α-truxillic acid dichloride | 17916-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-truxillic acid dichloride
• 英文别名: 2,4-diphenyl-cyclobutane-1,3-dicarbonyl chloride；2,4-Diphenyl-cyclobutan-1,3-dicarbonylchlorid；ε-Truxillsaeure-dichlorid；α-Truxilloylchlorid；2,4-Diphenylcyclobutane-1,3-dicarbonyl chloride
• CAS: 17916-52-8；20324-70-3
• 化学式: C₁₈H₁₄Cl₂O₂
• 分子量: 333.214
• InChiKey: RHZJLTRJKJIMFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-truxillic acid dichloride 、 alkaline earth salt of/the/ methylsulfuric acid 生成 γ-truxillic acid
  参考文献：
  名称：

  Liebermann; Drory, Chemische Berichte, 1889, vol. 22, p. 680

  摘要：

  DOI：
• 作为产物：
  描述：

  γ-truxillic acid 在 五氯化磷 作用下， 生成 α-truxillic acid dichloride
  参考文献：
  名称：

  Liebermann; Drory, Chemische Berichte, 1889, vol. 22, p. 680

  摘要：

  DOI：

文献信息

• Antinociceptive Activities of .ALPHA.-Truxillic Acid and .BETA.-Truxinic Acid Derivatives
  作者：Yu-Ming Chi、Motoyuki Nakamura、Xi-Ying Zhao、Toyokichi Yoshizawa、Wen-Mei Yan、Fumio Hashimoto、Junei Kinjo、Toshihiro Nohara、Shinobu Sakurada

  DOI：10.1248/bpb.29.580

  日期：——

  Our recent study demonstrated that the dimeric structure of α-truxillic acid derivatives played an important role in the expression of their anti-inflammatory activities. In the present report, to investigate the correlation between the structure and anti-inflammatory activity, α-truxillic acid (1) and its derivatives (2—6), β-truxinic acid (7) and its derivatives (8—10) were prepared, and their activities were evaluated in the formalin test. All compounds showed only weak or no activities against the neurogenic pain response, but demonstrated significant activities against the inflammatory pain response induced by formalin. The highest anti-inflammatory activities were observed for α-truxillic acid (1) and its derivative 4,4′-dihydroxy-α-truxillic acid (2). In addition, α-truxillic acid (1) and its derivative, α-truxillic acid bis(p-nitrophenyl)ester (5), showed higher anti-inflammatory activities than β-truxinic acid (7) and the corresponding derivative (10). Furthermore, free carboxylic acids (1, 2) showed higher activities than their dimethyl esters (3, 4) and bis(p-nitrophenyl)ester (5). These results confirmed that the α-formation of dimeric structure and the free carboxylic acid were also important for the expression of anti-inflammatory activities. Otherwise, 4,4′-dichloro-β-truxinic acid (8) had higher activity than its parent compound 7; furthermore, 1,3-dibenzoyl-2,4-di(4-chlorophenyl)cyclobutane (6) also showed strong anti-inflammatory activity. These results suggested that substituents in the phenyl groups were also important for the expression of anti-inflammatory activity. In order to gain information about their activity intensity, the anti-inflammatory activities of 2 and 4,4′-dichlorolated derivatives (6, 8) were compared with that of indomethacin (a nonsteroidal anti-inflammatory drug) in the formalin test. As a result, compounds 2, 6 and 8 showed stronger anti-inflammatory activities than indomethacin. These results suggested that α-truxillic acid and β-truxinic acid derivatives might be developed into a new type of anti-inflammatory drug.

  我们最近的研究表明，α-曲昔酸衍生物的二聚体结构对其抗炎活性的表达起着重要作用。为了研究结构与抗炎活性之间的相关性，本报告制备了α-曲昔酸（1）及其衍生物（2-6）、β-曲昔酸（7）及其衍生物（8-10），并在福尔马林试验中评估了它们的活性。所有化合物对神经源性疼痛反应的活性都很弱或没有，但对福尔马林诱导的炎症性疼痛反应有显著的活性。抗炎活性最高的是α-曲昔酸（1）及其衍生物 4,4′-二羟基-α-曲昔酸（2）。此外，α-曲昔酸（1）及其衍生物α-曲昔酸双（对硝基苯基）酯（5）的抗炎活性高于β-曲昔酸（7）及其相应衍生物（10）。此外，游离羧酸（1、2）的活性高于其二甲酯（3、4）和双（对硝基苯基）酯（5）。这些结果证实，二聚体结构的 α 形成和游离羧酸对抗炎活性的表达也很重要。此外，4,4′-二氯-β-曲辛酸（8）比其母体化合物 7 具有更高的活性；1,3-二苯甲酰基-2,4-二（4-氯苯基）环丁烷（6）也表现出很强的抗炎活性。这些结果表明，苯基中的取代基对于抗炎活性的表达也很重要。为了了解它们的活性强度，在福尔马林试验中将 2 和 4,4′-二氯衍生物（6、8）的抗炎活性与吲哚美辛（一种非甾体抗炎药）的抗炎活性进行了比较。结果表明，化合物 2、6 和 8 比吲哚美辛具有更强的抗炎活性。这些结果表明，α-曲昔酸和β-曲昔酸衍生物可能被开发成一种新型消炎药。
• CHASEY, K. L.;PAQUETTE, L. A.;BLOUNT, J. F., J. ORG. CHEM., 1982, 47, N 27, 5262-5270
  作者：CHASEY, K. L.、PAQUETTE, L. A.、BLOUNT, J. F.

  DOI：——

  日期：——
• Liebermann; Drory, Chemische Berichte, 1889, vol. 22, p. 680
  作者：Liebermann、Drory

  DOI：——

  日期：——