4,5,6,7-tetrahydro-5-methyl-6-(phenylmethyl)imidazo<4,5,1-jk><1,4>benzodiazepin-2-(1H)-one | 126233-82-7

• 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: 4,5,6,7-tetrahydro-5-methyl-6-(phenylmethyl)imidazo<4,5,1-jk><1,4>benzodiazepin-2-(1H)-one
• 英文别名: 4,5,6,7-tetrahydro-6-benzyl-5-methylimidazo<4,5,1-jk><1,4>benzodiazepin-2(1H)-one；4,5,6,7-tetrahydro-5-methyl-6-(phenylmethyl)-imidazo[4,5,1-jk][1,4]-benzodiazepin-2(1H)-one；4,5,6,7-tetrahydro-5-methyl-6-(phenylmethyl)imidazo(4,5,1-jk)[1,4]benzodiazepin-2-(1H)-one；10-Benzyl-11-methyl-1,3,10-triazatricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-2-one
• CAS: 126233-82-7
• 化学式: C₁₈H₁₉N₃O
• 分子量: 293.368
• InChiKey: VBGCNXIBJHLBHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5,6,7-tetrahydro-5-methyl-6-(phenylmethyl)imidazo<4,5,1-jk><1,4>benzodiazepin-2-(1H)-one 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 42.0 ℃ 、413.69 kPa 条件下， 反应 7.5h， 生成 6-Acetyl-4,5,6,7-tetrahydro-5-methylimidazo(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
• 作为产物：
  描述：

  2-溴-3-硝基苯甲酸甲酯 在 2-羟基吡啶 、 lithium aluminium tetrahydride 、 硫酸 、 sodium carbonate 作用下， 以 四氢呋喃 、 xylene 、 正丁醇 为溶剂， 反应 45.67h， 生成 4,5,6,7-tetrahydro-5-methyl-6-(phenylmethyl)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

• Pfaendler, Hans Rudolf; Weisner, Frank, Heterocycles, 1995, vol. 40, # 2, p. 717 - 728
  作者：Pfaendler, Hans Rudolf、Weisner, Frank

  DOI：——

  日期：——
• KUKLA, MICHAEL J.;BRESLIN, HENRY J.;PAUWELS, RUDI;FEDDE, CYNTHIA L.;MIRAN+, J. MED. CHEM., 34,(1991) N, C. 746-751
  作者：KUKLA, MICHAEL J.、BRESLIN, HENRY J.、PAUWELS, RUDI、FEDDE, CYNTHIA L.、MIRAN+

  DOI：——

  日期：——
• JPH01275582A
  申请人：——

  公开号：JPH01275582A

  公开（公告）日：1989-11-06
• US5270464A
  申请人：——

  公开号：US5270464A

  公开（公告）日：1993-12-14
• US5371079A
  申请人：——

  公开号：US5371079A

  公开（公告）日：1994-12-06