Arylnitro monocarbonyl curcumin analogues: Synthesis and in vitro antitubercular evaluation

Abstract

Curcumin is a natural product that has been reported to exhibit myriad pharmacological properties, one of which is antitubercular activity. It demonstrates antitubercular activity by directly inhibiting Mycobacterium tuberculosis (M.tb) and also enhances immune responses that ultimately lead to the elimination of M.tb by macrophages. This natural product is, however, unstable, and several analogues, noticeably monocarbonyl analogues, have been synthesized to overcome this challenge. Curcumin and its monocarbonyl analogues reported so far exhibit moderate antitubercular activity in the range of 7 to 16 μM. Herein, we report a straightforward synthesis of novel monocarbonyl curcumin analogues, their antitubercular activity, and the structure-activity relationship. The hit compound from this study, 3a, exhibits potent MIC 90 values in the range of 0.2 to 0.9 μM in both ADC and CAS media.

Novel quinoline derivatives with broad‐spectrum antiprotozoal activities

“…Intermediate 1 was then subjected to a Schiff base condensation reaction [ 37 ] with 5‐nitrofuran‐2‐carbaldehyde to yield compound 1a with a yield of 59%. Intermediate 2 was subjected to an Aldol condensation reaction [ 32 ] with various aldehydes, affording compounds 2a–2d in yields ranging from 30% to 100%. To synthesize compounds 3a–3d , intermediate 2 underwent N ‐alkylation with appropriate benzyl halide.…”

“…[36] This reaction afforded the desired compounds with yields varying from 10% to 80%. In addition, compounds 3a-3d were subjected to Aldol condensation [32] F I G U R E 1 Drugs used to treat trypanosomatids diseases. with various aldehydes in acetic acid, resulting in the formation of compounds 4a-4i with yields ranging from 5% to 50%.…”

“…[27] Among the various chalcone derivatives, aminochalcones have potential as antileishmanial, [28] antitrypanosomal, [29] and antibacterial agents. [30] Nitroaromatic chemicals have been found to exhibit inhibitory effects against various pathogenic organisms, including bacteria, [31,32] fungi, [33] viruses, and protozoans. [34] Typically, they function as prodrugs, wherein the nitro group is bioreduced to generate reactive nitrogen species, which are responsible for the anti-infective properties of this compound class.…”

Quinolone-3-amidoalkanol: A New Class of Potent and Broad-Spectrum Antimicrobial Agent

“…A 10 mL culture of Mtb pMSp12::GFP was grown in a Middlebrook 7H9 medium supplemented with either 0.03% casitone, 0.4% glucose, and 0.05% tyloxapol, or 0.03% albumine, 0.4% glucose, and 0.05% Tween 80, to an optical density (OD 600 ) of 0.6–0.7. The media cultures were diluted to 1:500 …”

Synthesis and In Vitro Antibacterial Evaluation of Mannich Base Nitrothiazole Derivatives

“…On day 14 following incubation, fluorescence readings were recorded for each well at 485 and 520 nM using a plate reader (FLUOstar OPTIMA, BMG LABTECH). These readings were standardized and used to generate dose-response curves from which the minimal inhibitory concentration (MIC 90 ) was estimated using the Levenberg-Marquardt damped least-squares (DLS) method, and it was found that the lowest concentration inhibited the growth of more than 90% of the bacterial population [19,20].…”