- Lipase-catalyzed resolution of both enantiomers of Ornidazole and some analogues
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The resolution of the enantiomers of the chemotherapeutic Ornidazole (Tiberal) 1a was achieved by acetylation of the racemic compound with vinylacetate in the presence of lipase Amano PS (from Pseudomonas cepacia). The halogen analogues 4a-6a and the corresponding 4-nitro-derivatives 1b and 4b-6b were also synthesized and the enantiomers were separated by kinetic enzymatic resolution. The absolute configuration of two compounds was determined by X-ray crystallography.
- Skupin, Rolf,Cooper, Trevor G.,Froehlich, Roland,Prigge, Joerg,Haufe, Guenter
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- 2-Methyl-4/5-nitroimidazole derivatives potentiated against sexually transmitted Trichomonas: Design, synthesis, biology and 3D-QSAR study
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Trichomoniasis is the most prevalent, non-viral sexually transmitted diseases (STD) caused by amitochondriate protozoan Trichomonas vaginalis. Increased resistance of T.?vaginalis to the marketed drug Metronidazole necessitates the development of newer chemical entities. A library of sixty 2-methyl-4/5-nitroimidazole derivatives was synthesized via nucleophilic ring opening reaction of epoxide and the efficacies against drug-susceptible and -resistant Trichomonas vaginalis were evaluated. All the molecules except two were found to be active against both susceptible and resistant strains with MICs ranging 8.55–336.70?μM and 28.80–1445.08?μM, respectively. Most of the compounds were remarkably more effective than the standard Metronidazole. This study analyzes the in?vitro and in?vivo activities of the new 5-nitroimidazoles, which were found to be safe against human cervical HeLa cells with good selectivity index. The exploration of SAR by the synthesis of four different prototypes and 3D-QSAR study has shown the importance of prototype 1 over other prototypes.
- Mandalapu, Dhanaraju,Kushwaha, Bhavana,Gupta, Sonal,Singh, Nidhi,Shukla, Mahendra,Kumar, Jitendra,Tanpula, Dilip K.,Sankhwar, Satya N.,Maikhuri, Jagdamba P.,Siddiqi, Mohammad I.,Lal, Jawahar,Gupta, Gopal,Sharma, Vishnu L.
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- 2-methyl-4-nitroimidazole derivatives and preparation method thereof, and application of pharmaceutical compositions
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The invention provides 2-methyl-4-nitroimidazole derivatives and a preparation method of the 2-methyl-4-nitroimidazole derivatives. Besides, pharmaceutical compositions containing the 2-methyl-4-nitroimidazole derivatives are applicable to treatment of many infectious diseases caused by Bacteroides fragilis, Bacteroides distasonis, Bacteroides ovatus, Bacteroides thetaiotaomicron, Bacteroides vulgatus, Clostridium, Eubacterium, Peptococcus and Peptostreptococcus, Helicobacter pylori, Bacteroides melaninogenicus, Fusobacterium, Capnocytophaga, Bacteroides gingivalis and other sensitive anaerobic bacteria.
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Paragraph 0023
(2017/10/22)
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