Synthesis and anticonvulsant activity of 6-Alkoxy-[1,2,4]Triazolo[3,4-a] Phthalazines

Chemical Biology and Drug Design

Volumn 73, Issue 3, 2009, Pages 313-319

  Zhang, Lei ^a   Guan, Li Ping ^a   Sun, Xian Yu ^a   Wei, Cheng Xi ^a   Chai, Kyu Yun ^b   Quan, Zhe Shan ^a  

^a YANBIAN UNIVERSITY   (China)

^b Wonkwang University   (South Korea)

Author keywords

1,2,4 triazolo 3,4 a phthalazines; Anticonvulsant activity; Synthesis

Indexed keywords

3 MERCAPTOPROPIONIC ACID; 6 (2 METHOXYLPHENOXYL) [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 (2 METHYLPHENOXYL) [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 (2,4 DICHLOROPHENOXYL) [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 (3 METHYLPHENOXYL) [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 (4 AMINOPHENOXYL) [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 (4 CHLOROBENZYLOXY) [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 (4 CHLOROPHENOXYL) [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 (4 FLUOROPHENOXYL) [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 (4 METHOXYLPHENOXYL) [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 (4 METHYLPHENOXYL) [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 (4 NITRYLPHENOXYL) [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 BUTYLOXY [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 DECYLOXY [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 ETHOXY [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 HEPTYLOXY [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 HEXYLOXY [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 ISOPROPY [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 METHOXY [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 NAPHTHALENOXYL [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 NONLOXY [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 OCTYLOXY [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 PENTYLOXY [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; 6 PHENOXYL [1,2,4]TRIAZOLO[3,4 A]PHTHALAZINE; ANTICONVULSIVE AGENT; ISONIAZID; PENTETRAZOLE; PHTHALAZINE DERIVATIVE; STRYCHNINE; THIOSEMICARBAZIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG ACTIVITY; ELECTRIC SHOCK; MOUSE; NEUROTOXICITY; NEUROTRANSMISSION; NONHUMAN; PRIORITY JOURNAL; ROTAROD TEST; SEIZURE; SYNTHESIS;

ANIMALS; ANTICONVULSANTS; ELECTROSHOCK; MICE; MICE, INBRED C57BL; PHTHALAZINES; ROTAROD PERFORMANCE TEST; SEIZURES; STRUCTURE-ACTIVITY RELATIONSHIP;

STRYCHNOS TOXIFERA;

EID: 60349106858     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00776.x     Document Type: Article

References (22)

1. Loscher W. (1998) New visions in the pharmacology of anticonvulsion. Eur J Pharmacol 342 : 1 13.
2. Leppik I.E. (1994) Antiepileptic drugs in development: prospects for the near future. Epilepsia 35 (Suppl. 4 29 40.
3. Perucca E. (1996) The new generation of antiepileptic drugs: advantages and disadvantages. Br J Clin Pharmacol 42 : 531 543.
4. Lin Z., Kadaba P.K. (1997) Molecular targets for the rational design of antiepileptic drugs and related neuroprotective agents. Med Res Rev 17 : 537 572.
5. Al-Soud Y.A., Al-Masoudi N.A., Ferwanah Ael.-R. (2003) Synthesis and properties of new substituted 1,2,4-triazoles: potential antitumor agents. Bioorg Med Chem 11 : 1701 1708.
6. Quan Z.S., Wang J.M., Rho J.R., Kwak K.C., Kang H.C., Jun C.S., Chai K.Y. (2005) Synthesis of 6-alkyloxyl-3,4-dihydro-2(1H)-quinoliones and their anticonvulsant activities. Bull Kor Chem Soc 26 : 1757 1760.
7. Cui L.J., Jin H.G., Xie Z.F., Piao H.R., Chai K.Y., Quan Z.S. (2005) Synthesis and anticonvulsant activity of 1-substituted-7-benzyloxy-4,5-dihydro- [1,2,4]triazolo[4,3-a] quinoline. Biol Pharm Bull 28 : 1216 1220.
8. Xie Z.F., Chai K.Y., Piao H.R., Kwak K.C., Quan Z.S. (2005) Synthesis and anticonvulsant activity of 7-alkoxyl-4,5-dihydro-[1,2,4]triazolo[4,3-a] quinolines. Bioorg Med Chem Lett 15 : 4803 4805.
9. Ramaiya S., Sundararaj K.G., Somasundaram R., Joseph T.L. (2002) Pharmacological evaluation of some new 1-substituted-4-hydroxy-phthalazines. Eur J Med Chem 37 : 793 801.
10. Krall R.L., Penry J.K., White B.G., Kupferberg H.J., Swinyard E.A. (1978) Antiepileptic drug development: II. Anticonvulsant drug screening. Epilepsia 19 : 409 428.
11. Porter R.J., Cereghino J.J., Gladding G.D., Hessie B.J., Kupferberg H.J., Scoville B., White B.G. (1984) Antiepileptic Drug Development Program. Cleve Clin Q 51 : 293 305.
12. Bernasconi R., Klein M., Martin P., Christe P., Hafner T., Portet C., Schmutz M. (1988) Gamma-vinyl GABA: comparison of neurochemical and anticonvulsant effects in mice. J Neural Transm 72 : 213 233.
13. Loscher W., Schmidt D. (1988) Which animal models should be used in the search for new antiepileptic drugs? A proposal based on experimental and clinical considerations Epilepsy Res 2 : 145 181.
14. Arnoldi A., Bonsignori A., Melloni P., Merlini L., Quadri M.L., Rossi A.C., Valsecchi M. (1990) Synthesis and anticonvulsant and sedative-hypnotic activity of 4-(alkylimino)-2,3-dihydro-4H-1-benzopyrans and -benzothiopyrans. J Med Chem 33 : 2865 2869.
15. Geurts M., Poupaert J.H., Scriba G.K., Lambert D.M. (1998) N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants. J Med Chem 41 : 24 30.
16. Sun X.Y., Jin Y.Z., Li F.N., Li G., Chai K.Y., Quan Z.S. (2006) Synthesis of 8-alkoxy-4,5-dihydro-[1,2,4]triazole[4,3-a]quinoline-1-ones and evaluation of their anticonvulsant properties. Arch Pharm Res 29 : 1080 1085.
17. Pal M., Batchu V.R., Parasuraman K., Yeleswarapu K.R. (2003) Aluminum chloride-induced heteroarylation of arenes and heteroarenes. 2. A new synthesis of 4-substituted phthalazin-1(2H)-ones. J Org Chem 68 : 6806 6809.
18. Carling R.W., Moore K.W., Street L.J., Wild D., Isted C., Leeson P.D., Thomas S. et al. (2004) 3-phenyl-6-(2-pyridyl)methyloxy-1,2,4-triazolo[3,4-a] phthalazines and analogues: high-affinity gamma-aminobutyric acid-A benzodiazepine receptor ligands with alpha 2, alpha 3, and alpha 5-subtype binding selectivity over alpha 1. J Med Chem 47 : 1807 1822.
19. Okada R., Negishi N., Nagaya H. (1989) The role of the nigrotegmental GABAergic pathway in the propagation of pentylenetetrazol-induced seizures. Brain Res 480 : 383 387.
20. Loscher W. (1979) 3-Mercaptopropionic acid: convulsant properties, effects on enzymes of the gamma-aminobutyrate system in mouse brain and antagonism by certain anticonvulsant drugs, aminooxyacetic acid and gabaculine. Biochem Pharmacol 28 : 1397 1407.
21. Gale K. (1992) GABA and epilepsy: basic concepts from preclinical research. Epilepsia 33 : S3 S12.
22. Sayin U., Cengiz S., Altug T. (1993) Vigabatrin as an anticonvulsant against pentylenetetrazol seizures. Pharmacol Res 28 : 325 331.