6268-73-1Relevant articles and documents
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.
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.
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.
