5-benzhydryloxy-7-(4-fluorobenzyl)-8-hydroxy-9-methoxy-1,2,3,4-tetrahydro-pyrrolo[3,4-g]quinoxaline-6,8-dione | 684286-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-benzhydryloxy-7-(4-fluorobenzyl)-8-hydroxy-9-methoxy-1,2,3,4-tetrahydro-pyrrolo[3,4-g]quinoxaline-6,8-dione
• 英文别名: 5-benzhydryloxy-7-(4-fluoro-benzyl)-9-methoxy-1,2,3,4-tetrahydro-pyrrolo[3,4-g]quinoxaline-6,8-dione；5-Benzhydryloxy-7-[(4-fluorophenyl)methyl]-9-methoxy-1,2,3,4-tetrahydropyrrolo[3,4-g]quinoxaline-6,8-dione
• CAS: 684286-95-1
• 化学式: C₃₁H₂₆FN₃O₄
• 分子量: 523.564
• InChiKey: RZPVDKFADGQCKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-benzhydryloxy-7-(4-fluorobenzyl)-8-hydroxy-9-methoxy-1,2,3,4-tetrahydro-pyrrolo[3,4-g]quinoxaline-6,8-dione 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以71%的产率得到7-(4-fluorobenzyl)-5-hydroxy-9-methoxy-1,2,3,4-tetrahydro-pyrrolo[3,4-g]quinoxaline-6,8-dione
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel tricyclic HIV-1 integrase inhibitors by modification of its pyridine ring

  摘要：

  This communication details both the syntheses and biological evaluation of a novel class of HIV-1 integrase inbibitors. When the quinoline moiety is replaced with the quinoxoline moiety, the antiviral activity is significantly compromised. Similarly, introduction of imidazole to replace the pyridine ring is deleterious to the potency of the compound against the enzyme. Substitution at the 3-position of the pyridine has been investigated. The presence of the pyridine ring in the tricyclic core is preferred for antiviral activity against HIV integrase. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.018
• 作为产物：
  描述：

  carbonic acid 9-benzhydryloxy-7-(4-fluorobenzyl)-6,8-dioxo-6,8-dihydro-7H-pyrrolo[3,4-g]quinoxalin-5-yl ester ethyl ester 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 5-benzhydryloxy-7-(4-fluorobenzyl)-8-hydroxy-9-methoxy-1,2,3,4-tetrahydro-pyrrolo[3,4-g]quinoxaline-6,8-dione
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel tricyclic HIV-1 integrase inhibitors by modification of its pyridine ring

  摘要：

  This communication details both the syntheses and biological evaluation of a novel class of HIV-1 integrase inbibitors. When the quinoline moiety is replaced with the quinoxoline moiety, the antiviral activity is significantly compromised. Similarly, introduction of imidazole to replace the pyridine ring is deleterious to the potency of the compound against the enzyme. Substitution at the 3-position of the pyridine has been investigated. The presence of the pyridine ring in the tricyclic core is preferred for antiviral activity against HIV integrase. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.018

文献信息

• Pre-organized tricyclic integrase inhibitor compounds
  申请人：Chen James M.

  公开号：US20090029939A1

  公开（公告）日：2009-01-29

  Tricyclic compounds according to the structure below, protected intermediates thereof, and methods for inhibition of HIV-integrase are disclosed. A 1 and A 2 are moieties forming a five, six, or seven membered ring. L is a bond or a linker connecting a ring atom of Ar to N. X is O, S, or substituted nitrogen. Ar is aryl or heteroaryl, Q is N, + NR, or CR 4 . The aryl carbons may be independently substituted with substituents other than hydrogen. The compounds may include prodrug moieties covalently attached at any site.

  本发明揭示了以下结构的三环化合物、其保护中间体以及抑制HIV整合酶的方法。其中，A1和A2是形成五、六或七元环的基团。L是连接Ar环原子和N的键或连接剂。X是O、S或取代的氮。Ar是芳基或杂环芳基，Q是N、+NR或CR4。芳基碳可以独立地被取代为除氢以外的取代基。这些化合物可以包括共价连接在任何位置的前药基团。
• Phosphonate Analogs Of Hiv Integrase Inhibitor Compounds
  申请人：Cai R. Zhenhong

  公开号：US20080076738A1

  公开（公告）日：2008-03-27

  Novel HIV integrase inhibitor compounds having at least one phosphonate group, protected intermediates thereof, and methods for inhibition of HIV-integrase are disclosed.

  本发明公开了至少具有一个膦酸酯基团的新型HIV整合酶抑制剂化合物、其受保护的中间体以及用于抑制HIV整合酶的方法。
• [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
• US7253180B2
  申请人：——

  公开号：US7253180B2

  公开（公告）日：2007-08-07