Preparation method of 1,4-benzodioxan-containing 1,3,4-oxadiazole derivatives and use of the 1,4-benzdioxan-containing 1,3,4-oxadiazole derivatives in anti-cancer drugs

A technology of benzodioxane and oxadiazole, applied to the preparation method of 1,3,4-oxadiazole derivatives containing 1,4-benzodioxane and its application field in anticancer drugs , which can solve problems such as application restrictions, many adverse reactions, and limited efficacy

Inactive Publication Date: 2012-09-26
NANJING UNIV
View PDF3 Cites 10 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These treatments have a certain effect on cancer, and some can cure some patients, but they all have serious adverse reactions or limited curative effects.
Chemotherapy is a relatively common treatment method. The commonly used drugs mainly include nitrogen mustards, pyrimidines, and platinums. However, most drugs have obvious disadvantages such as many adverse reactions, high toxicity, and low bioavailability. so that its application is limited

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
  • Preparation method of 1,4-benzodioxan-containing 1,3,4-oxadiazole derivatives and use of the 1,4-benzdioxan-containing 1,3,4-oxadiazole derivatives in anti-cancer drugs
  • Preparation method of 1,4-benzodioxan-containing 1,3,4-oxadiazole derivatives and use of the 1,4-benzdioxan-containing 1,3,4-oxadiazole derivatives in anti-cancer drugs
  • Preparation method of 1,4-benzodioxan-containing 1,3,4-oxadiazole derivatives and use of the 1,4-benzdioxan-containing 1,3,4-oxadiazole derivatives in anti-cancer drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: 2-(2,3-dihydrobenzo[b][1,4]dioxan-6-yl)-5-(3-methylbenzyl)-1,3,4-oxa Preparation of Oxadiazole (Compound 1).

[0021]

[0022] 1 mmol of 1,4-benzodioxane-6-carboxylic acid was subjected to esterification under the catalysis of concentrated sulfuric acid to obtain the corresponding ester. Then dissolve the obtained ester in an appropriate amount of methanol, add a slight excess of 85% hydrazine hydrate, and stir and reflux for 8-12 hours. The solvent was evaporated under reduced pressure, and then water was added. After the solid precipitated, it was filtered and washed with water, and recrystallized from ethanol to obtain a substituted hydrazide. After dissolving 1mmol hydrazide and 1mmol KOH in an appropriate amount of 95% ethanol, slowly add a little excess CS 2 Stir and reflux, evaporate the solvent ethanol after the reaction is terminated, pour it into cold water, adjust the pH value to 5-6 with dilute hydrochloric acid, produce a large amount of pre...

Embodiment 2

[0023] Example 2: 2-(2,3-dihydrobenzo[b][1,4]dioxan-6-yl)-5-(4-methylbenzyl)-1,3,4-oxa Preparation of Oxadiazole (Compound 2).

[0024]

[0025] The preparation method is the same as in Example 1. Substitute 4-methylbenzyl bromide for 3-methylbenzyl bromide to obtain the target compound. Yellow needle-like crystals, yield 76%; m.p.133-1°C; 1 H NMR (500MHz, CDCl 3 )δ: 3.4(m, 3H), 4.29-4.32(m, 4H), 4.47(s, 2H), 6.94(d, J=8.25Hz, 1H), 7.02(t, J=8.55, 2H) 7.33(d , J=7.9, 2H) 7.48 (d, J=9.15, 2H); MS (ESI): 341.09 (C 18 h 17 N 2 o 3 S, [M+H] + ).Anal.Calcd for C 18 h 16 N 2 o 3 S: C, 63.51; H, 4.74; N, 8.23%. Found: C, 63.36; H, 4.47; N, 8.48%.

Embodiment 3

[0026] Example 3: 2-(2,3-dihydrobenzo[b][1,4]dioxan-6-yl)-5-(2-fluorobenzyl)-1,3,4-oxadi Preparation of azole (compound 3).

[0027]

[0028] The preparation method is the same as in Example 1. Substitute 2-fluorobenzyl bromide for 3-methylbenzyl bromide to obtain the target compound. Pale yellow crystals. Yield 79.5%; mp: 108°C. 1 H NMR (500MHz, CDCl 3 )δ: 4.28-4.31 (m, 4H), 4.52 (s, 2H), 6.94 (d, J=8.2, 1H), 7.04-7.11 (m, 2H), 7.28 (d, J=7.8, 1H) 7.46 -7.49 (m, 2H), 7.52 (q, J=6.25, 1H); MS (ESI): 345.06 (C 17 h 14 N 2 o 3 S, [M+H] + ).Anal.Calcd for C 17 h 13 N 2 o 3 S: C, 59.29; H, 3.81; N, 8.13%. Found: C, 59.40; H, 3.82; N, 8.03%.

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 invention discloses 1,4-benzodioxan-containing 1,3,4-oxadiazole derivatives. The 1,4-benzodioxan-containing 1,3,4-oxadiazole derivatives have the general formula shown in the patent specification, wherein R represents a group shown in the patent specification. The 1,4-benzodioxan-containing 1,3,4-oxadiazole derivatives have obvious effects for inhibiting growth of a human hepatoma cell HEP-G2, a human colon cancer cell SW116 and a human cervical cancer cell HELA and thus the 1,4-benzodioxan-containing 1,3,4-oxadiazole derivatives can be used in preparation of anti-cancer drugs. The invention also discloses a preparation method of the 1,4-benzodioxan-containing 1,3,4-oxadiazole derivatives.

Description

technical field [0001] The invention relates to a preparation method of 1,3,4-oxadiazole derivatives containing 1,4-benzodioxane and its application in anticancer drugs. Background technique [0002] As one of the major diseases that seriously threaten human health, cancer is now gradually replacing cardiovascular disease as the disease with the largest number of deaths in the world. At present, there are many means and methods to treat cancer, such as surgery, chemical drug therapy, radiation therapy, traditional medical treatment represented by traditional Chinese medicine, immunotherapy and so on. These treatments have certain curative effects on cancer, and some can cure some patients, but all have serious adverse reactions, or limited curative effects and other disadvantages. Chemotherapy is a relatively common treatment method. The commonly used drugs mainly include nitrogen mustards, pyrimidines, and platinums. However, most drugs have obvious disadvantages such as m...

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): C07D413/04A61K31/4245A61P35/00
Inventor 朱海亮张晓敏孙娟刘凯杨雨顺燕茹张雁滨
Owner NANJING UNIV
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

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap