2. Academic Validation
  3. Design, synthesis and biological evaluation of diaziridinyl quinone isoxazole hybrids

Design, synthesis and biological evaluation of diaziridinyl quinone isoxazole hybrids

  • Eur J Med Chem. 2016 Jul 19:117:85-98. doi: 10.1016/j.ejmech.2016.03.042.
K Jones M Swapnaja 1,  Satyanarayana Yennam 2,  Murthy Chavali 3,  Y Poornachandra 4,  C Ganesh Kumar 4,  Krubakaran Muthusamy 5,  Venkatesh Babu Jayaraman 5,  Premkumar Arumugam 5,  Sridhar Balasubramanian 6,  Kiran Kumar Sriram 7
Affiliations

Affiliations

  • 1 Department of Medicinal Chemistry, GVK Biosciences Pvt. Ltd., Survey Nos: 125(part) & 126, IDA Mallapur, Hyderabad 500076, India; COEAMMPC & Division of Chemistry, Department of Sciences and Humanities, Vignan's Foundation for Science, Technology and Research University (VFSTRU; Vignan University), Vadlamudi, Guntur 522 213, India.
  • 2 Department of Medicinal Chemistry, GVK Biosciences Pvt. Ltd., Survey Nos: 125(part) & 126, IDA Mallapur, Hyderabad 500076, India. Electronic address: satya@gvkbio.com.
  • 3 COEAMMPC & Division of Chemistry, Department of Sciences and Humanities, Vignan's Foundation for Science, Technology and Research University (VFSTRU; Vignan University), Vadlamudi, Guntur 522 213, India.
  • 4 Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500007, India.
  • 5 Department of Biology, GVK Biosciences Pvt. Ltd., Survey Nos: 125(part) & 126, IDA Mallapur, Hyderabad 500076, India.
  • 6 Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500007, India.
  • 7 Department of Medicinal Chemistry, GVK Biosciences Pvt. Ltd., Survey Nos: 125(part) & 126, IDA Mallapur, Hyderabad 500076, India.
PMID: 27089214 DOI: 10.1016/j.ejmech.2016.03.042
Abstract

A series of novel diaziridinyl quinone isoxazole hybrids (9a-9j) were synthesized starting from 2, 5-dimethoxy acetophenone 1 via Claisen reaction, cyclisation, alkoxy carbonylation, hydrolysis, oxidation and aziridine insertion. All the compounds were screened for antimicrobial, anti-biofilm and cytotoxic activities. Among the screened compounds, the compound 9h showed good Antibacterial and anti-biofilm activities with MIC value of 3.9, 3.9, 3.9 and 7.8 μg/mL, respectively, and IC50 values of 1.9, 2.5, 2.8 and 5.1 μM, respectively, against Staphylococcus aureus MTCC 96, S. aureus MLS-16 MTCC 2940, Bacillus subtilis MTCC 121 and Klebsiella planticola MTCC 530, and also exhibited potent Antifungal activity against Candida albicans MTCC 227, C. albicans MTCC 854 and Candida krusei MTCC 3020 equipotent to standard miconazole (MIC value 7.8 μg/mL). All the synthesized compounds exhibited promising cytotoxicity against A549 and PC3 cell lines (IC50 values between 1 and 4 μM). Compounds 9b and 9j exhibited IC50 value of 0.5 μM which was similar to that of Mitomycin C against PC3 cell line.

Keywords

Anti-biofilm; Antibacterial activity; Antifungal; Cytotoxicity; Quinone diaziridinyl hybrids.

Figures
嗨！很高兴为您提供帮助！

尊敬的 MCE 客户您好，
请您选择所在区域，我们将转接对应客服为您服务！

热门区域

A

B

C

F

G

H

J

L

N

Q

S

T

X

Y

Z

热 A B C F G H J L N Q S T X Y Z