(5-cyano-6-fluoro-8-methyl-1-propyl-3,4-dihydro-1H-[1]benzothieno[2,3-c]pyran-1-yl)acetic acid | 845746-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡喃类
• 英文名称: (5-cyano-6-fluoro-8-methyl-1-propyl-3,4-dihydro-1H-[1]benzothieno[2,3-c]pyran-1-yl)acetic acid
• 英文别名: 2-(5-Cyano-6-fluoro-8-methyl-1-propyl-3,4-dihydrobenzothiopheno[2,3-c]pyran-1-yl)acetic acid；2-(5-cyano-6-fluoro-8-methyl-1-propyl-3,4-dihydro-[1]benzothiolo[2,3-c]pyran-1-yl)acetic acid
• CAS: 845746-06-7
• 化学式: C₁₈H₁₈FNO₃S
• 分子量: 347.41
• InChiKey: XEPYXSNMTYAXLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  98.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5-cyano-6-fluoro-8-methyl-1-propyl-3,4-dihydro-1H-[1]benzothieno[2,3-c]pyran-1-yl)acetic acid 生成 [(1S)-5-cyano-6-fluoro-8-methyl-1-propyl-3,4-dihydro-1H-[1]benzothieno[2,3-c]pyran-1-yl]acetic acid 、 [(1R)-5-cyano-6-fluoro-8-methyl-1-propyl-3,4-dihydro-1H-[1]benzothieno[2,3-c]pyran-1-yl]acetic acid
  参考文献：
  名称：

  [EN] PYRANOBENZOTHIOPHENE DERIVATIVES TO TREAT INFECTION WITH HEPATITIS C VIRUS
  [FR] DERIVES DE PYRANOBENZOTHIOPHENE DESTINES A TRAITER UNE INFECTION PAR LE VIRUS DE L'HEPATITE C

  摘要：

  该发明涉及一种化合物，其化学式为：(I)，其中R1、R2、R3 - R12和Y的取代基在规范中说明；包括该化合物的药物组合物；用有效量的该化合物或包括该化合物的药物组合物与哺乳动物接触来治疗或预防丙型肝炎病毒感染的方法；以及用有效量的该化合物或包括该化合物的药物组合物与丙型肝炎病毒接触来抑制丙型肝炎病毒复制的方法。

  公开号：

  WO2005016932A1
• 作为产物：
  描述：

  (5-Bromo-6-fluoro-8-methyl-1-propyl-3,4-dihydro-1H-benzo[4,5]thieno[2,3-c]pyran-1-yl)-acetic acid ethyl ester 在 N-甲基吡咯烷酮 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.25h， 生成 (5-cyano-6-fluoro-8-methyl-1-propyl-3,4-dihydro-1H-[1]benzothieno[2,3-c]pyran-1-yl)acetic acid
  参考文献：
  名称：

  Design and synthesis of 3,4-dihydro-1H-[1]-benzothieno[2,3-c]pyran and 3,4-dihydro-1H-pyrano[3,4-b]benzofuran derivatives as non-nucleoside inhibitors of HCV NS5B RNA dependent RNA polymerase

  摘要：

  A novel class of HCV NS513 RNA dependent RNA polymerase inhibitors containing 3,4-dihydro-1H-[1]-benzothieno[2,3-c]pyran and 3,4-dihydro-1H-pyrano[3,4-b]benzofuran scaffolds were designed and synthesized. Optimization of the alkyl substituent in the pyran ring showed preference for an n-propyl group, while 5,8-disubstitution pattern is preferred for the aromatic region. Analog 19 displayed potent activity with an IC50 of 50 nM against HCV NS513 enzyme and was selective over a panel of polymerases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.114

文献信息

• [EN] PYRANOBENZOTHIOPHENE DERIVATIVES TO TREAT INFECTION WITH HEPATITIS C VIRUS<br/>[FR] DERIVES DE PYRANOBENZOTHIOPHENE DESTINES A TRAITER UNE INFECTION PAR LE VIRUS DE L'HEPATITE C
  申请人：WYETH CORP

  公开号：WO2005016932A1

  公开（公告）日：2005-02-24

  The invention is directed to a compound of the formula: (I) wherein substitutions at R1, R2 , R3 - R12, and Y are set forth in the specification; pharmaceutical compositions comprising said compound, methods of treating or preventing a Hepatitis C viral infection in a mammal comprising contacting the mammal with an effective amount of said compound or pharmaceutical compositions including said compound and methods of inhibiting replication of a Hepatitis C virus comprising contacting the HCV virus with an effective amount of said compound or pharmaceutical compositions including said compound.

  该发明涉及一种化合物，其化学式为：(I)，其中R1、R2、R3 - R12和Y的取代基在规范中说明；包括该化合物的药物组合物；用有效量的该化合物或包括该化合物的药物组合物与哺乳动物接触来治疗或预防丙型肝炎病毒感染的方法；以及用有效量的该化合物或包括该化合物的药物组合物与丙型肝炎病毒接触来抑制丙型肝炎病毒复制的方法。
• Pyranobenzothiophene derivatives to treat infection with hepatitis c virus
  申请人：Gopalsamy Ariamala

  公开号：US20070276030A1

  公开（公告）日：2007-11-29

  The invention is directed to a compound of the formula: wherein substitutions fat R 1 , R 2 , R 3 -R 12 , and Y are set forth in the specification; pharmaceutical compositions comprising said compound, methods of treating or preventing a Hepatitis C viral infection in a mammal comprising contacting the mammal with an effective amount of said compound or pharmaceutical compositions including said compound and methods of inhibiting replication of a Hepatitis C virus comprising contacting the HCV virus with an effective amount of said compound or pharmaceutical compositions including said compound.

  本发明涉及一种化合物，其化学式如下： 其中，R1、R2、R3-R12和Y的取代基如说明书所述；包括该化合物的制药组合物；通过将哺乳动物与该化合物或包括该化合物的制药组合物的有效量接触来治疗或预防乙型肝炎病毒感染的方法；以及通过将乙型肝炎病毒与该化合物或包括该化合物的制药组合物的有效量接触来抑制乙型肝炎病毒复制的方法。
• Design and synthesis of 3,4-dihydro-1H-[1]-benzothieno[2,3-c]pyran and 3,4-dihydro-1H-pyrano[3,4-b]benzofuran derivatives as non-nucleoside inhibitors of HCV NS5B RNA dependent RNA polymerase
  作者：Ariamala Gopalsamy、Alexis Aplasca、Gregory Ciszewski、Kaapjoo Park、John W. Ellingboe、Mark Orlowski、Boris Feld、Anita Y.M. Howe

  DOI：10.1016/j.bmcl.2005.08.114

  日期：2006.1

  A novel class of HCV NS513 RNA dependent RNA polymerase inhibitors containing 3,4-dihydro-1H-[1]-benzothieno[2,3-c]pyran and 3,4-dihydro-1H-pyrano[3,4-b]benzofuran scaffolds were designed and synthesized. Optimization of the alkyl substituent in the pyran ring showed preference for an n-propyl group, while 5,8-disubstitution pattern is preferred for the aromatic region. Analog 19 displayed potent activity with an IC50 of 50 nM against HCV NS513 enzyme and was selective over a panel of polymerases. (c) 2005 Elsevier Ltd. All rights reserved.