Approach to thiazole-containing tetrahydropyridines via Aza-Rauhut-Currier reaction and their potent fungicidal and insecticidal activity / Zhu Yu-Jie,Guo Xiao-Feng,Fan Zhi-Jin,Chen Lai,Ma Liu-Yong,Wang Hai-Xia,Wei Yu,Xu Xuan-Ming,Lin Jian-Ping,Bakulev Vasiliy A. // RSC Advances. - 2016. - V. 6, l. 113. - P. 112704-112711.

ISSN/EISSN:

2046-2069 / нет данных

Type:

Article

Abstract:

A convenient and efficient synthesis of multi-substituted thiazole-containing tetrahydropyridine moieties was reported using the phosphine-catalyzed Aza-Rauhut-Currier reaction with excellent yields and diastereoselectivity. Thiazole-containing tetrahydropyridines were further transformed into the corresponding piperidine derivatives. The biological activity of the title compounds was explored; they exhibited moderate insecticidal activity against Aphis laburni Kaltenbach at 100 mg mL. A 3D QSAR model accurately predicted the insecticidal activity of the structurally diverse set of test compounds. Thiazole-containing tetrahydropyridines were active against normal fungi and also had good activity against resistant fungi mutations without cross resistance; thus, these compounds will be valuable for resistance management. The predicted potential fungicidal target of the title compounds is fumarate reductase.

Author keywords:

FUNCTIONALIZED TETRAHYDROPYRIDINES; NITROGEN-HETEROCYCLES; ACID-DERIVATIVES; 4+2 ANNULATION; DISCOVERY; KETONES; 1,2,3-TRIAZOLES; CYCLOADDITION; ALLENOATES; CONSTRUCT

DOI:

10.1039/c6ra24342h

Web of Science ID:

ISI:000389708700124

Соавторы в МНС:

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Другие поля

Поле	Значение
Publisher	ROYAL SOC CHEMISTRY
Address	THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Language	English
Keywords-Plus	FUNCTIONALIZED TETRAHYDROPYRIDINES; NITROGEN-HETEROCYCLES; ACID-DERIVATIVES; 4+2 ANNULATION; DISCOVERY; KETONES; 1,2,3-TRIAZOLES; CYCLOADDITION; ALLENOATES; CONSTRUCT
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	fanzj@nankai.edu.cn v.a.bakulev@urfu.ru
Funding-Acknowledgement	National Natural Science Foundation of China {[}31571991, 21372132]; International Science \& Technology Cooperation Program of China {[}2014DFR41030]; Tianjin Natural Science Foundation {[}14JCYBJC20400]; Ministry of Education and Science of the Russian Federation {[}State task 4.1626.2014/K]
Funding-Text	Z.J. Fan is grateful to the financial support from the National Natural Science Foundation of China (Grant No. 31571991, 21372132) and the International Science \& Technology Cooperation Program of China (Grant No. 2014DFR41030), and the Tianjin Natural Science Foundation (No. 14JCYBJC20400). V. A. Bakulev thanks the Ministry of Education and Science of the Russian Federation (State task 4.1626.2014/K). Resistant mutation fungi strains FJ1-10, T1-12 and T3-10 were kindly provided by Professor Liu Xili at China Agricultural University, and resistant mutation fungi strains BC2 were kindly provided by Professor Zhou Mingguo and Duan Yabing at Nanjing Agricutural University with multi-resistance characteristics.
Number-of-Cited-References	55
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	7
Journal-ISO	RSC Adv.
Doc-Delivery-Number	EE6GV