N-[(1,3-dihydro-6,7-dimethoxy-1-oxo-2H-isoindol-2-yl)-N'-(6,7-dimethoxy-1,1-dioxido-1,2-benzisothiazol-2(3H)-yl)]hydrazide | 1123212-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-[(1,3-dihydro-6,7-dimethoxy-1-oxo-2H-isoindol-2-yl)-N'-(6,7-dimethoxy-1,1-dioxido-1,2-benzisothiazol-2(3H)-yl)]hydrazide
• 英文别名: 2-(6,7-dimethoxy-1,1-dioxo-3H-1,2-benzothiazol-2-yl)-6,7-dimethoxy-3H-isoindol-1-one
• CAS: 1123212-47-4
• 化学式: C₁₉H₂₀N₂O₇S
• 分子量: 420.443
• InChiKey: QXDGDWPYWOQDHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[(1,3-dihydro-6,7-dimethoxy-1-oxo-2H-isoindol-2-yl)-N'-(6,7-dimethoxy-1,1-dioxido-1,2-benzisothiazol-2(3H)-yl)]hydrazide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 N-[(1,3-dihydro-6,7-dihydroxy-1-oxo-2H-isoindol-2-yl)]-N'-[(6,7-dihydroxy-1,1-dioxido-1,2-benzisothiazol-2(3H)-yl)] hydrazide
  参考文献：
  名称：

  2,3-Dihydro-6,7-dihydroxy-1H-isoindol-1-one-Based HIV-1 Integrase Inhibitors

  摘要：

  The bis-salicylhydrazides class of HIV-1 integrase (IN) inhibitors has been postulated to function by metal chelation. However, members of this series exhibit potent inhibition only when Mn2+ is used as cofactor. The current study found that bis-aroylhydrazides could acquire inhibitory potency in Mg2+ using dihydroxybenzoyl substituents as both the right and left components of the hydrazide moiety. Employing a 2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one ring system as a conformationally constrained 2,3-dihydroxybenzoyl equivalent provided good selectivity for IN-catalyzed strand transfer versus the 3'-processing reactions as well as antiviral efficacy in cells using HIV-1 based vectors.

  DOI：

  10.1021/jm070715d
• 作为产物：
  描述：

  2-(chloromethyl)-5,6-dimethoxybenzenesulfonyl chloride 在 三乙胺 作用下， 以 乙腈 为溶剂， 以47.8%的产率得到N-[(1,3-dihydro-6,7-dimethoxy-1-oxo-2H-isoindol-2-yl)-N'-(6,7-dimethoxy-1,1-dioxido-1,2-benzisothiazol-2(3H)-yl)]hydrazide
  参考文献：
  名称：

  [EN] HYDRAZIDE, AMIDE, PHTHALIMIDE AND PHTHALHYDRAZIDE ANALOGS AS INHIBITORS OF RETROVIRAL INTEGRASE
  [FR] ANALOGUES D'HYDRAZIDE, D'AMIDE, DE PHTALIMIDE ET DE PHTALHYDRAZIDE EN TANT QU'INHIBITEURS DE L'INTÉGRASE RÉTROVIRALE

  摘要：

  公开号：

  WO2009026248A3

文献信息

• 2,3-Dihydro-6,7-dihydroxy-1H-isoindol-1-one-Based HIV-1 Integrase Inhibitors
  作者：Xue Zhi Zhao、Elena A. Semenova、B. Christie Vu、Kasthuraiah Maddali、Christophe Marchand、Stephen H. Hughes、Yves Pommier、Terrence R. Burke

  DOI：10.1021/jm070715d

  日期：2008.1.1

  The bis-salicylhydrazides class of HIV-1 integrase (IN) inhibitors has been postulated to function by metal chelation. However, members of this series exhibit potent inhibition only when Mn2+ is used as cofactor. The current study found that bis-aroylhydrazides could acquire inhibitory potency in Mg2+ using dihydroxybenzoyl substituents as both the right and left components of the hydrazide moiety. Employing a 2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one ring system as a conformationally constrained 2,3-dihydroxybenzoyl equivalent provided good selectivity for IN-catalyzed strand transfer versus the 3'-processing reactions as well as antiviral efficacy in cells using HIV-1 based vectors.
• [EN] HYDRAZIDE, AMIDE, PHTHALIMIDE AND PHTHALHYDRAZIDE ANALOGS AS INHIBITORS OF RETROVIRAL INTEGRASE<br/>[FR] ANALOGUES D'HYDRAZIDE, D'AMIDE, DE PHTALIMIDE ET DE PHTALHYDRAZIDE EN TANT QU'INHIBITEURS DE L'INTÉGRASE RÉTROVIRALE
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2009026248A3

  公开（公告）日：2009-08-27