Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

4-alkyl-2-arylamino-5-(1,2,4-triazole-1-group) thiazole and application thereof to preparation of medicaments for resisting cancer

A technology of arylamino and alkyl, which is applied in the field of new compounds and their preparation, and can solve the problems of no research and development reports in the application

Inactive Publication Date: 2012-09-19
HUNAN UNIV
View PDF5 Cites 18 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

4-Alkyl-2-arylamino-5-(1,2,4-triazol-1-yl)thiazole and its preparation method and its application as preparation of anti-cervical cancer or human lung cancer drug have no research and development reports

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
  • 4-alkyl-2-arylamino-5-(1,2,4-triazole-1-group) thiazole and application thereof to preparation of medicaments for resisting cancer
  • 4-alkyl-2-arylamino-5-(1,2,4-triazole-1-group) thiazole and application thereof to preparation of medicaments for resisting cancer
  • 4-alkyl-2-arylamino-5-(1,2,4-triazole-1-group) thiazole and application thereof to preparation of medicaments for resisting cancer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0031] Preparation of Example 14-tert-butyl-2-phenylamino-5-(1,2,4-triazol-1-yl)thiazole and its hydrobromide

[0032]

[0033]3,3-Dimethyl-1-(1,2,4-triazol-1-yl)-1-bromo-2-butanone and phenylthiourea compounds are fed in a molar ratio of 1:1, in ethanol Heating to reflux reaction. After the reaction was completed, the solvent was distilled off under reduced pressure, washed with ethyl acetate, filtered, and dried to obtain 4-tert-butyl-2-phenylamino-5-(1,2,4-triazol-1-yl)thiazole hydrobromide Salt; hydrobromide was neutralized with ammonia water, extracted with ethyl acetate, distilled under reduced pressure, and recrystallized from ethanol to obtain 4-tert-butyl-2-phenylamino-5-(1,2,4-triazol-1-yl ) Thiazole, melting point 186-188°C. 1 H NMR (CDCl 3 , 400MHz), δ: 1.17(s, 9H, 3×CH 3 ), 1.83 (brs, 1H, NH), 7.10~7.40 (m, 5H, C 6 h 5 ), 8.10(s, 1H, C 2 h 2 N 3 3-H), 8.26(s, 1H, C 2 h 2 N 3 5-H).

Embodiment 24

[0034] Preparation of Example 24-tert-butyl-2-(3-methylanilino)-5-(1,2,4-triazol-1-yl)thiazole

[0035]

[0036] According to the method of Example 1, react 9.0h; Obtain 4-tert-butyl-2-(3-methylanilino)-5-(1,2,4-triazol-1-yl)thiazole; Melting point 98~ 100°C; 1 H NMR (CDCl 3 , 400MHz), δ: 1.16(s, 9H, 3×CH 3 ), 2.36(s, 3H, CH 3 ), 6.94 (d, J=8.0Hz, 1H, C 6 h 4 4-H), 7.12(d, J=6.4Hz, 1H, C 6 h 4 6-H), 7.13(s, 1H, C 6 h 4 2-H), 7.25(t, 1H, J = 7.2Hz, 1H, C 6 h 4 5-H), 8.08(s, 1H, C 2 h 2 N 3 3-H), 8.24(s, 1H, C 2 h 2 N 3 5-H).

Embodiment 34

[0037] Preparation of Example 34-tert-butyl-2-(4-methylanilino)-5-(1,2,4-triazol-1-yl)thiazole

[0038]

[0039] According to the method of Example 1, react 4.0h; Obtain 4-tert-butyl-2-(4-methylanilino)-5-(1,2,4-triazol-1-yl)thiazole; Melting point 147~ 150°C; 1 H NMR (CDCl 3 , 400MHz), δ: 1.17(s, 9H, 3×CH 3 ), 2.34(s, 3H, CH 3 ), 7.18 (d, J=8.8Hz, 2H, C 6 h 5 3,5-H), 7.22 (d, J=8.8Hz, 2H, C 6 h 5 2,6-H), 8.08(s,1H,C 2 h 2 N 3 3-H), 8.24(s, 1H, C 2 h 2 N 3 5-H).

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 4-alkyl-2-arylamino-5-(1,2,4-triazole-1-group) thiazole and salts thereof shown in a formula I, wherein R is selected from H, alkyl groups of C1-C2 and straight-chain alkyl groups or branched-chain alkyl groups of C3-C4; X1, X2, X3, X4 and X5 are selected from hydrogen, alkyl groups of C1-C2, hydroxide group, methoxy group, oxyethyl group, trifluoromethyl, fluorine, chlorine, bromine, nitryl, amino group, acetyl amino group, methanesulfamide, ethoxycarbonyl or carboxyl; and the salts of the 4-alkyl-2-arylamino-5-(1,2,4-triazole-1-group) thiazole are selected from hydrochloride, hydrobromide, nitrate, sulfate, phosphate, mesylate, p-toluene sulfonate, tartrate, lactate or malate. The 4-alkyl-2-arylamino-5-(1,2,4-triazole-1-group) thiazole is applied to preparation of medicaments for resisting cervical cancer or lung neoplasms.

Description

technical field [0001] The present invention relates to a class of novel compounds and their preparation methods and applications, specifically 4-alkyl-2-arylamino-5-(1,2,4-triazol-1-yl)thiazoles and their preparation methods and as preparation Application of anti-cervical cancer or human lung cancer drugs. Background technique [0002] Azole heterocyclic derivatives have always been paid attention to by drug and pesticide workers because of their good biological activity, high drug efficacy, wide bactericidal spectrum, and good systemic property [Comperhensive Heterocylic Chemistry. Pergamon Oxford, 1983, 5: 733-735], and triazoles are one of the more influential ones. The bactericidal mechanism of triazole fungicides is to affect the formation of fungal cell walls by hindering the biosynthesis of fungal ergosterol, and have good control effects on most fungal diseases that endanger crop growth. Triazole fungicides also have certain plant growth regulating activity [Pesti...

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
IPC IPC(8): C07D417/04A61P35/00
Inventor 胡艾希叶姣沈芳李婉陈懿
Owner HUNAN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com