6268-73-1Relevant academic research and scientific papers
Synthesis and anticonvulsant activity of novel purine derivatives
Wang, Shi-Ben,Jin, Peng,Li, Fu-Nan,Quan, Zhe-Shan
, p. 574 - 583 (2015/03/14)
A series of new purines containing triazole and other heterocycle substituents was synthesized and evaluated for their preliminary anticonvulsant activity and neurotoxicity by using the maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ) and rotarod neurotoxicity (TOX) tests. Among the compounds studied, 9-decyl-6-(1H-1,2,4-triazol-1-yl)-9H-purine (5e) was the most potent compound, with a median effective dose of 23.4 mg/kg and a high protective index of more than 25.6 after intraperitoneal administration in mice. Compound 5e showed significant oral activity against MESinduced seizures in mice, with an ED50 of 39.4 mg/kg and a PI above 31.6. These results demonstrate that compound 5e possesses better anticonvulsant activity and is safer than the commercially available drugs carbamazepine and valproate in MES, scPTZ and TOX models.
Synthesis and evaluation of anticonvulsant and antidepressant activities of 7-alkyl-7H-tetrazolo[1,5-g]purine derivatives
Wang, Shi-Ben,Deng, Xian-Qing,Liu, Da-Chuan,Zhang, Hong-Jian,Quan, Zhe-Shan
, p. 4619 - 4626 (2016/02/20)
Seventeen 7-alkyl-7H-tetrazolo[1,5-g]purine derivatives were synthesized, and their anticonvulsant and antidepressant activities were evaluated in a mouse model. The anticonvulsant effect and neurotoxicity of the compounds were evaluated with a maximal electroshock test and a rotated test in mice, respectively. Most of the compounds had anticonvulsant activity; among the compounds studied, 7-(3-chlorobenzyl)-7H-tetrazolo[1,5-g]purine (3h) was found to be the most potent compound with a median effective dose (ED50) value of 28.9 mg/kg and a protective index value of 15.8, possessing better anticonvulsant activity and higher safety than the marketed drug carbamazepine. To explain the possible mechanism of anticonvulsant activity, compound 3h was tested in pentylenetetrazole-induced seizures tests, and the results suggest that compound 3h exerts anticonvulsant activity through a GABA-mediated mechanism. Forced swimming test showed that at a dose of 40 mg/kg, five compounds have significant antidepressant activity, the most active compound was 7-(2-chlorobenzyl)-7H-tetrazolo[1,5-g]purine (3g), which decreased immobility time by 56 %.
Synthetic studies on compounds related to aminoimidazolecarboxamide: Synthesis of angularly fused purine derivatives and a solid phase ring transformation (ANRORC) to imidazo [1,5-a] pyrazine
Chattopadhyay, Gautam,Ray, Parlha Sinha
, p. 546 - 552 (2013/06/26)
l-Benzyl-5-aminoimidazole-4-carboxamide la has been used as a convenient precursor for the synthesis of new triazolo [3,4-i] purines 6 and the corresponding tetrazolo analogue 7. A mesoionic isomer 8 seems to exist along with 7. Interesting heteroaryl-purine motifs have also been prepared via suitably substituted 9-benzyIpurines. Imidazo |I,5-a| pyrazine derivative has been prepared in a solid phase exploitation of suitable imidazolium salt via ANRORC.
Reaction of 9-substituted 1-aminoadenine with hydrazine
Asano, Shoji,Itano, Keiji,Yamagata, Yuriko,Kohda, Kohfuku
, p. 1115 - 1121 (2007/10/03)
Reaction of 9-substituted (methyl or benzyl) 1-aminoadenines 1 with hydrazine afforded 9-substituted 6-hydrazinopurines 2 and 1-substituted 5-amino-4-(4-amino-1,2,4-triazol-3-yl)imidazole (4). The product ratio of 2 to 4 rose with increasing amounts of me
Rearrangements in Heterocyclic Synthesis: A Novel Translocation of an (N-Amino-N-methylamino)methylene Group from a Heterocyclic N-Amino-N-methylformamidine Side Chain to the Vinylogous Nitrile Function
Hosmane, Ramachandra S.,Lim, Benjamin B.,Burnett, Friedrich N.
, p. 382 - 386 (2007/10/02)
Reaction of the imidate 1-benzyl-4-cyano-5imidazole (5) with an equivalent of hydrazine provided 1-amino-9-benzyl-6-iminopurine (6), which, upon treatment which excess hydrazine, rearranged to 9-benzyl-6-hydrazinopurine (7).Reaction of 5 with methylhydrazine gave N-amino-N-methyl-N'-(1-benzyl-4-cyanoimidazol-5-yl)formamidine (8b).Thermolysis of 8b in refluxing toluene-methanol, catalyzed by trifluoroacetic acid, provided an equimolar mixture of 5-amino-1-benzyl-4-cyanoimidazole (9) and 3-(5-amino-1-benzylimidazol-4-yl)-1-methyl-1,2,4-triazole (10).Compound 9 was recycled to 8b via 5.The structure of 10 was established by spectral data coupled with an unequivocal synthesis.The conversion 8b to 10 represents a novel "translocative" rearrangement involoving the transfer of an NH2N(Me)CH= group from the imidazole 5-position to the nitrile function at position 4.Successful application of the rearrangement to the analogous pyrazole system is demonstrated.The rearrangement carries useful practical implications in the synthesis of the otherwise not easily accessible heterocycles of potential biological and medicinal significance.
