8-Chloro-10,10-dioxo-5-propyl-pyrrolo[1,2-b][1,2,5]benzothiadiazepin-4-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 8-Chloro-10,10-dioxo-5-propyl-pyrrolo[1,2-b][1,2,5]benzothiadiazepin-4-one
• 英文别名: 8-chloro-10,10-dioxo-5-propylpyrrolo[1,2-b][1,2,5]benzothiadiazepin-4-one
• 化学式: C₁₄H₁₃ClN₂O₃S
• 分子量: 324.788
• InChiKey: XVPBIARZILCZTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-[(2-amino-5-chlorophenyl)sulfonyl]-2-ethoxycarbonyl-1H-pyrrole 在 2-羟基吡啶 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 127.0h， 生成 8-Chloro-10,10-dioxo-5-propyl-pyrrolo[1,2-b][1,2,5]benzothiadiazepin-4-one
  参考文献：
  名称：

  5H-pyrrolo[1,2-b][1,2,5]benzothiadiazepines (PBTDs): A novel class of non-nucleoside reverse transcriptase inhibitors

  摘要：

  With the aim of developing novel inhibitors of human immunodeficiency virus, various derivatives (10-17) related to SH-pyrrolo[1,2-b][1,2,5]benzothiadiazepine (PBTD) were prepared and tested in vitro. The title tricyclic derivatives were obtained by intramolecular cyclization of the open-chain intermediate arylpyrrylsulfones, followed by N-alkylation at position 10. Among test derivatives some 10-alkyl-5H-pyrrolo[1,2-b][1,2,5]benzothiadiazepin-11(10H)-one-5,5-dioxides were found to exert potent and specific activity against HIV-1. In particular, 7-chloro derivatives 11i and j showed a potency comparable to that of nevirapine. However, when the chloro atom was shifted to the 8 position, the related products were scarcely active or totally inactive. Replacement of the pyrrole with pyrrolidine led to inactive products and the reduction of SO2 to S strongly diminished the antiviral potency. PBTD derivatives active in cell cultures were also inhibitory to the recombinant HIV-1 RT in enzyme assays, thus allowing the conclusion that PBTDs are a new class of non-nucleoside reverse transcriptase inhibitors (NNRTIs). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00075-2

文献信息

• 5H-pyrrolo[1,2-b][1,2,5]benzothiadiazepines (PBTDs): A novel class of non-nucleoside reverse transcriptase inhibitors
  作者：Marino Artico、Romano Silvestri、Eugenia Pagnozzi、Giorgio Stefancich、Silvio Massa、Anna Giulia Loi、Monica Putzolu、Simona Corrias、Maria Grazia Spiga、Paolo La Colla

  DOI：10.1016/0968-0896(96)00075-2

  日期：1996.6

  With the aim of developing novel inhibitors of human immunodeficiency virus, various derivatives (10-17) related to SH-pyrrolo[1,2-b][1,2,5]benzothiadiazepine (PBTD) were prepared and tested in vitro. The title tricyclic derivatives were obtained by intramolecular cyclization of the open-chain intermediate arylpyrrylsulfones, followed by N-alkylation at position 10. Among test derivatives some 10-alkyl-5H-pyrrolo[1,2-b][1,2,5]benzothiadiazepin-11(10H)-one-5,5-dioxides were found to exert potent and specific activity against HIV-1. In particular, 7-chloro derivatives 11i and j showed a potency comparable to that of nevirapine. However, when the chloro atom was shifted to the 8 position, the related products were scarcely active or totally inactive. Replacement of the pyrrole with pyrrolidine led to inactive products and the reduction of SO2 to S strongly diminished the antiviral potency. PBTD derivatives active in cell cultures were also inhibitory to the recombinant HIV-1 RT in enzyme assays, thus allowing the conclusion that PBTDs are a new class of non-nucleoside reverse transcriptase inhibitors (NNRTIs). Copyright (C) 1996 Elsevier Science Ltd