1-(6-chloro-1H-benzoxazol-2-yl)ethanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 1-(6-chloro-1H-benzoxazol-2-yl)ethanol
• 英文别名: 1-(6-chloro-2-benzoxazolyl)ethanol；1-(6-chloro-1,3-benzoxazol-2-yl)ethanol
• 化学式: C₉H₈ClNO₂
• 分子量: 197.621
• InChiKey: LZJCLZPZIGUGEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.26
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(6-chloro-1H-benzoxazol-2-yl)ethanol 在 chromium(VI) oxide 、 双(三甲基硅烷基)氨基钾 、 溶剂黄146 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Development of benzoxazole deoxybenzoin oxime and acyloxylamine derivatives targeting innate immune sensors and xanthine oxidase for treatment of gout

  摘要：

  Both the inhibition of inflammatory flares and the treatment of hyperuricemia itself are included in the management of gout. Extending our efforts to development of gout therapy, two series of benzoxazole deoxybenzoin oxime derivatives as inhibitors of innate immune sensors and xanthine oxidase (XOD) were discovered in improving hyperuricemia and acute gouty arthritis. In vitro studies revealed that most compounds not only suppressed XOD activity, but blocked activations of NOD-like receptor (NLRP3) inflammasome and Toll-like receptor 4 (TLR4) signaling pathway. More importantly, (E)-1-(6-methoxybenzo[d]oxazol-2-yl)-2-(4-methoxyphenyl)ethanone oxime (5d) exhibited anti-hyperuricemic and antiacute gouty arthritis activities through regulating XOD, NLRP3 and TLR4. Compound 5d may serve as a tool compound for further design of anti-gout drugs targeting both innate immune sensors and XOD. (c) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.02.013
• 作为产物：
  描述：

  乳酸 、 2-氨基-5-氯苯酚 反应 3.0h， 以51%的产率得到1-(6-chloro-1H-benzoxazol-2-yl)ethanol
  参考文献：
  名称：

  含有苯并五元不饱和杂环结构的α、β不饱和酮 类化合物及其制备方法和应用

  摘要：

  本发明提供公开了一类含有苯并五元不饱和杂环结构的α、β不饱和酮类化合物及其制备方法和用途，本发明的一类含有苯并五元不饱和杂环结构的α、β不饱和酮类化合物具有通式(Ⅰ)的结构。此外，本发明还提供了制备所述化合物的方法以及含有所述化合物作为活性成分的药物组合物。体外活性测试显示，本发明化合物表现出了对肿瘤细胞明显的抑制作用。因此，本发明为今后深入研究与开发抗肿瘤药物奠定了基础，同时也为肿瘤疾病的治疗提供了一种新的技术手段。

  公开号：

  CN104140415B

文献信息

• 含有苯并五元不饱和杂环结构的α、β不饱和酮 类化合物及其制备方法和应用
  申请人：中国医学科学院医药生物技术研究所

  公开号：CN104140415B

  公开（公告）日：2017-02-15

  本发明提供公开了一类含有苯并五元不饱和杂环结构的α、β不饱和酮类化合物及其制备方法和用途，本发明的一类含有苯并五元不饱和杂环结构的α、β不饱和酮类化合物具有通式(Ⅰ)的结构。此外，本发明还提供了制备所述化合物的方法以及含有所述化合物作为活性成分的药物组合物。体外活性测试显示，本发明化合物表现出了对肿瘤细胞明显的抑制作用。因此，本发明为今后深入研究与开发抗肿瘤药物奠定了基础，同时也为肿瘤疾病的治疗提供了一种新的技术手段。
• Photo-Induced α-Oxyalkylation of Aryl Chlorides with Ethers and Alcohols through Homolytic Aromatic Substitution
  作者：Eiji Shirakawa、Kohei Aoki、Kyohei Yonekura、Wataru Ejima、Shota Tanaka、Ami Shigeta

  DOI：10.1055/a-2273-2895

  日期：——

  The α-oxyalkylation of aryl chlorides with ethers and alcohols using a small amount of a peroxide was found to be induced by photoirradiation. The reaction proceeds through a homolytic aromatic substitution (HAS) mechanism consisting of addition of an α-oxyalkyl radical to an aryl chloride and elimination of the chlorine atom to give the α-oxyalkylation product, where photoirradiation is considered

  发现使用少量过氧化物的芳基氯与醚和醇的α-烷氧基化是通过光照射诱导的。该反应通过均解芳族取代（HAS）机制进行，包括将α-烷氧基加成到芳基氯上并消除氯原子，得到α-烷氧基化产物，其中光照射被认为不仅影响引发步骤促进过氧化物的均分解，同时也促进自由基链的增长。
• Development of benzoxazole deoxybenzoin oxime and acyloxylamine derivatives targeting innate immune sensors and xanthine oxidase for treatment of gout
  作者：Jun Huang、Zehao Zhou、Mengze Zhou、Mingxing Miao、Huanqiu Li、Qinghua Hu

  DOI：10.1016/j.bmc.2018.02.013

  日期：2018.5

  Both the inhibition of inflammatory flares and the treatment of hyperuricemia itself are included in the management of gout. Extending our efforts to development of gout therapy, two series of benzoxazole deoxybenzoin oxime derivatives as inhibitors of innate immune sensors and xanthine oxidase (XOD) were discovered in improving hyperuricemia and acute gouty arthritis. In vitro studies revealed that most compounds not only suppressed XOD activity, but blocked activations of NOD-like receptor (NLRP3) inflammasome and Toll-like receptor 4 (TLR4) signaling pathway. More importantly, (E)-1-(6-methoxybenzo[d]oxazol-2-yl)-2-(4-methoxyphenyl)ethanone oxime (5d) exhibited anti-hyperuricemic and antiacute gouty arthritis activities through regulating XOD, NLRP3 and TLR4. Compound 5d may serve as a tool compound for further design of anti-gout drugs targeting both innate immune sensors and XOD. (c) 2018 Elsevier Ltd. All rights reserved.