(10,10-Dioxo-4,5-dihydropyrrolo[1,2-b][1,2,5]benzothiadiazepin-4-yl)methyl methanesulfonate | 180905-78-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (10,10-Dioxo-4,5-dihydropyrrolo[1,2-b][1,2,5]benzothiadiazepin-4-yl)methyl methanesulfonate
• CAS: 180905-78-6
• 化学式: C₁₃H₁₄N₂O₅S₂
• 分子量: 342.397
• InChiKey: PBXMTMLTUHNGSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  氰化钾 、 (10,10-Dioxo-4,5-dihydropyrrolo[1,2-b][1,2,5]benzothiadiazepin-4-yl)methyl methanesulfonate 在 甲基三辛基氯化铵 作用下， 生成 2-(10,10-Dioxo-4,5-dihydropyrrolo[1,2-b][1,2,5]benzothiadiazepin-4-yl)acetonitrile
  参考文献：
  名称：

  Silvestri; Artico; Pagnozzi, Il Farmaco, 1996, vol. 51, # 6, p. 425 - 430

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 10,11-dihydropyrrolo<1,2-b><1,2,5>benzothiadiazepine-11-carboxylate 5,5-dioxide 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.75h， 生成 (10,10-Dioxo-4,5-dihydropyrrolo[1,2-b][1,2,5]benzothiadiazepin-4-yl)methyl methanesulfonate
  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
• Silvestri; Artico; Pagnozzi, Il Farmaco, 1996, vol. 51, # 6, p. 425 - 430
  作者：Silvestri、Artico、Pagnozzi、Stefancich、Massa、La Colla、Loi、Spiga、Corrias、Lichino

  DOI：——

  日期：——