7-(4-fluoro-benzyl)-6-hydroxy-5-methoxy-9-triisopropylsilanyloxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one | 684286-48-4

• 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: 7-(4-fluoro-benzyl)-6-hydroxy-5-methoxy-9-triisopropylsilanyloxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one
• 英文别名: 7-(4-fluoro-benzyl)-6,9-dihydroxy-5-methoxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one；7-[(4-fluorophenyl)methyl]-6-hydroxy-5-methoxy-9-tri(propan-2-yl)silyloxy-6H-pyrrolo[3,4-g]quinolin-8-one
• CAS: 684286-48-4
• 化学式: C₂₈H₃₅FN₂O₄Si
• 分子量: 510.681
• InChiKey: HYVXAPMFDVHQLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-(4-fluoro-benzyl)-6-hydroxy-5-methoxy-9-triisopropylsilanyloxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 在 lithium hydroxide 、 TEA 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 4-{3-[7-(4-fluoro-benzyl)-9-hydroxy-5-methoxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-6-ylsulfanyl]-propionyl}-piperazine-1-carboxylic acid tert-butyl 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
• 作为产物：
  描述：

  7-(4-fluoro-benzyl)-5,9-dihydroxy-pyrrolo[3,4-g]quinoline-6,8-dione 在 咪唑 、 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 46.0h， 生成 7-(4-fluoro-benzyl)-6-hydroxy-5-methoxy-9-triisopropylsilanyloxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one
  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] 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
• [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
• 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.