4-alkyl-2-aryl amino-5-(1,2,4-triazol-1-yl)thiazole and preparation method and application thereof
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A technology of arylamino and alkyl, applied in the field of new compounds and their preparation, can solve the problems of no research and development reports
Inactive Publication Date: 2012-07-25
HUNAN UNIV
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4-Alkyl-2-arylamino-5-(1,2,4-triazol-1-yl)thiazole and its preparation method
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Embodiment 1
[0036] Preparation of 4-tert-butyl-2-phenylamino-5-(1,2,4-triazol-1-yl)thiazole and its hydrobromide
[0037]
[0038] 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 Medium 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 neutralized with ammonia water, extracted with ethyl acetate, and distilled under reduced pressure to obtain 4-tert-butyl-2-phenylamino-5-(1,2,4-triazol-1-yl)thiazole, melting point 186~188℃. 1 HNMR (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 2
[0040] Preparation of 4-tert-butyl-2-(3-methylanilino)-5-(1,2,4-triazol-1-yl)thiazole and its hydrobromide
[0041]
[0042] According to the method of Example 1, react for 9.0h; get 4-tert-butyl-2-(3-methylanilino)-5-(1,2,4-triazol-1-yl)thiazole hydrobromide ; The hydrobromide was neutralized with ammonia water, extracted with ethyl acetate, and distilled under reduced pressure to obtain 4-tert-butyl-2-(3-methylanilino)-5-(1,2,4-triazole-1- Base) 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 3
[0044] Preparation of 4-tert-butyl-2-(4-methylanilino)-5-(1,2,4-triazol-1-yl)thiazole
[0045]
[0046] 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 HNMR (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).
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Abstract
The invention relates to 4-alkyl-2-aryl amino-5-(1,2,4-triazol-1-yl)thiazole shown as a chemical structural formula I and a salt thereof. The chemical structural formula I is shown in the specifications, wherein R is selected from H, alkyl with 1-2 carbon atoms, or straight chain alkyl or branch chain alkyl with 3-4 carbon atoms; and X1, X2, X3, X4 and X5 is selected from hydrogen, alkyl with 1-2 carbon atoms, hydroxyl, methoxyl, oxethyl, trifluoromethyl, fluorine, chlorine, bromine, nitro or amino. A preparation method of the 4-alkyl-2-aryl amino-5-(1,2,4-triazol-1-yl)thiazole comprises the following steps of: feeding 2-(1,2,4-triazol-1-yl)-2-bromoalkylketone and aryl thiourea in the molar ratio of 1:1, and carrying out a reflux reaction in ethanol; and after reacting, distilling under reduced pressure to remove a solvent, adding ethyl acetate for washing, filtering, drying to obtain 4-alkyl-2-aryl amino-5-(1,2,4-triazol-1-yl)thiazole hydrobromide, neutralizing the hydrobromide with ammonia water, extracting with ethyl acetate, drying, and distilling under reduced pressure to obtain 4-alkyl-2-aryl amino-5-(1,2,4-triazol-1-yl)thiazole. The 4-alkyl-2-aryl amino-5-(1,2,4-triazol-1-yl)thiazole has high antitumor activity, and can be applied to preparation of an anticancer medicament.
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 anti Application of 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 [Pesticides, 1994, 33 (4): 19-20; J Med Chem, 19...
Claims
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