11-ethyl-8-(2-hydroxyethyl)-2,5-dimethyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one | 380379-28-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 11-ethyl-8-(2-hydroxyethyl)-2,5-dimethyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one
• 英文别名: 5,11-dihydro-2,5-dimethyl-11-ethyl-8-(2-hydroxyethyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one；5,11-dihydro-2,5-dimethyl-11-ethyl-8-(2-hydroxyethyl)-6H-dipyrido[3,2-b:2',3'-e] [1,4]diazepin-6-one；2-ethyl-13-(2-hydroxyethyl)-5,9-dimethyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one
• CAS: 380379-28-2
• 化学式: C₁₇H₂₀N₄O₂
• 分子量: 312.371
• InChiKey: YUSKVVNQQJRXNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  11-ethyl-8-(2-hydroxyethyl)-2,5-dimethyl-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-(5-Ethyl-7,10-dimethyl-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：

  5,11-dihydro-2,5-dimethyl-11-ethyl-8-(2-propenyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one 在 氧气 、 臭氧 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以81%的产率得到11-ethyl-8-(2-hydroxyethyl)-2,5-dimethyl-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

• 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。
• NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
  申请人：BOEHRINGER INGELHEIM (CANADA) LTD.

  公开号：EP1294720B1

  公开（公告）日：2006-04-05
• US6420359B1
  申请人：——

  公开号：US6420359B1

  公开（公告）日：2002-07-16
• Novel 8-Substituted Dipyridodiazepinone Inhibitors with a Broad-Spectrum of Activity against HIV-1 Strains Resistant to Non-nucleoside Reverse Transcriptase Inhibitors
  作者：Jeff A. O'Meara、Christiane Yoakim、Pierre R. Bonneau、Michael Bös、Michael G. Cordingley、Robert Déziel、Louise Doyon、Jianmin Duan、Michel Garneau、Ingrid Guse、Serge Landry、Eric Malenfant、Julie Naud、William W. Ogilvie、Bounkham Thavonekham、Bruno Simoneau

  DOI：10.1021/jm050255t

  日期：2005.8.1

  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.