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Halogenated dihydropyran pyrrolidone compound as well as preparation method and application thereof

A technology of halogenated dihydropyranopyrrolone compounds and compounds, which is applied in the field of halogenated dihydropyranopyrrolone compounds and their preparation, and can solve problems such as halogenated dihydropyranopyrrolone compounds that have not been reported , achieve the effect of broad market application prospect, high yield and mild reaction

Active Publication Date: 2018-05-29
CHENGDU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Halogenated dihydropyranopyrrolone compounds of structure shown in the present invention have not been reported yet

Method used

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  • Halogenated dihydropyran pyrrolidone compound as well as preparation method and application thereof
  • Halogenated dihydropyran pyrrolidone compound as well as preparation method and application thereof
  • Halogenated dihydropyran pyrrolidone compound as well as preparation method and application thereof

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Experimental program
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Embodiment 1

[0039] Embodiment 1, the preparation of compound of the present invention

[0040] raw material

[0041] Quinidine squaramide catalyst: the structure is Purchased from Daicel Pharmaceutical Chiral Technology (Shanghai) Co., Ltd.

[0042] General synthetic route:

[0043]

[0044] Wherein, X is fluorine, chlorine, bromine, iodine; L 1 Is none or vinyl; ring A is naphthalene ring, benzene ring, thiophene ring; R 1 is benzyl, C 1 -C 8 Alkyl or (CH 2 ) n -O-Bn; n is an integer from 1 to 5; R 2 Be benzyl, allyl, p-methoxybenzyl; R 3 , R 4 independently selected from hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 3 Alkyl, nitro, methoxy.

[0045] The following compounds were prepared:

[0046]

[0047]

[0048]

[0049] 1. Preparation of compound 4a

[0050]

[0051] ①Take a 150mL round bottom flask, measure 30mmol of benzylamine, 10mL of absolute ethanol, and an equivalent amount of ethyl acrylate, and stir at room temperature for 16h. Weigh 1...

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Abstract

The invention provides a halogenated dihydropyran pyrrolidone compound of formula (I) as shown in the description, or a crystal form of the compound, in the formula, X is fluorine, chlorine, bromine and iodine; L1 is vacant or vinyl; ring A is a naphthalene ring, a benzene ring or a thiophene ring; R1 is benzyl, alkyl of C1-C8 or (CH2)n-O-Bn; n is an integer of 1-5; R2 is benzyl, allyl or p-methoxybenzyl; and R3 and R4 are respectively independently selected from hydrogen, fluorine, chlorine, bromine, iodine, alkyl of C1-C3, nitryl or methoxyl. The invention further provides a preparation method of the compound or the crystal form thereof. The compound provided by the invention is simple and convenient in preparation method, gentle in reaction and high in yield, and in addition has certainanti-tumor activity and wide market application prospects.

Description

technical field [0001] The invention relates to a halogenated dihydropyranopyrrolone compound and its preparation method and application. Background technique [0002] Multi-substituted pyran compounds, especially those based on the pyranocyclic skeleton, are widely present in natural products or pharmaceutical intermediates with physiological activity. Substituent modification of such compounds, derivatization of structural analogues and Further re-evaluation of biological activity has become a research hotspot. [0003] Huynh et al. (T.H.V.Huynh, I.Shim, H.Bohr, B.Abrahamsen, B.Nielsen, A.A.Jensen, L.Bunch, J.Med.Chem.2012,55,5403-5412.) reported the following Use of a series of polysubstituted compounds of the pyranocyclic skeleton as EAAT1-selective inhibitors. [0004] [0005] CN105541853A discloses multi-substituent type γ-pyranopyrrolidone compounds as shown below, which have good antibacterial activity. [0006] [0007] The halogenated dihydropyranopyrrolo...

Claims

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Application Information

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IPC IPC(8): C07D491/052A61P35/00
CPCC07B2200/07C07D491/052
Inventor 李俊龙沈旭东李强周亮朱红萍戴青松李青竹张翔曾荣冷海军刘悦杨开川张鹰刘宇
Owner CHENGDU UNIV
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