Journal ArticleDOI
Studies on antianaphylactic agents. 7. Synthesis of antiallergic 5-oxo-5H-[1]benzopyrano[2,3-b]pyridines.
Akira Nohara,Toshihiro Ishiguro,Kiyoshi Ukawa,Hirosada Sugihara,Yoshitaka Maki,Yasushi Sanno +5 more
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TLDR
Compounds bearing an alkyl group, especially an isopropyl group at the 7-position, were superior in activity to the corresponding unsubstituted compounds.Abstract:
5-Oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acids 23 and their tetrazole analogues 24 were synthesized from 4-oxo-4H-1-benzopyran-3-carbonitriles 3 or 2-amino-4-oxo-4H-1-benzopyran-3-carboxaldehydes 4. When administered intravenously, they exhibited antiallergic activity in a reaginic PCA test in rats. In the carboxylic acid series, the activity was influenced by the substituents at the 2-position and increased substantially in the following order: Me, OMe less than NH2 less than OH, H less than NHOMe. On the other hand, in the tetrazole series, 2-unsubstituted derivatives showed the highest activity. Regardless of the kinds of substituents at positions 2 and 3, compounds bearing an alkyl group, especially an isopropyl group at the 7-position, were superior in activity to the corresponding unsubstituted compounds. Among these alkyl derivatives, 3-carboxylic acid derivatives, i.e., 23c (7-ethyl), 23g (2-amino-7-isopropyl), 23r [2-(methoxyamino)-7-isopropyl], and a 3-tetrazole derivative 24c (7-isopropyl), were 41-184 times as potent as disodium cromoglycate. They also exhibited remarkable activity when administered orally; clinical studies on 23g (AA-673) are in progress.read more
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Synthesis, structure-activity relationships, and pharmacokinetic properties of dihydroorotate dehydrogenase inhibitors: 2-cyano-3-cyclopropyl-3-hydroxy-N-[3'-methyl-4'-(trifluoromethyl)phenyl ] propenamide and related compounds.
E. A. Kuo,P. Hambleton,David Kay,P. L. Evans,Saroop S. Matharu,E. Little,N. Mcdowall,C. B. Jones,C. J. R. Hedgecock,Yea Christopher Martyn,A. W. E. Chan,Peter W. Hairsine,Ian R. Ager,W. R. Tully,R. A. Williamson,Robert Westwood +15 more
TL;DR: The active metabolite of the novel immunosuppressive agent leflunomide has been shown to inhibit the enzyme dihydroorotate dehydrogenase (DHODH), which catalyzes the fourth step in de novo pyrimidine biosynthesis.
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Platinum-Catalyzed Michael Addition and Cyclization of Tertiary Amines with Nitroolefins by Dehydrogenation of α,β-sp3 C−H Bonds
Xiao-Feng Xia,Xing-Zhong Shu,Ke-Gong Ji,Yan-Fang Yang,Shaukat Ali,Xue-Yuan Liu,Yong-Min Liang,Yong-Min Liang +7 more
TL;DR: By using different functionalized nitroolefins compatible with the current oxidative conditions, two types of structurally divergent products, trisubstituted enamines and chromano[2,3-b]piperidines, could be expediently accessed, respectively.
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Synthesis of Aza Polycyclic Compounds Derived from Pyrrolidine, Indolizidine, and Indole via Intramolecular Diels−Alder Cycloadditions of Neutral 2-Azadienes
TL;DR: A method for the preparation of novel oxaza and diaza polycyclic 9-oxa-4-azaphenanthrene, 5H-pyrido[2,3-a]pyrrolizine, and 5H,6H- pyrido,[3,2-g]indolizine is described, based on tandem reactions.
Journal ArticleDOI
Synthesis and anti-inflammatory activities of 4H-chromene and chromeno[2,3-b]pyridine derivatives
Shu-Ting Chung,Wen-Hsin Huang,Chih-Kuo Huang,Feng-Cheng Liu,Ren-Yeong Huang,Chin-Chen Wu,An-Rong Lee +6 more
TL;DR: The results herein suggest that 4H-chromene and chromeno[2,3-b]pyridine may have potential as structural templates in the design and development of new anti-inflammatory drugs.
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Aldo-X Bifunctional Building Blocks for the Synthesis of Heterocycles
TL;DR: This review summarizes the synthesis of important heterocycles by using aldo-X bifunctional building blocks as pivotal components in establishing multicomponent reactions, tandem reactions, and so forth.
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