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Novel genipin derivatives and preparation method and application thereof

A technology of genipin and derivatives, which is applied in the field of preparation of new genipin derivatives, and can solve problems such as lack of Scp1 inhibitors

Pending Publication Date: 2021-06-22
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In summary, there is still a lack of new Scp1 inhibitors in the field

Method used

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  • Novel genipin derivatives and preparation method and application thereof
  • Novel genipin derivatives and preparation method and application thereof
  • Novel genipin derivatives and preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0081] The invention provides a preparation method and application of novel genipin derivatives. Based on the structural characteristics of Scp1, the present invention designs novel genipin derivatives. There is a hydrophobic end in its structure, and there is a carboxylic acid group as the hydrophilic end, which are respectively larger than the hydrophobic pocket of Scp1 and the magnesium ion in the active center and the surrounding magnesium ions. Hydrophilic pocket binding. The exposed carboxyl group in the molecule can form intermolecular hydrogen bonds with Ser211, Asp206, Lys190 or Asp96 in the Scp1 pocket, and the benzyl group in the side chain can form π with any or more residues in Phe106, Tyr188, and Tyr158 in the active pocket -π interaction, improving the stability of small molecules and protein binding. The evaluation of Scp1 inhibitory activity shows that the novel compound prepared by the present invention has good Scp1 inhibitory activity and can be used to pr...

Embodiment 1

[0145] The synthesis of embodiment 1 compound III

[0146]

[0147] Dissolve geniposide (1g, 2.58mmol) in DMF (10mL), slowly add 60% sodium hydride (0.618g, 15.46mmol) under ice-water bath, after reacting for 1h, slowly add benzyl bromide (15.46mmol), and React overnight. After the reaction, the reaction solution was added to ice water (60mL), extracted three times with ethyl acetate (90mL), the organic phases were combined, washed three times with 1M hydrochloric acid solution (30mL), saturated brine (60mL) successively, and anhydrous Dry over sodium sulfate, concentrate under reduced pressure, and separate and purify by silica gel chromatography to obtain light yellow oily liquid with a yield of 70%. 1 H NMR (400MHz, Chloroform-d) δ7.54(s, 1H), 7.38(d, J=4.2Hz, 1H), 7.33(q, J=5.3, 4.6Hz, 22H), 7.22(d, J= 7.2Hz, 2H), 5.87(s, 1H), 5.36(d, J=5.8Hz, 1H), 5.29(s, 1H), 4.95(t, J=10.7Hz, 2H), 4.87(d, J= 9.2Hz, 2H), 4.70–4.50(m, 7H), 4.22(d, J=13.7Hz, 2H), 3.75(d, J=11.1Hz, 1...

Embodiment 2

[0149]

[0150] Referring to Example 1, a light yellow oily liquid was obtained with a yield of 61%. 1H NMR (400MHz, Chloroform-d) δ7.60(s,1H),7.35–7.10(m,20H),5.91(s,1H),5.42(s,1H),4.96(s,1H),4.90( dd,J=12.2,3.0Hz,2H),4.85(s,1H),4.75–4.47(m,8H),4.27(s,2H),3.74(s,3H),3.71–3.62(m,2H) ,3.52(s,2H),3.41–3.34(m,1H),3.05(s,1H),2.95(s,1H),2.41(s,15H),2.31(s,1H),2.26(s,1H ).

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Abstract

The invention provides novel genipin derivatives and a preparation method thereof. The novel genipin derivatives comprise geniposide derivatives and genipin derivatives. The invention belongs to the field of pharmaceutical chemistry. The geniposide derivative has a structure shown as a formula (I).

Description

technical field [0001] The invention relates to a compound in the technical field of medicine and chemical industry and its preparation, specifically a preparation method and application of a novel genipin derivative. Background technique [0002] Brain tumors refer to tumors that grow in the brain, which can be divided into primary and secondary intracranial tumors. Primary tumors are tumors originating from brain, meninges, pituitary gland, cranial nerves, cerebrovascular and embryonic remnants. Secondary intracranial tumors are metastases to the brain from malignant tumors in other parts of the body. Among the most common brain tumors are gliomas, such as astrocytoma, oligodendroglioma, ependymoma, and medulloblastoma. Because the boundary between malignant brain tumors and normal brain tissue is unclear, surgery is difficult to completely remove, and some deep tumors are not suitable for surgical treatment, which is difficult, disabled, and has a high mortality rate. I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/04C07D311/94A61P25/00A61P35/00A61K31/7048A61K31/352
CPCC07H17/04C07D311/94A61P25/00A61P35/00
Inventor 姜发琴雷纾雯吕丹张勇杜溢
Owner SHANGHAI JIAO TONG UNIV
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