Triazole-diazepine-5-ketone compound

A technology of ketone compounds and diazepines, which is applied in the field of medicine and can solve problems that have not been reported

Active Publication Date: 2018-10-12
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of compound is used as an anti-tumor activity research, and there is no report at present.

Method used

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  • Triazole-diazepine-5-ketone compound
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  • Triazole-diazepine-5-ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Example 1: 2-phenyl-8-(3,4,5-trimethoxyphenyl)-2,6-dihydro-[1,2,3]triazolo[4,5-e][ 1,4] Preparation of diazepin-5(4H)-one (compound 1)

[0098] Add 2-phenyl-4-(3,4,5-benzoyl)-5-amino-1,2,3-triazole (354mg, 1.0mmol) into a 100mL eggplant-shaped bottle, anhydrous di Chloromethane (30mL) dissolved, N 2 Protect, pre-cool at 0°C, add chloroacetyl chloride (0.15 mL, 2.0 mmol) dropwise, and transfer to room temperature after the addition is complete. The reaction was continued for 24 hours. After the reaction was detected by TLC, the solvent was evaporated under reduced pressure, washed with ethyl acetate, and filtered with suction to obtain compound I. Compound 2-chloro-N-(2-phenyl-5-(3,4,5-trimethoxybenzoyl)-2H-1,2,3-triazol-4-yl)acetamide (430mg , 1.0mmol), urotropine (701mg, 5.0mmol), ammonium acetate (386mg, 5.0mmol) was dissolved in 95% ethanol, reflux reaction for 5h, after the reaction was detected by TLC, the solvent was evaporated under reduced pressure, dichlorom...

Embodiment 2

[0099] Example 2: 2-p-tolyl-8-(3,4,5-trimethoxyphenyl)-2,6-dihydro-[1,2,3]triazolo[4,5-e] Preparation of [1,4]diazepin-5(4H)-one (Compound 2)

[0100] Compound 2 was prepared in the same manner as in Example 1 except that the corresponding raw materials were used; the yield was 74%. 1 H NMR (600MHz, CDCl 3 )δ9.61(s,1H),7.96(d,J=8.4Hz,2H),7.31(d,J=8.4Hz,2H),7.30(s,2H),4.59(s,2H),3.92( s,3H),3.89(s,6H),2.42(s,3H)ppm; 13 C NMR (100MHz, CDCl 3 )δ168.0, 162.2, 152.9(×2), 147.1, 140.8, 139.0, 137.0, 134.3, 131.7, 130.1(×2), 118.8(×2), 106.7(×2), 61.0, 57.5, 56.2(×2) ,21.1ppm.

Embodiment 3

[0101] Example 3: 2-o-tolyl-8-(3,4,5-trimethoxyphenyl)-2,6-dihydro-[1,2,3]triazolo[4,5-e] Preparation of [1,4]diazepin-5(4H)-one (compound 3)

[0102] Compound 3 was prepared in the same manner as in Example 1 except that the corresponding raw materials were used; the yield was 76%. 1 H NMR (600MHz, CDCl 3 )δ9.74(s,1H),7.63(m,0.5H),7.55(d,J=7.7Hz,1H),7.43(m,0.5H),7.30(m,1H),7.26(m,1H ),7.18(s,2H),4.51(s,2H),3.82(s,3H),3.79(s,6H),2.39(s,3H)ppm; 13 C NMR (100MHz, CDCl 3)δ167.8, 162.5, 153.0(×2), 146.8, 141.0, 138.7, 134.3, 132.3, 132.0, 129.6, 126.9(×2), 125.0, 106.8(×2), 60.9, 57.2, 56.2(×2), 19.4 ppm.

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PUM

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Abstract

The invention belongs to the technical field of drugs, and relates to a triazole-diazepine-5-ketone compound and application thereof, in particular to application of the compound, which serves as a tumor cell proliferation inhibitor, in the aspect of preparing antineoplastic drugs. According to the compound, the pharmaceutically accepted salt, solvate or isomer thereof has a structural formula asshown in the description, wherein the definitions of R1 to R8 are as described in the claims and the description.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a triazolodiazepin-5-one compound and its application, specifically, relates to the use of this type of compound as a tumor cell proliferation inhibitor in the preparation of antitumor drugs application. Background technique [0002] Malignant tumor is a serious disease that threatens human health and life, and it is the leading cause of death in China. Searching for and discovering new drugs for the treatment and prevention of tumors is a major issue at present. 4-Substituted methoxybenzoyl-aryl-thiazole (SMART) is a tubulin polymerization inhibitor obtained by structural optimization of natural products as lead compounds. It exerts its anticancer activity by acting on the colchicine binding site to inhibit tubulin polymerization , and it can overcome the problem of Pgp-mediated multidrug resistance, and has lower neurotoxicity compared with vinblastine. The in vivo efficacy o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/551A61P35/00
Inventor 张为革冯东杰吴英良王灏包凯关奇左代英
Owner SHENYANG PHARMA UNIVERSITY
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