dimethylsulfamic acid 7-(4-fluoro-benzyl)-6,8-dioxo-9-triisopropylsilanyloxy-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester | 684285-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: dimethylsulfamic acid 7-(4-fluoro-benzyl)-6,8-dioxo-9-triisopropylsilanyloxy-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester
• 英文别名: [7-[(4-fluorophenyl)methyl]-6,8-dioxo-9-tri(propan-2-yl)silyloxypyrrolo[3,4-g]quinolin-5-yl] N,N-dimethylsulfamate
• CAS: 684285-24-3
• 化学式: C₂₉H₃₆FN₃O₆SSi
• 分子量: 601.771
• InChiKey: CCHPKFQUGASOMD-UHFFFAOYSA-N

物化性质

• 沸点：
  668.2±65.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  dimethylsulfamic acid 7-(4-fluoro-benzyl)-6,8-dioxo-9-triisopropylsilanyloxy-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester 在 甲基溴化镁 、 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 1.5h， 以87%的产率得到dimethylsulfamic acid 7-(4-fluoro-benzyl)-6-methylene-8-oxo-9-triisopropylsilanyloxy-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester
  参考文献：
  名称：

  [EN] PHOSPHONATE ANALOGS OF HIV INTEGRASE INHIBITOR COMPOUNDS
  [FR] ANALOGUES DE PHOSPHONATE DE COMPOSES INHIBITEURS DE L'INTEGRASE DU VIH

  摘要：

  公开号：

  WO2005117904A3
• 作为产物：
  描述：

  7-(4-fluoro-benzyl)-5,9-dihydroxy-pyrrolo[3,4-g]quinoline-6,8-dione 在 咪唑 、 4-二甲氨基吡啶 、 TEA 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 dimethylsulfamic acid 7-(4-fluoro-benzyl)-6,8-dioxo-9-triisopropylsilanyloxy-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester
  参考文献：
  名称：

  Effect of substitution on novel tricyclic HIV-1 integrase inhibitors

  摘要：

  A series of novel tricyclic inhibitors of HIV-1 integrase enzyme was prepared. The effect of substitution at C-6 of the 9-hydroxy-6,7-dihydropyrrolo[3,4-glquinolin-8-one compounds was studied in vitro. Inhibitors with small side chains at C-6 were generally well tolerated by the enzyme, and the physicochemical properties of the inhibitors were improved by substitution of a small alkyl group at this position. A second series of analogs bearing a sulfamate at the C-5 position with various C-6 substituents were prepared to explore the interplay between the two groups. The SAR of the two classes are not parallel; modification at C-5 impacts the effect of substitutions at C-6. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.008

文献信息

• [EN] PRE-ORGANIZED TRICYCLIC INTEGRASE INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS TRICYCLIQUES PRÉORGANISÉS INHIBITEURS D'INTÉGRASE
  申请人：GILEAD SCIENCES INC

  公开号：WO2004035576A3

  公开（公告）日：2004-06-24
• [EN] PHOSPHONATE ANALOGS OF HIV INTEGRASE INHIBITOR COMPOUNDS<br/>[FR] ANALOGUES DE PHOSPHONATE DE COMPOSES INHIBITEURS DE L'INTEGRASE DU VIH
  申请人：GILEAD SCIENCES INC

  公开号：WO2005117904A3

  公开（公告）日：2006-07-27
• Effect of substitution on novel tricyclic HIV-1 integrase inhibitors
  作者：Maria Fardis、Haolun Jin、Salman Jabri、Ruby Z. Cai、Michael Mish、Manuel Tsiang、Choung U. Kim

  DOI：10.1016/j.bmcl.2006.05.008

  日期：2006.8

  A series of novel tricyclic inhibitors of HIV-1 integrase enzyme was prepared. The effect of substitution at C-6 of the 9-hydroxy-6,7-dihydropyrrolo[3,4-glquinolin-8-one compounds was studied in vitro. Inhibitors with small side chains at C-6 were generally well tolerated by the enzyme, and the physicochemical properties of the inhibitors were improved by substitution of a small alkyl group at this position. A second series of analogs bearing a sulfamate at the C-5 position with various C-6 substituents were prepared to explore the interplay between the two groups. The SAR of the two classes are not parallel; modification at C-5 impacts the effect of substitutions at C-6. (c) 2006 Elsevier Ltd. All rights reserved.