Synthesis and Antimycobacterial Evaluation of Piperazyl‐alkyl‐Ether Linked 7‐Chloroquinoline‐Chalcone/Ferrocenyl Chalcone Conjugates

Abstract

A series of piperazyl‐alkyl‐ether linked 7‐chloroquinoline‐chalcone/ferrocenyl chalcone conjugates were synthesized and evaluated for their anti‐mycobacterial activities against the mc26230 strain of Mycobacterium tuberculosis and cytotoxicity against the Vero cell line. While all the compounds showed limited cytotoxicity, the ferrocenyl‐chalcone conjugate with pentyl chain as spacer proved to be most potent among the series with a Minimum Inhibitory Concentration (MIC) of 14 μg/mL.

Structural and biological survey of 7‐chloro‐4‐(piperazin‐1‐yl)quinoline and its derivatives

“…However, all compounds were less active and more toxic than the standards (Quinine and Camptothecin) (Ansari et al, 2017). However, Singh et al proved that the introduction of ferrocene ring improved the antitubercular activities in general with conjugate 49 exhibiting MIC of 14 μg/ml comparable to the most active conjugate 50 in the series which does not have ferrocene ring MIC of 15 μg/ml (Singh, Viljoen, Kremer, & Kumar, 2018). In 2018, Shalini et al identified compound 51 against M. tuberculosis , it exhibited activity (MIC 50 : 2.2 μg/ml) against mc26230 strain.…”

A Study on Biologically Active Chalcone Based Benzodiazepines

“…[3] Further studies on benzodiazepines led to the conclusion that they exhibited good anti-cancer [4,5] , antibacterial [6] , antifungal [7] , anti-inflammatory [8,9] , antitubercular [10] , and anticonvulsant properties [11,12] Chalcone, a biologically active compound was extracted naturally from plants and was used for the formation of many flavonoids and isoflavonoids heterocycles. [13][14][15][16] Chalcone being a biologically active compound itself reported many properties like antibacterial 17] , antioxidant [18] , antimycobacterial [19] , antitumor [20] , antituberculosis [14] , and cytotoxicity [21] . Apart from this, they are also used to synthesise many heterocycles such as benzodiazepines [22] , pyrazolines [23,24] , isoxazoles [25] etc.…”

Experimental and Theoretical Studies on the Molecular Structure, FT-IR, NMR, HOMO, LUMO, MESP, and Reactivity Descriptors of (E)-1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

“…Chalcones are considered as vital intermediates to synthesize wide variety of heterocyclic compounds with broad-spectrum of biological activities. [11][12][13][14][15][16] The extraordinary pharmacological profile of chalcones and their hybrid derivatives include anticancer, [17][18][19][20] anti-tubercular, 21,22 antibacterial, [23][24][25][26] anti-HIV, [27][28][29][30] antimalarial, [31][32][33][34] antioxidants, [35][36][37] antiviral, [38][39][40] antifungal, [41][42][43][44][45] cardiovascular, 46,47 antitumor, [48][49][50] antiulcer, 51 anticonvulsant, 52,53 anti-inflammatory, [54][55][56][57][58]…”