4zxxwxpUoNPBvpeB4hzUnXDCMGC3Upf_iVdxXkMeVRZRQVjnBP0R7XUuQEfXMzvmi1UtQ1leURCkqw6_Y8qLwuDNzlKzuf6ngHvDGaMKY3g7nvESG0Tp_5JXPa8eDice8fviJFfGFDUMg
CitedBy_id crossref_primary_10_1002_vjch_202300123
crossref_primary_10_1111_cbdd_14370
crossref_primary_10_3390_M1739
crossref_primary_10_3390_molecules28114518
crossref_primary_10_1186_s43094_024_00652_y
Cites_doi 10.1021/acs.molpharmaceut.6b00129
10.1039/C9TB01957J
10.1016/j.ejmech.2021.113738
10.1016/j.steroids.2021.108912
10.1007/s10600-014-0821-3
10.1007/s12257-013-0798-y
10.3390/ijms22189796
10.3390/molecules24050877
10.1016/j.ejmech.2019.111653
10.1021/acsmedchemlett.1c00374
10.1016/j.steroids.2019.108530
10.1016/j.bmcl.2019.126645
10.3390/molecules23092300
10.1016/S0166-3542(02)00185-7
10.3390/molecules26072102
10.1016/j.ejmech.2021.113242
10.1016/j.steroids.2016.07.007
10.2174/1568026621666211105101231
10.1016/j.ejmech.2017.07.013
10.1248/cpb.c19-00485
10.3390/biomedicines9080951
10.3390/ijms231810309
10.1016/j.ejmech.2019.111622
10.3390/antibiotics11010094
10.1186/s12906-021-03402-2
10.1016/j.steroids.2012.07.009
10.1023/B:CONC.0000033930.76751.b7
10.1039/B918846K
10.1016/j.bmc.2019.115147
10.3390/ijms23031075
10.1039/C5NP00015G
10.1016/j.bioorg.2016.08.004
10.1016/j.ejmech.2017.04.062
10.1038/s41429-022-00514-w
10.1016/j.ejmech.2015.02.029
10.1021/acsanm.1c04374
10.1021/cc9800071
10.2174/1389557521666210810153627
10.3390/M1078
10.3390/molecules25235557
10.1007/s10600-011-0050-y
ContentType Journal Article
Copyright COPYRIGHT 2022 MDPI AG
2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
2022 by the authors. 2022
Copyright_xml – notice: COPYRIGHT 2022 MDPI AG
– notice: 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
– notice: 2022 by the authors. 2022
DBID CGR
CUY
CVF
ECM
EIF
NPM
AAYXX
CITATION
3V.
7X7
7XB
88E
8FI
8FJ
8FK
ABUWG
AFKRA
AZQEC
BENPR
CCPQU
COVID
DWQXO
FYUFA
GHDGH
K9.
M0S
M1P
PIMPY
PQEST
PQQKQ
PQUKI
PRINS
7X8
5PM
DOA
DOI 10.3390/molecules27238499
DatabaseName Medline
MEDLINE
MEDLINE (Ovid)
MEDLINE
MEDLINE
PubMed
CrossRef
ProQuest Central (Corporate)
Health & Medical Collection
ProQuest Central (purchase pre-March 2016)
Medical Database (Alumni Edition)
Hospital Premium Collection
Hospital Premium Collection (Alumni Edition)
ProQuest Central (Alumni) (purchase pre-March 2016)
ProQuest Central (Alumni)
ProQuest Central
ProQuest Central Essentials
AUTh Library subscriptions: ProQuest Central
ProQuest One Community College
Coronavirus Research Database
ProQuest Central Korea
Health Research Premium Collection
Health Research Premium Collection (Alumni)
ProQuest Health & Medical Complete (Alumni)
Health & Medical Collection (Alumni Edition)
Medical Database
Publicly Available Content (ProQuest)
ProQuest One Academic Eastern Edition (DO NOT USE)
ProQuest One Academic
ProQuest One Academic UKI Edition
ProQuest Central China
MEDLINE - Academic
PubMed Central (Full Participant titles)
Directory of Open Access Journals
DatabaseTitle MEDLINE
Medline Complete
MEDLINE with Full Text
PubMed
MEDLINE (Ovid)
CrossRef
Publicly Available Content Database
ProQuest Central Essentials
ProQuest One Academic Eastern Edition
ProQuest Health & Medical Complete (Alumni)
Coronavirus Research Database
ProQuest Central (Alumni Edition)
ProQuest One Community College
ProQuest Hospital Collection
Health Research Premium Collection (Alumni)
ProQuest Central China
ProQuest Hospital Collection (Alumni)
ProQuest Central
ProQuest Health & Medical Complete
Health Research Premium Collection
ProQuest Medical Library
ProQuest One Academic UKI Edition
Health and Medicine Complete (Alumni Edition)
ProQuest Central Korea
ProQuest One Academic
ProQuest Medical Library (Alumni)
ProQuest Central (Alumni)
MEDLINE - Academic
DatabaseTitleList

Publicly Available Content Database

MEDLINE
CrossRef
Database_xml – sequence: 1
  dbid: DOA
  name: Directory of Open Access Journals
  url: https://www.doaj.org/
  sourceTypes: Open Website
– sequence: 2
  dbid: NPM
  name: PubMed
  url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed
  sourceTypes: Index Database
– sequence: 3
  dbid: EIF
  name: MEDLINE
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search
  sourceTypes: Index Database
– sequence: 4
  dbid: 7X7
  name: Health & Medical Collection
  url: https://search.proquest.com/healthcomplete
  sourceTypes: Aggregation Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1420-3049
ExternalDocumentID oai_doaj_org_article_6674901da53d452e9626f48bb861e9b7
A745960893
10_3390_molecules27238499
36500593
Genre Journal Article
GeographicLocations China
GeographicLocations_xml – name: China
GrantInformation_xml – fundername: Russian Foundation for Basic Research
  grantid: e-Asia Helth 21-53-70201
– fundername: MOE
  grantid: HE-098
– fundername: MOST
– fundername: MOE project
  grantid: HE-098
– fundername: RFBR
  grantid: 21-53-70201
GroupedDBID ---
0R~
123
2WC
3V.
53G
5VS
7X7
88E
8FE
8FG
8FH
8FI
8FJ
A8Z
AADQD
AAFWJ
AAHBH
ABDBF
ABJCF
ABUWG
ACGFO
ACIWK
ACPRK
AEGXH
AENEX
AFKRA
AFPKN
AFRAH
AFZYC
AIAGR
ALIPV
ALMA_UNASSIGNED_HOLDINGS
BBNVY
BENPR
BHPHI
BPHCQ
BVXVI
CCPQU
CGR
CS3
CUY
CVF
D1I
DIK
DU5
E3Z
EBD
ECM
EIF
EMOBN
ESTFP
ESX
FYUFA
GROUPED_DOAJ
GX1
HCIFZ
HH5
HMCUK
HYE
HZ~
I09
IAO
ITC
KB.
KQ8
LK8
M1P
M7P
MODMG
M~E
NPM
O-U
O9-
OK1
P2P
PDBOC
PIMPY
PQQKQ
PROAC
PSQYO
RIG
RPM
SV3
TR2
TUS
UKHRP
~8M
AAYXX
CITATION
7XB
8FK
AZQEC
COVID
DWQXO
K9.
PQEST
PQUKI
PRINS
7X8
5PM
ID FETCH-LOGICAL-c560t-cb8e8cd79ffec58f8de06e0d66a96018d6b0487b310df901d163b7ff10e9fdb43
IEDL.DBID RPM
ISSN 1420-3049
IngestDate Tue Oct 22 15:08:27 EDT 2024
Tue Sep 17 21:30:55 EDT 2024
Wed Dec 04 00:07:17 EST 2024
Thu Dec 05 07:30:58 EST 2024
Tue Nov 19 21:21:03 EST 2024
Tue Nov 12 23:19:28 EST 2024
Fri Dec 06 08:39:34 EST 2024
Sat Sep 28 08:20:35 EDT 2024
IsDoiOpenAccess true
IsOpenAccess true
IsPeerReviewed true
IsScholarly true
Issue 23
Keywords polyamine
influenza A (H1N1)
indole
Ugi derivatives
oleanolic acid
triterpenoids
antiviral activity
Dengue virus
benzylidene
Language English
License https://creativecommons.org/licenses/by/4.0
Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-c560t-cb8e8cd79ffec58f8de06e0d66a96018d6b0487b310df901d163b7ff10e9fdb43
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ORCID 0000-0002-5224-3771
0000-0003-2910-6805
0000-0002-1107-7332
0000-0002-5606-1588
OpenAccessLink https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9738632/
PMID 36500593
PQID 2748556630
PQPubID 2032355
ParticipantIDs doaj_primary_oai_doaj_org_article_6674901da53d452e9626f48bb861e9b7
pubmedcentral_primary_oai_pubmedcentral_nih_gov_9738632
proquest_miscellaneous_2753318532
proquest_journals_2748556630
gale_infotracmisc_A745960893
gale_infotracacademiconefile_A745960893
crossref_primary_10_3390_molecules27238499
pubmed_primary_36500593
PublicationCentury 2000
PublicationDate 2022-12-01
PublicationDateYYYYMMDD 2022-12-01
PublicationDate_xml – month: 12
  year: 2022
  text: 2022-12-01
  day: 01
PublicationDecade 2020
PublicationPlace Switzerland
PublicationPlace_xml – name: Switzerland
– name: Basel
PublicationTitle Molecules (Basel, Switzerland)
PublicationTitleAlternate Molecules
PublicationYear 2022
Publisher MDPI AG
MDPI
Publisher_xml – sequence: 0
  name: MDPI AG
– name: MDPI AG
– name: MDPI
References Crance (ref_50) 2003; 58
Yu (ref_10) 2016; 13
ref_13
ref_12
ref_53
ref_52
Salvador (ref_2) 2014; 41
Salvador (ref_4) 2017; 142
Pai (ref_6) 2016; 54
Bildziukevich (ref_25) 2017; 117
Gupta (ref_11) 2022; 22
Hodon (ref_46) 2019; 15
Alvarenga (ref_49) 2012; 1
Vetal (ref_8) 2014; 19
Song (ref_40) 2015; 93
Orzechowska (ref_48) 2021; 225
Heller (ref_21) 2016; 68
Smirnova (ref_47) 2022; 75
Su (ref_18) 2019; 182
ref_20
Khusnutdinova (ref_32) 2021; 36
ref_28
ref_27
ref_26
Li (ref_15) 2021; 215
Kvasnica (ref_1) 2015; 32
Meng (ref_17) 2019; 27
Vistica (ref_54) 1991; 51
Spivak (ref_22) 2020; 154
Baltina (ref_51) 2019; 29
Kazakova (ref_35) 2021; 175
Smirnova (ref_43) 2018; 13
Wrzeciono (ref_38) 1973; 47
Scudiero (ref_55) 1988; 48
Shao (ref_19) 2021; 12
Li (ref_14) 2019; 67
ref_36
ref_34
Gupta (ref_45) 2010; 5
Vida (ref_23) 2012; 77
Khusnutdinova (ref_33) 2018; 13
Boreko (ref_41) 2002; 3
Javed (ref_7) 2016; 10
Kazakova (ref_37) 2011; 47
Hao (ref_30) 2016; 35
Huang (ref_16) 2010; 8
Ghose (ref_39) 1999; 1
Nonappa (ref_29) 2022; 5
Gupta (ref_31) 2017; 135
Tolmacheva (ref_44) 2014; 49
ref_3
Flekhter (ref_42) 2004; 40
Bildziukevich (ref_24) 2020; 8
ref_5
Wang (ref_9) 2022; 22
References_xml – volume: 13
  start-page: 1699
  year: 2016
  ident: ref_10
  article-title: Pharmacokineti Partially in vitro and in vivo of two novel prodrugs of oleanolic acid in rats and its hepatoprotective effects against liver injury induced by CCl4
  publication-title: Mol. Pharm.
  doi: 10.1021/acs.molpharmaceut.6b00129
  contributor:
    fullname: Yu
– volume: 8
  start-page: 484
  year: 2020
  ident: ref_24
  article-title: Spermine amides of selected triterpenoid acids: Dynamic supramolecular system formation influences the cytotoxicity of the drugs
  publication-title: J. Mater. Chem. B.
  doi: 10.1039/C9TB01957J
  contributor:
    fullname: Bildziukevich
– volume: 225
  start-page: 113738
  year: 2021
  ident: ref_48
  article-title: Novel betulin dicarboxylic acid ester derivatives as potent antiviral agents: Design, synthesis, biological evaluation, structure-activity relationship and in-silico study
  publication-title: Eur. J. Med. Chem.
  doi: 10.1016/j.ejmech.2021.113738
  contributor:
    fullname: Orzechowska
– volume: 175
  start-page: 108912
  year: 2021
  ident: ref_35
  article-title: Synthesis of erythrodiol C-ring derivatives and their activity against Chlamydia trachomatis
  publication-title: Steroids
  doi: 10.1016/j.steroids.2021.108912
  contributor:
    fullname: Kazakova
– volume: 49
  start-page: 1050
  year: 2014
  ident: ref_44
  article-title: Synthesis and antiviral activity of C-3(C-28)-substituted 2,3-seco-triterpenoids
  publication-title: Chem. Nat. Compd.
  doi: 10.1007/s10600-014-0821-3
  contributor:
    fullname: Tolmacheva
– volume: 1
  start-page: 122
  year: 2012
  ident: ref_49
  article-title: Evaluation of Cuspidaria pulchra and its isolated compounds against Schistosoma mansoni Adult Worms
  publication-title: Int. J. Biotechn. Wellness Ind.
  contributor:
    fullname: Alvarenga
– volume: 54
  start-page: 196
  year: 2016
  ident: ref_6
  article-title: Determination of betulinic acid, oleanolic acid and ursolic acid from Achyranthes aspera L. using RP-UFLC-DAD analysis and evaluation of various parameters for their optimum yield
  publication-title: Indian J. Exp. Biol.
  contributor:
    fullname: Pai
– volume: 19
  start-page: 720
  year: 2014
  ident: ref_8
  article-title: Microwave assisted extraction of ursolic acid and oleanolic acid from Ocimum sanctum
  publication-title: Biotechnol. Bioprocess Eng.
  doi: 10.1007/s12257-013-0798-y
  contributor:
    fullname: Vetal
– ident: ref_34
  doi: 10.3390/ijms22189796
– ident: ref_36
  doi: 10.3390/molecules24050877
– volume: 15
  start-page: 111653
  year: 2019
  ident: ref_46
  article-title: Design and synthesis of pentacyclic triterpene conjugates and their use in medicinal research
  publication-title: Eur. J. Med.Chem.
  doi: 10.1016/j.ejmech.2019.111653
  contributor:
    fullname: Hodon
– volume: 12
  start-page: 1759
  year: 2021
  ident: ref_19
  article-title: Design and Synthesis of Oleanolic Acid Trimers to Enhance Inhibition of Influenza Virus Entry
  publication-title: ACS Med. Chem. Lett.
  doi: 10.1021/acsmedchemlett.1c00374
  contributor:
    fullname: Shao
– volume: 35
  start-page: 1167
  year: 2016
  ident: ref_30
  article-title: Synthesis, crystal structure and antitumor activity of a new indolequinone derivative of ursolic acid. Chin
  publication-title: J. Struct. Chem.
  contributor:
    fullname: Hao
– volume: 154
  start-page: 108530
  year: 2020
  ident: ref_22
  article-title: Antimicrobial properties of amine- and guanidine-functionalized derivatives of betulinic, ursolic and oleanolic acids: Synthesis and structure-activity evaluation
  publication-title: Steroids
  doi: 10.1016/j.steroids.2019.108530
  contributor:
    fullname: Spivak
– volume: 29
  start-page: 126645
  year: 2019
  ident: ref_51
  article-title: Glycyrrhizic acid derivatives as Dengue virus inhibitors
  publication-title: Bioorg. Med. Chem. Lett.
  doi: 10.1016/j.bmcl.2019.126645
  contributor:
    fullname: Baltina
– ident: ref_12
  doi: 10.3390/molecules23092300
– volume: 58
  start-page: 73
  year: 2003
  ident: ref_50
  article-title: Interferon, Ribavirin, 6-Azauridine and Glycyrrhizin: Antiviral Compounds. Active against Pathogenic Flaviviruses
  publication-title: Antivir. Res.
  doi: 10.1016/S0166-3542(02)00185-7
  contributor:
    fullname: Crance
– ident: ref_5
  doi: 10.3390/molecules26072102
– volume: 215
  start-page: 113242
  year: 2021
  ident: ref_15
  article-title: Discovery and structural optimization of 3-O-b-chacotriosyl oleanane-type triterpenoids as potent entry inhibitors of SARS-CoV-2 virus infections
  publication-title: Eur J Med Chem.
  doi: 10.1016/j.ejmech.2021.113242
  contributor:
    fullname: Li
– volume: 117
  start-page: 90
  year: 2017
  ident: ref_25
  article-title: Spectral and microscopic study of self-assembly of novel cationic spermine amides of betulinic acid
  publication-title: Steroids
  doi: 10.1016/j.steroids.2016.07.007
  contributor:
    fullname: Bildziukevich
– volume: 22
  start-page: 3
  year: 2022
  ident: ref_9
  article-title: Recent Progress in Oleanolic Acid: Structural Modification and Biological Activity
  publication-title: Curr. Top. Med. Chem.
  doi: 10.2174/1568026621666211105101231
  contributor:
    fullname: Wang
– volume: 142
  start-page: 95
  year: 2017
  ident: ref_4
  article-title: Oleanane-, ursane-, and quinone methide friedelane-type triterpenoid derivatives: Recent advances in cancer treatment
  publication-title: Eur. J. Med. Chem.
  doi: 10.1016/j.ejmech.2017.07.013
  contributor:
    fullname: Salvador
– volume: 67
  start-page: 1201
  year: 2019
  ident: ref_14
  article-title: Synthesis, Structure Activity Relationship and Anti-influenza A Virus Evaluation of Oleanolic Acid-Linear Amino Derivatives
  publication-title: Chem. Pharm. Bull.
  doi: 10.1248/cpb.c19-00485
  contributor:
    fullname: Li
– volume: 3
  start-page: 86
  year: 2002
  ident: ref_41
  article-title: Inhibition of virus reproduction and proteinase activity by lupane and some other terpenes
  publication-title: J. Biomed. Sci.
  contributor:
    fullname: Boreko
– ident: ref_20
  doi: 10.3390/biomedicines9080951
– volume: 10
  start-page: 782
  year: 2016
  ident: ref_7
  article-title: Isolation, Identification and Antiproliferative Activity of Triterpenes from the Genus Monotheca A. DC
  publication-title: Rec. Nat. Prod.
  contributor:
    fullname: Javed
– ident: ref_52
  doi: 10.3390/ijms231810309
– volume: 5
  start-page: 1567
  year: 2010
  ident: ref_45
  article-title: Cytotoxic Evaluation of Semisynthetic Ester and Amide Derivatives of Oleanolic Acid
  publication-title: Nat. Prod. Comm.
  contributor:
    fullname: Gupta
– ident: ref_53
– volume: 182
  start-page: 111622
  year: 2019
  ident: ref_18
  article-title: Design, synthesis of oleanolic acid-saccharide conjugates using click chemistry methodology and study of their anti-influenza activity
  publication-title: Europ. J. Med. Chem.
  doi: 10.1016/j.ejmech.2019.111622
  contributor:
    fullname: Su
– ident: ref_27
  doi: 10.3390/antibiotics11010094
– volume: 47
  start-page: 955
  year: 1973
  ident: ref_38
  article-title: Nitrogen derivatives of triterpenes. VII. Products of the reduction of oleanonic acid oxime and its methyl ester
  publication-title: Roczniki Chem.
  contributor:
    fullname: Wrzeciono
– ident: ref_13
  doi: 10.1186/s12906-021-03402-2
– volume: 77
  start-page: 1212
  year: 2012
  ident: ref_23
  article-title: Polyamine conjugates of stigmasterol
  publication-title: Steroids
  doi: 10.1016/j.steroids.2012.07.009
  contributor:
    fullname: Vida
– volume: 13
  start-page: 1267
  year: 2018
  ident: ref_43
  article-title: Structure—Anti-influenza type A activity relationship among a series of nitrogen lupane triterpenoids
  publication-title: Nat. Prod. Comm.
  contributor:
    fullname: Smirnova
– volume: 48
  start-page: 4827
  year: 1988
  ident: ref_55
  article-title: Evaluation of a soluble tetrazolium/formazan assay for cellgrowth and drug sensitivity in culture using human and other tumor cell lines
  publication-title: Cancer Res.
  contributor:
    fullname: Scudiero
– volume: 40
  start-page: 141
  year: 2004
  ident: ref_42
  article-title: Selective oxidation of triterpene alcohols by sodium hypochlorite
  publication-title: Chem. Nat. Comp.
  doi: 10.1023/B:CONC.0000033930.76751.b7
  contributor:
    fullname: Flekhter
– volume: 8
  start-page: 632
  year: 2010
  ident: ref_16
  article-title: Synthesis and anti-human hepatocellular carcinoma activity of new nitric oxide-releasing glycosyl derivatives of oleanolic acid
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/B918846K
  contributor:
    fullname: Huang
– volume: 27
  start-page: 115147
  year: 2019
  ident: ref_17
  article-title: Design, synthesis and biological evaluation of amino acids-oleanolic acid conjugates as influenza virus inhibitors
  publication-title: Bioorg. Med. Chem.
  doi: 10.1016/j.bmc.2019.115147
  contributor:
    fullname: Meng
– ident: ref_28
  doi: 10.3390/ijms23031075
– volume: 41
  start-page: 33
  year: 2014
  ident: ref_2
  article-title: Chapter 2—Highlights of pentacyclic triterpenoids in the cancer settings
  publication-title: Studies in Nat. Prod. Chem.
  contributor:
    fullname: Salvador
– volume: 32
  start-page: 1303
  year: 2015
  ident: ref_1
  article-title: Pentacyclic triterpenoids with nitrogen- and sulfur-containing heterocycles: Synthesis and medicinal significance
  publication-title: Nat. Prod. Rep.
  doi: 10.1039/C5NP00015G
  contributor:
    fullname: Kvasnica
– volume: 68
  start-page: 137
  year: 2016
  ident: ref_21
  article-title: Synthesis and proapoptotic activity of oleanolic acid derived amides
  publication-title: Bioorg. Chem.
  doi: 10.1016/j.bioorg.2016.08.004
  contributor:
    fullname: Heller
– volume: 135
  start-page: 517
  year: 2017
  ident: ref_31
  article-title: Synthesis of novel benzylidene analogues of betulinic acid as potent cytotoxic agents
  publication-title: Eur. J. Med. Chem.
  doi: 10.1016/j.ejmech.2017.04.062
  contributor:
    fullname: Gupta
– volume: 75
  start-page: 258
  year: 2022
  ident: ref_47
  article-title: Azepanodipterocarpol is potential candidate for inhibits influenza H1N1 type among other lupane, oleanane, and dammarane A-ring amino-triterpenoids
  publication-title: J. Antibiot.
  doi: 10.1038/s41429-022-00514-w
  contributor:
    fullname: Smirnova
– volume: 36
  start-page: 1
  year: 2021
  ident: ref_32
  article-title: Synthesis of messagenin and platanic acid chalcone derivatives and their biological potential
  publication-title: Nat. Prod. Res.
  contributor:
    fullname: Khusnutdinova
– volume: 93
  start-page: 431
  year: 2015
  ident: ref_40
  article-title: Structure-activity relationships of 3-O-beta-chacotriosyl ursolic acid derivatives as novel H5N1 entry inhibitors
  publication-title: Eur. J. Med. Chem.
  doi: 10.1016/j.ejmech.2015.02.029
  contributor:
    fullname: Song
– volume: 5
  start-page: 3799
  year: 2022
  ident: ref_29
  article-title: Aging-Induced Structural Transition of Nanoscale Oleanolic Acid Amphiphiles and Selectivity against Gram-Positive Bacteria
  publication-title: ACS Appl. Nano Mater.
  doi: 10.1021/acsanm.1c04374
  contributor:
    fullname: Nonappa
– volume: 1
  start-page: 55
  year: 1999
  ident: ref_39
  article-title: A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases
  publication-title: Combinat. Chem.
  doi: 10.1021/cc9800071
  contributor:
    fullname: Ghose
– volume: 22
  start-page: 600
  year: 2022
  ident: ref_11
  article-title: A Review on Recent Developments in the Anticancer Potential of Oleanolic Acid and its Analogs (2017–2020)
  publication-title: Mini Rev. Med. Chem.
  doi: 10.2174/1389557521666210810153627
  contributor:
    fullname: Gupta
– ident: ref_26
  doi: 10.3390/M1078
– ident: ref_3
  doi: 10.3390/molecules25235557
– volume: 13
  start-page: 665
  year: 2018
  ident: ref_33
  article-title: Synthesis and cytotoxicity of 28-N-propargylaminoalkylated 2,3-indolotriterpenic acids
  publication-title: Nat. Prod. Commun.
  contributor:
    fullname: Khusnutdinova
– volume: 47
  start-page: 752
  year: 2011
  ident: ref_37
  article-title: Conjugates of several lupane, oleanane, and ursane triterpenoids with the antituberculosis drug isoniazid and pyridinecarboxaldehydes
  publication-title: Chem. Nat. Compd.
  doi: 10.1007/s10600-011-0050-y
  contributor:
    fullname: Kazakova
– volume: 51
  start-page: 2515
  year: 1991
  ident: ref_54
  article-title: Tetrazolium-based assays for cellular viability: A critical examination of selected parameters affecting formazan production
  publication-title: Cancer Res.
  contributor:
    fullname: Vistica
SSID ssj0021415
Score 2.456649
Snippet A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) oleanonic acid derivatives, holding some cyclic amines, linear polyamines and...
SourceID doaj
pubmedcentral
proquest
gale
crossref
pubmed
SourceType Open Website
Open Access Repository
Aggregation Database
Index Database
StartPage 8499
SubjectTerms Amides
Amides - therapeutic use
Amines
Antimicrobial agents
Antiviral activity
Antiviral agents
Antiviral Agents - therapeutic use
benzylidene
Cancer
Cell cycle
Cytotoxicity
Dengue
Dengue fever
E coli
Herbal medicine
Humans
indole
Influenza
Influenza A
Influenza A Virus, H1N1 Subtype
Influenza, Human - drug therapy
Methicillin
oleanolic acid
polyamine
Polyamines
Polyamines - pharmacology
Polyamines - therapeutic use
Selectivity
Serotypes
Severe acute respiratory syndrome coronavirus 2
Triterpenes - therapeutic use
triterpenoids
Ugi derivatives
Vector-borne diseases
Viruses
SummonAdditionalLinks – databaseName: Directory of Open Access Journals
  dbid: DOA
  link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV1ba9VAEB6kL_oi3o22ZQVBEIO5bJLNY9pajkKrqIW-LXutgTYRc45Qf31nsjnHE_rgi6_ZDcnuzGS-IbPfB_BaZ06luTcx2tvH3HiMubxM4qSyNtc6VWL8FXNyWi7O-Kfz4nxL6ot6wgI9cNg4UuvjmLOsKnLLi8zViMA9F1qLMnW1DufIk2xdTE2lVop5KfzDzLGof38VpGbdkJHGFh-JXv9moZGs__YneSsnzfsltxLQ8QO4PyFH1oQ3fgh3XPcI7h6uBdseQ__tukM4N7TDO9Z0yzb-GARI_ii2SE9Tpjobrh-57mLlWGOCcgTrPWvir5jD2ElvW4-glH2-dKoj1lyc1Vr2pb-8VlcISNkReuzvkSx8eAJnxx--Hy7iSU8hNohrlrHRwgljq5o6RQrhhXVJ6RJblgrrmFTYUmM8VxoRn_W054jVdOV9mrjaW83zp7CDj3bPgRlbFyoxLiPCLmcxjIVRta0Kbj1CLB_B2_X-yp-BNkNiuUHGkLeMEcEBWWAzkRivxwvoB3LyA_kvP4jgDdlPUlyikYyajhfg-xLDlWwqXuAqEZ5FsDubiVYy8-G1B8gpngeJtbsoEPnmSQSvNsN0J_Woda5f0RyEzgR_sgieBYfZLClHIEziiRFUM1earXk-0rU_RrbvmmRZ8-zF_9ikl3Avo-MbYzvOLuwsf63cHoKqpd4f4-cG3McgbA
  priority: 102
  providerName: Directory of Open Access Journals
– databaseName: ProQuest Technology Collection
  dbid: 8FG
  link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1ba9VAEB60fdAX0XqLVllBEMTQXHc3T5K2Ho9Cq6iFvoW91kCb1OYcof76ziQ5pw0FX3c3ZDczs_PN7mQ-gLc6cSpOvQlR3j7MjEebS3kURsLaVOtYyf4q5uCQz4-yr8f58Xjg1o1plas9sd-obWvojHwHoyeZI_ZIo4_nf0JijaLb1ZFC4y5sxonglNInZ5_XAVeM3mm4yUwxtN85GwhnXZcQ01bWl3u99kV9yf7bG_MNzzTNmrzhhmYP4cGIH1k5CPwR3HHNFtzbW9G2PYb252WDoK6ruw-sbBZ1-GWgIfmn2Dw-jJlq7NC-75qTpWOlGfgjWOtZGf5AT8YOWlt7hKbs26lTDdXOxVG1Zd_b00t1hrCU7aPe_u1LhndP4Gj26dfePBxZFUKD6GYRGi2dNFYUlC-SSy-ti7iLLOcKo5lYWq7RqoVG3Gc9ogWLiE0L7-PIFd7qLH0KG_hq9xyYsUWuIuMSKtvlLBqzNKqwIs-sR6DlA3i_-r7V-VA8o8Kgg4RR3RJGALskgfVAqnvdN7QXJ9VoRhXnIqM5qTy1WZ64AuMxn0mtJY9doUUA70h-FVknCsmo8ScDnC_VuapKkeW4SgRpAWxPRqKUzLR7pQHVaNVdda2DAbxZd9OTlKnWuHZJYxBAEwhKAng2KMx6SSnCYaJQDEBMVGmy5mlPU__ua34XRM6aJi_-P62XcD-h3zP6dJtt2FhcLN0rBE0L_bq3jCsKOhjb
  priority: 102
  providerName: ProQuest
Title Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives
URI https://www.ncbi.nlm.nih.gov/pubmed/36500593
https://www.proquest.com/docview/2748556630
https://search.proquest.com/docview/2753318532
https://pubmed.ncbi.nlm.nih.gov/PMC9738632
https://doaj.org/article/6674901da53d452e9626f48bb861e9b7
Volume 27
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1La9tAEB6S9NBeSvqM2tRsoVAoVay3VkfHjusU7Ji0Kb6JfaYCWwqxHUh_fWdXkhuRWy8SaFdoVzOj-UY7-w3AJx4o5odauChv7UZCo82Fied6qZQh5z6jdilmOksmV9H3RbzYg7jdC2OT9gUvTsrl6qQsftvcypuV6Ld5Yv35dJiZSpVh0N-HfXS_bYjeRFk-uqR6-TLEeL6_qqvMqnVgymtFluP1nwOyPP2Pv8YP3FE3VfKB7xkfwvMGNJJBPbgXsKfKl_B02NZqewXVj_sSkdy6WH8lg3JTuOd17ZE_jEz8mU9YKevrI1VebxUZiLpoBKk0GbiX6L7ItJKFRjxKLpaKlYYwF3sVksyr5T1bIRYlI1TWO8sTvn4NV-Ozn8OJ25RScAVCmo0rOFVUyDQzSSIx1VQqL1GeTBKGIYxPZcLRlFOOYE9qhAgSYRpPtfY9lWnJo_ANHOCj1REQIbOYeUIFhqtLSbRgKlgm0ziSGtGVduBL-37zm5oxI8dIwwgjfyQMB06NBHYdDdm1vVDdXueNyPMkSSMzJhaHMooDlWEQpiPKOU18lfHUgc9GfrkxSRSSYM3OAhyvIbfKB2kU4ywRmTlw3OmJUhLd5lYD8saU1zmG7TRG0Bt6DnzcNZs7TXpaqaqt6YOo2SCfwIG3tcLsphQiBjZ1Ex1IO6rUmXO3BfXeEn03ev7uv-98D88Cs13Dpt8cw8Hmdqs-IIja8B6aziLFIx1_68GT07PZ_BLPw4tf56Oe_THRs2b1F9BSJho
link.rule.ids 230,314,727,780,784,864,885,2102,12056,12765,21388,27924,27925,31719,31720,33373,33374,33744,33745,38516,43310,43600,43805,43895,53791,53793,73745,74035,74302,74412
linkProvider National Library of Medicine
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1Lb9QwEB7B9lAuiHcDBYyEhISImnecE9q-tIXuUpVW6s3ys0Rqk9LsIpVfz0yS3TaqxDV2FDszY38TT74P4KOKrAxjp320t_MT7TDm4izwg9yYWKlQ8vYoZjrLJqfJt7P0rP_g1vRllcs1sV2oTa3pG_kWZk88RewRB1-vfvukGkWnq72ExkNYI-b0dARr23uzo-NVyhXi_tSdZcaY3G9ddpKztolIaytpCV9vd6OWtP_-0nxnbxrWTd7ZiPafwOMeQbJxZ_Kn8MBWz2B9Zync9hzqnzcVwrqmbL6wcTUv_YNOiOSvZJNwFjJZme76rq3OF5aNdacgwWrHxv4x7mVsWpvSIThlPy6srIg9F3uVhh3VFzfyEoEp20XP_dOShjcv4HR_72Rn4ve6Cr5GfDP3teKWa5MXVDGScseNDTIbmCyTmM-E3GQK4zpXiPyMQ7xgELOp3LkwsIUzKolfwggfbTeAaVOkMtA2IuIuazCcuZaFydPEOIRazoPPy_crrjr6DIFpBxlD3DOGB9tkgVVHYr5uL9TX56IPJJFleUJjkmlskjSyBWZkLuFK8Sy0hco9-ET2ExSfaCQt-98McLzEdCXGeZLiLBGmebA56IlW0sPmpQeIPq4bceuFHnxYNdOdVKtW2XpBfRBCEwyKPHjVOcxqSjECYhJR9CAfuNJgzsOWqvzVsn4XJM8aR6__P6z3sD45mR6Kw4PZ9zfwKKKfNdrim00Yza8X9i1CqLl618fJPw-mHSw
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV3bbtNAEB1BKgEviGsxFFgkJCSEFd-9fkJu0ygFGqJCpb5Zey2WWrvUCVL5emZsJ61ViVfvRtnNzOycyY7PAXgvAyP80CoX7W3dSFmMuTDxXC_VOpTSF7y9ijmcJ7Pj6MtJfNL3PzV9W-X6TGwPal0r-o98jNUTjxF7hN7Y9m0Ri8n088VvlxSk6Ka1l9O4C1uYFb1gBFu7-_PF0ab88jFXdfeaIRb64_NOftY0AeluRS3563Vmagn8bx_TN_LUsIfyRlKaPoKHPZpkeWf-x3DHVE_g_t5axO0p1D-uKoR4Tdl8Ynm1LN2DTpTkr2Azf-4zUenu-cRUpyvDctWpSbDastw9wrzGDmtdWgSq7PuZERUx6eKsUrNFfXYlzhGksgl68Z-WQLx5BsfT_Z97M7fXWHAVYp2lqyQ3XOk0o-6RmFuujZcYTyeJwNrG5zqRGOOpRBSoLWIHjfhNptb6nsmsllH4HEb41eYFMKWzWHjKBETiZTSGNlci02kcaYuwyzrwcf37FhcdlUaBJQgZo7hlDAd2yQKbicSC3T6oL0-LPqiKJEkjWpOIQx3FgcmwOrMRl5Invslk6sAHsl9BsYpGUqJ_5QDXS6xXRZ5GMe4SIZsDO4OZaCU1HF57QNHHeFNce6QD7zbD9EnqW6tMvaI5CKcJEgUObHcOs9lSiOCYBBUdSAeuNNjzcKQqf7UM4BlJtYbBy_8v6y3cwxApvh3Mv76CBwG9t9H24ezAaHm5Mq8RTS3lmz5M_gFCqSFZ
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Synthesis%2C+Anti-Influenza+H1N1+and+Anti-Dengue+Activity+of+A-Ring+Modified+Oleanonic+Acid+Polyamine+Derivatives&rft.jtitle=Molecules+%28Basel%2C+Switzerland%29&rft.au=Smirnova%2C+Irina&rft.au=Petrova%2C+Anastasiya&rft.au=Giniyatullina%2C+Gul%E2%80%99nara&rft.au=Smirnova%2C+Anna&rft.date=2022-12-01&rft.pub=MDPI+AG&rft.issn=1420-3049&rft.eissn=1420-3049&rft.volume=27&rft.issue=23&rft_id=info:doi/10.3390%2Fmolecules27238499&rft.externalDocID=A745960893
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1420-3049&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1420-3049&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1420-3049&client=summon