Beta-amino acid esters having optical activity and containing benzothiazole groups and synthetic method and application thereof
A benzothiazole-based, optically active technology applied in the field of benzothiazole-containing beta-amino acid ester compounds
Inactive Publication Date: 2010-09-01
GUIZHOU UNIV
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But so far there is no research about the Mannich reaction catalyzed by benzothiazole imine and malonate with cinchonaline thiourea organocatalyst. Therefore, it is of great significance to study the synthesis of β-amino acid compounds containing benzothiazole groups by organocatalytic Mannich reaction
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Abstract
The invention discloses a synthetic method and bioactivity of beta-amino acid esters which have optical activity and contain benzothiazole groups. The beta-amino acid esters which have optical activity and contain the benzothiazole groups have the structure shown in the general formula (I), and in the formula, R1 is a group of hydrogen, p-chloro, o-chloro, p-fluoro, o-fluoro, p-methyl, o-methoxy and the like; R2 is a group of 4-methyl, 6-methoxy and the like; and R3 is a group of methyl, ethyl, propyl, isopropyl and the like. The invention introduces Mannich reaction which uses organic catalyst of cinchona alkaloid thiourea to catalyze benzothiazole imine and malonate, the product is obtained by one-step synthesis, and the reaction yield and the selectivity to enantiomer are both high. Compounds c, d and e in the inveniton have high therapeutic and passivation inhibiting effects towards tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) and show good anti-plant virus activity.
Description
technical field The invention relates to an optically active β-amino acid ester compound containing a benzothiazole group with an anti-plant virus effect and a preparation method thereof. Background technique Thiazole compounds have broad-spectrum biological activities and can be used in the research of pesticides and medicines. Since Merck company successfully developed thiabendazole (Triabendazole) in 1962, the research on the biological activity of thiazole compounds has caused people's great interest, and has successfully developed a lot of thiazole pesticide varieties (Fitzjohn, S.; Robinson, M.P. Bezoxazole and benzothiazole Derivatives [P]. WO 9406783, 1994-03-31. Naka, I.P.; Matsuno, H., Inami, S. et al. Preparation of epalrestat [P]. JP08291155, 1997-10-21.). At the same time, the research on thiazole compounds in medicine has also attracted more and more interest from chemists (Sebrell, L.B.; Boord, C.E. Preparation and properties of 1-mercaptobenzothiazole its ho...
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IPC IPC(8): C07D277/82A01N43/78A01P1/00
Inventor 宋宝安李为华杨松胡德禹金林红魏学范会涛薛伟李良
Owner GUIZHOU UNIV
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