(+)-(S)-4,5,6,7-Tetrahydro-5-methyl-6-(2-propenyl)-imidazo-(4,5,1-jk)(1,4)-benzodiazepin-2(1H)-one | 126233-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: (+)-(S)-4,5,6,7-Tetrahydro-5-methyl-6-(2-propenyl)-imidazo-(4,5,1-jk)(1,4)-benzodiazepin-2(1H)-one
• 英文别名: (11S)-11-methyl-10-prop-2-enyl-1,3,10-triazatricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-2-one
• CAS: 126233-91-8
• 化学式: C₁₄H₁₇N₃O
• 分子量: 243.308
• InChiKey: OYQVBYVHKBMZGU-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-2,3,4,5-tetrahydro-3-methyl-1H-<1,4>benzodiazepine-9-amine 在 N-甲基吗啉 、 sodium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.75h， 生成 (+)-(S)-4,5,6,7-Tetrahydro-5-methyl-6-(2-propenyl)-imidazo-(4,5,1-jk)(1,4)-benzodiazepin-2(1H)-one
  参考文献：
  名称：

  Synthesis and anti-HIV-1 activity of 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-one (TIBO) derivatives

  摘要：

  A series of 6-substituted 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-ones (9) have been synthesized and tested for their ability to inhibit the replication of the HIV-1 virus in MT-4 cells. Two synthetic methods are described, one of which allows the synthesis of single enantiomers of the final products. A structure-activity study was done within the series of compounds to determine the optimum group for the 6-position substitution and to determine whether the activity was enantiospecific at the 5-position, which was substituted with a methyl group. The best analogue, 9jj, inhibited HIV-1 with an IC50 of 4-mu-M, which is comparable to the activity level of DDI, a 2',3'-dideoxynucleoside-type structure undergoing clinical trials as an anti-AIDS therapy.

  DOI：

  10.1021/jm00106a040

文献信息

• Synthesis and anti-HIV-1 activity of 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-one (TIBO) derivatives
  作者：Michael J. Kukla、Henry J. Breslin、Rudi Pauwels、Cynthia L. Fedde、Milton Miranda、Malcolm K. Scott、Ronald G. Sherrill、Alfons Raeymaekers、Jozef Van Gelder

  DOI：10.1021/jm00106a040

  日期：1991.2

  A series of 6-substituted 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-ones (9) have been synthesized and tested for their ability to inhibit the replication of the HIV-1 virus in MT-4 cells. Two synthetic methods are described, one of which allows the synthesis of single enantiomers of the final products. A structure-activity study was done within the series of compounds to determine the optimum group for the 6-position substitution and to determine whether the activity was enantiospecific at the 5-position, which was substituted with a methyl group. The best analogue, 9jj, inhibited HIV-1 with an IC50 of 4-mu-M, which is comparable to the activity level of DDI, a 2',3'-dideoxynucleoside-type structure undergoing clinical trials as an anti-AIDS therapy.