Structural development of 1H-pyrazolo-[3,4-b]pyridine-4-carboxylic acid derivatives as human peroxisome proliferator-activated receptor alpha (PPARα)-selective agonists

[Display omitted] We previously reported that 1H-pyrazolo-[3,4-b]pyridine-4-carboxylic acid derivative 6 is an agonist of human peroxisome proliferator-activated receptor alpha (hPPARα). Here, we prepared a series of 1H-pyrazolo-[3,4-b]pyridine-4-carboxylic acid derivatives in order to examine the s...

Full description

Saved in:
Bibliographic Details
Published inBioorganic & medicinal chemistry letters Vol. 29; no. 16; pp. 2124 - 2128
Main Authors Miyachi, Hiroyuki, Yuzuriha, Tomohiro, Tabata, Ryotaro, Fukuda, Syohei, Nunomura, Kazuto, Lin, Bangzhong, Kobayashi, Tadayuki, Ishimoto, Kenji, Doi, Takefumi, Tachibana, Keisuke
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.08.2019
Elsevier
Subjects
1H-Pyrazolo-[3,4-b]pyridine-4-carboxylic acid
Agonist
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Life Sciences & Biomedicine
Peroxisome proliferator-activated receptor alpha
Pharmacology & Pharmacy
Physical Sciences
PPAR
PPARα agonist
Science & Technology
Structure-activity relationship
Peroxisome proliferator-activated receptor alpha
1H-Pyrazolo-[3,4-b]pyridine-4-carboxylic acid
Agonist
PPAR
PPARα agonist
Structure-activity relationship
PPAR alpha agonist
PPAR-ALPHA
METABOLISM
BINDING
STRUCTURE-BASED DESIGN
Online AccessGet full text

Cover

Abstract [Display omitted] We previously reported that 1H-pyrazolo-[3,4-b]pyridine-4-carboxylic acid derivative 6 is an agonist of human peroxisome proliferator-activated receptor alpha (hPPARα). Here, we prepared a series of 1H-pyrazolo-[3,4-b]pyridine-4-carboxylic acid derivatives in order to examine the structure-activity relationships (SAR). SAR studies clearly indicated that the steric bulkiness of the substituent on 1H-pyrazolo-[3,4-b]pyridine ring, the position of the distal hydrophobic tail part, and the distance between the distal hydrophobic tail part and the acidic head part are critical for hPPARα agonistic activity. These SAR results are somewhat different from those reported for fibrate-class hPPARα agonists. A representative compound (10f) was as effective as fenofibrate in reducing the elevated plasma triglyceride levels in a high-fructose-fed rat model.
AbstractList [Display omitted] We previously reported that 1H-pyrazolo-[3,4-b]pyridine-4-carboxylic acid derivative 6 is an agonist of human peroxisome proliferator-activated receptor alpha (hPPARα). Here, we prepared a series of 1H-pyrazolo-[3,4-b]pyridine-4-carboxylic acid derivatives in order to examine the structure-activity relationships (SAR). SAR studies clearly indicated that the steric bulkiness of the substituent on 1H-pyrazolo-[3,4-b]pyridine ring, the position of the distal hydrophobic tail part, and the distance between the distal hydrophobic tail part and the acidic head part are critical for hPPARα agonistic activity. These SAR results are somewhat different from those reported for fibrate-class hPPARα agonists. A representative compound (10f) was as effective as fenofibrate in reducing the elevated plasma triglyceride levels in a high-fructose-fed rat model.
We previously reported that 1H-pyrazolo-[3,4-b] pyridine-4-carboxylic acid derivative 6 is an agonist of human peroxisome proliferator-activated receptor alpha (hPPAR alpha). Here, we prepared a series of 1H-pyrazolo-[3,4-b] pyridine-4-carboxylic acid derivatives in order to examine the structure-activity relationships (SAR). SAR studies clearly indicated that the steric bulkiness of the substituent on 1H-pyrazolo[3,4-b]pyridine ring, the position of the distal hydrophobic tail part, and the distance between the distal hydrophobic tail part and the acidic head part are critical for hPPAR alpha agonistic activity. These SAR results are somewhat different from those reported for fibrate-class hPPAR alpha agonists. A representative compound (10f) was as effective as fenofibrate in reducing the elevated plasma triglyceride levels in a high-fructose-fed rat model.
We previously reported that 1H-pyrazolo-[3,4-b]pyridine-4-carboxylic acid derivative 6 is an agonist of human peroxisome proliferator-activated receptor alpha (hPPARα). Here, we prepared a series of 1H-pyrazolo-[3,4-b]pyridine-4-carboxylic acid derivatives in order to examine the structure-activity relationships (SAR). SAR studies clearly indicated that the steric bulkiness of the substituent on 1H-pyrazolo-[3,4-b]pyridine ring, the position of the distal hydrophobic tail part, and the distance between the distal hydrophobic tail part and the acidic head part are critical for hPPARα agonistic activity. These SAR results are somewhat different from those reported for fibrate-class hPPARα agonists. A representative compound (10f) was as effective as fenofibrate in reducing the elevated plasma triglyceride levels in a high-fructose-fed rat model.
Author Miyachi, Hiroyuki
Doi, Takefumi
Ishimoto, Kenji
Fukuda, Syohei
Nunomura, Kazuto
Kobayashi, Tadayuki
Lin, Bangzhong
Yuzuriha, Tomohiro
Tabata, Ryotaro
Tachibana, Keisuke
Author_xml – sequence: 1
  givenname: Hiroyuki
  orcidid: 0000-0002-7693-7022
  surname: Miyachi
  fullname: Miyachi, Hiroyuki
  organization: Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, 1-1-1, Tsushima-Naka, Kita-ku, Okayama 700-8530, Japan
– sequence: 2
  givenname: Tomohiro
  surname: Yuzuriha
  fullname: Yuzuriha, Tomohiro
  organization: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan
– sequence: 3
  givenname: Ryotaro
  surname: Tabata
  fullname: Tabata, Ryotaro
  organization: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan
– sequence: 4
  givenname: Syohei
  surname: Fukuda
  fullname: Fukuda, Syohei
  organization: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan
– sequence: 5
  givenname: Kazuto
  surname: Nunomura
  fullname: Nunomura, Kazuto
  organization: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan
– sequence: 6
  givenname: Bangzhong
  surname: Lin
  fullname: Lin, Bangzhong
  organization: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan
– sequence: 7
  givenname: Tadayuki
  surname: Kobayashi
  fullname: Kobayashi, Tadayuki
  organization: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan
– sequence: 8
  givenname: Kenji
  surname: Ishimoto
  fullname: Ishimoto, Kenji
  organization: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan
– sequence: 9
  givenname: Takefumi
  surname: Doi
  fullname: Doi, Takefumi
  organization: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan
– sequence: 10
  givenname: Keisuke
  surname: Tachibana
  fullname: Tachibana, Keisuke
  organization: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan
BackLink https://www.ncbi.nlm.nih.gov/pubmed/31320147$$D View this record in MEDLINE/PubMed
BookMark eNqNkd9qFDEUxoNU7Lb6Al5ILiuaNf92dge8KYtaoWDRXggiIZOcsVkyk2mSWbu-kZe-iM9khl17KcIhfw6_75B83wk66kMPCD1ldM4oq15t5k1n_JxTVs9pVYo_QDMmK0mEpIsjNKN1Rcmqlp-P0UlKG0qZpFI-QseCiaKSyxn6-SnH0eQxao8tbMGHoYM-49BidkGGXdQ_gg_ki3gpSfO13J11PRBJjI5NuNt5Z7A2zhZxdFud3RYS1gnfjJ3u8QAx3LkUOsBDDN61EHUOkWiTJxgsjmBgKC2s_XCj8dnV1fnH37-ekwQeJgiw_hZ6l3J6jB622id4cthP0fXbN9frC3L54d379fklMbKqMllJYYQ1DQMrl5ZLXjO20C3XxrS1EUwbUbcLwUCIZW0rY2xZVsKUZtsuhThFZ_ux5cG3I6SsOpcMeK97CGNSnFeMi2IgKyjfoyaGlCK0aoiu03GnGFVTQmqjpoTUlJCiVSleRM8O88emA3sv-RtJAVZ74Ds0oU3GQW_gHqOUyhXlYrEsJ87WLhfPQ78OY5-L9MX_Swv9ek9DcXPrIKqDwrqSSlY2uH995A9vxcml
CitedBy_id crossref_primary_10_1002_slct_202002538
crossref_primary_10_1021_acs_joc_1c02165
crossref_primary_10_1016_j_scp_2020_100316
crossref_primary_10_1016_j_inoche_2020_108321
crossref_primary_10_3390_molecules27072237
crossref_primary_10_1248_bpb_b21_00220
crossref_primary_10_1007_s11172_022_3487_1
crossref_primary_10_1038_s41598_020_64527_x
crossref_primary_10_1055_a_2145_5916
crossref_primary_10_1111_ics_12767
Cites_doi 10.1074/jbc.RA118.002077
10.1021/jm2014293
10.1016/S0960-894X(03)00715-7
10.1172/JCI27989
10.1016/j.bbadis.2011.02.014
10.1016/j.bmc.2011.03.064
10.1038/415813a
10.1248/cpb.56.1357
10.1515/bchm.1997.378.7.651
10.1677/jme.0.0110037
10.5551/jat.28720
10.1016/S0022-2275(20)30037-7
10.1038/25931
ContentType Journal Article
Copyright 2019 Elsevier Ltd
Copyright © 2019 Elsevier Ltd. All rights reserved.
Copyright_xml – notice: 2019 Elsevier Ltd
– notice: Copyright © 2019 Elsevier Ltd. All rights reserved.
DBID 1KM
AAWJD
BLEPL
DTL
NPM
AAYXX
CITATION
7X8
DOI 10.1016/j.bmcl.2019.06.062
DatabaseName Index Chemicus
Web of Science - Science Citation Index Expanded - 2019
Web of Science Core Collection
Science Citation Index Expanded
PubMed
CrossRef
MEDLINE - Academic
DatabaseTitle Web of Science
PubMed
CrossRef
MEDLINE - Academic
DatabaseTitleList
Web of Science
PubMed
Database_xml – sequence: 1
  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: 2
  dbid: 1KM
  name: Index Chemicus
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC
  sourceTypes:
    Enrichment Source
    Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Medicine
Anatomy & Physiology
Chemistry
EISSN 1464-3405
EndPage 2128
ExternalDocumentID 10_1016_j_bmcl_2019_06_062
31320147
000480235700021
S0960894X19304445
Genre Research Support, Non-U.S. Gov't
Journal Article
GrantInformation_xml – fundername: Japan Agency for Medical Research and Development (AMED)
  sequence: 0
  grantid: JP18am0101085
– fundername: Grants-in-Aid for Scientific Research; Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT); Japan Society for the Promotion of Science; Grants-in-Aid for Scientific Research (KAKENHI)
  sequence: 0
  grantid: 16K13044; 15H02896
– fundername: JSPS KAKENHI; Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT); Japan Society for the Promotion of Science; Grants-in-Aid for Scientific Research (KAKENHI)
  sequence: 0
  grantid: 15H02896; 16K13044; 18H03190
– fundername: Takeda Science Foundation; Takeda Science Foundation (TSF)
  sequence: 0
– fundername: Ministry of Education, Culture, Sports, Science and Technology, Japan; Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT)
  sequence: 0
– fundername: AMED
  sequence: 0
  grantid: JP19am0101085
GroupedDBID ---
--K
--M
.~1
0R~
1B1
1RT
1~.
1~5
23N
4.4
457
4G.
5GY
5VS
7-5
71M
8P~
9JM
9JN
AABNK
AACTN
AAEDT
AAEDW
AAIAV
AAIKJ
AAKOC
AALRI
AAOAW
AAQFI
AARLI
AAXUO
ABBQC
ABFNM
ABGSF
ABJNI
ABMAC
ABMZM
ABUDA
ABZDS
ACDAQ
ACGFS
ACIUM
ACRLP
ADBBV
ADECG
ADEZE
ADUVX
AEBSH
AEHWI
AEKER
AENEX
AFKWA
AFTJW
AFXIZ
AFZHZ
AGHFR
AGUBO
AGYEJ
AIEXJ
AIKHN
AITUG
AJOXV
AJRQY
AJSZI
AKRWK
ALCLG
ALMA_UNASSIGNED_HOLDINGS
AMFUW
AMRAJ
ANZVX
AXJTR
BKOJK
BLXMC
BNPGV
CS3
D0L
EBS
EFJIC
EJD
EO8
EO9
EP2
EP3
F5P
FDB
FIRID
FLBIZ
FNPLU
FYGXN
G-Q
GBLVA
IHE
J1W
KOM
LZ2
M29
M2Z
M34
M41
MO0
N9A
O-L
O9-
OAUVE
OGGZJ
OZT
P-8
P-9
P2P
PC.
Q38
RIG
ROL
RPZ
SCC
SDF
SDG
SDP
SES
SPC
SPCBC
SSH
SSK
SSP
SSU
SSZ
T5K
YK3
ZMT
~02
~G-
1KM
AAXKI
BLEPL
DTL
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
NPM
.HR
53G
6TJ
AAQXK
AAYXX
ABTAH
ABXDB
ACNNM
ACRPL
ADMUD
ADNMO
AFFNX
AFJKZ
AGRDE
AHHHB
ASPBG
AVWKF
AZFZN
CITATION
FEDTE
FGOYB
G-2
HEA
HMK
HMO
HMS
HMT
HVGLF
HZ~
R2-
SAE
SCB
SEW
SOC
SPT
WUQ
XPP
Y6R
ZY4
7X8
ID FETCH-LOGICAL-c466t-843c3dcb1ed47d2429115af2accf9c31ac39f531e3379d6ccdd6c83c9f5ff733
IEDL.DBID .~1
ISICitedReferencesCount 11
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000480235700021
ISSN 0960-894X
IngestDate Fri Oct 25 01:57:43 EDT 2024
Fri Dec 06 01:20:16 EST 2024
Sat Sep 28 08:27:00 EDT 2024
Tue Dec 17 11:10:08 EST 2024
Fri Dec 13 18:09:13 EST 2024
Tue Jul 16 04:30:30 EDT 2024
IsDoiOpenAccess false
IsOpenAccess true
IsPeerReviewed true
IsScholarly true
Issue 16
Keywords Peroxisome proliferator-activated receptor alpha
1H-Pyrazolo-[3,4-b]pyridine-4-carboxylic acid
Agonist
PPAR
PPARα agonist
Structure-activity relationship
PPAR alpha agonist
PPAR-ALPHA
METABOLISM
BINDING
STRUCTURE-BASED DESIGN
Language English
License Copyright © 2019 Elsevier Ltd. All rights reserved.
LinkModel DirectLink
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-c466t-843c3dcb1ed47d2429115af2accf9c31ac39f531e3379d6ccdd6c83c9f5ff733
Notes KAKEN
SourceType-Other Sources-1
ObjectType-Article-2
content type line 63
ObjectType-Correspondence-1
ORCID 0000-0002-7693-7022
OpenAccessLink http://manuscript.elsevier.com/S0960894X19304445/pdf/S0960894X19304445.pdf
PMID 31320147
PQID 2261233131
PQPubID 23479
PageCount 5
ParticipantIDs pubmed_primary_31320147
proquest_miscellaneous_2261233131
crossref_primary_10_1016_j_bmcl_2019_06_062
webofscience_primary_000480235700021CitationCount
webofscience_primary_000480235700021
elsevier_sciencedirect_doi_10_1016_j_bmcl_2019_06_062
PublicationCentury 2000
PublicationDate 2019-08-15
PublicationDateYYYYMMDD 2019-08-15
PublicationDate_xml – month: 08
  year: 2019
  text: 2019-08-15
  day: 15
PublicationDecade 2010
PublicationPlace OXFORD
PublicationPlace_xml – name: OXFORD
– name: England
PublicationTitle Bioorganic & medicinal chemistry letters
PublicationTitleAbbrev BIOORG MED CHEM LETT
PublicationTitleAlternate Bioorg Med Chem Lett
PublicationYear 2019
Publisher Elsevier Ltd
Elsevier
Publisher_xml – sequence: 0
  name: Elsevier
– name: Elsevier Ltd
References Nolte, Wisely, Westin (b0040) 1998; 395
Raza-Iqbal, Tanaka, Anai (b0065) 2015; 22
Varga, Czimmerer, Nagy (b0005) 2011; 1812
Miyachi, Uchiki (b0060) 2003; 13
Kuwabara, Oyama, Tomioka (b0030) 2012; 55
Philippe, Giulia, Jean-Charles, Bart (b0010) 2006; 116
Tachibana, Yuzuriha, Tabata (b0035) 2018; 293
Xu, Stanley, Montana (b0050) 2002; 415
Araya, Kasuga, Toyota (b0025) 2008; 56
Physico-chemical properties of compound 10fNa: 1H NMR (300 MHz, CDCl3) δ 8.32 (2H, dd, J = 6.9, 2.2 Hz), 7.48 (2H, dd, J = 7.0, 2.3 Hz), 7.08 (1H, s), 3.78 (1H, sep, J = 6.9 Hz), 2.65 (3H, s), 1.40 (6H, d, J = 6.9 Hz). Mp. >300 °C. HPLC purity was estimated to be 99.8% by means of reversed-phase HPLC, using a Pegasil ODS sp100 column (4.6 mm × 250 mm, Senshu Chemical, Japan) fitted on a JASCO HPLC system, with CH3CN:0.1% TFA = 2:1 v/v as the eluent and detection at 254 nm.
Issemann, Prince, Tugwood, Green (b0015) 1993; 11
Park, Lemieux, Lewis, Kuksis, Steiner (b0075) 1997; 38
Physico-chemical properties of compound 10f: 1H NMR (300 MHz, DMSO-d6) δ 8.31 (2H, dd, J = 6.8, 2.1 Hz), 7.56 (1H, s), 7.47 (2H, dd, J = 6.9, 2.2 Hz), 3.86 (1H, sep, J = 6.8Hz), 2.76 (3H, s), 1.42 (6H, d, J = 6.7 Hz). 13C NMR (100 MHz, DMSO-d6) δ 167.27, 159.11, 151.12, 151.04, 137.95, 135.63, 129.52, 128.99, 121.83, 117.60, 109.29, 27.41, 24.45, 21.96. MS 329 (M+H)+. Mp. 270.6–271.4 °C. HPLC purity was estimated to be 99.5% by means of reversed-phase HPLC, using a Pegasil ODS sp100 column (4.6 mm × 250 mm, Senshu Chemical, Japan) fitted on a JASCO HPLC system, with CH3CN:0.1% TFA = 2:1 v/v as the eluent and detection at 254 nm.
Keller, Devchand, Perround, Wali (b0055) 1997; 378
Ban, Kasuga, Nakagome (b0020) 2011; 15
Xu, HE (WOS:000173833900052) 2002; 415
Tachibana, K (WOS:000437096700031) 2018; 293
Ban, S (WOS:000290299100015) 2011; 19
Park, J (WOS:000071277200014) 1997; 38
Nolte, RT (WOS:000075829900031) 1998; 395
Varga, T (WOS:000292350400023) 2011; 1812
Miyachi, H (WOS:000185322500005) 2003; 13
Lefebvre, P (WOS:000235854300003) 2006; 116
ISSEMANN, I (WOS:A1993LY83600005) 1993; 11
Raza-Iqbal, S (WOS:000365179900004) 2015; 22
Keller, H (WOS:A1997XQ68200011) 1997; 378
Araya, Y (WOS:000259078100030) 2008; 56
Kuwabara, N (WOS:000299453300029) 2012; 55
Ban (10.1016/j.bmcl.2019.06.062_b0020) 2011; 15
Issemann (10.1016/j.bmcl.2019.06.062_b0015) 1993; 11
Kuwabara (10.1016/j.bmcl.2019.06.062_b0030) 2012; 55
Nolte (10.1016/j.bmcl.2019.06.062_b0040) 1998; 395
Miyachi (10.1016/j.bmcl.2019.06.062_b0060) 2003; 13
Xu (10.1016/j.bmcl.2019.06.062_b0050) 2002; 415
Varga (10.1016/j.bmcl.2019.06.062_b0005) 2011; 1812
Keller (10.1016/j.bmcl.2019.06.062_b0055) 1997; 378
Araya (10.1016/j.bmcl.2019.06.062_b0025) 2008; 56
10.1016/j.bmcl.2019.06.062_b0070
10.1016/j.bmcl.2019.06.062_b0045
Tachibana (10.1016/j.bmcl.2019.06.062_b0035) 2018; 293
Raza-Iqbal (10.1016/j.bmcl.2019.06.062_b0065) 2015; 22
Philippe (10.1016/j.bmcl.2019.06.062_b0010) 2006; 116
Park (10.1016/j.bmcl.2019.06.062_b0075) 1997; 38
References_xml – volume: 11
  start-page: 37
  year: 1993
  ident: b0015
  publication-title: J. Mol. Endocrinol.
  contributor:
    fullname: Green
– volume: 22
  start-page: 754
  year: 2015
  ident: b0065
  publication-title: J. Atheroscler. Thromb.
  contributor:
    fullname: Anai
– volume: 1812
  start-page: 1007
  year: 2011
  ident: b0005
  publication-title: Biochim. Biophys. Acta
  contributor:
    fullname: Nagy
– volume: 55
  start-page: 893
  year: 2012
  ident: b0030
  publication-title: J. Med. Chem.
  contributor:
    fullname: Tomioka
– volume: 13
  start-page: 3145
  year: 2003
  ident: b0060
  publication-title: Bioorg. Med. Chem. Lett.
  contributor:
    fullname: Uchiki
– volume: 395
  start-page: 137
  year: 1998
  ident: b0040
  publication-title: Nature
  contributor:
    fullname: Westin
– volume: 38
  start-page: 2529
  year: 1997
  ident: b0075
  publication-title: J. Lipid Res.
  contributor:
    fullname: Steiner
– volume: 293
  start-page: 10333
  year: 2018
  ident: b0035
  publication-title: J. Biol. Chem.
  contributor:
    fullname: Tabata
– volume: 415
  start-page: 813
  year: 2002
  ident: b0050
  publication-title: Nature.
  contributor:
    fullname: Montana
– volume: 116
  start-page: 571
  year: 2006
  ident: b0010
  publication-title: J. Clin. Invest.
  contributor:
    fullname: Bart
– volume: 378
  start-page: 651
  year: 1997
  ident: b0055
  publication-title: Biol. Chem
  contributor:
    fullname: Wali
– volume: 15
  start-page: 3183
  year: 2011
  ident: b0020
  publication-title: Bioorg. Med. Chem.
  contributor:
    fullname: Nakagome
– volume: 56
  start-page: 1357
  year: 2008
  ident: b0025
  publication-title: Chem Pharm Bull (Tokyo)
  contributor:
    fullname: Toyota
– volume: 11
  start-page: 37
  year: 1993
  ident: WOS:A1993LY83600005
  article-title: THE PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR RETINOID-X RECEPTOR HETERODIMER IS ACTIVATED BY FATTY-ACIDS AND FIBRATE HYPOLIPEMIC DRUGS
  publication-title: JOURNAL OF MOLECULAR ENDOCRINOLOGY
  contributor:
    fullname: ISSEMANN, I
– volume: 293
  start-page: 10333
  year: 2018
  ident: WOS:000437096700031
  article-title: Discovery of peroxisome proliferator-activated receptor (PPARα) activators with a ligand-screening system using a human PPAR-expressing cell line
  publication-title: JOURNAL OF BIOLOGICAL CHEMISTRY
  doi: 10.1074/jbc.RA118.002077
  contributor:
    fullname: Tachibana, K
– volume: 22
  start-page: 754
  year: 2015
  ident: WOS:000365179900004
  article-title: Transcriptome Analysis of K-877 (a Novel Selective PPARα Modulator (SPPARMα))-Regulated Genes in Primary Human Hepatocytes and the Mouse Liver
  publication-title: JOURNAL OF ATHEROSCLEROSIS AND THROMBOSIS
  contributor:
    fullname: Raza-Iqbal, S
– volume: 395
  start-page: 137
  year: 1998
  ident: WOS:000075829900031
  article-title: Ligand binding and co-activator assembly of the peroxisome proliferator-activated receptor-γ
  publication-title: NATURE
  contributor:
    fullname: Nolte, RT
– volume: 378
  start-page: 651
  year: 1997
  ident: WOS:A1997XQ68200011
  article-title: PPAR alpha structure-function relationships derived from species-specific differences in responsiveness to hypolipidemic agents
  publication-title: BIOLOGICAL CHEMISTRY
  contributor:
    fullname: Keller, H
– volume: 415
  start-page: 813
  year: 2002
  ident: WOS:000173833900052
  article-title: Structural basis for antagonist-mediated recruitment of nuclear co-repressors by PPARα
  publication-title: NATURE
  contributor:
    fullname: Xu, HE
– volume: 55
  start-page: 893
  year: 2012
  ident: WOS:000299453300029
  article-title: Peroxisome Proliferator-Activated Receptors (PPARs) Have Multiple Binding Points That Accommodate Ligands in Various Conformations: Phenylpropanoic Acid-Type PPAR Ligands Bind to PPAR in Different Conformations, Depending on the Subtype
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm2014293
  contributor:
    fullname: Kuwabara, N
– volume: 56
  start-page: 1357
  year: 2008
  ident: WOS:000259078100030
  article-title: Structure-based design and synthesis of fluorescent PPARα/δ co-agonist and its application as a probe for fluorescent polarization assay of PPARδ ligands
  publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN
  contributor:
    fullname: Araya, Y
– volume: 13
  start-page: 3145
  year: 2003
  ident: WOS:000185322500005
  article-title: Analysis of the critical structural determinant(s) of species-selective peroxisome proliferator-activated receptor alpha (PPARα)-activation by phenylpropanoic acid-type PPARα agonists
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/S0960-894X(03)00715-7
  contributor:
    fullname: Miyachi, H
– volume: 116
  start-page: 571
  year: 2006
  ident: WOS:000235854300003
  article-title: Sorting out the roles of PPARα in energy metabolism and vascular horneostasis
  publication-title: JOURNAL OF CLINICAL INVESTIGATION
  doi: 10.1172/JCI27989
  contributor:
    fullname: Lefebvre, P
– volume: 38
  start-page: 2529
  year: 1997
  ident: WOS:000071277200014
  article-title: Chronic exogenous insulin and chronic carbohydrate supplementation increase de novo VLDL triglyceride fatty acid production in rats
  publication-title: JOURNAL OF LIPID RESEARCH
  contributor:
    fullname: Park, J
– volume: 1812
  start-page: 1007
  year: 2011
  ident: WOS:000292350400023
  article-title: PPARs are a unique set of fatty acid regulated transcription factors controlling both lipid metabolism and inflammation
  publication-title: BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR BASIS OF DISEASE
  doi: 10.1016/j.bbadis.2011.02.014
  contributor:
    fullname: Varga, T
– volume: 19
  start-page: 3183
  year: 2011
  ident: WOS:000290299100015
  article-title: Structure-based design, synthesis, and nonalcoholic steatohepatitis (NASH)-preventive effect of phenylpropanoic acid peroxisome proliferator-activated receptor (PPAR) α-selective agonists
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY
  doi: 10.1016/j.bmc.2011.03.064
  contributor:
    fullname: Ban, S
– volume: 1812
  start-page: 1007
  year: 2011
  ident: 10.1016/j.bmcl.2019.06.062_b0005
  publication-title: Biochim. Biophys. Acta
  doi: 10.1016/j.bbadis.2011.02.014
  contributor:
    fullname: Varga
– volume: 415
  start-page: 813
  year: 2002
  ident: 10.1016/j.bmcl.2019.06.062_b0050
  publication-title: Nature.
  doi: 10.1038/415813a
  contributor:
    fullname: Xu
– volume: 116
  start-page: 571
  year: 2006
  ident: 10.1016/j.bmcl.2019.06.062_b0010
  publication-title: J. Clin. Invest.
  doi: 10.1172/JCI27989
  contributor:
    fullname: Philippe
– ident: 10.1016/j.bmcl.2019.06.062_b0045
– volume: 55
  start-page: 893
  year: 2012
  ident: 10.1016/j.bmcl.2019.06.062_b0030
  publication-title: J. Med. Chem.
  doi: 10.1021/jm2014293
  contributor:
    fullname: Kuwabara
– volume: 293
  start-page: 10333
  year: 2018
  ident: 10.1016/j.bmcl.2019.06.062_b0035
  publication-title: J. Biol. Chem.
  doi: 10.1074/jbc.RA118.002077
  contributor:
    fullname: Tachibana
– volume: 13
  start-page: 3145
  year: 2003
  ident: 10.1016/j.bmcl.2019.06.062_b0060
  publication-title: Bioorg. Med. Chem. Lett.
  doi: 10.1016/S0960-894X(03)00715-7
  contributor:
    fullname: Miyachi
– volume: 56
  start-page: 1357
  year: 2008
  ident: 10.1016/j.bmcl.2019.06.062_b0025
  publication-title: Chem Pharm Bull (Tokyo)
  doi: 10.1248/cpb.56.1357
  contributor:
    fullname: Araya
– volume: 378
  start-page: 651
  year: 1997
  ident: 10.1016/j.bmcl.2019.06.062_b0055
  publication-title: Biol. Chem
  doi: 10.1515/bchm.1997.378.7.651
  contributor:
    fullname: Keller
– volume: 15
  start-page: 3183
  year: 2011
  ident: 10.1016/j.bmcl.2019.06.062_b0020
  publication-title: Bioorg. Med. Chem.
  doi: 10.1016/j.bmc.2011.03.064
  contributor:
    fullname: Ban
– volume: 11
  start-page: 37
  year: 1993
  ident: 10.1016/j.bmcl.2019.06.062_b0015
  publication-title: J. Mol. Endocrinol.
  doi: 10.1677/jme.0.0110037
  contributor:
    fullname: Issemann
– ident: 10.1016/j.bmcl.2019.06.062_b0070
– volume: 22
  start-page: 754
  year: 2015
  ident: 10.1016/j.bmcl.2019.06.062_b0065
  publication-title: J. Atheroscler. Thromb.
  doi: 10.5551/jat.28720
  contributor:
    fullname: Raza-Iqbal
– volume: 38
  start-page: 2529
  year: 1997
  ident: 10.1016/j.bmcl.2019.06.062_b0075
  publication-title: J. Lipid Res.
  doi: 10.1016/S0022-2275(20)30037-7
  contributor:
    fullname: Park
– volume: 395
  start-page: 137
  year: 1998
  ident: 10.1016/j.bmcl.2019.06.062_b0040
  publication-title: Nature
  doi: 10.1038/25931
  contributor:
    fullname: Nolte
SSID ssj0014044
Score 2.3909643
Snippet [Display omitted] We previously reported that 1H-pyrazolo-[3,4-b]pyridine-4-carboxylic acid derivative 6 is an agonist of human peroxisome...
We previously reported that 1H-pyrazolo-[3,4-b] pyridine-4-carboxylic acid derivative 6 is an agonist of human peroxisome proliferator-activated receptor alpha...
We previously reported that 1H-pyrazolo-[3,4-b]pyridine-4-carboxylic acid derivative 6 is an agonist of human peroxisome proliferator-activated receptor alpha...
Source Web of Science
SourceID proquest
crossref
pubmed
webofscience
elsevier
SourceType Aggregation Database
Index Database
Enrichment Source
Publisher
StartPage 2124
SubjectTerms 1H-Pyrazolo-[3,4-b]pyridine-4-carboxylic acid
Agonist
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Life Sciences & Biomedicine
Peroxisome proliferator-activated receptor alpha
Pharmacology & Pharmacy
Physical Sciences
PPAR
PPARα agonist
Science & Technology
Structure-activity relationship
Title Structural development of 1H-pyrazolo-[3,4-b]pyridine-4-carboxylic acid derivatives as human peroxisome proliferator-activated receptor alpha (PPARα)-selective agonists
URI https://dx.doi.org/10.1016/j.bmcl.2019.06.062
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000480235700021
https://www.ncbi.nlm.nih.gov/pubmed/31320147
https://search.proquest.com/docview/2261233131
Volume 29
WOS 000480235700021
WOSCitedRecordID wos000480235700021
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1fa9RAEF9KC-qL1Kt_Tm1ZoYii2zPZzW7yeByWU2kptsKBSNjsbiTiJeFySs8Hv4-P_SJ-Jmc2yan4B_ElkM1kSTKTmV-yM78hZD-2ABsSZVjGhWHCGMt0HDqWAUSKFZe5yLB2-OhYTl-J57NotkEmfS0MplV2vr_16d5bdyOj7mmO6qIYnSL4jhMxAwiCpGdYaC6iJ9jF4ODzOs0D2WM8hRQIM5TuCmfaHK9sbnD5IUg8h6cM_xScfgWfv41TPiYdbpOrHZik4_Z6r5ENVw7IzriED-n5it6nPr3T_zcfkMuTvrXbgFw66lbUd8iXU08gi-Qb1H5PIKJVToMpq1cL_QkmYK_5Y8GyN7BfQLBzTDCjF1l1vnpfGKpNYeHkhW-U9tE1VDfU9_6jyEJ-XjTV3NEa2wPlzq_qM6ymAGFnKTx8V8MQ9UW_9MHJyfjl14uHrPH9eWA2qt9WyO7bXCdnh0_PJlPWtW9gRki5ZLHghluTBc4KZQEKgF-NdB5qY_LE8EAbnuTgAhznKrESzAQ2MTcwmOeK8xtks6xKd4vQ0EicUoYQO_H7KYmUVULHgC6tVUk4JI96taV1S9KR9tlr71JUcopKTjGFT4J01Gs2_cnUUogifz3vXm8GKegLF1Z06aoPTRoiDxvnAQ-G5GZrH-vrQGpMsEI1JPs_Gsz6eFvVj6RDGJxgguBfxCYdgTsSFyxv_-cN3SFXcA__kAfRXbIJ9uZ2AWItsz3_Du2RrfGzF9Pjb5FiJ94
link.rule.ids 314,780,784,4502,24116,27924,27925,45585,45679
linkProvider Elsevier
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1fa9RAEF9qBdsXqVe1p1VXKKLoeiS7-fd4HJZTe6XYEw5Els3uRiJeEi6n9Hzo9-mjX8TP5MwmORX_IL4EspksSWYy80t25jeEHMQGYEMSaZZyoZnQ2jAV-5alAJHiiIeZSLF2eHIcjl-LF7NgtkFGXS0MplW2vr_x6c5btyOD9mkOqjwfnCL4jhMxAwiCpGfBJXJZBIB-waifnq_zPJA-xnFIgTRD8bZypknySuca1x-8xJF4hv6fotOv6PO3gcoFpcMdcrVFk3TYXPA1smGLHtkdFvAlPV_RB9Tld7of5z2yNep6u_XIlUm7pL5LLk4dgyyyb1DzPYOIlhn1xqxaLdRnmIC94U8ES9_Cfg7RzjLBtFqk5dnqQ66p0rmBkxeuU9onW1NVU9f8jyIN-Vlel3NLK-wPlFm3rM-wnAKEraHw9G0FQ9RV_dKHJyfDV1-_PGK1a9ADs1H1rkR63_o6mR4-m47GrO3fwLQIwyWLBdfc6NSzRkQGsAA41kBlvtI6SzT3lOZJBj7Ach4lJgQ7gU3MNQxmWcT5DbJZlIXdI9TXIU4Z-hA88QMqCSITCRUDvDQmSvw-edypTVYNS4fs0tfeS1SyRCVLzOELQTroNCt_sjUJYeSv593vzECCvnBlRRW2_FhLH4nYOPe41yc3G_tYXwdyY4IVRn1y8KPBrI83Zf3IOoTRCSbw_kVs1DK4I3PB8tZ_3tA9sjWeTo7k0fPjl7fJNh7B3-VesE82wfbsHcBby_Sue5--AUOQKXs
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=Structural+development+of+1H-pyrazolo-%5B3%2C4-b%5Dpyridine-4-carboxylic+acid+derivatives+as+human+peroxisome+proliferator-activated+receptor+alpha+%28PPAR%CE%B1%29-selective+agonists&rft.jtitle=Bioorganic+%26+medicinal+chemistry+letters&rft.au=Miyachi%2C+Hiroyuki&rft.au=Yuzuriha%2C+Tomohiro&rft.au=Tabata%2C+Ryotaro&rft.au=Fukuda%2C+Syohei&rft.date=2019-08-15&rft.pub=Elsevier+Ltd&rft.issn=0960-894X&rft.eissn=1464-3405&rft.volume=29&rft.issue=16&rft.spage=2124&rft.epage=2128&rft_id=info:doi/10.1016%2Fj.bmcl.2019.06.062&rft.externalDocID=S0960894X19304445
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0960-894X&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0960-894X&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0960-894X&client=summon