(2-(4-chlorophenyl)benzoxazol-5-yl) acetic acid | 851703-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2-(4-chlorophenyl)benzoxazol-5-yl) acetic acid
• 英文别名: CBA；2-(4-Chlorophenyl)-1,3-benzoxazol-5-ol；2-(4-chlorophenyl)-1,3-benzoxazol-5-ol
• CAS: 851703-47-4
• 化学式: C₁₃H₈ClNO₂
• 分子量: 245.665
• InChiKey: GKOUEQBLBYIIQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氨基-4-羟基-苯乙酸甲酯 在 盐酸 、 lead(IV) tetraacetate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 7.0h， 生成 (2-(4-chlorophenyl)benzoxazol-5-yl) acetic acid
  参考文献：
  名称：

  Synthesis and In-Vivo Evaluation of Benzoxazole Derivatives as Promising Anti-Psoriatic Drugs for Clinical Use

  摘要：

  2-(4-氯苯基)-5-苯并噁唑乙酸（CBA）及其酯，甲基-2-(4-氯苯基)-5-苯并噁唑乙酸酯（MCBA），已合成并通过1HNMR、IR和质谱确认了它们的结构。使用imiquimod（IMQ）诱导的牛皮癣小鼠模型测试了CBA和MCBA的抗牛皮癣活性，小鼠经过局部（1% w/w）和口服（125 mg/kg）治疗14天。通过计算牛皮癣区域严重指数（PASI）评分来评估牛皮癣的红斑强度、厚度和脱屑。研究还包括对治疗小鼠皮肤组织的组织病理学改变的确定。CBA和MCBA的局部和口服给药导致牛皮癣的红斑强度、厚度和脱屑减少，这表现为PASI值显著降低。此外，CBA和MCBA处理的小鼠皮肤组织显示出较少的牛皮癣改变证据，如角化过度、不完全角化、鳞屑皮屑、水肿、类牛皮癣和增生。在局部或口服给药后，MCBA处理的小鼠的抗牛皮癣效果比CBA处理的小鼠更强。这些效果与参考药Clobetasol propionate相当。这种药物发现可能被转化为未来在牛皮癣治疗中的潜在新药。

  DOI：

  10.3390/molecules27093023

文献信息

• Synthesis and In-Vivo Evaluation of Benzoxazole Derivatives as Promising Anti-Psoriatic Drugs for Clinical Use
  作者：Rami Ayoub、Jamal Jilani、Qais Jarrar、Raad Alani、Chrismawan Ardianto、Khang Wen Goh、Dalia Ali、Said Moshawih

  DOI：10.3390/molecules27093023

  日期：——

  2-(4-Chlorophenyl)-5-benzoxazoleacetic acid (CBA) and its ester, methyl-2-(4-chloro-phenyl)-5-benzoxazoleacetate (MCBA), were synthesized, and their structures were confirmed by 1HNMR, IR, and mass spectrophotometry. The anti-psoriatic activities of CBA and MCBA were tested using an imiquimod (IMQ)-induced psoriatic mouse model, in which mice were treated both topically (1% w/w) and orally (125 mg/kg) for 14 days. The erythema intensity, thickness, and desquamation of psoriasis were scored by calculating the psoriasis area severity index (PASI). The study also included the determination of histopathological alterations in the skin tissues of treated mice. Topical and oral administration of CBA and MCBA led to a reduction in erythema intensity, thickness, and desquamation, which was demonstrated by a significant decrease in the PASI value. In addition, skin tissues of mice treated with CBA and MCBA showed less evidence of psoriatic alterations, such as hyperkeratosis, parakeratosis, scale crust, edema, psoriasiform, and hyperplasia. After administration of either topical or oral dosing, the anti-psoriatic effects were found to be stronger in MCBA-treated than in CBA-treated mice. These effects were comparable to those produced by Clobetasol propionate, the reference drug. This drug discovery could be translated into a potential new drug for future clinical use in psoriasis treatment.

  2-(4-氯苯基)-5-苯并噁唑乙酸（CBA）及其酯，甲基-2-(4-氯苯基)-5-苯并噁唑乙酸酯（MCBA），已合成并通过1HNMR、IR和质谱确认了它们的结构。使用imiquimod（IMQ）诱导的牛皮癣小鼠模型测试了CBA和MCBA的抗牛皮癣活性，小鼠经过局部（1% w/w）和口服（125 mg/kg）治疗14天。通过计算牛皮癣区域严重指数（PASI）评分来评估牛皮癣的红斑强度、厚度和脱屑。研究还包括对治疗小鼠皮肤组织的组织病理学改变的确定。CBA和MCBA的局部和口服给药导致牛皮癣的红斑强度、厚度和脱屑减少，这表现为PASI值显著降低。此外，CBA和MCBA处理的小鼠皮肤组织显示出较少的牛皮癣改变证据，如角化过度、不完全角化、鳞屑皮屑、水肿、类牛皮癣和增生。在局部或口服给药后，MCBA处理的小鼠的抗牛皮癣效果比CBA处理的小鼠更强。这些效果与参考药Clobetasol propionate相当。这种药物发现可能被转化为未来在牛皮癣治疗中的潜在新药。