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Chiral 1, 4-dihydropyran (2, 3-c) pyrazole derivative as well as synthesis method and application of chiral 1, 4-dihydropyran (2, 3-c) pyrazole derivative

A technology of pyrazole derivatives and dihydropyran, which is applied in the direction of organic active ingredients, chemicals used for biological control, medical preparations containing active ingredients, etc., can solve the problems that there are no literature reports on pyrazole derivatives, etc. Achieving the effects of flexible reaction time, wide application range and high yield

Active Publication Date: 2014-07-09
惠州拓康生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] According to literature review, there is no literature report on the asymmetric synthesis of chiral multi-substituted dihydropyrano[2,3-c]pyrazole derivatives

Method used

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  • Chiral 1, 4-dihydropyran (2, 3-c) pyrazole derivative as well as synthesis method and application of chiral 1, 4-dihydropyran (2, 3-c) pyrazole derivative
  • Chiral 1, 4-dihydropyran (2, 3-c) pyrazole derivative as well as synthesis method and application of chiral 1, 4-dihydropyran (2, 3-c) pyrazole derivative
  • Chiral 1, 4-dihydropyran (2, 3-c) pyrazole derivative as well as synthesis method and application of chiral 1, 4-dihydropyran (2, 3-c) pyrazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Add pyrazolone derivative 2a (0.10mmol), malononitrile (0.10mmol) and Takemoto catalyst (0.02mmol) as shown in formula (IV) to a 5mL reaction test tube, then add 1ml of toluene, and the mixture is heated at a temperature of 15 °C and stirred for 12 hours. Then the solvent was removed under reduced pressure, and column chromatography was performed with a mixture of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate was 10:1) as the eluent to obtain chiral 1,4- Dihydropyran(2,3-c)pyrazole derivative 3a (31 mg, 95% yield).

[0040] The reaction equation is as follows:

[0041]

[0042] The structure of the chiral 1,4-dihydropyran(2,3-c)pyrazole derivative 3a obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1 H NMR(400MHz,DMSO)δ(ppm)7.79(d,J=8.1Hz,2H),7.49(t,J=7.9Hz,2H),7.37-7.22(m,8H),4.67(s,1H) ,1.77(s,3H); 13 C NMR (101MHz, CDCl 3)δ (ppm) 159.50, 145.36, 143.94, 143.67, 137.60...

Embodiment 2

[0046] Add pyrazolone derivative 2b (0.10mmol), malononitrile (0.10mmol) and Takemoto catalyst (0.02mmol) as shown in formula (IV) to a 5mL reaction test tube, then add 1ml of toluene, and the mixture is heated at a temperature of 15 °C and stirred for 12 hours. Then the solvent was removed under reduced pressure, and column chromatography was carried out with a mixture of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate was 10:1) as the eluent to obtain the chiral 1,4- Dihydropyran(2,3-c)pyrazole derivative 3b (32 mg, yield 93%).

[0047] The reaction equation is as follows:

[0048]

[0049] The structure of the chiral 5-chloro-1,4-dihydropyran(2,3-c)pyrazole derivative 3b obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1 H NMR(600MHz,DMSO)δ(ppm)7.78(d,J=7.8Hz,2H),7.49(t,J=7.9Hz,2H),7.33-7.25(m,5H),7.17(t,J= 8.8Hz,2H),4.72(s,1H),1.78(s,3H); 13 C NMR (151MHz, DMSO) δ (ppm) 162.02...

Embodiment 3

[0052] Add pyrazolone derivative 2c (0.10mmol), malononitrile (0.10mmol) and Takemoto catalyst (0.02mmol) as shown in formula (IV) to a 5mL reaction test tube, then add 1ml of toluene, and the mixture is heated at a temperature of 15 °C and stirred for 12 hours. Then the solvent was removed under reduced pressure, and column chromatography was performed with a mixture of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate was 10:1) as the eluent to obtain chiral 1,4- Dihydropyran(2,3-c) pyrazole derivative 3c (35 mg, 97% yield).

[0053] The reaction equation is as follows:

[0054]

[0055] The structure of the 5-chloro-1,4-dihydropyran(2,3-c)pyrazole derivative 3c obtained above was identified by NMR and high-resolution mass spectrometry, 1 H NMR(600MHz,DMSO)δ(ppm)7.78(d,J=7.7Hz,2H),7.49(t,J=7.9Hz,2H),7.41(d,J=8.4Hz,2H),7.30(t ,J=8.0Hz,5H),4.72(s,1H),1.78(s,3H); 13 C NMR (151MHz, DMSO) δ (ppm) 159.53, 145.26, 143.96, 142.73, 137.54...

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Abstract

The invention discloses a chiral 1, 4-dihydropyran (2, 3-c) pyrazole derivative as well as a synthesis method and application of the chiral 1, 4-dihydropyran (2, 3-c) pyrazole derivative. The synthesis method comprises the steps of with methylbenzene as a solvent, enabling a substituted or unsubstituted imidazolone derivative and propanedinitrile to react under the analysis of a Takemoto catalyst, and carrying out after-treatment on a reaction product to obtain the chiral 1, 4-dihydropyran (2, 3-c) pyrazole derivative. The method has the advantages of flexible reaction time, relatively high yield, simplicity and convenience in operation and the like, and is wide in application range. The chiral 1, 4-dihydropyran (2, 3-c) pyrazole derivative has an inhibiting effect on gram positive bacteria and gram negative bacteria.

Description

technical field [0001] The invention belongs to the field of synthetic medicine and chemical industry, and mainly relates to a synthesis method of a heterocyclic compound, in particular to a chiral 1,4-dihydropyran (2,3-c) pyrazole derivative with antibacterial activity and their synthesis methods and applications. Background technique [0002] Multi-substituted dihydropyrano[2,3-c]pyrazole compounds are an important class of heterocyclic compounds, which have certain potential medicinal functions, such as: anti-inflammatory (Zaki, M.E.A.; Saliman, H.A.; Hickal, O.A.; Rashad, A.E.Z. Naturforsch., C: Biosci.2006, 61, 1; Sheng, C.K.; Li, J.H.; Hideo, N.J. Med. Chem. 1984, 27, 539.), antibacterial (Smith, W.P.; Sollis, L.S. ; Howes, D.P.; Cherry, C.P.; Starkey, D.I.; Cobley, N.K.J. Med. Chem. 1998, 41, 787; Mazaahir, K.; , 15, 4295.), anticancer (Wang, J.L.; Liu, D.; Zheng, Z.J.; Shan, S.; Han, X.; Srinivasula, S.M.; Croce, C.M.; Alnemri, E.S.; Huang, Z.Proc .Natl.Acad.Sci.U...

Claims

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Application Information

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IPC IPC(8): C07D491/052A61K31/4162A01P1/00
CPCC07D491/052Y02A50/30
Inventor 谢建武孙平
Owner 惠州拓康生物科技有限公司
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