吐昔酸 | 4462-95-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 吐昔酸
• 中文别名: 2,4-二苯基环丁烷-1,3-二羧酸；2,4-二苯環丁-1,2-二甲酸
• 英文名称: α-truxillic acid
• 英文别名: epi-truxillic acid；truxillic acid；2,4-diphenyl-cyclobutane-1,3-dicarboxylic acid；2,4-Diphenyl-cyclobutan-1,3-dicarbonsaeure；2,4-Diphenyl-cyclobutan-dicarbonsaeure-(1,3)；α-Truxillsaeure；2,4-diphenylcyclobutane-1,3-dicarboxylic acid
• CAS: 4462-95-7
• 化学式: C₁₈H₁₆O₄
• mdl: MFCD00984993
• 分子量: 296.323
• InChiKey: QWFRRFLKWRIKSZ-UHFFFAOYSA-N

物化性质

• 熔点：
  228 °C
• 沸点：
  470.5±45.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2917399090

反应信息

• 作为反应物：
  描述：

  吐昔酸 以 乙腈 为溶剂， 反应 4.0h， 生成 肉桂酸
  参考文献：
  名称：

  Optimisation of two-photon induced cleavage of molecular linker systems for drug delivery

  摘要：

  Photoreactive linker systems for drug delivery in modern ophthalmology are crucial for the efficiency of such applications. We compare 5 different linker molecule candidates (truxillic acid and 4 dimers of coumarin derivates) in solution regarding their chemical stability and two-photon induced cleavage efficiency, and shed light into the role of molecular structure in the cleavage reaction. Dimers of the coumarin family showed much higher two-photon induced cleavage efficiency, achieving the highest reaction cross-section when tert-Butyldimethylsilyl (TBS) was used as a substituent, being almost 5-times higher than the unsubstituted coumarin dimer. Coumarin-based linker systems react promptly with nucleophilic solvents, in particular with short chain alcohols. The polarity of such solvents which do not cause a lactone ring opening seems not to influence the cleavage of the cyclobutane ring in coumarin dimers. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2009.12.016
• 作为产物：
  描述：

  (E)-1,1-dichloro-5-phenylpenta-1,4-dien-3-one 在 potassium permanganate 作用下， 生成 吐昔酸
  参考文献：
  名称：

  Pochat,F.; Levas,E., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1971, vol. 273, p. 382 - 385

  摘要：

  DOI：

文献信息

• Compound having silsesquioxane skeleton and its polymer
  申请人：Inagaki Jyun-ichi

  公开号：US20050009982A1

  公开（公告）日：2005-01-13

  The present invention relates to a compound represented by Formula (1) and a polymer obtained using the compound: wherein R 1 is phenyl which may have substituents, Q 1 is hydrogen, halogen, alkyl having 1 to 10 carbon atoms, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl or phenyl in which optional hydrogen may be replaced by halogen or alkyl having 1 to 5 carbon atoms, and Q 2 is a group represented by Formula (2) wherein the code < represents a bonding point with silicon, l, m, n and p are independently 0, 1, 2 or 3, A 1 to A 4 are independently a single bond, 1,4-cyclohexylene, 1,4-cyclohexenylene, a condensed ring group having 6 to 10 carbon atoms which is a divalent group, or 1,4-phenylene, Z 0 to Z 3 are independently a single bond, —CH═CR—, —C≡C—, —COO—, —OCO—, or alkylene having 1 to 20 carbon atoms, and Z 4 is a single bond, —CH═CH—, —C≡C—, —COO—, —OCO—, or alkylene having 1 to 20 carbon atoms. And Y 1 in Formula (1) is the group defined in Claim 1.

  本发明涉及一种由式（1）表示的化合物和使用该化合物获得的聚合物：其中R1是苯基，可能具有取代基；Q1是氢、卤素、具有1至10个碳原子的烷基、环丙基、环丁基、环戊基、环己基、环己烯基或苯基，其中可选的氢原子可被卤素或具有1至5个碳原子的烷基取代；Q2是由式（2）表示的基团，其中代码<表示与硅的连接点，l、m、n和p独立地为0、1、2或3，A1至A4独立地为单键、1,4-环己亚基、1,4-环己烯亚基、具有6至10个碳原子的缩合环基团，为二价基团，或1,4-苯亚基，Z0至Z3独立地为单键、—CH═CR—、—C≡C—、—COO—、—OCO—或具有1至20个碳原子的烷基，Z4为单键、—CH═CH—、—C≡C—、—COO—、—OCO—或具有1至20个碳原子的烷基。式（1）中的Y1是权利要求1中定义的基团。
• Nickel-Catalyzed Reductive [2+2] Cycloaddition of Alkynes
  作者：Santiago Cañellas、John Montgomery、Miquel À. Pericàs

  DOI：10.1021/jacs.8b09677

  日期：2018.12.19

  The nickel-catalyzed synthesis of tetrasubstituted cyclobutenes from alkynes is reported. This transformation is uniquely promoted by the use of a primary aminophosphine, an unusual ligand in nickel catalysis. Mechanistic insights for this new transformation are provided, and postreaction modifications of the cyclobutene products to stereodefined cyclic and acyclic compounds are reported, including

  报道了镍催化从炔烃合成四取代环丁烯的方法。这种转化是通过使用伯氨基膦（镍催化中一种不常见的配体）来独特促进的。提供了这种新转化的机理见解，并报道了环丁烯产物对立体定义的环状和无环化合物的反应后修饰，包括表-特鲁昔酸的合成。
• [EN] alpha-AND gamma-TRUXILLIC ACID DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THEREOF<br/>[FR] DÉRIVÉS D'ACIDE Alpha- ET Gamma-TRUXILLIQUE ET LEURS COMPOSITIONS PHARMACEUTIQUES
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2014015276A1

  公开（公告）日：2014-01-23

  The present invention provides a compound, and method of inhibiting the activity of a Fatty Acid Binding Protein (FABP) comprising contacting the FABP with a compound, having the structure: Formula (I).

  本发明提供了一种化合物，以及一种抑制脂肪酸结合蛋白（FABP）活性的方法，包括将该化合物与FABP接触，该化合物具有结构：Formula (I)。
• [EN] α-TRUXILLIC ACID DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THEREOF<br/>[FR] DÉRIVÉS D'ACIDE Α-TRUXILLIQUE ET COMPOSITIONS PHARMACEUTIQUES ASSOCIÉES
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2017156354A1

  公开（公告）日：2017-09-14

  The present invention provides a compound, and method of inhibiting the activity of a Fatty Acid Binding Protein (FABP) comprising contacting the FABP with a compound, said compound having the structure : Formula (I)

  本发明提供了一种化合物，以及一种抑制脂肪酸结合蛋白（FABP）活性的方法，包括将该化合物与FABP接触，所述化合物具有结构：Formula (I)。
• 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。