Faculty Publications
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Item Synthesis and anticonvulsant activity of some new bishydrazones derived from 3,4-dipropyloxythiophene(2009) Kulandasamy, R.; Vasudeva Adhikari, A.V.; Stables, J.P.A series of new 3,4-dipropyloxy-N2,N5-bis(substituted)thiophene-2,5-dicarbohydrazides (4-30) were synthesized from ethyl thiodiglycolate and diethyloxalate through multistep reactions. Following Dieckmann-Komppa reaction, the required precursor 3,4-dihydroxythiophene-2,5-diester (1) was prepared. This was derivatized with propyl bromide and further converted to corresponding hydrazide (3), which was finally transformed to targeted hydrazones (4-30) by conventional methods. The newly synthesized compounds were characterized using FT-IR, 1H and 13C NMR, EI-MS and elemental analyses. The anticonvulsant activity of all the title compounds was investigated against maximal electroshock induced seizures (MES) and subcutaneous pentylenetetrazole (scMET) models and their neurotoxicity was also evaluated. Some of the selected compounds were subjected to 6 Hz test in order to evaluate their uncover activities. Compound 3,4-dipropyloxy-N2,N5-bis[1-(2-thienyl)ethylidene]thiophene-2,5-dicarbohydrazide (15) has emerged as a lead in this series with less neurotoxicity. © 2009 Elsevier Masson SAS. All rights reserved.Item A new class of anticonvulsants possessing 6 Hz activity: 3,4-Dialkyloxy thiophene bishydrazones(2009) Kulandasamy, R.; Vasudeva Adhikari, A.V.; Stables, J.P.Thirty nine new 3,4-di(substituted)oxy-N2,N5-bis(substituted)thiophene-2,5-dicarbohydrazides were synthesized starting from ethyl thiodiglycolate through multi-step reactions. In the synthetic sequence, 3,4-dihydroxythiophene-2,5-diester (1) was obtained by condensing the ethyl thiodiglycolate with diethyl oxalate. It was derivatized using different alkyl halides to give disubstituted thiophene esters (2-5), which were then converted to corresponding hydrazides (6-9) following usual methods. Finally, these hydrazides, on treatment with various substituted carbonyl compounds underwent smooth condensation to yield target hydrazones (10-13). The new compounds were characterized using FT-IR, 1H NMR and 13C NMR, mass spectral and elemental analyses. The anticonvulsant activity of the title compounds was established after intraperitoneal (ip) administration in three seizure models, which include maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ) and 6 Hz screens and their neurotoxicity was also evaluated. Compound 11f has emerged as an active compound with no neurotoxicity in this series. Also, the structure-activity relationship of the tested compounds was discussed. © 2009 Elsevier Masson SAS. All rights reserved.Item Design and synthesis of some new quinoline-3-carbohydrazone derivatives as potential antimycobacterial agents(Elsevier Ltd, 2010) Eswaran, S.; Vasudeva Adhikari, A.V.; Pal, N.K.; Chowdhury, I.H.A series of 26 new quinoline derivatives carrying active pharmacophores has been synthesized and evaluated for their in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv (MTB), Mycobacterium smegmatis (MC2), and Mycobacterium fortuitum following the broth micro dilution assay method. Compounds 13e, 13i, 13k, 14a, 14c, 14i, and 14k exhibited significant minimum inhibition concentrations, when compared with first line drugs isoniazid (INH) and rifampicin (RIF) and could be ideally suited for further modifications to obtain more efficacious compounds in the fight against multi-drug resistant tuberculosis. © 2009 Elsevier Ltd. All rights reserved.Item Synthesis, anticonvulsant and anti-inflammatory studies of new 1,4-dihydropyridin-4-yl-phenoxyacetohydrazones(Elsevier Masson SAS infos@masson.fr 62 rue Camille Desmoulins Issy les Moulineaux Cedex 92442, 2013) Ulloora, S.; Shabaraya, R.; Ranganathan, R.; Vasudeva Adhikari, A.V.The present work involves design and synthesis of new substituted 1,4-dihydropyridin-4-yl-phenoxyacetohydrazones (4a-s, 5a-h), starting from 4-hydroxybenzaldehyde. The final compounds were screened for their in vivo anticonvulsant activity by MES, scPTZ and 6 Hz methods, while their anti-inflammatory screening was performed by Carrageenan induced Paw Edema method. The results indicated that compounds carrying electron donating groups are anticonvulsant active, while most of the tested compounds exhibited significant anti-inflammatory activity. Compounds 4k, l, 4p-s, and 5c showed rapid anti-inflammatory activity within 30 min and appeared as lead compounds. Further, Neurotoxicity study revealed that all the tested compounds are non-toxic up to 300 mg/kg doses. Selected compounds were also subjected to analgesic screening following Tail immersion method and they exhibited good activity. © 2013 Elsevier Masson SAS. All rights reserved.