6-[4-(Trifluoromethoxy)phenoxy]hexan-1-ol | 1383151-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-[4-(Trifluoromethoxy)phenoxy]hexan-1-ol
• CAS: 1383151-29-8
• 化学式: C₁₃H₁₇F₃O₃
• 分子量: 278.271
• InChiKey: MBKIMANEEOWXPR-UHFFFAOYSA-N

物化性质

• 沸点：
  327.2±42.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-[4-(Trifluoromethoxy)phenoxy]hexan-1-ol 在 silica gel 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 6-(4-(trifluoromethoxy)phenoxy)hexanal
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of N-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection

  摘要：

  We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENY) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENY in BHK cells of 6.5 mu M, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 mu M) against DENY infection, while maintaining low cytotoxicity (CC50 > 500 mu M, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 +/- 4%).

  DOI：

  10.1021/jm300171v
• 作为产物：
  描述：

  6-溴正己醇 、 对三氟甲氧基苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 6-[4-(Trifluoromethoxy)phenoxy]hexan-1-ol
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of N-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection

  摘要：

  We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENY) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENY in BHK cells of 6.5 mu M, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 mu M) against DENY infection, while maintaining low cytotoxicity (CC50 > 500 mu M, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 +/- 4%).

  DOI：

  10.1021/jm300171v

文献信息

• 2,3-Dihydro-6-Nitroimidazo (2,1-b) Oxazole Compounds for the Treatment of Tuberculosis
  申请人：Tsubouchi Hidetsugu

  公开号：US20080119478A1

  公开（公告）日：2008-05-22

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: (1) in the above formula (1), R1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R1 and —(CH2) n R2 may form a spiro ring represented by the formula (30) below, together with the adjacent carbon atom (in the formula below, RRR represents a piperidyl group which may have substituents on the piperidine ring), (30) and R2 represents a benzothiazolyloxy group, quinolyloxy group, pyridyloxy group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis , multi-drug-resistant Mycobacterium tuberculosis , and atypical acid-fast bacteria.

  本发明提供了一种由下述通式（1）表示的2,3-二氢-6-硝基咪唑[2,1-b]噁唑化合物： 在上述式（1）中，R1代表氢原子或C1-C6烷基，n代表0到6的整数，R1和—(CH2)nR2可以与相邻的碳原子形成如下式（30）所示的螺环，其中，在下式中，RRR代表可能在哌啶环上具有取代基的哌啶基： （30）且R2代表苯并噻唑氧基、喹啉氧基、吡啶氧基或类似基团。该化合物对结核分枝杆菌、多重耐药结核分枝杆菌和非典型酸杆菌具有优异的杀菌作用。
• 2,3-DIHYDRO-6-NITROIMIDAZO [2,1-B] OXAZOLE COMPOUNDS FOR THE TREATMENT OF TUBERCULOSIS
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP1678185B1

  公开（公告）日：2008-10-08
• US8163753B2
  申请人：——

  公开号：US8163753B2

  公开（公告）日：2012-04-24
• Design, Synthesis, and Biological Evaluation of <i>N</i>-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection
  作者：Wenquan Yu、Tina Gill、Lijuan Wang、Yanming Du、Hong Ye、Xiaowang Qu、Ju-Tao Guo、Andrea Cuconati、Kang Zhao、Timothy M. Block、Xiaodong Xu、Jinhong Chang

  DOI：10.1021/jm300171v

  日期：2012.7.12

  We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENY) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENY in BHK cells of 6.5 mu M, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 mu M) against DENY infection, while maintaining low cytotoxicity (CC50 > 500 mu M, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 +/- 4%).