Novel 3-fluoro-4-morpholinoaniline derivatives: synthesis and assessment of anti-cancer activity in breast cancer cells

TitleNovel 3-fluoro-4-morpholinoaniline derivatives: synthesis and assessment of anti-cancer activity in breast cancer cells
Publication TypeJournal Article
Year of Publication2022
AuthorsMore, NA, Jadhao, NL, Meshram, RJ, Tambe, P, Salve, RA, Sabane, JK, Sawant, SN, Gajbhiye, V, Gajbhiye, JM
JournalJournal of Molecular Structure
Date PublishedAPR
Type of ArticleArticle
KeywordsAnticancer activity, Apoptosis, Breast cancer, Heterocyclic compounds, Morpholine, Sulfonamide
AbstractHeterocyclic morpholine compounds are well-known for their anti-cancer activity. In this study, novel morpholine and its sulfonamide derivatives were designed and synthesized as potential anti-tumor agents. The new compounds were obtained from amine derivatives via nucleophilic addition reactions, providing the desired products in 70 to 90% yield. The docking analysis was performed for all thirty-one compounds. Out of them, we represent the docking poses for compounds NAM-5 and NAM-7 as representatives. After docking analysis, compounds NAM-5 and NAM- 7 were tested for in vitro antitumor activity against breast cancer cell lines (MCF-7 and MDA-MB-231) and healthy mouse embryonic fibroblast cell line (3T3L-1). Amongst these, sulfonamide group-containing compound NAM-5 showed significant anti-proliferative activity with IC50 of 1.811 mu M and 2.143 mu M for MCF-7 and MDA-MB-231 cells, respectively. On the other hand, NAM-7 showed good anti-proliferative activity against MCF-7 (IC50 1.883 mu M) but slightly lower activity against MDA-MB-231 cells (IC50 4.688 mu M). The activity of both the compound was also tested on 3T3L-1 Cell line which showed activity similar to clinically approved anti-cancer drug doxorubicin (DOX). The cell death analysis by flow-cytometry confirmed apoptosis mediated cell death in 3T3L-1, MCF-7 and MDA-MB-231 cells when treated with the NAM-5 and NAM-7, respectively. The results demonstrated that the synthesized sulfonamide derivatives have significant potential as anti-cancer agents and have a substantial importance in cancer therapeutics with favourable safety profile. Structural analysis of docked poses of sulfonamide derivatives attempts to shed light on the structural basis of sulfonamide derivatives based anti-cancer effect. (C) 2021 Elsevier B.V. All rights reserved.
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)3.196
Divison category: 
Organic Chemistry

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