4-(Difluoromethoxy)-8-(trifluoromethyl)dibenzofuran-1-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4-(Difluoromethoxy)-8-(trifluoromethyl)dibenzofuran-1-carboxamide
• 英文别名: 4-(difluoromethoxy)-8-(trifluoromethyl)dibenzofuran-1-carboxamide
• 化学式: C₁₅H₈F₅NO₃
• 分子量: 345.225
• InChiKey: QDHZDKAOHFEAEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(Difluoromethoxy)-8-(trifluoromethyl)dibenzofuran-1-carboxamide 在 4-二甲氨基吡啶 、 tetraphosphorus decasulfide 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸酐 、 potassium hydroxide 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.33h， 生成 (2-(4-(difluoromethoxy)-8-(trifluoromethyl)dibenzo[b,d]furan-1-yl)-1,3-thiazol-4-yl)(4-hydroxypiperidin-1-yl)methanone
  参考文献：
  名称：

  In vivo effective dibenzo[b,d]furan-1-yl-thiazoles as novel PDE-4 inhibitors

  摘要：

  Herein we report the synthesis, PDE-4B and TNF-alpha inhibitory activities of a few dibenzo[b,d]furan-1-yl-thiazole derivatives. The hydroxycyclohexanol amide derivatives 14, 18, 24, 29, 31 and 33 exhibited promising in vitro PDE-4B and TNF-alpha inhibitory activities. Compound 24 showed good systemic availability in preclinical animal models and was also found to be non-toxic (exploratory mutagenicity test). Further it exhibited promising results in in vivo asthma/COPD and Uveitis models. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.09.011
• 作为产物：
  描述：

  4-difluoromethoxy-8-trifluoromethyl-dibenzo[b,d]furan-1-carboxylic acid 在 氯甲酸乙酯 、 三乙胺 、 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-(Difluoromethoxy)-8-(trifluoromethyl)dibenzofuran-1-carboxamide
  参考文献：
  名称：

  In vivo effective dibenzo[b,d]furan-1-yl-thiazoles as novel PDE-4 inhibitors

  摘要：

  Herein we report the synthesis, PDE-4B and TNF-alpha inhibitory activities of a few dibenzo[b,d]furan-1-yl-thiazole derivatives. The hydroxycyclohexanol amide derivatives 14, 18, 24, 29, 31 and 33 exhibited promising in vitro PDE-4B and TNF-alpha inhibitory activities. Compound 24 showed good systemic availability in preclinical animal models and was also found to be non-toxic (exploratory mutagenicity test). Further it exhibited promising results in in vivo asthma/COPD and Uveitis models. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.09.011

文献信息

• In vivo effective dibenzo[b,d]furan-1-yl-thiazoles as novel PDE-4 inhibitors
  作者：Gopalan Balasubramanian、Sukunath Narayanan、Lavanya Andiappan、Thirunavukkarasu Sappanimuthu、Saravanan Thirunavukkarasu、Shamundeeswari Sundaram、Saravanakumar Natarajan、Naresh Sivaraman、Sridharan Rajagopal、Fakrudeen Ali Ahamed Nazumudeen、Sanjeev Saxena、Santosh L. Vishwakarma、Shridhar Narayanan、Ganapavarapu V.R. Sharma、Chidambaram V. Srinivasan、Narasimhan Kilambi

  DOI：10.1016/j.bmc.2016.09.011

  日期：2016.11

  Herein we report the synthesis, PDE-4B and TNF-alpha inhibitory activities of a few dibenzo[b,d]furan-1-yl-thiazole derivatives. The hydroxycyclohexanol amide derivatives 14, 18, 24, 29, 31 and 33 exhibited promising in vitro PDE-4B and TNF-alpha inhibitory activities. Compound 24 showed good systemic availability in preclinical animal models and was also found to be non-toxic (exploratory mutagenicity test). Further it exhibited promising results in in vivo asthma/COPD and Uveitis models. (C) 2016 Elsevier Ltd. All rights reserved.