TY  - JOUR
N1  - The copyright of this article belongs to RSC Publishing 
ID  - open3187
UR  - https://pubs.rsc.org/en/content/articlelanding/2024/nj/d3nj04485h
A1  - Kumar, Pankaj
A1  - Kaur, Jaswinder
A1  - Kumari, Sumeeta
A1  - Paliwal, Sakshi
A1  - Berry, Shiwani
A1  - Pinnaka, Anil Kumar
A1  - Bhalla, Aman
Y1  - 2023/11/16/
N2  - Herein, a novel synthetic methodology was devised to synthesize cis-3-aroyl-urea-?-lactams by reacting aroyl isoselenocyanates with cis-3-amino-?-lactams in a THF?:?H2O mixture (9?:?1). This synthetic approach eliminates the previous requirement for the challenging synthesis of unstable aroyl isocyanates and the low-yield acylation of urea to obtain aroyl urea derivatives. Further optimized conditions for nucleophilic reaction of aroyl isothiocyanates with cis-3-amino-?-lactams to obtain cis-3-aroyl-thiourea-?-lactams were developed. The stereochemistry of cis-3-aroyl-thiourea/urea-?-lactams (5a?f/8a?f) was elucidated by analyzing the J values of C3?H and C4?H of ?-lactams. Subsequently, we evaluated the antibacterial activity of these compounds against both Gram-positive bacteria (S. aureus and B. cereus) and Gram-negative bacteria (P. aeruginosa and E. coli). Remarkably, among all the synthesized compounds, 8e exhibited potent activity against all bacterial strains, with a notable MIC value of 6.25 ?g mL?1 against B. cereus, surpassing ampicillin (MIC = 25 ?g mL?1) by four-fold. Additionally, compounds 8d and 8e demonstrated promising antifungal properties, with an MIC value of 1.5 ?g mL?1 against C. tropicalis, comparable to fluconazole (MIC = 1 ?g mL?1). Furthermore, compounds 8d and 8e exhibited 80% and 75% cell viability against THLE-2 cells at a concentration of 25 ?g mL?1. Molecular docking analysis provided additional support for the observed in vitro antibacterial and antifungal activities of compound 8e.


PB  - RSC Publishing 
JF  - New Journal of Chemistry
VL  - 48
TI  - Aroyl-isothiocyanates/isoselenocyanates as precursors to obtain novel cis-3-aroyl-thiourea/urea-?-lactams: design, synthesis, docking and biological evaluation
SP  - 67
EP  - 78
ER  -