Synthesis and anti-trypanosomal activity of novel 5-nitro-2-furaldehyde and 5-nitrothiophene-2-carboxaldehyde semicarbazone derivatives
ABSTRACT Several novel semicarbazones derivatives were prepared from 5-nitro-2-furaldehyde or 5-nitrothiophene-2-carboxaldehyde, and tested in vitro as potential anti-trypanosomal agents. The compounds were prepared in good to excellent yields in 2–3 steps from readily available starting materials. Some derivatives were found to be active against Trypanosoma cruzi with an activity similar to that of Nifurtimox.
- SourceAvailable from: Mohamed Jawed Ahsan[Show abstract] [Hide abstract]
ABSTRACT: Semicarbazone analogs are synthesized by the condensation of semicarbazide and aldehyde/ketone. The literature survey revealed that semicarbazones had been emerged as compounds with biological activities including anticonvulsant, antitubercular, anticancer and antimicrobial activities and so forth. The anticonvulsant activity of semicarbazones is mainly attributed due to the presence of an aryl binding site with aryl/alkyl hydrophobic group, a hydrogen bonding domain and an electron donor group and they are suggested to act by inhibiting sodium ion (Na+) channel. Dimmock et al., reported an extensive series of semicarbazones and reported 4-(4-fluorophenoxy) benzaldehyde semicarbazone (C0102862, V102862) as lead molecule. In MES (oral) screening C0102862 showed protective index (PI > 315) more than carbamazepine (PI 101), phenytoin (PI > 21.6) and valproate (PI > 2.17). This review briefly describes the information available about semicarbazone analogs with their anticonvulsant activity.Central Nervous System Agents in Medicinal Chemistry(Formerly Current Medicinal Chemistry - Central Nervous System Agents) 06/2013; 13(2):148-158.
Article: Antituberculosis agents VIII[Show abstract] [Hide abstract]
ABSTRACT: A series of alkyl α-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio]acetic acid esters 6a–e were synthesized and evaluated for in vitro antituberculosis activity against Mycobacterium tuberculosis strain H37Rv using the BACTEC 460 radiometric system and BACTEC 12B medium. The antituberculosis data indicated that methyl, propyl, buthyl and benzyl esters showed a significant in vitro antimycobacterium tuberculosis activity (MIC=0.39–0.78 μg/ml) and the ethyl analogue did not show a good activity (MIC>6.25 μg/ml, %inhibition=58). The most active compound of the series was n-propyl α-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio]acetate (6c) with MIC value of 0.39 μg/ml.Il Farmaco 11/2003; 58(11):1073-1076.
- Archiv Der Pharmazie - ARCH PHARM. 01/2000; 333(11):387-393.