An efficient one-pot cyclization of quinoline thiosemicarbazones to quinolines derivatized with 1,3,4-thiadiazole as anticancer and anti-tubercular agents

Abstract

A series of 6,7,8-substituted thiosemicarbazones (2a-j) of 2-chloro-3-formyl-quinoline derivatives were cyclized to the title compounds (3a-j) using acetic anhydride. The structures of the final compounds (3a-j) were confirmed by elemental and spectral (IR, 1 H NMR and MS) analysis. Some of the title compounds have shown promising anticancer and antitubercular activities.

N-[4-Acetyl-5-(4-fluorophenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide

“…For biological applications of 1,3,4-thiadiazole derivatives, see: ; Kumar et al (2012); Oruç et al (2004); Kadi et al (2007); Noolvi et al (2011);; Marganakop et al (2012). For a related structure, see: Zhang (2009).…”

“…of naturally occurring compounds and also pharmacologically potent molecules. These derivatives are known to exhibit a broad spectrum of activities including antiproliferative, antituberculosis, anti-inflammatory, anticancer and antimicrobial activities Kumar et al, 2012;Oruç et al, 2004;Kadi et al, 2007;Noolvi et al, 2011;Marganakop et al, 2012).…”

Synthesis and Antiproliferative Activity of Some Quinoline and Oxadiazole Derivatives

“…The biological potential of quinoline inspired us to explore further the quinoline derivatives. The quinoline derivatives showed promising antiproliferative activity against HeLa (human cervix cancer cell line) and MDA-MB-435 (melanoma) cell lines [6,7,14]. Hence we selected HeLa and MDA-MB-435 to test the in vitro antiproliferative activity of quinoline derivatives (5a-j) reported here in the present investigation.…”

“…Several quinoline analogues were reported as anticancer agents [6][7][8][9][10][11][12][13]. The structure of some of the quinoline anticancer drug is shown in Figure 1 [6].…”

An Efficient One‐Pot Synthesis of 7,7‐Dimethyl‐2‐(2‐oxo‐2H‐chromen‐3‐yl)‐4‐aryl‐7,8‐dihydroquinolin‐5(6H)‐one Derivatives Using Chitosan–SO3H as Biodegradable Organocatalyst

“…Quinoline and its derivatives are an important class of N‐containing heterocycles; they are present in a wide variety of naturally occurring alkaloids with pharmacological properties, and they are useful for dyes and intermediates in organic synthesis . Quinoline compounds possess a broad spectrum of biological activity such as antitumor , acetylcholinesterase inhibitors , anticonvulsant , cardiovascular , leishmanicidal activity , topo I/II inhibitor activities , anti‐proliferative activity , and antitubercular activities .…”