Synthesis and in Vitro Evaluation of New Nitro-Substituted Thiazolyl Hydrazone Derivatives as Anticandidal and Anticancer Agents

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ALTINTOP M. D., ÖZDEMİR A., Turan-Zitouni G., ILGIN S., ATLI EKLİOĞLU Ö., DEMİRCİ F., ...More

MOLECULES, vol.19, no.9, pp.14809-14820, 2014 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 19 Issue: 9
  • Publication Date: 2014
  • Doi Number: 10.3390/molecules190914809
  • Journal Name: MOLECULES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.14809-14820
  • Keywords: thiazole, hydrazone, furan, anticancer activity, anticandidal activity, BIOLOGICAL-ACTIVITIES, ANTIPROLIFERATIVE ACTIVITY, ANTIFUNGAL AGENTS, DRUG-RESISTANCE, CANCER-CELLS, INFECTIONS, HYDRAZIDES, INHIBITORS, ANALOGS, MOIETY
  • Anadolu University Affiliated: Yes

Abstract

Fourteen new thiazolyl hydrazone derivatives were synthesized and evaluated for their anticandidal activity using a broth microdilution assay. Among the synthesized compounds, 2-[2-((5-(4-chloro-2-nitrophenyl) furan-2-yl) methylene) hydrazinyl]-4-(4-fluorophenyl) thiazole and 2-[2-((5-(4-chloro-2-nitrophenyl) furan-2-yl) methylene) hydrazinyl]-4-(4-methoxyphenyl) thiazole were found to be the most effective antifungal compounds against Candida utilis, with a MIC value of 250 mu g/mL, when compared with fluconazole (MIC = 2 mu g/mL). Additionally, the synthesized compounds were evaluated for their in vitro cytotoxic effects on the MCF-7 and NIH/3T3 cell lines. As a result, 2-[2-((5-(4-chloro-2-nitrophenyl) furan-2-yl) methylene) hydrazinyl]-4-(4-chlorophenyl) thiazole was identified as the most promising anticancer compound against MCF-7 cancer cells due to its inhibitory effects (IC50 = 125 mu g/mL) and relatively low toxicity towards the NIH/3T3 cell line (IC50 > 500 mu g/mL).