5-(3-甲氧基苯基)-2-噻吩甲醛 | 249504-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-(3-甲氧基苯基)-2-噻吩甲醛
• 英文名称: 5-(3-methoxyphenyl)thiophene-2-carbaldehyde
• CAS: 249504-37-8
• 化学式: C₁₂H₁₀O₂S
• 分子量: 218.276
• InChiKey: DLXLICDIIBNILO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  2-(3-甲氧基苯基)噻吩	2-(3-methoxyphenyl)thiophene	17595-93-6	C11H10OS	190.266

反应信息

• 作为反应物：
  描述：

  5-(3-甲氧基苯基)-2-噻吩甲醛 在 甲醇 、 sodium tetrahydroborate 、 potassium tert-butylate 、 氧气 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 2-(3-甲氧基苯基)噻吩
  参考文献：
  名称：

  含杂芳基的伯醇和仲醇中的无金属好氧氧化选择性C–C键裂解。

  摘要：

  据报道，伯和仲杂芳基醇中无过渡金属的需氧氧化选择性C–C键断裂反应。该反应是高效的并且耐受各种杂芳基醇，产生羧酸衍生物和中性杂芳族化合物。实验研究与密度泛函理论计算相结合，揭示了选择性C–C键断裂的机理。该策略还提供了另一种简单的羧化反应方法。

  DOI：

  10.1021/acs.orglett.9b00563
• 作为产物：
  描述：

  2-噻吩甲醛 、 邻甲氧基苯甲酸 在 dipotassium hydrogenphosphate 、 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以55%的产率得到5-(3-甲氧基苯基)-2-噻吩甲醛
  参考文献：
  名称：

  Rh（III）催化的羧酸为无痕导向基团的芳族羧酸的脱羧邻-杂芳基化反应

  摘要：

  芳香族羧酸与各种杂芳烃的高选择性脱羧邻杂芳基化反应是通过Rh（III）催化的2倍C–H活化而开发的，这显示了芳香族羧酸和杂芳烃的广泛底物范围。使用天然存在的羧酸作为导向基团避免了麻烦的用于安装和除去外部导向基团的额外步骤。

  DOI：

  10.1021/acs.orglett.5b00532

文献信息

• Propionic Acid Derivatives and Methods of Use Thereof
  申请人：Biediger Ronald J.

  公开号：US20180312523A1

  公开（公告）日：2018-11-01

  Provided herein are compounds and pharmaceutical compositions of formula I where R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as described herein. Also provided pharmaceutically acceptable salts or stereoisomers of these compounds. In addition methods are provided for inhibiting the binding of an integrin to treat various pathophysiological conditions.

  本文提供了公式I的化合物和药物组合物，其中R1、R2、R3、R4、R5和R6如本文所述。还提供了这些化合物的药用可接受盐或立体异构体。此外，还提供了用于抑制整合素结合以治疗各种病理生理条件的方法。
• Propionic acid derivatives and methods of use thereof
  申请人：Biediger Ronald J.

  公开号：US10875875B2

  公开（公告）日：2020-12-29

  Provided herein are compounds and pharmaceutical compositions of formula I where R1, R2, R3, R4, R5 and R6 are as described herein. Also provided pharmaceutically acceptable salts or stereoisomers of these compounds. In addition methods are provided for inhibiting the binding of an integrin to treat various pathophysiological conditions.

  本文提供了式 I 的化合物和药物组合物 其中 R1、R2、R3、R4、R5 和 R6 如本文所述。还提供了这些化合物的药学上可接受的盐或立体异构体。此外，还提供了抑制整合素结合以治疗各种病理生理状况的方法。
• 10.1039/d4md00210e
  作者：Saruengkhanphasit, Rungroj、Ngiwsara, Lukana、Lirdprapamongkol, Kriengsak、Chatwichien, Jaruwan、Niwetmarin, Worawat、Eurtivong, Chatchakorn、Kittakoop, Prasat、Svasti, Jisnuson、Ruchirawat, Somsak

  DOI：10.1039/d4md00210e

  日期：——

  new indole derivatives comprising of seven furanyl-3-phenyl-1H-indole-carbohydrazide derivatives and fourteen thiophenyl-3-phenyl-1H-indole-carbohydrazide derivatives were synthesised and biologically evaluated for their microtubule-destabilising effects, and antiproliferative activities against the National Cancer Institute 60 (NCI60) human cancer cell line panel. Among the derivatives, 6i showed

  合成了二十一种新型吲哚衍生物，包括七种呋喃基-3-苯基-1H-吲哚-碳酰肼衍生物和十四种噻吩基-3-苯基-1H-吲哚-碳酰肼衍生物，并对其微管不稳定作用进行了生物学评估，以及针对国家癌症研究所 60 (NCI60) 人类癌细胞系小组的抗增殖活性。在衍生物中， 6i显示出最佳的细胞毒活性，对 COLO 205 结肠癌 (LC 50 = 71 nM)、SK-MEL-5 黑色素瘤细胞 (LC 50 = 75 nM) 和 MDA-MB-435 (LC 50 = 259纳米）。衍生物6j显示出最强的微管不稳定作用。 6i和6j均能够诱导 MDA-MB-231 三阴性乳腺癌细胞的 G2/M 细胞周期停滞和细胞凋亡。分子对接模拟结果表明这些衍生物通过与秋水仙碱位点结合来抑制微管蛋白。计算的分子描述符表明，最有效的衍生物具有可接受的药代动力学特征，并且有利于口服药物给药。
• Exploration of a Series of 5-Arylidene-2-thioxoimidazolidin-4-ones as Inhibitors of the Cytolytic Protein Perforin
  作者：Julie A. Spicer、Gersande Lena、Dani M. Lyons、Kristiina M. Huttunen、Christian K. Miller、Patrick D. O’Connor、Matthew Bull、Nuala Helsby、Stephen M. F. Jamieson、William A. Denny、Annette Ciccone、Kylie A. Browne、Jamie A. Lopez、Jesse Rudd-Schmidt、Ilia Voskoboinik、Joseph A. Trapani

  DOI：10.1021/jm401604x

  日期：2013.12.12

  A series of novel 5-arylidene-2-thioxoimidazolidin-4-ones were investigated as inhibitors of the lymphocyte-expressed pore-forming protein perform. Structure activity relationships were explored through variation of an isoindolinone or 3,4-dihydroisoquinolinone subunit on a fixed 2-thioxoimidazolidin-4-one/thiophene core. The ability of the resulting compounds to inhibit the lytic activity of both isolated perform protein and perforin delivered in situ by natural killer cells was determined. A number of compounds showed excellent activity at concentrations that were nontoxic to the killer cells, and several were a significant improvement on previous classes of inhibitors, being substantially more potent and soluble. Representative examples showed rapid and reversible binding to immobilized mouse perforin at low concentrations (<= 2.5 mu M) by surface plasmon resonance and prevented formation of perforin pores in target cells despite effective target cell engagement, as determined by calcium influx studies. Mouse PK studies of two analogues showed T-1/2 values of 1.1-1.2 h (dose of 5 mg/kg iv) and MTDs of 60-80 mg/kg (ip).
• Preparation of 5-Aryl Furfurals and Aryl Thiophene-2-carboxaldehydes via Palladium-Catalyzed C−C Bond Formation in Aqueous Media¹
  作者：Jacqueline C. Bussolari、Diana C. Rehborn

  DOI：10.1021/ol990708m

  日期：1999.10.1

  [GRAPHICS]A series of 5-aryl furfurals and aryl thiophene-2-carboxaldehydes was synthesized. To this end, efficient and effective palladium-catalyzed C-C bond-forming reactions were carried out at room temperature in aqueous media. This mild process allowed the cross-coupling reaction of the bromides to occur in the presence of electrophilic functional groups, which is a valuable advantage over previously reported methods.