Reactions of 3-Acylchromones with Heterocyclic Ketene Aminals: One-Pot Synthesis and Phosphatase Inhibitory Activity of Fused Pyridine Derivatives / Savych Iryna,Ejaz Syeda Abida,Shah Syed Jawad Ali,Iaroshenko Viktor O.,Villinger Alexander,Sosnovskikh Vyacheslav Ya.,Iqbal Jamshed,Abbasi Afshin,Langer Peter // EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - 2017. - V. , l. 1. - P. 186-202.

ISSN/EISSN:

1434-193X / 1099-0690

Type:

Article

Abstract:

Domino reactions of 3-acylchromones, namely 3- methoxalyl-, 3-aroyl- and 3-cinnamoylchromones, with heterocyclic ketene aminals (HKAs) proceed by attack of the nucleophile on the C-2 atom of the chromone moiety, pyrone ringopening and subsequent formal {[}3+3] cyclocondensation with formation of functionalized tetracyclic fused chromeno{[}2,3-b]-pyridines or 2H, 3H-imidazo{[}1,2-a] pyridines. The product distribution depends on the type of acyl group located at the 3-position of the chromone and on the size of the heterocyclic moiety of the HKAs. The products show considerable activity as selective phosphatase inhibitors.

Author keywords:

Drug discovery; Fused-ring systems; Heterocyclic ketene aminals; Domino reactions; Nitrogen heterocycles 1,3-BIS-SILYL ENOL ETHERS; REGIOSELECTIVE SYNTHESIS; BIOLOGICAL-ACTIVITY; EFFICIENT SYNTHESIS; DIMETHYL 1,3-ACETONEDICARBOXYLATE; XANTHENEDIONE DERIVATIVES; DIHYDROFOLATE REDUCTASES; 1,3-DICARBONYL COMPOUNDS; RECEPTOR ANTAGONISTS; MEDICINAL CHEMISTRY

DOI:

10.1002/ejoc.201601138

Web of Science ID:

ISI:000393328200023

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	JAN 3
Publisher	WILEY-V C H VERLAG GMBH
Address	POSTFACH 101161, 69451 WEINHEIM, GERMANY
Language	English
EISSN	1099-0690
Keywords-Plus	1,3-BIS-SILYL ENOL ETHERS; REGIOSELECTIVE SYNTHESIS; BIOLOGICAL-ACTIVITY; EFFICIENT SYNTHESIS; DIMETHYL 1,3-ACETONEDICARBOXYLATE; XANTHENEDIONE DERIVATIVES; DIHYDROFOLATE REDUCTASES; 1,3-DICARBONYL COMPOUNDS; RECEPTOR ANTAGONISTS; MEDICINAL CHEMISTRY
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	iva108@google-mail.com peter.langer@uni-rostock.de
Funding-Acknowledgement	State of Mecklenburg-Vorpommern; Deutscher Akademischer Austausch-Dienst (DAAD) (program Deutsch-Pakistanische Hochschulzusammenarbeit); Bundesministerium fur Bildung und Forschung (BMBF) (REMEDIS project) {[}03IS2081A]; Organization for the Prohibition of Chemical Weapons (OPCW); Higher Education Commission of Pakistan {[}20-3733/NRPU/RD/ 14/520]
Funding-Text	Financial support by the State of Mecklenburg-Vorpommern (scholarship for I. S.), by the Deutscher Akademischer Austausch-Dienst (DAAD) (program Deutsch-Pakistanische Hochschulzusammenarbeit), by the Bundesministerium fur Bildung und Forschung (BMBF) (REMEDIS project, Grant No. 03IS2081A), by the Organization for the Prohibition of Chemical Weapons (OPCW), and by the Higher Education Commission of Pakistan (Project No. 20-3733/NRPU/R\&D/ 14/520) is gratefully acknowledged.
Number-of-Cited-References	118
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	7
Journal-ISO	Eur. J. Org. Chem.
Doc-Delivery-Number	EJ6KN