2-chloro-11-ethyl-8-(2-hydroxyethyl)-5-methyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one | 189391-94-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-chloro-11-ethyl-8-(2-hydroxyethyl)-5-methyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one
• 英文别名: 2-chloro-5,11-dihydro-11-ethyl-8-(β-hydroxy)ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one；2-chloro-5,11-dihydro-11-ethyl-8-(2-hydroxyethyl)-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one；2-chloro-5,11-dihydro-11-ethyl-8-(beta-hydroxy)ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one；5-chloro-2-ethyl-13-(2-hydroxyethyl)-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: 189391-94-4
• 化学式: C₁₆H₁₇ClN₄O₂
• 分子量: 332.79
• InChiKey: MWSSQCWMKGFBIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-11-ethyl-8-(2-hydroxyethyl)-5-methyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one 在 lithium hydroxide 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4-[2-(7-Chloro-5-ethyl-10-methyl-11-oxo-10,11-dihydro-5H-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-2-yl)-ethoxy]-3-methyl-benzoic acid
  参考文献：
  名称：

  Novel 8-Substituted Dipyridodiazepinone Inhibitors with a Broad-Spectrum of Activity against HIV-1 Strains Resistant to Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  A series of novel 8-substituted dipyridodiazepinone-based inhibitors were investigated for their antiviral activity against wild type human immunodeficiency virus (HIV-1) and the clinically prevalent K103N/Y181C mutant virus. Our efforts have resulted in a series of benzoic acid analogues that are potent inhibitors of HIV-1 replication against a panel of HIV-1 strains resistant to non-nucleoside reverse transcriptase inhibitors (NNRTIS). Furthermore, the combination of good antiviral potency, a broad spectrum of activity, and an excellent pharmacokinetic profile provides strong justification for the further development of compound 7 as a potential treatment for wild type and NNRTI-resistant HIV-1 infection.

  DOI：

  10.1021/jm050255t
• 作为产物：
  描述：

  8-溴-2-氯-11-乙基-5-甲基-5,11-二氢-6H-二吡啶并[3,2-B:2',3'-E][1,4]二氮杂卓-6-酮 在 四(三苯基膦)钯 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-chloro-11-ethyl-8-(2-hydroxyethyl)-5-methyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one
  参考文献：
  名称：

  Novel 8-Substituted Dipyridodiazepinone Inhibitors with a Broad-Spectrum of Activity against HIV-1 Strains Resistant to Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  A series of novel 8-substituted dipyridodiazepinone-based inhibitors were investigated for their antiviral activity against wild type human immunodeficiency virus (HIV-1) and the clinically prevalent K103N/Y181C mutant virus. Our efforts have resulted in a series of benzoic acid analogues that are potent inhibitors of HIV-1 replication against a panel of HIV-1 strains resistant to non-nucleoside reverse transcriptase inhibitors (NNRTIS). Furthermore, the combination of good antiviral potency, a broad spectrum of activity, and an excellent pharmacokinetic profile provides strong justification for the further development of compound 7 as a potential treatment for wild type and NNRTI-resistant HIV-1 infection.

  DOI：

  10.1021/jm050255t

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。
• Non-nucleoside reverse transcriptase inhibitors
  申请人：——

  公开号：US20020028807A1

  公开（公告）日：2002-03-07

  Provided are compounds of the general formula I: 1 wherein R 2 is selected from the group consisting of H, F, Cl, (C 1-4 ) alkyl, (C 3-4 ) cycloalkyl and CF 3 ; R 4 is H or Me; R 5 is H, Me or Et, with the proviso that R 4 and R 5 are not both Me, and if R 4 is Me then R 5 cannot be Et; R 11 is Et, cyclopropyl, propyl, isopropyl, or isobutyl; and is selected from the group consisting of: 2 and pharmaceutically acceptable salts thereof, as inhibitors of HIV reverse transcriptase, wild-type and several mutant strains.

  提供的是一般式I的化合物：其中R2从H、F、Cl、(C1-4)烷基、(C3-4)环烷基和CF3组成的群体中选择；R4为H或Me；R5为H、Me或Et，但R4和R5不能同时为Me，如果R4为Me，则R5不能为Et；R11为Et、环丙基、丙基、异丙基或异丁基；并选择自以下组合物：2和其药学上可接受的盐，作为HIV逆转录酶、野生型和几种突变株的抑制剂。
• 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
• NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
  申请人：BOEHRINGER INGELHEIM (CANADA) LTD.

  公开号：EP1294720B1

  公开（公告）日：2006-04-05
• US5705499A
  申请人：——

  公开号：US5705499A

  公开（公告）日：1998-01-06