Synthesis of novel benzimidazole functionalized chiral thioureas and evaluation of their antibacterial and anticancer activities

Madabhushi, Sridhar; Mallu, Kishore Kumar Reddy; Vangipuram, Venkata Sairam; Kurva, Srinivas; Poornachandra, Y.; Kumar, C. Ganesh

doi:10.1016/j.bmcl.2014.08.064

Cited by 37 publications

(21 citation statements)

References 19 publications

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“…The antimicrobial activities of thioureas were reported in which few derivatives were found to be good against E. coli (Zhong et al, 2008). Madabhushi et al (2014) reported the benzimidazole linked chiral thioureas as antibacterial and anti-cancer agents. The biological applications of acyl/aryl thioureas have comprehensively been discussed .…”

Section: Discussionmentioning

confidence: 99%

New 1-octanoyl-3-aryl thiourea derivatives: Solvent-free synthesis, characterization and multi-target biological activities

Larik

Saeed

Channar

et al. 2016

Bangladesh J Pharmacol

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An efficient solvent-free synthesis of a 10-member library of octanoyl linked substituted aryl thioureas was accomplished successfully. The octanoyl isothiocyanate was freshly prepared in excellent yield and purity by the reaction of potassium thiocyanate with octanoyl chloride followed by removal of potassium chloride by filtration. The reaction of the latter with a series of ten different substituted anilines by stirring at 60-65°C lead to the formation of the title compounds. The in vitro antifungal activity of newly synthesized compounds was evaluated against Aspergillus niger, A. flavus and Fusarium solani strains of pathogenic fungi. Antibacterial assay was carried out against Gram positive (Staphylococcus aureus, Micrococcus luteus) and Gram negative bacterial strains (Escherichia coli, Enterobacter aerogens). Furthermore, anti-oxidant potential and enzyme inhibition studies against α-amylase and butyryl cholinestrase were performed. The results obtained indicated moderate to excellent activities of most of the compounds whilst some derivatives showed potency higher than the standard used.Video Clips:<a href="https://www.youtube.com/v/GJ8JFPUHdo4">Antibacterial assay</a>: 2 min 16 sec<a href="https://www.youtube.com/v/1j73_wjZaOE">Enzyme inhibition</a>: 1 min 27 sec

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Section: Discussionmentioning

confidence: 99%

New 1-octanoyl-3-aryl thiourea derivatives: Solvent-free synthesis, characterization and multi-target biological activities

Larik

Saeed

Channar

et al. 2016

Bangladesh J Pharmacol

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“…Structural assignments of the synthesized N-acyl-1Himidazole-1-carbothioamide derivatives (5a -5j) are based on their spectral (FT-IR, 1 H-NMR, 13 C-NMR) and elemental analysis (CHNS) data. FT-IR spectra of the synthesized compounds (5a -5j) display broader absorption peaks at 3460 -3117.88 cm À 1 which are attributed to NH group protons.…”

Section: Spectroscopic Characterizationsmentioning

confidence: 99%

“…The NH protons are present in the 1 H-NMR spectra as broader singlets at 10.06 -11.20 ppm. The amide linkage displays sharp singlets at 169.03 -176.30 ppm in the 13 C-NMR spectra. The para-substituted pattern of the phenyl ring resulted in the formation of double doublets at 7.84 -7.27 ppm in the 1 H-NMR spectra.…”

Section: Spectroscopic Characterizationsmentioning

confidence: 99%

“…TU based heterocycles include thiohydantoins, iminothiazolidinones, imidazole‐2‐thiones, thiazolines and thiazolamines associated with a broader spectrum of synthetic and biological applications . TU pharmacophores possess specific binding sites like hydrogen binding area (NH), complementary area (S) and auxiliary binding area (1,3‐substituents) . This favorable pharmacokinetic profile impart TU based heterocycles potent biological applications including antimalarial, antitubercular, anti‐HIV, analgesic and anticancer .…”

Section: Introductionmentioning

confidence: 99%

“…[11,12] TU pharmacophores possess specific binding sites like hydrogen binding area (NH), complementary area (S) and auxiliary binding area (1,3-substituents). [13] This favorable pharmacokinetic profile impart TU based heterocycles potent biological applications including antimalarial, [14] antitubercular, [15] anti-HIV, [16] analgesic [17] and anticancer. [18] Symmetrical and asymmetrical TU derivatives serve as potent antimicrobial drug candidates.…”

Section: Introductionmentioning

confidence: 99%

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Novel N‐Acyl‐1H‐imidazole‐1‐carbothioamides: Design, Synthesis, Biological and Computational Studies

Aziz

Saeed

Khan

et al. 2020

Chemistry & Biodiversity

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The present study reports the convenient synthesis, spectroscopic characterization, bio‐assays and computational evaluation of a novel series of N‐acyl‐1H‐imidazole‐1‐carbothioamides. The screened derivatives displayed excellent antioxidant activity, moderate antibacterial and antifungal potential. The screened derivatives were found to be highly biocompatible against hRBCs. Molecular docking ascertained the mechanism and mode of action towards the molecular target delineating that ligands and complexes were stabilized at the active site by electrostatic and hydrophobic forces in accordance to the corresponding experimental results. Docking simulation provided additional information about the possibilities of inhibitory potential of the compounds against RNA. Computational evaluation predicted that N‐acyl‐1H‐imidazole‐1‐carbothioamides 5c and 5g can serve as potential surrogates for hit to lead generation and design of novel antioxidant and antibacterial agents.

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Microwave-assisted synthesis and in vitro antiproliferative activity of some novel 1,2,3-triazole-based pyrazole aldehydes and their benzimidazole derivatives

et al. 2020

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Synthesis of novel benzimidazole functionalized chiral thioureas and evaluation of their antibacterial and anticancer activities

Cited by 37 publications

References 19 publications

New 1-octanoyl-3-aryl thiourea derivatives: Solvent-free synthesis, characterization and multi-target biological activities

New 1-octanoyl-3-aryl thiourea derivatives: Solvent-free synthesis, characterization and multi-target biological activities

Novel N‐Acyl‐1H‐imidazole‐1‐carbothioamides: Design, Synthesis, Biological and Computational Studies

Microwave-assisted synthesis and in vitro antiproliferative activity of some novel 1,2,3-triazole-based pyrazole aldehydes and their benzimidazole derivatives

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