1H‑1,2,3-Triazole-Tethered Isatin–Ferrocene and Isatin–Ferrocenylchalcone Conjugates: Synthesis and in Vitro Antitubercular Evaluation

A Cu-mediated azide–alkyne cycloaddition protocol has been employed for the synthesis of 16 different triazoles to probe the antitubercular structure–activity relationships within the isatin–ferrocene–triazole conjugate family. The antitubercular evaluation studies revealed a marked improvement in a...

Full description

Saved in:
Bibliographic Details
Published inOrganometallics Vol. 32; no. 20; pp. 5713 - 5719
Main Authors Kumar, Kewal, Carrère-Kremer, Séverine, Kremer, Laurent, Guérardel, Yann, Biot, Christophe, Kumar, Vipan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.10.2013
Amer Chemical Soc
Subjects
Online AccessGet full text

Cover

Loading…
Abstract A Cu-mediated azide–alkyne cycloaddition protocol has been employed for the synthesis of 16 different triazoles to probe the antitubercular structure–activity relationships within the isatin–ferrocene–triazole conjugate family. The antitubercular evaluation studies revealed a marked improvement in activity with the introduction of ferrocene nucleus among precursors N-alkylazido isatins with a prefernce for halogen (F, Cl) substituent at C-5 position of isatin as well as propyl chain length as a spacer. The induction of a chalcone nucleus resulted in the enhanced antimycobacterial efficacy irrespective of the subtituent and alkyl chain length as evidenced by the isatin–ferrocenylchalcone hybrids. The described protocol is the first successful attempt of the amalgamation of ferrocene–isatin nuclei tethered via a triazole linker.
AbstractList A Cu-mediated azide–alkyne cycloaddition protocol has been employed for the synthesis of 16 different triazoles to probe the antitubercular structure–activity relationships within the isatin–ferrocene–triazole conjugate family. The antitubercular evaluation studies revealed a marked improvement in activity with the introduction of ferrocene nucleus among precursors N-alkylazido isatins with a prefernce for halogen (F, Cl) substituent at C-5 position of isatin as well as propyl chain length as a spacer. The induction of a chalcone nucleus resulted in the enhanced antimycobacterial efficacy irrespective of the subtituent and alkyl chain length as evidenced by the isatin–ferrocenylchalcone hybrids. The described protocol is the first successful attempt of the amalgamation of ferrocene–isatin nuclei tethered via a triazole linker.
A Cu-mediated azide-alkyne cycloaddition protocol has been employed for the synthesis of 16 different triazoles to probe the antitubercular structure activity relationships within the isatin-ferrocene-triazole conjugate family. The antitubercular evaluation studies revealed a marked improvement in activity with the introduction of ferrocene nucleus among precursors N-alkylazido isatins with a prefernce for halogen (F, Cl) substituent at C-S position of isatin as well as propyl chain length as a spacer. The induction of a chalcone nucleus resulted in the enhanced antimycobacterial efficacy irrespective of the subtituent and alkyl chain length as evidenced by the isatin-ferrocenylchalcone hybrids. The described protocol is the first successful attempt of the amalgamation of ferrocene isatin nuclei tethered via a triazole linker.
Author Kumar, Kewal
Carrère-Kremer, Séverine
Biot, Christophe
Kumar, Vipan
Guérardel, Yann
Kremer, Laurent
AuthorAffiliation DIMNP
Université Montpellier 2I
CNRS
Université Lille 1
Guru Nanak Dev University
AuthorAffiliation_xml – name: DIMNP
– name: Université Montpellier 2I
– name: Guru Nanak Dev University
– name: Université Lille 1
– name: CNRS
Author_xml – sequence: 1
  givenname: Kewal
  surname: Kumar
  fullname: Kumar, Kewal
– sequence: 2
  givenname: Séverine
  surname: Carrère-Kremer
  fullname: Carrère-Kremer, Séverine
– sequence: 3
  givenname: Laurent
  surname: Kremer
  fullname: Kremer, Laurent
– sequence: 4
  givenname: Yann
  surname: Guérardel
  fullname: Guérardel, Yann
– sequence: 5
  givenname: Christophe
  surname: Biot
  fullname: Biot, Christophe
  email: christophe.biot@univ-lille1.fr, vipan_org@yahoo.com
– sequence: 6
  givenname: Vipan
  surname: Kumar
  fullname: Kumar, Vipan
  email: christophe.biot@univ-lille1.fr, vipan_org@yahoo.com
BookMark eNqNUbtOAzEQtFCQCI-CP7iGCg68du5FF50SiBSJgkB7cnx7xNHFRrYPFKp8AA3iD_MlmIeoKKj2oZnRzs4-6WmjkZBjoOdAGVyYFacASfayQ_qQMBqndAA90qcsS-OMc75H9p1bUkrTjLM-eYXr7eYNztgZj2dWiRfTYjxDv0CLdTRxwiu93byP0VojUWMk9B_rdSsXopXhlKg0etk9CI_uMrpd6yDklPtiKR3dK29NNNRe-W6OVnatsNHoSbRdEDT6kOw2onV49FMPyN14NCuv4-nN1aQcTmMBOfhYyobWQFPARKZsUBdNxuoaGpZJLDBJRA4Uc46sFjXkiFgIKoowzSWHokn4ATn91n3GuWmcVKglVo9WrYRdV-E3nKU8TYrQ0Tyg8_-jS-W_rJSm0z5QT76pQrpqaTqrg60KaPWZVfWbFf8AtjGMZw
Cites_doi 10.1038/nature09657
10.1016/j.ejmech.2006.09.019
10.1016/j.ejmech.2011.10.033
10.1002/cbic.201200159
10.1016/j.ejmech.2005.12.004
10.1016/j.bmc.2007.03.031
10.1021/jm900513a
10.1016/S0968-0896(03)00233-5
10.1016/j.vaccine.2006.05.097
10.1016/j.bmc.2004.03.014
10.1016/S0140-6736(12)60734-X
10.1021/jo802097m
10.1039/c2dt12460b
10.1016/j.cbi.2004.04.004
10.1021/jm901120h
10.1016/j.ejmech.2010.10.004
10.1016/j.bmcl.2011.03.082
10.1021/om300296n
10.1128/AAC.47.4.1449-1451.2003
10.1016/j.bmcl.2011.11.082
10.1007/978-3-642-13185-1_1
10.1021/jm0708331
10.1002/anie.200502925
10.1016/j.bmc.2009.06.019
10.1016/j.ejmech.2012.06.057
10.1021/cr800500u
10.1093/jac/dkn507
10.1039/c2dt32148c
10.1038/nri1704
10.1021/jm049913k
10.1016/j.ejmech.2012.10.008
10.1016/j.ejmech.2010.07.020
10.1002/anie.200461471
10.1039/c2dt30514c
10.1021/cr0101510
10.1016/j.bmcl.2010.12.051
10.1016/S0223-5234(03)00085-0
10.1183/09031936.05.00109904
10.1016/j.bmc.2012.06.038
10.1016/j.ejmech.2011.06.037
10.1016/j.bmc.2005.08.008
10.1016/S0140-6736(06)69573-1
10.1021/jm301077m
10.1016/j.poly.2011.11.034
ContentType Journal Article
Copyright Copyright © 2013 American Chemical Society
Copyright_xml – notice: Copyright © 2013 American Chemical Society
DBID 1KM
BLEPL
DTL
GKMDS
DOI 10.1021/om301157z
DatabaseName Index Chemicus
Web of Science Core Collection
Science Citation Index Expanded
Web of Science - Science Citation Index Expanded - 2013
DatabaseTitle Web of Science
DatabaseTitleList
Web of Science
Database_xml – sequence: 1
  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 Chemistry
EISSN 1520-6041
EndPage 5719
ExternalDocumentID 000326365900008
c171663537
GrantInformation_xml – fundername: Department of Science and Technology, New Delhi, under Innovation in Science Pursuit for Inspired Research (INSPIRE) Fellowship; Department of Science & Technology (India)
GroupedDBID 123
4.4
55A
7~N
AABXI
ABMVS
ABPTK
ABUCX
ABUFD
ACGFS
ACJ
ACNCT
ACS
AEESW
AENEX
AFEFF
AFFNX
ALMA_UNASSIGNED_HOLDINGS
AQSVZ
CS3
D0L
DU5
DZ
EBS
ED
ED~
EJD
F20
F5P
GNL
IH9
IHE
JG
JG~
LG6
P2P
ROL
TN5
TWZ
UI2
VF5
VG9
VQA
W1F
X
XFK
XKZ
YNT
YZZ
-DZ
-~X
1KM
5VS
6P2
AALRI
AAXUO
ABJNI
ABQRX
ACGFO
ADHLV
AGXLV
AHGAQ
BAANH
BLEPL
CUPRZ
DTL
FDB
GGK
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
XSW
ID FETCH-LOGICAL-a181t-ccf0d1061e5c624d9f72dd1f27ce9e55a810e83e2dad18eee9a0a92dabc319f53
IEDL.DBID ACS
ISICitedReferencesCount 83
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000326365900008
ISSN 0276-7333
IngestDate Wed Sep 18 02:07:29 EDT 2024
Fri Oct 25 20:15:14 EDT 2024
Thu Aug 27 13:42:08 EDT 2020
IsPeerReviewed true
IsScholarly true
Issue 20
Keywords ORGANOMETALLIC COMPOUNDS
DESIGN
CYCLOADDITION EN-ROUTE
CHALCONE DERIVATIVES
ANTICANCER
ANALOGS
TUBERCULOSIS
BIOLOGICAL EVALUATION
AGENTS
BETA-LACTAM-FERROCENE
Language English
LinkModel DirectLink
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-a181t-ccf0d1061e5c624d9f72dd1f27ce9e55a810e83e2dad18eee9a0a92dabc319f53
ORCID 0000-0002-7396-1959
0000-0003-4967-9512
0000-0002-6604-4458
0000-0002-1853-1059
PageCount 7
ParticipantIDs webofscience_primary_000326365900008
webofscience_primary_000326365900008CitationCount
acs_journals_10_1021_om301157z
ProviderPackageCode JG~
55A
AABXI
GNL
VF5
XKZ
7~N
ACJ
VG9
W1F
ACS
AEESW
AFEFF
ABMVS
ABUCX
IH9
AQSVZ
ED~
UI2
PublicationCentury 2000
PublicationDate 2013-10-28
PublicationDateYYYYMMDD 2013-10-28
PublicationDate_xml – month: 10
  year: 2013
  text: 2013-10-28
  day: 28
PublicationDecade 2010
PublicationPlace WASHINGTON
PublicationPlace_xml – name: WASHINGTON
PublicationTitle Organometallics
PublicationTitleAbbrev ORGANOMETALLICS
PublicationTitleAlternate Organometallics
PublicationYear 2013
Publisher American Chemical Society
Amer Chemical Soc
Publisher_xml – name: American Chemical Society
– name: Amer Chemical Soc
References Liu, M (WOS:000183590100008) 2003; 11
Gursoy, A (WOS:000184333500011) 2003; 38
HEYM, B (WOS:A1994NZ23300007) 1994; 344
Sharma, VM (WOS:000177603200010) 2002; 12
Sriram, Dharmarajan (MEDLINE:16787323) 2005; 1
Kolb, HC (WOS:000187217100009) 2003; 8
Boumendjel, A (WOS:000254709100037) 2008; 51
Dalton, T (WOS:000310196500030) 2012; 380
Moon, MJ (WOS:000233708900024) 2006; 14
Marrapu, VK (WOS:000295237400083) 2011; 46
Kumar, K (WOS:000312745100015) 2012; 58
Lunardi, F (WOS:000181842000048) 2003; 47
Singh, P (WOS:000309494100046) 2012; 55
Yogeeswari, P. (BCI:BCI200510028467) 2005; 60
Singh, P (WOS:000301169800064) 2012; 47
Navarro, M (WOS:000308263500006) 2012; 31
EDWARDS, EI (WOS:A1979GN95100014) 1979; 168
Hindi, KM (WOS:000269042400019) 2009; 109
Martin, C (WOS:000230498200024) 2005; 26
Hillard, E (WOS:000234441900022) 2006; 45
Maguene, GM (WOS:000286905400004) 2011; 46
Patra, M (WOS:000305186000001) 2012; 13
Pasqualoto, KFM (WOS:000222530700006) 2004; 47
Pandeya, Surendra Nath (BCI:BCI200510084601) 2005; 55
Koul, A (WOS:000286596500023) 2011; 469
World Health Organization (000326365900008.1) 1000
Kumar, K (WOS:000313616600023) 2013; 42
Nabi, G (WOS:000286455300013) 2011; 21
Sambandamurthy, VK (WOS:000240702200018) 2006; 24
Slayden, RA (WOS:000263419700005) 2009; 63
Lloyd, NC (WOS:000226825900018) 2005; 44
Rao, YK (WOS:000221366000019) 2004; 12
Gandhi, NR (WOS:000242180900026) 2006; 368
Zhang, J (WOS:000267873000003) 2009; 17
Patra, M (WOS:000310120700018) 2012; 55
Nowakowska, Z (WOS:000245248300001) 2007; 42
Abadi, AH (WOS:000237184000002) 2006; 41
Aboul-Fadl, T (WOS:000282112700020) 2010; 45
Cabrera, M (WOS:000246257900006) 2007; 15
Huber, D (WOS:000271427900037) 2009; 52
Patra, M (WOS:000303775000003) 2012; 41
Kremer, L (WOS:000087392200065) 2000; 275
Aminake, MN (WOS:000307828600024) 2012; 20
Mahajan, A (WOS:000290024200014) 2011; 21
Jagasia, R (WOS:000265073700007) 2009; 74
Sabzevari, O (WOS:000222745100007) 2004; 148
Nunn, P (WOS:000232229600017) 2005; 5
Bouhfid, R (WOS:000234174800010) 2005; 65
Kumar, K (WOS:000303166800005) 2012; 41
Muller, TJ (WOS:000300643100035) 2012; 33
Garden, SJ (WOS:000073555900019) 1998; 28
Gibaud, S (WOS:000282667000001) 2010; 32
Pieroni, M (WOS:000270671200014) 2009; 52
van Staveren, DR (WOS:000225757500006) 2004; 104
Singh, P (WOS:000298636700005) 2012; 22
References_xml – volume: 469
  start-page: 483
  year: 2011
  ident: WOS:000286596500023
  article-title: The challenge of new drug discovery for tuberculosis
  publication-title: NATURE
  doi: 10.1038/nature09657
  contributor:
    fullname: Koul, A
– volume: 42
  start-page: 125
  year: 2007
  ident: WOS:000245248300001
  article-title: A review of anti-infective and anti-inflammatory chalcones
  publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1016/j.ejmech.2006.09.019
  contributor:
    fullname: Nowakowska, Z
– volume: 47
  start-page: 594
  year: 2012
  ident: WOS:000301169800064
  article-title: 1,2,3-Triazole tethered beta-lactam-Chalcone bifunctional hybrids: Synthesis and anticancer evaluation
  publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1016/j.ejmech.2011.10.033
  contributor:
    fullname: Singh, P
– volume: 168
  start-page: 259
  year: 1979
  ident: WOS:A1979GN95100014
  article-title: SYNTHESIS AND REACTIONS OF HOMONUCLEAR FERROCENE ACID ANHYDRIDES AND THEIR USE IN THE PREPARATION OF FERROCENYL-PENICILLINS AND FERROCENYL-CEPHALOSPORINS
  publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  contributor:
    fullname: EDWARDS, EI
– volume: 13
  start-page: 1232
  year: 2012
  ident: WOS:000305186000001
  article-title: Organometallic Compounds: An Opportunity for Chemical Biology?
  publication-title: CHEMBIOCHEM
  doi: 10.1002/cbic.201200159
  contributor:
    fullname: Patra, M
– volume: 41
  start-page: 296
  year: 2006
  ident: WOS:000237184000002
  article-title: Synthesis of 3-substituted-2-oxoindole analogues and their evaluation as kinase inhibitors, anticancer and antiangiogenic agents
  publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1016/j.ejmech.2005.12.004
  contributor:
    fullname: Abadi, AH
– volume: 15
  start-page: 3356
  year: 2007
  ident: WOS:000246257900006
  article-title: Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure-activity relationships
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY
  doi: 10.1016/j.bmc.2007.03.031
  contributor:
    fullname: Cabrera, M
– volume: 52
  start-page: 6287
  year: 2009
  ident: WOS:000270671200014
  article-title: Synthesis, Biological Evaluation, and Structure-Activity Relationships for 5-[(E)-2-Arylethenyl]-3-isoxazolecarboxylic Acid Alkyl Ester Derivatives as Valuable Antitubercular Chemotypes
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm900513a
  contributor:
    fullname: Pieroni, M
– volume: 11
  start-page: 2729
  year: 2003
  ident: WOS:000183590100008
  article-title: Structure-activity relationships of antileishmanial and antimalarial chalcones
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY
  doi: 10.1016/S0968-0896(03)00233-5
  contributor:
    fullname: Liu, M
– volume: 24
  start-page: 6309
  year: 2006
  ident: WOS:000240702200018
  article-title: Mycobacterium tuberculosis Delta RD1 Delta panCD: A safe and limited replicating mutant strain that protects immunocompetent and immunocompromised mice against experimental tuberculosis
  publication-title: VACCINE
  doi: 10.1016/j.vaccine.2006.05.097
  contributor:
    fullname: Sambandamurthy, VK
– volume: 12
  start-page: 2679
  year: 2004
  ident: WOS:000221366000019
  article-title: Differential effects of synthesized 2'-oxygenated chalcone derivatives: modulation of human cell cycle phase distribution
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY
  doi: 10.1016/j.bmc.2004.03.014
  contributor:
    fullname: Rao, YK
– volume: 275
  start-page: 16857
  year: 2000
  ident: WOS:000087392200065
  article-title: Thiolactomycin and related analogues as novel anti-mycobacterial agents targeting KasA and KasB condensing enzymes in Mycobacterium tuberculosis
  publication-title: JOURNAL OF BIOLOGICAL CHEMISTRY
  contributor:
    fullname: Kremer, L
– year: 1000
  ident: 000326365900008.1
  publication-title: Tuberculosis: Data and Country Profiles
  contributor:
    fullname: World Health Organization
– volume: 344
  start-page: 293
  year: 1994
  ident: WOS:A1994NZ23300007
  article-title: IMPLICATIONS OF MULTIDRUG-RESISTANCE FOR THE FUTURE OF SHORT-COURSE CHEMOTHERAPY OF TUBERCULOSIS - A MOLECULAR STUDY
  publication-title: LANCET
  contributor:
    fullname: HEYM, B
– volume: 28
  start-page: 1679
  year: 1998
  ident: WOS:000073555900019
  article-title: A convenient methodology for the N-alkylation of isatin compounds
  publication-title: SYNTHETIC COMMUNICATIONS
  contributor:
    fullname: Garden, SJ
– volume: 380
  start-page: 1406
  year: 2012
  ident: WOS:000310196500030
  article-title: Prevalence of and risk factors for resistance to second-line drugs in people with multidrug-resistant tuberculosis in eight countries: a prospective cohort study
  publication-title: LANCET
  doi: 10.1016/S0140-6736(12)60734-X
  contributor:
    fullname: Dalton, T
– volume: 74
  start-page: 2964
  year: 2009
  ident: WOS:000265073700007
  article-title: Peptide Cyclization and Cyclodimerization by Cu-I-Mediated Azide-Alkyne Cycloaddition
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo802097m
  contributor:
    fullname: Jagasia, R
– volume: 1
  start-page: 277
  year: 2005
  ident: MEDLINE:16787323
  article-title: Aminopyrimidinimino isatin analogues: design and synthesis of novel non- nucleoside HIV-1 reverse transcriptase inhibitors with broad-spectrum anti-microbial properties.
  publication-title: Medicinal chemistry (Shariqah (United Arab Emirates))
  contributor:
    fullname: Sriram, Dharmarajan
– volume: 41
  start-page: 6350
  year: 2012
  ident: WOS:000303775000003
  article-title: Small organometallic compounds as antibacterial agents
  publication-title: DALTON TRANSACTIONS
  doi: 10.1039/c2dt12460b
  contributor:
    fullname: Patra, M
– volume: 148
  start-page: 57
  year: 2004
  ident: WOS:000222745100007
  article-title: Molecular cytotoxic mechanisms of anticancer hydroxychalcones
  publication-title: CHEMICO-BIOLOGICAL INTERACTIONS
  doi: 10.1016/j.cbi.2004.04.004
  contributor:
    fullname: Sabzevari, O
– volume: 52
  start-page: 6860
  year: 2009
  ident: WOS:000271427900037
  article-title: 1,1 '-Disubstituted Ferrocenes as Molecular Hinges in Mono- and Bivalent Dopamine Receptor Ligands
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm901120h
  contributor:
    fullname: Huber, D
– volume: 46
  start-page: 31
  year: 2011
  ident: WOS:000286905400004
  article-title: Synthesis and antimycobacterial activity of a series of ferrocenyl derivatives
  publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1016/j.ejmech.2010.10.004
  contributor:
    fullname: Maguene, GM
– volume: 65
  start-page: 2949
  year: 2005
  ident: WOS:000234174800010
  article-title: An efficient synthesis of new spiro[indolo-3(1H),2 '(3 ' H)-oxadiazolyl] and 1-(triazol-4-ylmethyl)isatin derivatives
  publication-title: HETEROCYCLES
  contributor:
    fullname: Bouhfid, R
– volume: 21
  start-page: 2866
  year: 2011
  ident: WOS:000290024200014
  article-title: Synthesis and in vitro antitubercular activity of ferrocene-based hydrazones
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2011.03.082
  contributor:
    fullname: Mahajan, A
– volume: 31
  start-page: 5715
  year: 2012
  ident: WOS:000308263500006
  article-title: Bioorganometallic Compounds with Antimalarial Targets: Inhibiting Hemozoin Formation
  publication-title: ORGANOMETALLICS
  doi: 10.1021/om300296n
  contributor:
    fullname: Navarro, M
– volume: 47
  start-page: 1449
  year: 2003
  ident: WOS:000181842000048
  article-title: Trypanocidal and leishmanicidal properties of substitution-containing chalcones
  publication-title: ANTIMICROBIAL AGENTS AND CHEMOTHERAPY
  doi: 10.1128/AAC.47.4.1449-1451.2003
  contributor:
    fullname: Lunardi, F
– volume: 22
  start-page: 57
  year: 2012
  ident: WOS:000298636700005
  article-title: Synthesis, docking and in vitro antimalarial evaluation of bifunctional hybrids derived from beta-lactams and 7-chloroquinoline using click chemistry
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2011.11.082
  contributor:
    fullname: Singh, P
– volume: 32
  start-page: 1
  year: 2010
  ident: WOS:000282667000001
  article-title: Arsenic-Based Drugs: From Fowler's Solution to Modern Anticancer Chemotherapy
  publication-title: MEDICINAL ORGANOMETALLIC CHEMISTRY
  doi: 10.1007/978-3-642-13185-1_1
  contributor:
    fullname: Gibaud, S
– volume: 51
  start-page: 2307
  year: 2008
  ident: WOS:000254709100037
  article-title: Antimitotic and antiproliferative activities of chalcones: Forward structure-activity relationship
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm0708331
  contributor:
    fullname: Boumendjel, A
– volume: 45
  start-page: 285
  year: 2006
  ident: WOS:000234441900022
  article-title: Ferrocene-mediated proton-coupled electron transfer in a series of ferrocifen-type breast-cancer drug candidates
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200502925
  contributor:
    fullname: Hillard, E
– volume: 17
  start-page: 4873
  year: 2009
  ident: WOS:000267873000003
  article-title: 'Click' D-1 receptor agonists with a 5-HT1A receptor pharmacophore producing D-2 receptor activity
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY
  doi: 10.1016/j.bmc.2009.06.019
  contributor:
    fullname: Zhang, J
– volume: 55
  start-page: 455
  year: 2012
  ident: WOS:000309494100046
  article-title: Azide-alkyne cycloaddition en route to novel 1H-1,2,3-triazole tethered isatin conjugates with in vitro cytotoxic evaluation
  publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1016/j.ejmech.2012.06.057
  contributor:
    fullname: Singh, P
– volume: 109
  start-page: 3859
  year: 2009
  ident: WOS:000269042400019
  article-title: The Medicinal Applications of Imidazolium Carbene-Metal Complexes
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr800500u
  contributor:
    fullname: Hindi, KM
– volume: 63
  start-page: 451
  year: 2009
  ident: WOS:000263419700005
  article-title: Morphological features and signature gene response elicited by inactivation of FtsI in Mycobacterium tuberculosis
  publication-title: JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY
  doi: 10.1093/jac/dkn507
  contributor:
    fullname: Slayden, RA
– volume: 42
  start-page: 1492
  year: 2013
  ident: WOS:000313616600023
  article-title: Azide-alkyne cycloaddition en route towards 1H-1,2,3-triazole-tethered beta-lactam-ferrocene and beta-lactam-ferrocenylchalcone conjugates: synthesis and in vitro anti-tubercular evaluation
  publication-title: DALTON TRANSACTIONS
  doi: 10.1039/c2dt32148c
  contributor:
    fullname: Kumar, K
– volume: 5
  start-page: 819
  year: 2005
  ident: WOS:000232229600017
  article-title: Tuberculosis control in the era of HIV
  publication-title: NATURE REVIEWS IMMUNOLOGY
  doi: 10.1038/nri1704
  contributor:
    fullname: Nunn, P
– volume: 8
  start-page: 1128
  year: 2003
  ident: WOS:000187217100009
  article-title: The growing impact of click chemistry on drug discovery
  publication-title: DRUG DISCOVERY TODAY
  contributor:
    fullname: Kolb, HC
– volume: 47
  start-page: 3755
  year: 2004
  ident: WOS:000222530700006
  article-title: Rational design of new antituberculosis agents: Receptor-independent four-dimensional quantitative structure-activity relationship analysis of a set of isoniazid derivatives
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm049913k
  contributor:
    fullname: Pasqualoto, KFM
– volume: 58
  start-page: 153
  year: 2012
  ident: WOS:000312745100015
  article-title: Synthesis of novel 1H-1,2,3-triazole tethered C-5 substituted uracil isatin conjugates and their cytotoxic evaluation
  publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1016/j.ejmech.2012.10.008
  contributor:
    fullname: Kumar, K
– volume: 45
  start-page: 4578
  year: 2010
  ident: WOS:000282112700020
  article-title: Schiff bases of indoline-2,3-dione (isatin) derivatives and nalidixic acid carbohydrazide, synthesis, antitubercular activity and pharmacophoric model building
  publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1016/j.ejmech.2010.07.020
  contributor:
    fullname: Aboul-Fadl, T
– volume: 44
  start-page: 941
  year: 2005
  ident: WOS:000226825900018
  article-title: The composition of Ehrlich's salvarsan: Resolution of a century-old debate
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200461471
  contributor:
    fullname: Lloyd, NC
– volume: 41
  start-page: 5778
  year: 2012
  ident: WOS:000303166800005
  article-title: Synthesis and in vitro anti-tubercular evaluation of 1,2,3-triazole tethered beta-lactam-ferrocene and beta-lactam-ferrocenylchalcone chimeric scaffolds
  publication-title: DALTON TRANSACTIONS
  doi: 10.1039/c2dt30514c
  contributor:
    fullname: Kumar, K
– volume: 55
  start-page: 27
  year: 2005
  ident: BCI:BCI200510084601
  article-title: Biological activities of isatin and its derivatives
  publication-title: Acta Pharmaceutica (Zagreb)
  contributor:
    fullname: Pandeya, Surendra Nath
– volume: 104
  start-page: 5931
  year: 2004
  ident: WOS:000225757500006
  article-title: Bioorganometallic chemistry of ferrocene
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr0101510
  contributor:
    fullname: van Staveren, DR
– volume: 21
  start-page: 944
  year: 2011
  ident: WOS:000286455300013
  article-title: Radical-scavenging properties of ferrocenyl chalcones
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2010.12.051
  contributor:
    fullname: Nabi, G
– volume: 38
  start-page: 633
  year: 2003
  ident: WOS:000184333500011
  article-title: Synthesis and primary cytotoxicity evaluation of 3-[[(3-phenyl-4(3H)quinazolinone-2-yl)mercaptoacetyl] hydrazono]-1H-2-indolinones
  publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1016/S0223-5234(03)00085-0
  contributor:
    fullname: Gursoy, A
– volume: 12
  start-page: 2303
  year: 2002
  ident: WOS:000177603200010
  article-title: Novel indolo[2,1-b]quinazoline analogues as cytostatic agents: Synthesis, biological evaluation and structure-activity relationship
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  contributor:
    fullname: Sharma, VM
– volume: 60
  start-page: 1
  year: 2005
  ident: BCI:BCI200510028467
  article-title: Anticonvulsant and neurotoxicity evaluation of some 6-substituted benzothiazolyl-2-thiosemicarbazones
  publication-title: Farmaco (Lausanne)
  contributor:
    fullname: Yogeeswari, P.
– volume: 26
  start-page: 162
  year: 2005
  ident: WOS:000230498200024
  article-title: The dream of a vaccine against tuberculosis; new vaccines improving or replacing BCG?
  publication-title: EUROPEAN RESPIRATORY JOURNAL
  doi: 10.1183/09031936.05.00109904
  contributor:
    fullname: Martin, C
– volume: 20
  start-page: 5277
  year: 2012
  ident: WOS:000307828600024
  article-title: Synthesis and evaluation of hybrid drugs for a potential HIV/AIDS-malaria combination therapy
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY
  doi: 10.1016/j.bmc.2012.06.038
  contributor:
    fullname: Aminake, MN
– volume: 46
  start-page: 4302
  year: 2011
  ident: WOS:000295237400083
  article-title: Novel aryloxy azolyl chalcones with potent activity against Mycobacterium tuberculosis H37Rv
  publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1016/j.ejmech.2011.06.037
  contributor:
    fullname: Marrapu, VK
– volume: 14
  start-page: 237
  year: 2006
  ident: WOS:000233708900024
  article-title: Synthesis and structure-activity relationships of novel indirubin derivatives as potent anti-proliferative agents with CDK2 inhibitory activities
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY
  doi: 10.1016/j.bmc.2005.08.008
  contributor:
    fullname: Moon, MJ
– volume: 368
  start-page: 1575
  year: 2006
  ident: WOS:000242180900026
  article-title: Extensively drug-resistant tuberculosis as a cause of death in patients co-infected with tuberculosis and HIV in a rural area of South Africa
  publication-title: LANCET
  doi: 10.1016/S0140-6736(06)69573-1
  contributor:
    fullname: Gandhi, NR
– volume: 55
  start-page: 8790
  year: 2012
  ident: WOS:000310120700018
  article-title: Ferrocenyl Derivatives of the Anthelmintic Praziquantel: Design, Synthesis, and Biological Evaluation
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm301077m
  contributor:
    fullname: Patra, M
– volume: 33
  start-page: 257
  year: 2012
  ident: WOS:000300643100035
  article-title: A spectroscopic, electrochemical and DFT study of para-substituted ferrocene-containing chalcone derivatives: Structure of FcCOCHCH(p-(BuC6H4)-Bu-t)
  publication-title: POLYHEDRON
  doi: 10.1016/j.poly.2011.11.034
  contributor:
    fullname: Muller, TJ
SSID ssj0006732
Score 2.4451656
Snippet A Cu-mediated azide–alkyne cycloaddition protocol has been employed for the synthesis of 16 different triazoles to probe the antitubercular structure–activity...
A Cu-mediated azide-alkyne cycloaddition protocol has been employed for the synthesis of 16 different triazoles to probe the antitubercular structure activity...
Source Web of Science
SourceID webofscience
acs
SourceType Enrichment Source
Index Database
Publisher
StartPage 5713
SubjectTerms Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
Title 1H‑1,2,3-Triazole-Tethered Isatin–Ferrocene and Isatin–Ferrocenylchalcone Conjugates: Synthesis and in Vitro Antitubercular Evaluation
URI http://dx.doi.org/10.1021/om301157z
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000326365900008
Volume 32
WOS 000326365900008
WOSCitedRecordID wos000326365900008
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3JTsMwEB2xHODCjiibLMERQ21ncbhVgaogwYWCuFWOPRFlSVGTHuiJD-CC-EO-BDtdhMR6TGQnVmYmz-NZHsBuGgrtyNEoGo9Ta4kBVdokNLW6xNGEHLWrRj47DxqX3um1fz0BOz9E8Dk76Dw4HfTD_iRMc4uHzsOqxRfj320Qlixk1r0KaCiEGLUP-jzVQY_Ov8WWEkfq83A0qsYZpI_c7feKZF_3vzZn_G2JCzA33EeS2kDwizCB2RLMxCP6tmV4YY3351e2x_cEbVot63fukTbL8l405MQl8WTvz2917DoIy5Co7JvbT_f6RrmYFZK4k9323KFbfkgunjL7oLydl7PaGblqF90Oqbma316C3TK5lRyPO4mvwGX9uBk36JB6gSoL-QXVOq0a5y2irwPumSgNuTEs5aHGCH1fSVZFKZAbZZhExEhVVWSvEm1tOvXFKkxldm1rQBJPJsYLVRAJ63pJqexYEfkJC7T0lE4rsG1l0xqaTt4qo-KctcYftQK7n8XWehy04XBhc7v3FEHJe1qVFWD_GRYPW5-7kv9i_a93b8Asd_wXFqy43ISpotvDLbsLKZLtUgs_AKD93F4
link.rule.ids 315,786,790,27107,27955,27956,57091,57141
linkProvider American Chemical Society
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3NTtwwELZaeqAXoBTEQgEfOGK6tvPjcFtFrJbfC0vFLXLsidgWsmiTPbAnHoAL6hvyJIy9YUEVUjkmsp2RM5MZZ2a-j5CdIpbGkaMxsIFgaIkR08bmrEBdEmBjAcZ1I5-eRb2L4OgyvGxgclwvDApR4UqVT-K_ogvwn8Mbp4phPPlMvuDaiTPCTno---pGsScjw1NWxGIp5QuK0NupzgOZ6l0X491Jd3HKS-QF8VUkf_bGdb5nJv9gNH5M0iWy0ESVtDNVg2_kE5TLZD59IXP7Th547-n-ke-KXcn6qHOT4TWwvm_2BUsPXUlP-XT_twsj59BKoLp85_bdtbnSLoMFNB2Wv8fuF1y1T8_vSlyoGlR-1qCkvwb1aEg7rgN4nMPIl7rSgxmu-Aq56B700x5riBiYxgCgZsYUbevOjhCaSAQ2KWJhLS9EbCCBMNSKt0FJEFZbrgAg0W2d4FVu0MKLUK6SuRJlWyM0D1Rug1hHicSDmFIax8okzHlkVKBN0SJbuKdZY0hV5nPkgmezTW2RnbdvL7udgnK4JDpGojLyLKht1SL8I8PSBgjdAQDU6_979jaZ7_VPT7KTw7PjDfJVOGYMdGNC_SBz9WgMmxif1PmWV8xnhcXkyQ
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3NTtwwELZaKrVcCi2t2JYfHzhiWNtJ7PS2CqyW0tJKLBW3yLEn6rY0izbZA3viAXpBvCFPwtiEFaqQyjGR7YycmcxMxvN9hGyVSlpPjsbARYKhJSbMWFewEnVJgFMCrO9G_nqUDE6iz6fxaZso-l4YFKLGlepQxPdWfe7KFmGA747_eHWM1ew5eRErHnlD7GXH8y9vogIhGWZaCVNSynskoYdTvRey9aNuJriU_hL5NhcmnCT5vTNtih07-wen8enSLpPXbXRJe3fq8IY8g-oteZXdk7qtkL98cHN5xbfFtmRD1L3Z-AzYMDT9gqMH_mhPdXN53YeJd2wVUFM9cvvizP40vpIFNBtXv6b-V1z9iR5fVLhQParDrFFFf4yayZj2fCfwtIBJOPJK9-f44u_ISX9_mA1YS8jADAYCDbO27DqfQ0JsExG5tFTCOV4KZSGFODaad0FLEM44rgEgNV2T4lVh0dLLWL4nCxXKtkpoEenCRcokqcSETGuDY2UaFzyxOjK27JAN3Ne8Nag6D7VywfP5pnbI1sM3mJ_fgXP4YjpGpDIJbKhd3SH8KcOyFhDdAwE0H_737E3y8vteP_9ycHT4kSwKT5CB3kzoNbLQTKawjmFKU2wE3bwFyOXnQw
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=1H-1%2C2%2C3-Triazole-Tethered+Isatin-Ferrocene+and+Isatin-Ferrocenylchalcone+Conjugates%3A+Synthesis+and+in+Vitro+Antitubercular+Evaluation&rft.jtitle=Organometallics&rft.au=Kumar%2C+Kewal&rft.au=Carrere-Kremer%2C+Severine&rft.au=Kremer%2C+Laurent&rft.au=Guerardel%2C+Yann&rft.date=2013-10-28&rft.pub=Amer+Chemical+Soc&rft.issn=0276-7333&rft.eissn=1520-6041&rft.volume=32&rft.issue=20&rft.spage=5713&rft.epage=5719&rft_id=info:doi/10.1021%2Fom301157z&rft.externalDBID=n%2Fa&rft.externalDocID=000326365900008
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0276-7333&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0276-7333&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0276-7333&client=summon