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Azide-Alkyne Cycloaddition En Route to 1H-1,2,3-Triazole-Tethered Isatin-Ferrocene, Ferrocenylmethoxy-Isatin, and Isatin-Ferrocenylchalcone Conjugates: Synthesis and Antiproliferative Evaluation.


ABSTRACT: Diverse series of isatin-ferrocene conjugates were synthesized via Cu-promoted azide-alkyne cycloaddition reaction with an aim of probing their antiproliferative structure-activity relationship against MCF-7 (estrogen receptor positive) and MDA-MB-231 (triple negative) cell lines. Among the synthesized conjugates, isatin-ferrocenes proved to be more potent against MCF-7, whereas ferrocenylmethoxy-isatins exhibited activity against MDA-MB-231 cell lines. However, the introduction of chalcone moiety among these hybrids resulted in the complete loss of activity against the tested cell lines, as evident by isatin-ferrocenylchalcones. The conjugates 5a and 9c proved to be the most potent among the series against MCF-7 and MDA-MB-213 cell lines, exhibiting IC50 values of 31.62 and 20.26 ?M, respectively.

SUBMITTER: Singh A 

PROVIDER: S-EPMC6044575 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Azide-Alkyne Cycloaddition En Route to 1<i>H</i>-1,2,3-Triazole-Tethered Isatin-Ferrocene, Ferrocenylmethoxy-Isatin, and Isatin-Ferrocenylchalcone Conjugates: Synthesis and Antiproliferative Evaluation.

Singh Amandeep A   Saha Sourav Taru ST   Perumal Shanen S   Kaur Mandeep M   Kumar Vipan V  

ACS omega 20180130 1


Diverse series of isatin-ferrocene conjugates were synthesized via Cu-promoted azide-alkyne cycloaddition reaction with an aim of probing their antiproliferative structure-activity relationship against MCF-7 (estrogen receptor positive) and MDA-MB-231 (triple negative) cell lines. Among the synthesized conjugates, isatin-ferrocenes proved to be more potent against MCF-7, whereas ferrocenylmethoxy-isatins exhibited activity against MDA-MB-231 cell lines. However, the introduction of chalcone moie  ...[more]

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