Design, synthesis, and anticonvulsant evaluation of some novel 1, 3 benzothiazol-2-yl hydrazones/acetohydrazones

Medicinal Chemistry Research

Volumn 21, Issue 9, 2012, Pages 2428-2442

  Kumar, Praveen ^a   Shrivastava, Birendra ^a   Pandeya, Surendra N ^b   Tripathi, Laxmi ^c   Stables, James P ^d  

^a JAIPUR NATIONAL UNIVERSITY   (India)

^b Saroj Institute of Technology and Management   (India)

^c SD College of Pharmacy & Vocational Studies   (India)

^d NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

2 (1,3 benzothiazol 2 ylsulfanyl) N (substituted)acetohydrazide; 2 2 (Substituted)hydrazinyl 1,3 benzothiazole; 6 Hz psychomotor seizure test; Computational study; Neurotoxicity

Indexed keywords

1,3 BENZOTHIAZOL 2 YL ACETOHYDRAZONE DERIVATIVE; 1,3 BENZOTHIAZOL 2 YL HYDRAZONE DERIVATIVE; 2 (1,3 BENZOTHIAZOL 2 YLSULFANYL) N' [4 (4 BROMOPHENOXY)BENZYLIDENE]ACETOHYDRAZIDE; 4 AMINOBUTYRIC ACID A RECEPTOR ALPHA1; ANTICONVULSIVE AGENT; SODIUM PROTON EXCHANGE PROTEIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CLONIC SEIZURE; CONTROLLED STUDY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; GENETIC ALGORITHM; MALE; MOLECULAR DOCKING; MOTOR DYSFUNCTION; MOUSE; NEUROPROTECTION; NEUROTOXICITY; NONHUMAN; PHARMACOPHORE; PREDICTION; ROTAROD TEST; SEIZURE;

EID: 84866392970     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9768-0     Document Type: Article

References (19)

1. Bell GS, Sander JW (2002) The epidemiology of epilepsy: the size of the problem. Seizure 11(Suppl A):306-314
2. Camerman A, Camerman N (1980) Stereochemical similarities in chemically different antiepileptic drugs. In: Glaser GH, Penry JK, Woodbury JM (eds) Antiepileptic drugs: mechanism of action. Raven Press, New York, pp 223-231
3. Chopade RS, Bahekar RH, Khedekar PB, Bhusari KP, Rao AR (2000) Synthesis and anticonvulsant activity of 3-(5-substituted-benzothiazol-2-yl)-6-phenyl-[1, 3]-oxazinane-2-thiones. Arch Pharm (Weinheim) 335:881
4. Ertl P, Rohde B, Selzer P (2000) Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem 43:3714-3717
5. Farrar VA, Ciechanowicz MR, Grochowski J, Serda P, Pilati T, Filippini G, Hinko CN, El-Assadi E, Moore JA, Edafiogho IO, Andrews CW, Cory M, Nicholson JM, Scott JR (1993) Synthesis and CLOGP correlation of imidooxy anticonvulsants. J Med Chem 36:3517-3525 (Pubitemid 24004347)
6. Hays SJ, Rice MJ, Ortwine DF, Johnson G, Schwarz RD, Boyd DK (1994) Substituted 2-benzothiazolamines as sodium flux inhibitors: quantitative structure activity relationships and anticonvulsant activity. J Pharm Sci 83:1425
7. Jones GL, Woodbury DM (1982) Principles of drug action: structure activity relationships and mechanisms. In: Woodbury DM, Penry JK, Pippenger CE (eds) Antiepileptic drugs. Raven Press, New York, pp 83-109
8. Landmark CJ (2007) Targets for antiepileptic drugs in the synapse. Med Sci Monit 13:RA1-RA7 (Pubitemid 46045538)
9. Lipinski CA, Lombardo L, Dominy BW, Feeney PJ (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 46:3-26 (Pubitemid 33653411)
10. Mizoule J, Meldrum B, Martine M, Croucher M, Ollat C, Uzar A (1985) 2-amino-6-trifluromethoxy benzothiazole, a possible antagonist of excitatory amino acid neurotransmission-1. Anticonvulsant properties. Neuropharmacology 24:767
11. Molinspiration Cheminformatics, Bratislava, Slovak Republic, http://www.molinspiration.com/services/properties.html. Accessed September 16, 2010
12. Perucen E (1996) The new generation of antiepileptic drugs: advantages and disadvantages. Br J Clin Pharmacol 42:531-543
13. Sabers A, Gram L (2000) Newer anticonvulsants: comparative review of drug interactions and adverse effects. Drugs 60:23-33 (Pubitemid 30598818)
14. Siddiqui N, Rana A, Khan SA, Bhat MA, Haque SE (2007) Synthesis of benzothiazole semicarbazones as novel anticonvulsants-the role of hydrophobic domain. Bioorg Med Chem Lett 17(15): 4178-4182 (Pubitemid 47021404)
15. Unverferth K, Engel J, Hofgen N, Rostock A, Gunther R, Lankau HJ, Menzer M, Rolfs A, Liebscher J, Muller B, Hofmann HJ (1998) Synthesis, anticonvulsant activity, and structure-activity relationships of sodium channel blocking 3-aminopyrroles. J Med Chem 41:63-73 (Pubitemid 28070468)
16. Wang Y, Cai S, Lan N, Keana J, Ilyin V, Weber E (1998) Carbocyclic and heterocyclic substituted semicarbazones and thiosemicarbazones and the use thereof. PCT/US98/08004:1-81
17. Yogeeshwari P, Sriram D, Thirumurgan R, Jit LR, Ragavendran JV, Kavya R, Rakhra K, Saraswat V (2006) Synthesis of N4-(2, 4-dimethylphenyl) semicarbazones as 4-aminobutyrate aminotransferase inhibitors. Acta Pharm 56:259-272 (Pubitemid 44422507)
18. Yogeeswari P, Sriram D, Thirumurugan R, Raghavendran JV, Sudhan K, Pavana RK, Stables JP (2005) Discovery of N-(2, 6-dimethylphenyl)-substituted semicarbazones as anticonvulsants: hybrid pharmacophore-based design. J Med Chem 48:6202-6211 (Pubitemid 41428975)
19. Zhao Y, Abraham MH, Lee J, Hersey A, Luscombe NC, Beck G, Sherborne B, Cooper I (2002) Rate-limited steps of human oral absorption and QSAR studies. Pharm Res 19:1446-1457 (Pubitemid 35266548)