Molecules p. 8567 - 8581 (2010)
Update date:2022-07-29
Topics:
Dolezal, Martin
Zitko, Jan
Osicka, Zdenek
Kunes, Jiri
Vejsova, Marcela
Buchta, Vladimir
Dohnal, Jiri
Jampilek, Josef
Kralova, Katarina
A series of sixteen pyrazinamide analogues with the -CONH- linker connecting the pyrazine and benzene rings was synthesized by the condensation of chlorides of substituted pyrazinecarboxylic acids with ring-substituted (chlorine) anilines. The prepared compounds were characterized and evaluated for their antimycobacterial and antifungal activity, and for their ability to inhibit photosynthetic electron transport (PET). 6-Chloro-N-(4-chlorophenyl) pyrazine-2-carboxamide manifested the highest activity against Mycobacterium tuberculosis strain H37Rv (65% inhibition at 6.25 μg/mL). The highest antifungal effect against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 6-chloro-5-tert-butyl-N-(3,4-dichlorophenyl) pyrazine-2-carboxamide (MIC = 62.5 μmol/L). 6-Chloro-5-tert-butyl-N-(4- chlorophenyl)pyrazine-2-carboxamide showed the highest PET inhibition in spinach chloroplasts (Spinacia oleracea L.) chloroplasts (IC50 = 43.0 μmol/L). For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds as well as their structureactivity relationships are discussed.
View MoreShanghai SMEC Trading Co., Ltd.
website:http://www.shanghaismec.com
Contact:+86-21-68811293
Address:ROOM 1101,NO.800 SHANGCHENG RD,SHANGHAI,CHINA
Zhejiang Kente Chemical Co.,Ltd.
Contact:86-0576-87651912
Address:No.7, Fengxi West Road, Modern Industrial Zone
Contact:+86-717-6370352
Address:168 Chengdong Avenue, Yichang, Hubei 443003, P. R.China
Beijing Huikang Boyuan Chemical Tech Co.,LTD
Contact:+86-10-68862197
Address:No.7 Haiying Road,Science City,Fengtai District,Beijing,China
Yueyang Hudex Pharmaceuticals Ltd.
Contact:0730-8748800
Address:Wujiang Bridge,Yueyang Economy & Technology Development Zone
Doi:10.1016/j.ejmech.2010.08.046
(2010)Doi:10.1016/S0040-4039(01)80319-1
(1989)Doi:10.1021/ja207869f
(2011)Doi:10.1039/c0cc02997a
(2010)Doi:10.1039/jr9640001151
(1964)Doi:10.1039/c0ob00299b
(2010)