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6 - methyl - 4 - phenyl - 5 - ( phenyl or cycloalkyl) carbamoyl - 1,2,3, 4 - tetrahydropyrimidin- 2 - one derivatives as antitubercular agents

A technology of ectoine and phenyl, applied in the field of preparing these compounds

Inactive Publication Date: 2013-03-13
COUNCIL OF SCI & IND RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Furthermore, this could be a strategy to overcome multi-drug resistant bacilli that are increasingly rendering traditional treatment options ineffective

Method used

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  • 6 - methyl - 4 - phenyl - 5 - ( phenyl or cycloalkyl) carbamoyl - 1,2,3, 4 - tetrahydropyrimidin- 2 - one derivatives as antitubercular agents
  • 6 - methyl - 4 - phenyl - 5 - ( phenyl or cycloalkyl) carbamoyl - 1,2,3, 4 - tetrahydropyrimidin- 2 - one derivatives as antitubercular agents
  • 6 - methyl - 4 - phenyl - 5 - ( phenyl or cycloalkyl) carbamoyl - 1,2,3, 4 - tetrahydropyrimidin- 2 - one derivatives as antitubercular agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Example 1: N-(3-chlorophenyl)-4-(2,4-dichlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5 - amides. (1)

[0105] Synthesized using Experimental Procedure Method "A". (3-Chloroacetylacetylanilide, 2,4-dichlorobenzaldehyde)

[0106] Yield: 46%; melting point (m.p.) 201-202°C; infrared spectrum (IR) (KBr, cm-1): 3227, 2953, 1703, 1680, 1472, 1236, 772; 1 H NMR spectrum ( 1 H NMR) (400MHz, DMSO-d6) δppm 1.71 (s, 3H, CH3), 5.49 (s, 1H, CH) 7.02-7.53 (m, 7H, Ar-H), 7.6 (s, 1H, NH), 8.95 (s, 1H, NH) 9.45 (s, 1H, NH).

Embodiment 2

[0107] Example 2: N-(4-nitro-phenyl)-4-(2,4-dichloro-phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro Pyrimidine-5-amide. (2)

[0108] Synthesized using Experimental Procedure Method "A". (3-Nitroacetylacetoanilide, 2,4-dichlorobenzaldehyde)

[0109] Yield: 55%; Melting point (m.p.) 225-227°C; Infrared spectrum (IR) (KBr, cm-1): 3375, 2924, 1693, 1545, 1237, 756; 1 H NMR spectrum ( 1 H NMR) (400MHz, DMSO-d6) δppm2.05 (s, 3H, CH3), 5.78 (s, 1H, CH), 7.42-8.17 (m, 7H, Ar-H), 7.69 (s, 1H, NH ), 9.03 (s, 1H, NH), 10.32 (s, 1H, NH).

Embodiment 3

[0110] Example 3: N-(2,3-dichloro-phenyl)-4-(2,4-dichloro-phenyl)-6-methyl-2-oxo-1,2,3,4- Tetrahydropyrimidine-5-amide. (3)

[0111] Synthesized using Experimental Procedure Method "A". (2,3-dichloroacetoacetanilide, 2,4-dichlorobenzaldehyde) yield: 60%; melting point (m.p.) 264-266°C; infrared spectrum (IR) (KBr, cm-1): 3286 ,2928,1707,1458,1214,765; 1 H NMR spectrum ( 1 H NMR) (400MHz, DMSO-d6) δppm 2.14 (s, 3H, CH3), 5.74 (s, 1H, CH), 7.36-7.70 (m, 6H, Ar-H), 7.46 (s, 1H, NH) , 8.95(s,1H,NH), 9.45(s,1H,NH).

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Abstract

The present invention discloses antitubercular compounds selected from tetrahydropyrimidones / tetrahydrothiopyrimidone derivatives of Formula (1) and its pharmaceutically acceptable salts for the treatment of Mycobacterium in the dormant phase. Formula (1) wherein, R is H, halogen, dihalogen, O-alkyl, di- O-alkyl, R1 is phenyl, chlorophenyl, nitrophenyl, diclorophenyl, cycloalkyl, preferably cyclohexyl, X is O or S.

Description

technical field [0001] The present invention relates to compounds of formula 1 which exhibit anti-tuberculosis activity. In particular, the invention relates to compounds which exhibit anti-tuberculosis properties during the dormant phase of mycobacteria, and to methods of preparing these compounds. [0002] [0003] chemical formula 1 [0004] Wherein, R is H, halogen, dihalogenated, O-alkyl, di-O-alkyl, R 1 is phenyl, chlorophenyl, nitrophenyl, dichlorophenyl, cycloalkyl preferably cyclohexyl, and X is O or S. Background technique [0005] As we all know, about 8 million people suffer from tuberculosis every year, and 2 million people die from tuberculosis every year. The Indian population has the highest incidence rate, with up to 1.8 million people affected by TB. The neglect of TB control programs has led to a resurgence of TB as HIV infection rises. From 2000 to 2004, the emergence of drug-resistant strains also contributed to this new epidemic, with 20% of TB ...

Claims

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Application Information

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IPC IPC(8): C07D239/22A61K31/513A61P31/06
CPCC07D239/22A61P31/06
Inventor 迪曼·萨卡萨帕·萨卡罗西特·拉曼什·罗什维杰·穆里德哈·凯德卡拉古维尔·拉马卡恩特·彼苏莱恩卡埃文斯·克利夫顿·科蒂纽阿纳米克·坎蒂拉尔·沙哈
Owner COUNCIL OF SCI & IND RES