3-(4-(methylthio)phenyl)thiophene-2-carbaldehyde | 572912-98-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(4-(methylthio)phenyl)thiophene-2-carbaldehyde
• 英文别名: 3-[4-(methylthio)phenyl]thiophene-2-calbaldehyde；3-(4-Methylsulfanylphenyl)thiophene-2-carbaldehyde
• CAS: 572912-98-2
• 化学式: C₁₂H₁₀OS₂
• 分子量: 234.343
• InChiKey: GEMVDZWZUYLHHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  70.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-(methylthio)phenyl)thiophene-2-carbaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 双氧水 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以50%的产率得到3-(4-methylsulfonylphenyl)thiophene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and COX-2 inhibitory properties of N-phenyl- and N-benzyl-substituted amides of 2-(4-methylsulfonylphenyl)cyclopent-1-ene-1-carboxylic acid and of their pyrazole, thiophene and isoxazole analogs

  摘要：

  Some N-phenyl- (7a-10a) and N-benzyl-substituted (7b-10b) amido analogs of cyclooxygenase (COX-2) selective tricyclic non-steroidal anti-inflammatory drugs have been synthesized with the aim to obtain information on the structural requirements for the COX-inhibitory activity. Compounds 7-10 were tested in vitro for their inhibitory properties only towards COX-2 enzyme by measuring prostaglandin E2 (PGE2) production on activated J774.2 macrophages. Some of the new compounds (7a, 8a, 9a and 9b) showed a modest activity, with percentage inhibition values near 30% at a concentration of 10 microM. These data have been tentatively explained by a conformational study which indicates that at least the N-phenyl-substituted amides 7a-9a present steric hindrances which may prevent a good interaction with COX-2 active site.

  DOI：

  10.1016/j.farmac.2003.09.003
• 作为产物：
  描述：

  3-溴噻吩-2-甲醛 在 四(三苯基膦)钯 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.5h， 生成 3-(4-(methylthio)phenyl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  吡啶氮在钯催化亚胺水解中的作用：(E)-1-(3-溴噻吩-2-基)-N-(4-甲基吡啶-2-基)甲胺的案例研究

  摘要：

  在本研究中，4-甲基吡啶-2-胺与 3-溴噻吩-2-甲醛和席夫碱 (E)-1-(3-溴噻吩-2-基)-N-(4-甲基吡啶-2) 反应-基)甲胺以79%的产率获得。在 Suzuki 偶联反应条件下，使用 Pd(PPh3)4 作为催化剂，席夫碱与芳基/杂芳基硼酸的偶联，产生亚胺键（5a-5k，6a-6h）水解良好至中等的产物产量。为了深入了解过渡金属催化的化合物水解，进行了密度泛函理论 (DFT) 计算。理论计算有力地支持了实验，并提供了对过渡金属催化亚胺水解的深入了解。

  DOI：

  10.3390/molecules24142609

文献信息

• Synthesis of heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors: effects on the inhibitory activity of the replacement of the cyclopentene central core with pyrazole, thiophene or isoxazole ring
  作者：Aldo Balsamo、Isabella Coletta、Angelo Guglielmotti、Carla Landolfi、Francesca Mancini、Adriano Martinelli、Claudio Milanese、Filippo Minutolo、Susanna Nencetti、Elisabetta Orlandini、Mario Pinza、Simona Rapposelli、Armando Rossello

  DOI：10.1016/s0223-5234(02)01448-4

  日期：2003.2

  Several heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors, in which the cyclopentene moiety was replaced by pyrazole, thiophene or isoxazole ring, were synthesized, in order to verify the influence of the different nature of the central core on the COX inhibitory properties of these kinds of molecules. Among the compounds tested, only the 3-(p-methylsulfonylphenyl) substituted thiophene derivatives 17 and 22, showed a certain COX-2 inhibitory activity, accompanied by an appreciable COX-2 versus COX-1 selectivity. Only one of the 1-(p-methylsulfonylphenyl)pyrazole compounds (16) displayed a modest inhibitory activity towards both type of isoenzymes. while the pyrazole 1-(p-aminosulfonylphenyl) substituted 12 proved to be significantly active only towards COX-1. All the isoxazole derivatives were inactive on both COX isoforms. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Role of Pyridine Nitrogen in Palladium-Catalyzed Imine Hydrolysis: A Case Study of (E)-1-(3-bromothiophen-2-yl)-N-(4-methylpyridin-2-yl)methanimine
  作者：Ahmad、Rasool、Rizwan、Altaf、Rashid、Mahmood、Ayub

  DOI：10.3390/molecules24142609

  日期：——

  In the present study, 4-methylpyridin-2-amine was reacted with 3-bromothiophene-2-carbaldehyde and the Schiff base (E)-1-(3-bromothiophen-2-yl)-N-(4-methylpyridin-2-yl)methanimine was obtained in a 79% yield. Coupling of the Schiff base with aryl/het-aryl boronic acids under Suzuki coupling reaction conditions, using Pd(PPh3)4 as catalyst, yielded products with the hydrolysis of the imine linkages

  在本研究中，4-甲基吡啶-2-胺与 3-溴噻吩-2-甲醛和席夫碱 (E)-1-(3-溴噻吩-2-基)-N-(4-甲基吡啶-2) 反应-基)甲胺以79%的产率获得。在 Suzuki 偶联反应条件下，使用 Pd(PPh3)4 作为催化剂，席夫碱与芳基/杂芳基硼酸的偶联，产生亚胺键（5a-5k，6a-6h）水解良好至中等的产物产量。为了深入了解过渡金属催化的化合物水解，进行了密度泛函理论 (DFT) 计算。理论计算有力地支持了实验，并提供了对过渡金属催化亚胺水解的深入了解。
• Synthesis and COX-2 inhibitory properties of N-phenyl- and N-benzyl-substituted amides of 2-(4-methylsulfonylphenyl)cyclopent-1-ene-1-carboxylic acid and of their pyrazole, thiophene and isoxazole analogs
  作者：Simona Rapposelli、Annalina Lapucci、Filippo Minutolo、Elisabetta Orlandini、Gabriella Ortore、Mario Pinza、Aldo Balsamo

  DOI：10.1016/j.farmac.2003.09.003

  日期：2004.1

  Some N-phenyl- (7a-10a) and N-benzyl-substituted (7b-10b) amido analogs of cyclooxygenase (COX-2) selective tricyclic non-steroidal anti-inflammatory drugs have been synthesized with the aim to obtain information on the structural requirements for the COX-inhibitory activity. Compounds 7-10 were tested in vitro for their inhibitory properties only towards COX-2 enzyme by measuring prostaglandin E2 (PGE2) production on activated J774.2 macrophages. Some of the new compounds (7a, 8a, 9a and 9b) showed a modest activity, with percentage inhibition values near 30% at a concentration of 10 microM. These data have been tentatively explained by a conformational study which indicates that at least the N-phenyl-substituted amides 7a-9a present steric hindrances which may prevent a good interaction with COX-2 active site.