Design & synthesis of hybrid pharmacophore of β-lactam, 1,8-naphthyridine, and secondary amines; Discover their in vitro antimicrobial, anticancer properties & DFT and ADMET prediction studies

An efficient synthetic strategy was developed for the synthesis of hybrid pharmacophores; encompass the merging of β -lactams, 1,8-naphthyridine and secondary amines/pyridines. With a simple unified synthetic protocol, we prepared a series of substituted 3-chloro-1-((3-(2-(trifluoromethyl)phenyl)-1,...

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Published inMedicinal chemistry research Vol. 32; no. 6; pp. 1098 - 1108
Main Authors Pandya, Keyur M., Battula, Satyanarayana, Kumar, K. A. Aravinda, Patel, Rajesh J., Patel, Navin B.
Format Journal Article
LanguageEnglish
Published New York Springer US 01.06.2023
Springer Nature B.V
Subjects
Amides
Amines
Ampicillin
Antibiotics
Anticancer properties
Antiinfectives and antibacterials
Biochemistry
Biomedical and Life Sciences
Biomedicine
Bioorganic Chemistry
Ciprofloxacin
Cisplatin
Gram-negative bacteria
Gram-positive bacteria
Inorganic Chemistry
Medicinal Chemistry
Original Research
Pharmacology/Toxicology
Pharmacophores
Pyridines
Streptomycin
Synthesis
β-Lactam antibiotics
1,8-naphthyridine
lactam
Amines
Antibacterial
Molecular conjugates
Anticancer
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Summary:An efficient synthetic strategy was developed for the synthesis of hybrid pharmacophores; encompass the merging of β -lactams, 1,8-naphthyridine and secondary amines/pyridines. With a simple unified synthetic protocol, we prepared a series of substituted 3-chloro-1-((3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridin-2-yl)amino)azetidin-2-one compounds ( 8a – 8j ) and evaluated for their antimicrobial, and anticancer activities (against MDA-MB-231 cell line). Notably, compounds 8d , 8g , and 8j were identified as potent anticancer molecules and comparable to Cisplatin. Compounds 8d and 8g were found to have promising antitubercular efficacy even greater than the standards Streptomycin and Ciprofloxacin. Compounds 8a , 8d , 8g , 8i , and 8j also displayed potency against both Gram-positive and Gram-negative bacteria and comparable to Ampicillin & Ciprofloxacin. Further, the biological activities were supported and studied by DFT studies and ADMET predictions. Graphical Abstract
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-023-03058-2