A multi‐step synthetic protocol was employed to accomplish the synthesis of (2Z)‐2‐((E)‐4‐(benzylideneamino)phenyl)‐3‐(1‐methyl‐1H‐imidazol‐2‐yl)acrylonitrile derivatives. The title compounds were screened for antitubercular activity. Amongst them, three of the compounds appeared promising with a MIC value 0.2 to 0.4 μg/mL whereas the other compounds have also exhibited lower MIC than the standards. Docking study was performed to check their binding interaction and to deduce the possible mechanism of action involved in the inhibition process which revealed that the newly synthesized molecules act by inhibiting the DprE1 enzymatic pathway.
The present article reports the synthesis of 2‐chloro‐N‐(4‐(6‐chloroH‐imidazo[1,2‐a]pyridin‐2‐yl)phenyl)acetamide derivatives (PINRAc 1–12) using 5‐chloropyridin‐2‐amine and 2‐bromo‐1‐(4‐nitrophenyl)ethanone in a multi‐step protocol. The structures of all the compounds were characterized by NMR, FT‐IR and GCMS. The compounds were screened for their antitubercular activity against Mycobacterium tuberculosis H37Rv using the microplate Alamar Blue assay. Most of them exhibited good antitubercular activity with MIC in the range of 1.6–25 μg/mL and the cytotoxicity study carried out on human embryonic kidney cell line showed no toxicity on the normal cells. The docking study was performed on mycolic acid transporter protein MmpL3 from Mycobacterium smegmatis which supported the in vitro results.
This paper reports a novel Donor‐π‐Acceptor type of π‐conjugated triphenylamine (TPA) dyes bearing a 4‐nitrophenyl acrylonitrile units (abbreviated as TPA‐4(a–e) which were synthesized by Knoevenagel condensation followed by palladium catalyzed Suzuki‐Miyaura cross coupling reaction with good yield. These dyes contain TPA as electron donor (D) and 4‐nitrophenyl acrylonitrile as electron acceptor (A) and probes were confirmed by standard spectroscopic techniques viz.,1H, 13C NMR, FT‐IR, GC‐MS and ESI‐MS. Herein, for the D‐π‐A push‐pull structure, TPA and 4‐nitrophenyl acrylonitrile are connected by vinylene bond as the π‐bridge. Optical/Solvatochromic properties were studied in detail by UV‐Vis absorption and fluorescence spectroscopy. The intramolecular charge transfer properties were studied using DFT model with the CAM‐B3LYP function and solvatochromism by experimental method. The synthesized materials have shown moderate quantum yields. Optical bandgap values range from 2.33 to 2.39 eV and these derivatives exhibit well judged thermal stability and their 5 % weight loss temperature are in the range 178–220 °C. Cyclic voltametery study of the title compounds indicated that
values ranging from 1.05–1.25 eV. Quantum yields (Φ) of the probes are experimentally measured in the 1, 4‐dioxane and the Stokes shifts are observed to be in the range of 4882–5545 cm−1. The results displayed that these novel (D−A−D) chromophores could play an important role in the organic optoelectronics.
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