6-chloro-4-hydroxy-3-propyl-1H-quinol-2-one | 345913-36-2

• 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: 6-chloro-4-hydroxy-3-propyl-1H-quinol-2-one
• 英文别名: 6-chloro-4-hydroxy-3-propyl-2(1H)-quinolinone；6-chloro-4-hydroxy-3-propyl-1H-quinolin-2-one
• CAS: 345913-36-2
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: WPSGQRYUSTVFMF-UHFFFAOYSA-N

物化性质

• 熔点：
  245 °C
• 沸点：
  441.9±45.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-4-hydroxy-3-propyl-1H-quinol-2-one 在 lithium 、 sodium hydride 、 silver(l) oxide 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.58h， 生成 6-chloro-4-[(2-cyclopropylethynyl)oxy]-2-[(4-methoxybenzyl)oxy]-3-propyl-4-quinoline
  参考文献：
  名称：

  Design of Non-nucleoside Inhibitors of HIV-1 Reverse Transcriptase with Improved Drug Resistance Properties. 2.

  摘要：

  HIV-1 nonnucleoside reverse transcriptase inhibitors (NNRTIs) are part of the combination therapy currently used to treat HIV infection. The features of a new NNRTI drug for HIV treatment must include selective potent activity against both wild-type virus as well as against mutant virus that have been selected by use of current antiretroviral treatment regimens. Based on analogy with known HIV-1 NNRTI inhibitors and modeling studies utilizing the X-ray crystal structure of inhibitors bound in the HIV-1 RT, a series of substituted 2-quinolones was synthesized and evaluated as HIV-1 inhibitors.

  DOI：

  10.1021/jm040072r
• 作为产物：
  描述：

  对氯苯胺 、 丙基丙二酸二乙酯 在 正己烷 作用下， 以 二苯醚 为溶剂， 反应 16.0h， 生成 6-chloro-4-hydroxy-3-propyl-1H-quinol-2-one
  参考文献：
  名称：

  Quinolone compounds for use in treating viral infections

  摘要：

  本发明涉及喹诺酮化合物及其在治疗病毒感染中的应用。

  公开号：

  US20030069271A1

文献信息

• Bifunctional molecules and vectors complexed therewith for targeted gene delivery
  申请人：The Scripps Research Institute

  公开号：US20020164333A1

  公开（公告）日：2002-11-07

  Methods and products for targeting delivery vectors, such as adenoviral gene delivery particles, to selected cell types are provided. The methods rely on targeting by a bifunctional molecule that specifically complexes with a protein on the vector particle surface and with targeted cell surface proteins. The targeted cell surface proteins are any that activate the phosphatidylinositol-3-OH kinases. The bifunctional molecules, compositions, kits, and methods of preparation and use of the vector/bifunctional molecules for gene therapy are provided.

  本研究提供了将载体（如腺病毒基因载体颗粒）靶向选定细胞类型的方法和产品。这些方法依赖于一种双功能分子的靶向作用，这种分子能与载体颗粒表面的蛋白质和靶细胞表面蛋白质特异性地复合物。目标细胞表面蛋白是激活磷脂酰肌醇-3-OH 激酶的任何蛋白。本文提供了用于基因治疗的双功能分子、组合物、试剂盒以及载体/双功能分子的制备和使用方法。
• Design of Non-Nucleoside Inhibitors of HIV-1 Reverse Transcriptase with Improved Drug Resistance Properties. 1.
  作者：Andrew L. Hopkins、Jingshan Ren、John Milton、Richard J. Hazen、Joseph H. Chan、David I. Stuart、David K. Stammers

  DOI：10.1021/jm040071z

  日期：2004.11.1

  We have used a structure-based approach to design a novel series of non-nucleoside inhibitors of HIV-1 RT (NNRTIs). Detailed analysis of a wide range of crystal structures of HIV-1 RT-NNRTI complexes together with data on drug resistance mutations has identified factors important for tight binding of inhibitors and resilience to mutations. Using this approach we have designed and synthesized a novel series of quinolone NNRTIs. Crystal structure analysis of four of these compounds in complexes with HIV-1 RT confirms the predicted binding modes. Members of this quinolone series retain high activity against the important resistance mutations in RT at Tyr181Cys and Leu100Ile.
• QUINOLONE COMPOUNDS FOR USE IN TREATING VIRAL INFECTIONS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1244629A2

  公开（公告）日：2002-10-02
• US6232107B1
  申请人：——

  公开号：US6232107B1

  公开（公告）日：2001-05-15
• [EN] QUINOLONE COMPOUNDS FOR USE IN TREATING VIRAL INFECTIONS<br/>[FR] COMPOSES DE QUINOLONE UTILISES DANS LE TRAITEMENT D'INFECTIONS VIRALES
  申请人：GLAXO GROUP LTD

  公开号：WO2001046150A2

  公开（公告）日：2001-06-28

  The present invention relates to quinolone compounds, such as compounds of formula (Ia) wherein: R1 is hydrogen; R2 is oxygen or sulfur; R3 is trifluoromethyl; cyano; C¿1-8?alkyl optionally substituted with C1-8alkyl or trifluoromethyl; or OR?15¿, wherein R15 is C¿1-8?alkyl optionally substituted with C1-8alkyl; R?4 is OR11¿, wherein R11 is C¿2-8?alkenyl optionally substituted with C1-8alkyl; C1-8alkyl optionally substituted with C1-8alkyl; C6-14arylalkyl; C3-6cycloalkyl; C3-6cycloalkylalkyl; heterocyclealkyl; heterocyclealkynyl; C3-6cycloalkylalkenyl; C6-14arylalkynyl; C3-6cycloalkylalkynyl; SR?12¿, wherein R12 is C¿3-6?cycloalkyl; S(O)R?12¿, wherein R12 is C¿3-6?cycloalkyl; or NR?13R14¿ wherein R?13 and R14¿, which may be the same or different, are hydrogen or C¿1-8?alkyl, optionally substituted with C1-8alkyl; R?5¿ is hydrogen; nitro; halogen; C¿1-8?alkyl, optionally substituted with C1-8alkyl or trifluoromethyl; R?6¿ is hydrogen; halogen; C¿1-8?alkyl; cyano: trifluoromethyl; or OR?10¿ wherein R10 is C¿1-8?alkyl or trifluoromethyl; R?7¿ is hydrogen; C¿1-8?alkyl; halogen; C6-14aryl; C1-8alkylaryl; C2-8alkynyl; heteroaryl; or OR?9¿ wherein R9 is C¿1-8?alkyl; R?8¿ is hydrogen; halogen; cyano; nitro; or OR16, wherein R16 is hydrogen or C¿1-8?alkyl optionally substituted with C1-8alkyl or trifluoromethyl; and their use in the treatment of viral infections.