2-chloro-5,11-dihydro-11-ethyl-8-ethynyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one | 189393-63-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-chloro-5,11-dihydro-11-ethyl-8-ethynyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
• 英文别名: 5-chloro-2-ethyl-13-ethynyl-9-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one
• CAS: 189393-63-3
• 化学式: C₁₆H₁₃ClN₄O
• 分子量: 312.758
• InChiKey: FGWWTXJQUWEOGY-UHFFFAOYSA-N

物化性质

• 熔点：
  157-159 °C
• 沸点：
  542.1±50.0 °C(predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-5,11-dihydro-11-ethyl-8-ethynyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one 在 platinum(IV) oxide 四(三苯基膦)钯 、 2,6-二叔丁基-4-甲基苯酚 、 硫酸 、 氢气 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2-Chloro-5,11-dihydro-11-ethyl-5-methyl-8-[2-(2-carbomethoxypyrid-4-yl)ethyl]-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
  参考文献：
  名称：

  Novel Nonnucleoside Inhibitors of HIV-1 Reverse Transcriptase. 7. 8-Arylethyldipyridodiazepinones as Potent Broad-Spectrum Inhibitors of Wild-Type and Mutant Enzymes

  摘要：

  Like other nonnucleoside inhibitors of HIV-1 reverse transcriptase, the dipyridodiazepinone nevirapine (Viramune, 1) selects for drug resistant variants of HIV-1, both in cell culture and in patients. In particular, the mutation of residue 181 from tyrosine to cysteine (Y181C) is associated with resistance to most reported nonnucleoside inhibitors. Introduction of an arylethyl substituent at the 8-position of the tricyclic dipyridodiazepinone skeleton confers enhanced potency against Y181C RT. Several analogues of this series display good broad spectrum potency against a panel of mutant enzymes.

  DOI：

  10.1021/jm9707028
• 作为产物：
  描述：

  13-Amino-5-chloro-2-ethyl-9-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 2,6-二叔丁基-4-甲基苯酚 、 硫酸 、 四丁基氟化铵 、 三乙胺 、 sodium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 2.83h， 生成 2-chloro-5,11-dihydro-11-ethyl-8-ethynyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
  参考文献：
  名称：

  Novel Nonnucleoside Inhibitors of HIV-1 Reverse Transcriptase. 7. 8-Arylethyldipyridodiazepinones as Potent Broad-Spectrum Inhibitors of Wild-Type and Mutant Enzymes

  摘要：

  Like other nonnucleoside inhibitors of HIV-1 reverse transcriptase, the dipyridodiazepinone nevirapine (Viramune, 1) selects for drug resistant variants of HIV-1, both in cell culture and in patients. In particular, the mutation of residue 181 from tyrosine to cysteine (Y181C) is associated with resistance to most reported nonnucleoside inhibitors. Introduction of an arylethyl substituent at the 8-position of the tricyclic dipyridodiazepinone skeleton confers enhanced potency against Y181C RT. Several analogues of this series display good broad spectrum potency against a panel of mutant enzymes.

  DOI：

  10.1021/jm9707028

文献信息

• 8-arylalkyl- and
  申请人：Boehringer Ingelheim Pharmaceuticals, Inc.

  公开号：US05705499A1

  公开（公告）日：1998-01-06

  Disclosed are novel 8-arylalkyl-5,11-dihydro-6H-dipyrido\x9b3,2-b:2',3'-e!\x9b1,4!diazepines. These are useful in the treatment of HIV-1 infection.

  公开的是新型的8-芳基烷基-5,11-二氢-6H-二吡啶[3,2-b:2',3'-e]![1,4]二氮杂环。这些化合物在治疗HIV-1感染中是有用的。
• 8-Arylalkyl- and 8-arylheteroalkyl-5, 11-dihydro-6H-dipyrido-[3,2-b:2', 3'-e][1,4]diazepines and their use in the prevention or treatment of HIV infection
  申请人：BOEHRINGER INGELHEIM PHARMACEUTICALS INC.

  公开号：EP0767172B1

  公开（公告）日：2003-03-26
• US5705499A
  申请人：——

  公开号：US5705499A

  公开（公告）日：1998-01-06