苯酚,4-[3-(氯甲基)-1,2,4-噁二唑-5-基]-2,6-二(1,1-二甲基乙基)- | 130116-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 苯酚,4-[3-(氯甲基)-1,2,4-噁二唑-5-基]-2,6-二(1,1-二甲基乙基)-
• 英文名称: 2,6-Di-tert-butyl-4-(3-chloromethyl-[1,2,4]oxadiazol-5-yl)-phenol
• 英文别名: 2,6-ditert-butyl-4-[3-(chloromethyl)-1,2,4-oxadiazol-5-yl]phenol
• CAS: 130116-50-6
• 化学式: C₁₇H₂₃ClN₂O₂
• 分子量: 322.835
• InChiKey: HDQCOPSVEOOJGR-UHFFFAOYSA-N

物化性质

• 沸点：
  407.9±55.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 苯酚,4-[3-(氯甲基)-1,2,4-噁二唑-5-基]-2,6-二(1,1-二甲基乙基)- 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以75%的产率得到2,6-Bis(1,1-dimethylethyl)-4-[3-(1-pyrrolidinylmethyl)-1,2,4-oxadiazol-5-yl]phenol
  参考文献：
  名称：

  Novel 1,2,4-oxadiazoles and 1,2,4-thiadiazoles as dual 5-lipoxygenase and cyclooxygenase inhibitors

  摘要：

  A series of 1,2,4-oxadiazoles and 1,2,4-thiadiazoles containing a 2,6-di-tert-butylphenol substituent were prepared and evaluated as dual inhibitors of 5-lipoxygenase and cyclooxygenase in rat basophilic leukemia (RBL-1) cells. Several of these compounds show oral efficacy in the rat carageenan footpad edema (CFE) and mycobacterium footpad edema (MFE) antiinflammatory models, without concomitant gastric ulceration. Structure-activity relationships are discussed. The best compounds (ID40 values in MFE of 3-8 mg/kg po) contain guanidine-derived substituents on the heterocyclic ring.

  DOI：

  10.1021/jm00098a015
• 作为产物：
  描述：

  3,5-二叔丁基-4-羟基苯甲酸 在 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.0h， 生成 苯酚,4-[3-(氯甲基)-1,2,4-噁二唑-5-基]-2,6-二(1,1-二甲基乙基)-
  参考文献：
  名称：

  Novel 1,2,4-oxadiazoles and 1,2,4-thiadiazoles as dual 5-lipoxygenase and cyclooxygenase inhibitors

  摘要：

  A series of 1,2,4-oxadiazoles and 1,2,4-thiadiazoles containing a 2,6-di-tert-butylphenol substituent were prepared and evaluated as dual inhibitors of 5-lipoxygenase and cyclooxygenase in rat basophilic leukemia (RBL-1) cells. Several of these compounds show oral efficacy in the rat carageenan footpad edema (CFE) and mycobacterium footpad edema (MFE) antiinflammatory models, without concomitant gastric ulceration. Structure-activity relationships are discussed. The best compounds (ID40 values in MFE of 3-8 mg/kg po) contain guanidine-derived substituents on the heterocyclic ring.

  DOI：

  10.1021/jm00098a015

文献信息

• 3,5-di-tertiary-butyl-4-hydroxyphenyl-1,3,4-thiadiazoles, and
  申请人：Warner-Lambert Company

  公开号：US05155122A1

  公开（公告）日：1992-10-13

  The present invention is novel compounds which are 3,5-di-tertiary-butyl-4-hydroxyphenyl substituted 1,2,4- and 1,3,4-thiadazoles and oxadiazoles, and 1,2,4-triazoles, and pharmaceutically acceptable additions and base salts thereof, pharmaceutical compositions and methods of use therefor. The invention compounds are now found to have activity as inhibitors of 5-lipoxygenase and/or cyclooxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever, and the like.

  本发明涉及新型化合物，其为3,5-二叔丁基-4-羟基苯基取代的1,2,4-和1,3,4-噻二唑和噁二唑以及1,2,4-三唑，以及其药学上可接受的加合物和碱盐、制药组合物和使用方法。现发现该发明化合物具有作为5-脂氧合酶和/或环氧合酶抑制剂的活性，从而提供治疗因此类抑制而受益的疾病的方法，包括炎症、关节炎、疼痛、发热等。
• 3,5-Di-tertiary-butyl-4-hydroxyphenyl-1,3,4-thiadiazoles, and oxadiazoles and 3,5-di-tertiary-butyl-4-hydroxiphenyl- 1,2,4-thiadiazoles, -oxadiazoles as antiinflammatory agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0371438A2

  公开（公告）日：1990-06-06

  The present invention is novel compounds which are 3,5-di-tertiary-butyl-4-hydroxyphenyl substituted 1,2,4-and 1,3,4-thiadazoles and oxadiazoles, and 1,2,4-triazoles, and pharmaceutically acceptable additions and base salts thereof, pharmaceutical compositions and methods of use therefor. The invention compounds are now found to have activity as inhibitors of 5-lipoxygenase and/or cyclooxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever, and the like.

  本发明是3,5-二叔丁基-4-羟基苯基取代的1,2,4和1,3,4-噻二唑和噁二唑以及1,2,4-三唑的新型化合物及其药学上可接受的添加剂和基盐、药物组合物和使用方法。现在发现，本发明化合物具有作为 5-脂氧合酶和/或环氧合酶抑制剂的活性，可治疗受这种抑制影响的有利病症，包括炎症、关节炎、疼痛、发热等。
• US5155122A
  申请人：——

  公开号：US5155122A

  公开（公告）日：1992-10-13
• US5256680A
  申请人：——

  公开号：US5256680A

  公开（公告）日：1993-10-26
• US5376670A
  申请人：——

  公开号：US5376670A

  公开（公告）日：1994-12-27