Oleanolic acid derivative, preparation method and application thereof

A technology for oleanolic acid and derivatives, applied in the field of oleanolic acid derivatives and their preparation, can solve the problems of poor water solubility, less research on hypoglycemic activity, weak biological activity and the like

Active Publication Date: 2018-06-08
GUANGDONG UNIV OF TECH
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, as a widely distributed and cheap and easy-to-obtain natural product, its biological activity is weak, and its bioavailability is low due to its poor water solubility and poor lipid-water distribution coefficient.
Therefore, in recent years, in order to improve the bioavailability and biological activity of oleanolic acid, domestic and foreign researchers have modified its active group and active site, synthesized a series of derivatives and carried out anti-tumor, anti- HIV and other activity studies, but there are few studies on the hypoglycemic activity of such derivatives

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Oleanolic acid derivative, preparation method and application thereof
  • Oleanolic acid derivative, preparation method and application thereof
  • Oleanolic acid derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0041] The following will clearly and completely describe the technical solutions in the embodiments of the present invention with reference to the accompanying drawings in the embodiments of the present invention. Obviously, the described embodiments are only some, not all, embodiments of the present invention. Based on the embodiments of the present invention, all other embodiments obtained by persons of ordinary skill in the art without making creative efforts belong to the protection scope of the present invention.

[0042] 1. Table 1 shows the structures of the compounds prepared in the examples of the present invention and their half-inhibitory concentrations, figure 1 Its chemical reaction formula and its structural formula.

[0043] Table 1

[0044]

[0045]

[0046]

[0047] 2. Taking compound 10 as an example, describe in detail the preparation method of the oleanolic acid derivative of the present invention

[0048] 1) Weigh 300mg (0.66mmol) of oleanolic ac...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The application belongs to the technical field of medicament synthesis, and particularly relates to an oleanolic acid derivative, a preparation method and application thereof. The invention claims theoleanolic acid derivative which is as shown in general formula (I), or a corresponding isomer, a non-corresponding isomer, medically acceptable salt, prodrug and active metabolite, and a mixture thereof, wherein R is selected from an aryl or heteroaryl which is optionally substituted by any one or more groups of a hydrogen atom, X, alkyl, substituted alkyl, alkoxyl or heteroaryl. The oleanolic acid derivative is obtained by performing chemical modifying on a natural product oleanolic acid serving as a lead compound, and is novel in structure, high in bioavailability and high in bioactivity. In vitro pharmacological experiments show that the oleanolic acid derivative is a noncompetitive alpha-glucosidase inhibitor, which has an obvious effect on inhibiting the activity of the alpha-glucosidase inhibitor; the activity of the oleanolic acid derivative is far higher than that of a positive drug, namely, acarbose, and has a very upbeat prospect in the application of a hypoglycemic drug.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to an oleanolic acid derivative and its preparation method and application. Background technique [0002] Diabetes mellitus (DM) is a syndrome of metabolic disorders of fat, sugar, electrolyte and protein caused by immune dysfunction, genetic factors, microbial infection and other factors leading to hypofunction of pancreatic islets. The main symptoms are polydipsia, polyphagia, Polyuria, weight loss, etc. [0003] The main harm of diabetes is not itself but the various serious complications caused by it. The complications caused by diabetes mainly include limb gangrene, blindness, cardiovascular and cerebrovascular sclerosis and renal failure. Studies have shown that 30% to 40% of patients with diabetes will develop at least one complication 10 years after the onset of diabetes. Such a high complication rate leads to high mortality and disability in diabetic pat...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/585A61P3/10
CPCC07J63/008
Inventor 赵肃清钟颖颖陈惠生吴盼盼张炳杰杨洋朱秋雁张春国
Owner GUANGDONG UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products