2,4-dibromo-6-chloro-3-propylquinoline | 345913-46-4

• 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: 2,4-dibromo-6-chloro-3-propylquinoline
• CAS: 345913-46-4
• 化学式: C₁₂H₁₀Br₂ClN
• 分子量: 363.479
• InChiKey: STKSVUCTGDJTDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4-dibromo-6-chloro-3-propylquinoline 在 溶剂黄146 作用下， 反应 8.0h， 以97.5%的产率得到4-bromo-6-chloro-3-propyl-1H-quinol-2-one
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1021/jm040071z
• 作为产物：
  描述：

  丙基丙二酸二乙酯 在 三溴化磷 作用下， 以 二苯醚 为溶剂， 反应 24.5h， 生成 2,4-dibromo-6-chloro-3-propylquinoline
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1021/jm040071z

文献信息

• Quinolone compounds for use in treating viral infections
  申请人：——

  公开号：US20030069271A1

  公开（公告）日：2003-04-10

  The present invention relates to quinolone compounds and their use in the treatment of viral infections.

  本发明涉及喹诺酮化合物及其在治疗病毒感染中的应用。
• 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
• [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.
• 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.