Medicinal Chemistry Research p. 1578 - 1586 (2013)
Update date:2022-07-30
Topics:
Husain, Asif
Ahmad, Aftab
Mkhalid, Ibraheem Ahmed I.
Mishra, Ravinesh
Rashid, Mohd
Several bischalcones (2a-h and 5a-e) and flavones (3a-f) were synthesized and evaluated for their antimicrobial actions. Bischalcones were prepared by condensing 1,1′-(4,6-dimethyl-1,3-phenylene)diethanone (1) or 1-(5-acetyl-2,4-dimethoxyphenyl)-1-ethanone (4) with arylaldehydes. Bischalcones were cyclized in presence of iodine to give corresponding flavones (3a-f). An alternative route to synthesize the flavones consisted in preparing the diester derivatives (6a-f) of (1) with different aromatic acids, which could be converted to β-diketones followed by cyclization to give the corresponding flavones. However, all the attempts in this direction were unsuccessful and it could not be possible to proceed beyond diester stage; six diester derivatives (6a-f) were synthesized. The structures of the synthesized compounds were assigned on the basis of 1H NMR, mass spectral data and microanalyses results. The antimicrobial screening was performed at a concentration of 100 μg/mL by cup plate method; the compounds inhibiting growth of one or more of the microorganisms were further tested for their minimum inhibitory concentration (MIC) by turbidity method. Preliminary antimicrobial results revealed that the compounds 2a-h and 3a-f were significant in their antibacterial and antifungal activities. MICs results showed that the compound 2f exhibited very good activity against E. coli, P. aeruginosa, and C. albicans with MIC-12.5 μg/mL. Similar type of activity was shown the compound 3a against S. aureus and C. albicans with MIC-12.5 μg/mL. Another compound, 3f, was active against P. aeruginosa and C. albicans with MIC-12.5 μg/mL. Methylation of the two chelated hydroxyls (5a-e) significantly reduced the activity. However, oxidative cyclization of bischalcones resulted in compounds (3a-f) which were found to be considerably active. Diesters (6a-f) were insignificant in their antimicrobial activities.
View MoreHangzhou Eastbiopharm Co.,Ltd.
Contact:+86-571-88931780
Address:Hangzhou,China
Chengdu Pukang Biotechnology Co., Ltd
Contact:+86-28-82550498
Address:No. 558 Rulin Road,Xinjin county,Chengdu city, China
Ji'an Hairui Natural Plant Co. Ltd.
Contact:0796-8105528
Address:Meilin industry park, Qingyuan district Ji'an City, Jiangxi Province
Springchem New Material Technology Co.,Limited
website:http://www.spring-chem.com
Contact:86-21-62885108
Address:602B, Building 1, No. 641, Tianshan Road
Chengdu Boon Stream Chemical Industry Co.,Ltd.
Contact:+86-28-83156758
Address:No.859,Dongzikou Road,Jinniu District,Chengdu,Sichuan,P.R.China
Doi:10.1021/om4000133
(2013)Doi:10.1021/jo4001367
(2013)Doi:10.1021/ja400883q
(2013)Doi:10.1016/S0040-4020(01)88483-0
(1992)Doi:10.1016/j.poly.2012.12.032
(2013)Doi:10.1021/jo4001564
(2013)