Synthesis and biological evaluation of some bicyclic [2-(2,4-dimethylphenylthio)phenyl] aniline and its amide derivatives as potential antitubercular agents

Abstract

In the present investigation, a series of bicyclic [2-(2,4-dimethylphenylthio)phenyl] aniline analogues were synthesized and characterized by IR, NMR (1 H and 13 C) and mass spectra. All newly synthesized 15 compounds were inspected for their in vitro antitubercular activity against Mycobacterium tuberculosis (MTB) H 37 Ra in both active and dormant state using an established XTT Reduction Menadione assay (XRMA). The titled compounds exhibited minimum inhibitory concentration (MIC90) ranging from 0.05 to >30 (μg/mL). The potent four compounds were further evaluated in THP-1 infection model where they demonstrated significant antitubercular activity. All the ex vivo active were further evaluated for cytotoxic activity against THP-1, MCK-7 and HeLa cell lines in order to check selectivity index. All compounds were further screened against four different bacteria to assess their selectivity towards MTB. These derivatives could be considered as a precursor structure for further design of antituberculosis agent.

Environmentally Benign Large-Scale Synthesis of a Precursor to Vortioxetine

“…The pH of the aqueous phase containing hydrochloric salt of 2-[(2,4-dimethylphenyl)thio]aniline was adjusted to 7 with the addition of solid NaHCO 3 and extracted with EtOAc (3 × 100 mL). The combined organic layers were dried (Na 2 SO 4 ) and evaporated to give 2-[(2,4-dimethylphenyl)thio]aniline (3) as a pure product (5.4 g, 99%) with spectral and physical data in agreement to those reported in the literature; 18 mp 34-36 °C (Lit. 18 mp 34-36 °C).…”

“…The combined organic layers were dried (Na 2 SO 4 ) and evaporated to give 2-[(2,4-dimethylphenyl)thio]aniline (3) as a pure product (5.4 g, 99%) with spectral and physical data in agreement to those reported in the literature; 18 mp 34-36 °C (Lit. 18 mp 34-36 °C). The mixture was stirred for another 30 min at the same temperature, then HPF 6 (60% solution in H 2 O, 0.61 mL) was added and the mixture was heated to 100 °C for 12 h. Upon completion of the reaction, the precipitated solid was filtered off, washed with EtOAc and the organic layer was washed with brine (3 mL) and aq NaHCO 3 (3 mL).…”

Synthesis of some novel piperidine fused 5-thioxo-1H-1,2,4-triazoles as potential antimicrobial and antitubercular agents

“…6 All the aforementioned facts demanded a vital requirement to develop new anti-TB agents with an exceptional mechanism of action, high potency, well-tolerance, low toxicity and short therapy duration profiles. 7 The presence of heterocyclic framework in biologically active molecules highlights the significance of synthesizing novel compounds by incorporating these architectures for developing new anti-tubercular agents. Fully decorated heterocyclic architectures involving derivatives of pyrrole, 8 benzimidazole, 9 indole, 10 imidazole, 11 furan, 12 and benzotriazole, 13 are reported to show excellent antimycobacterial properties.…”

Microwave‐Assisted Synthesis and Antituberculosis Screening of Some 4‐((3‐(Trifluoromethyl)‐5,6‐dihydro‐[1,2,4]triazolo[4,3‐a]pyrazin‐7(8H)‐l)methyl)benzenamine Hybrids

“…We have recently reported few heterocyclic hybrids as a potential antimicrobial and antituberculosis activity. In continuation with our research efforts, 4‐((3‐(trifluoromethyl)‐5,6‐dihydro‐[1,2,4]triazolo[4,3‐ a ]pyrazin‐7(8 H )‐yl)methyl)benzenamine ( 5 ) and its analogs 6a–o were inspected for their in vitro antitubercular activity against Mycobacterium tuberculosis H 37 Ra using an established XTT reduction menadione assay.…”