5-氯-3-(羟基甲基)苯并恶唑-2(3H)-酮 | 17929-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 5-氯-3-(羟基甲基)苯并恶唑-2(3H)-酮
• 英文名称: 5-chloro-3-(hydroxymethyl)benzo[d]oxazol-2(3H)-one
• 英文别名: 5-chloro-3-hydroxymethyl-3H-benzooxazol-2-one；3-Hydroxymethyl-5-chlor-2-benzoxazolinon；5-Chlor-3-hydroxymethyl-2-benzoxazolinon；3-Hydroxymethyl-5-chlorbenzoxazolon；2-Benzoxazolinone, 5-chloro-3-hydroxymethyl-；5-chloro-3-(hydroxymethyl)-1,3-benzoxazol-2-one
• CAS: 17929-34-9
• 化学式: C₈H₆ClNO₃
• 分子量: 199.594
• InChiKey: FSCPTWHCVYVMGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-氯-3-(羟基甲基)苯并恶唑-2(3H)-酮 在 三溴化磷 作用下， 以 乙醚 为溶剂， 生成 3-bromomethyl-5-chloro-3H-benzooxazol-2-one
  参考文献：
  名称：

  某些3-取代的苯并恶唑啉酮的合成和抗菌活性。

  摘要：

  DOI：

  10.1002/jps.2600570108
• 作为产物：
  描述：

  聚合甲醛 、 氯唑沙宗 以 水 为溶剂， 反应 3.0h， 以87.5%的产率得到5-氯-3-(羟基甲基)苯并恶唑-2(3H)-酮
  参考文献：
  名称：

  Chlorzoxazone esters of some non-steroidal anti-inflammatory (NSAI) carboxylic acids as mutual prodrugs: Design, synthesis, pharmacological investigations and docking studies

  摘要：

  The discovery of the inducible isoform of cyclooxygenase enzyme (COX-2) spurred the search for anti-inflammatory agents devoid of the undesirable effects associated with classical NSAIDs. New chlorzoxazone ester prodrugs (6-8) of some acidic NSAIDs (1-3) were designed, synthesized and evaluated as mutual prodrugs with the aim of improving the therapeutic potency and retard the adverse effects of gastrointestinal origin. The structure of the synthesized mutual ester prodrugs (6-8) were confirmed by IR, H-1 NMR, mass spectroscopy (MS) and their purity was ascertained by TLC and elemental analyses. In vitro chemical stability revealed that the synthesized ester prodrugs (6-8) are chemically stable in hydrochloric acid buffer pH 1.2 as a non-enzymatic simulated gastric fluid (SGF) and in phosphate buffer pH 7.4 as non-enzymatic simulated intestinal fluid (SIF). In 80% human plasma, the mutual prodrugs were found to be susceptible to enzymatic hydrolysis at relatively faster rate (t(1/2) approximate to 37 and 34 min for prodrugs 6 and 7, respectively). Mutual ester prodrugs (6-8) were evaluated for their anti-inflammatory and muscle relaxation activities. Scanning electromicrographs of the stomach showed that the ester prodrugs induced very little irritancy in the gastric mucosa of rats after oral administration for 4 days. In addition, docking of the mutual ester prodrugs (6-8) into COX-2 active site was conducted in order to predict the affinity and orientation of these prodrugs at the enzyme active site. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.065

文献信息

• Synthesis and Antibacterial Activity of Certain 3-Substituted Benzoxazolinones
  作者：Rajendra S. Varma、W.Lewis Nobles

  DOI：10.1002/jps.2600570108

  日期：1968.1
• Chlorzoxazone esters of some non-steroidal anti-inflammatory (NSAI) carboxylic acids as mutual prodrugs: Design, synthesis, pharmacological investigations and docking studies
  作者：Ahmed Z. Abdel-Azeem、Atef A. Abdel-Hafez、Gamal S. El-Karamany、Hassan H. Farag

  DOI：10.1016/j.bmc.2009.03.065

  日期：2009.5

  The discovery of the inducible isoform of cyclooxygenase enzyme (COX-2) spurred the search for anti-inflammatory agents devoid of the undesirable effects associated with classical NSAIDs. New chlorzoxazone ester prodrugs (6-8) of some acidic NSAIDs (1-3) were designed, synthesized and evaluated as mutual prodrugs with the aim of improving the therapeutic potency and retard the adverse effects of gastrointestinal origin. The structure of the synthesized mutual ester prodrugs (6-8) were confirmed by IR, H-1 NMR, mass spectroscopy (MS) and their purity was ascertained by TLC and elemental analyses. In vitro chemical stability revealed that the synthesized ester prodrugs (6-8) are chemically stable in hydrochloric acid buffer pH 1.2 as a non-enzymatic simulated gastric fluid (SGF) and in phosphate buffer pH 7.4 as non-enzymatic simulated intestinal fluid (SIF). In 80% human plasma, the mutual prodrugs were found to be susceptible to enzymatic hydrolysis at relatively faster rate (t(1/2) approximate to 37 and 34 min for prodrugs 6 and 7, respectively). Mutual ester prodrugs (6-8) were evaluated for their anti-inflammatory and muscle relaxation activities. Scanning electromicrographs of the stomach showed that the ester prodrugs induced very little irritancy in the gastric mucosa of rats after oral administration for 4 days. In addition, docking of the mutual ester prodrugs (6-8) into COX-2 active site was conducted in order to predict the affinity and orientation of these prodrugs at the enzyme active site. (C) 2009 Elsevier Ltd. All rights reserved.