55149-47-8Relevant academic research and scientific papers
Synthesis of 2-aminoquinoline-3-carboamides and pyrimido[4,5-b]quinolin-4-ones through copper-catalyzed one-pot multicomponent reactions
Zhang, Xin-Ying,Guo, Xiao-Jie,Fan, Xue-Sen
supporting information, p. 106 - 111 (2015/02/05)
Pyrimido[4,5-b]quinolinones have attracted considerable interest from both chemical and medicinal scientists as these compounds display remarkable antimicrobial, anti-inflammatory, antitumor, antiallergy, analgesic, and antioxidant activities. The importance of pyrimido[4,5-b]quinolinones has stimulated enormous efforts to develop efficient methodologies for their synthesis. Herein, we disclose a novel synthetic protocol toward pyrimido[4,5-b]quinolin-4-ones through Cu(OAc)2-catalyzed one-pot four-component reactions of 2-bromobenzaldehydes, aqueous ammonia, cyanoacetamides and aldehydes. The synthetic procedure combines amination/condensation/cyclization/dehydrogenation reactions in one pot, allowing synthesis of complex compounds in a simple and practical manner. Compared with literature procedures, the synthetic strategies developed herein showed advantages such as readily available and economically sustainable starting materials, structural diversity of products, good functional group tolerance, and a remarkably simple operation process.
Structure-Activity Relationships in a Series of Novel 3,4-Dihydro-4-oxopyrimidoquinoline-2-carboxylic Acid Antiallergy Agents
Althuis, T. H.,Kadin, S. B.,Czuba, L. J.,Moore, P. F.,Hess, H.-J.
, p. 262 - 269 (2007/10/02)
A series of more than 50 new 3,4-dihydro-4-oxopyrimidoquinoline-2-carboxylic acid derivatives and related compounds with substituent variations at the 2, 3, and 5-9 positions was prepared and evaluated for antiallergy activity using the rat PCA assay.These compounds were obtained by the condensation of the appropriately substituted 2-aminoquinoline-3-carboxamides with dialkyl oxalates, followed by further chemical transformations.More than two-thirds of the compounds prepared exhibited intravenous activity ranging from 1 to 400 times disodium cromoglycate (DSCG).Structure-activity data suggest that the presence of a carboxylic acid moiety at the 2 position affords optimal potency and that esters are preferred for good oral absorption.Best oral activity, with ED50 values ranging from 0.3 to 3.0 mg/kg, was displayed by ethyl esters with methoxy and/or ethoxy groups at the 7 and 8 positions.
