Aroyl-isothiocyanates/isoselenocyanates as precursors to obtain novel <i>cis</i>-3-aroyl-thiourea/urea-β-lactams: design, synthesis, docking and biological evaluation

Kumar, Pankaj; Kaur, Jaswinder; Kumari, Sumeeta; Paliwal, Sakshi; Berry, Shiwani; Pinnaka, Anil Kumar; Bhalla, Aman

doi:10.1039/d3nj04485h

New J. Chem.

2024

DOI: 10.1039/d3nj04485h

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Aroyl-isothiocyanates/isoselenocyanates as precursors to obtain novel cis-3-aroyl-thiourea/urea-β-lactams: design, synthesis, docking and biological evaluation

Pankaj Kumar,

Jaswinder Kaur,

Sumeeta Kumari

et al.

Abstract: Herein, a novel synthetic methodology was devised to synthesize cis-3-aroyl-urea-β-lactams by reacting aroyl isoselenocyanates with cis-3-amino-β-lactams in a THF:H2O mixture (9:1). This synthetic approach eliminates the previous requirement for the...

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Cited by 2 publications

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Design, Synthesis and Biological Evaluation of C3‐Indolyl/(3‐chloro‐indolyl)‐C4‐aryl/heteroaryl‐azetidin‐2‐ones

Yadav,

Fatimah,

Sahoo

et al. 2024

ChemMedChem

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Herein, trans‐ and cis‐azetidin‐2‐ones 3‐6 were strategically synthesized, capitalizing on the bioactivity of azetidin‐2‐ones and indole pharmacophore, followed by a comprehensive characterization using a diverse array of spectroscopic techniques. The sixteen azetidin‐2‐ones were examined for antimicrobial activities against both Gram‐negative (P. aeruginosa, E. coli, A. baumannii) and Gram‐positive bacteria (S. aureus, E. faecium, B. cereus), as well as against C. albicans and C. tropicalis fungal strains. The highly potent compounds (5a, 6b, 6d) demonstrated maximum inhibition against all multidrug‐resistant strains, with minimum inhibitory concentrations ranging from 0.97‐3.9 μg/mL, surpassing the potency of standard ampicillin (MIC: 3.12‐50 μg/mL). Moreover, 6b and 6d exhibited significant inhibitory effects on C. albicans (MIC: 0.97 μg/mL), comparable to fluconazole. The presence of C3‐(3‐chloro‐indolyl) scaffold, combined with diverse electronic effects at N1/C4‐centers, particularly the inclusion of thiophen‐2‐yl motif, greatly influenced the activity of target compounds. Assessment of 4d, 4i‐k and 6d on THLE‐2 cell lines revealed their preferential safety. Molecular docking studies revealed seven compounds with active dual targeting of DNA GyrB and PBP2a proteins, demonstrating a potent broad‐spectrum antibacterial effect. In silico ADME analysis affirms positive drug‐likeness and favorable pharmacokinetic characteristics of indole‐derived hybrids, indicating a promising potential for addressing challenges in evolving multidrug resistance.

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Design, Synthesis and Biological Evaluation of C3‐Indolyl/(3‐chloro‐indolyl)‐C4‐aryl/heteroaryl‐azetidin‐2‐ones

Yadav,

Fatimah,

Sahoo

et al. 2024

ChemMedChem

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Dual site reactivity of indole-3-Schiff bases with S/Se/Cl substituted ketenes for stereoselective C-4 substituted indole-β-lactams, biological evaluations, magic chloro effect and molecular docking studies

Sharma,

kumar,

Sharma

et al. 2024

Bioorganic Chemistry

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Aroyl-isothiocyanates/isoselenocyanates as precursors to obtain novel cis-3-aroyl-thiourea/urea-β-lactams: design, synthesis, docking and biological evaluation

Abstract: Herein, a novel synthetic methodology was devised to synthesize cis-3-aroyl-urea-β-lactams by reacting aroyl isoselenocyanates with cis-3-amino-β-lactams in a THF:H2O mixture (9:1). This synthetic approach eliminates the previous requirement for the...

Cited by 2 publications

References 32 publications

Design, Synthesis and Biological Evaluation of C3‐Indolyl/(3‐chloro‐indolyl)‐C4‐aryl/heteroaryl‐azetidin‐2‐ones

Design, Synthesis and Biological Evaluation of C3‐Indolyl/(3‐chloro‐indolyl)‐C4‐aryl/heteroaryl‐azetidin‐2‐ones

Dual site reactivity of indole-3-Schiff bases with S/Se/Cl substituted ketenes for stereoselective C-4 substituted indole-β-lactams, biological evaluations, magic chloro effect and molecular docking studies

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