8-Amino-5,11-dihydro-11-ethyl-5-methyl6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one | 135795-10-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 8-Amino-5,11-dihydro-11-ethyl-5-methyl6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
• 英文别名: 8-Substituted Dipyridodiazepinone 5；13-amino-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
• CAS: 135795-10-7
• 化学式: C₁₄H₁₅N₅O
• 分子量: 269.306
• InChiKey: ZQEDJHKILXMIFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  75.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-Amino-5,11-dihydro-11-ethyl-5-methyl6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one 在 硫酸 、 sodium iodide 、 sodium nitrite 作用下， 生成 5,11-dihydro-11-ethyl-8-iodo-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
• 作为产物：
  描述：

  2-氯-3-硝基吡啶 在 盐酸 、 sodium hydride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 xylene 为溶剂， 反应 12.0h， 生成 8-Amino-5,11-dihydro-11-ethyl-5-methyl6H-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

• Method and compositions for identifying anti-hiv therapeutic compounds
  申请人：Birkus Gabriel

  公开号：US20070190523A1

  公开（公告）日：2007-08-16

  The invention relates to methods and compositions for identifying compounds having therapeutic activity against human immunodeficiency virus (HIV).

  本发明涉及用于鉴定具有治疗人类免疫缺陷病毒（HIV）活性的化合物的方法和组合物。
• 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
• Synthesis and biological evaluation of phosphonate analogues of nevirapine
  作者：Jay Parrish、Leah Tong、Michael Wang、Xiaowu Chen、Eric B. Lansdon、Carina Cannizzaro、Xubin Zheng、Manoj C. Desai、Lianhong Xu

  DOI：10.1016/j.bmcl.2012.12.049

  日期：2013.3

  A series of nevirapine-based analogues containing the phosphonate functionality were prepared and evaluated in vitro against HIV RT. The effect of the phosphonate was evaluated against the wild type and Y181C HIV replication. An in vivo PK study was performed on a select analogue. (c) 2012 Elsevier Ltd. All rights reserved.
• 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：EP0429987B1

  公开（公告）日：1999-03-17
• US5366972A
  申请人：——

  公开号：US5366972A

  公开（公告）日：1994-11-22