3-(5-甲酰基-2-噻吩基)苯甲酸 | 606970-74-5

• 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: 3-(5-甲酰基-2-噻吩基)苯甲酸
• 英文名称: 5-(3-carboxyphenyl)thiophene-2-carbaldehyde
• 英文别名: 3-(5-formylthiophen-2-yl)benzoic acid；3-(5-Formyl-thiophen-2-yl)-benzoic acid
• CAS: 606970-74-5
• 化学式: C₁₂H₈O₃S
• 分子量: 232.26
• InChiKey: VIKAAKFSYUCLTJ-UHFFFAOYSA-N

物化性质

• 熔点：
  251-257°C
• 沸点：
  476.4±40.0 °C(Predicted)
• 密度：
  1.379±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H319
• 危险性防范说明：
  P305 + P351 + P338
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(5-甲酰基-2-噻吩基)苯甲酸 、 (9ci)-5-甲基-1H-苯并咪唑-2-乙腈 在 哌啶 作用下， 以 乙醇 为溶剂， 以54%的产率得到(E)-3-(5-(2-cyano-2-(5-methyl-1H-benzo[d]imidazol-2-yl)vinyl)thiophen-2-yl)benzoic acid
  参考文献：
  名称：

  以结构为导向的针对促旋酶ATPase结构域的抗结核药的发现

  摘要：

  在这项研究中，我们探索了DNA回旋酶（GyrB）的药物开发不足的ATPase域，作为开发针对结核分枝杆菌的新型药物的潜在平台。在这项工作中，结合了基于配体和结构的药效团模型，基于具有吡咯酰胺抑制剂的酶的晶体结构，鉴定了分枝杆菌GyrB结构域的结构多样的小分子抑制剂（PDB ID：4BAE）。药效团建模和随后的体外筛选产生了初次打击的化合物5 [（E）‐5‐（5‐（2‐（1 H‐苯并[ d ]咪唑‐2‐yl] ‐2‐氰基乙烯基）呋喃‐2‐ yl）间苯二甲酸; IC 50 = 4.6±0.1μ米]，随后结合分子建模和合成化学方法对其进行了定制，以产生优化的铅化合物24 [（E）-3-（5-（2-氰基-2-2-（5-甲基-1 H-苯并[ d] ]咪唑-2-基）乙烯基）噻吩-2-基）苯甲酸; IC 50 = 0.3±0.2μ米]，它被发现显示针对GyrB的纯化的酶和效力针对为H的体外功效相当37的

  DOI：

  10.1002/cmdc.201500556
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 、 3-羧基苯硼酸 在 palladium dichloride 乙二胺四乙酸 、 四丁基溴化铵 、 potassium carbonate 作用下， 反应 0.17h， 以86%的产率得到3-(5-甲酰基-2-噻吩基)苯甲酸
  参考文献：
  名称：

  Pd-EDTA是水中铃木-宫浦反应的有效催化剂

  摘要：

  PdCl 2 -EDTA络合物1是在20-100°C的水中，芳基和杂芳基卤化物与芳基（杂芳基）硼酸的Suzuki-Miyaura反应的有效催化剂。芳基碘化物和溴化物进行交叉耦合，其周转数（TON）高达97,000，周转频率（TOF）高达582,000 h -1。

  DOI：

  10.1016/j.tetlet.2005.06.085

文献信息

• Synthesis and biological evaluation of 2-arylimino-3-pyridin-thiazolineone derivatives as antibacterial agents
  作者：Ming-Guang Cai、Yang Wu、Jun Chang

  DOI：10.1016/j.bmcl.2016.03.089

  日期：2016.5

  With an intention to find more potent antibacterial agents, four halogen disubstituted thiazolineone derivatives (2a-d), five halogen monosubstituted thiazolineone derivatives (2e-i), and eleven 2-arylimino-3-pyridin-thiazolineone derivatives (2j-t) were synthesized and screened for their antibacterial activity, bactericidal activity, cytotoxicity, and erythrocyte hemolysis. Most of the synthesized

  为了寻找更有效的抗菌剂，分别开发了四种卤素二取代的噻唑啉酮衍生物（2a-d），五个卤素单取代的噻唑啉酮衍生物（2e-i）和十一种2-芳基氨基-3-吡啶-噻唑啉酮衍生物（2j-t）。合成并筛选了它们的抗菌活性，杀菌活性，细胞毒性和红细胞溶血作用。大多数合成衍生物在抑制表皮葡萄球菌和MRSA的生长中显示出抗菌活性，并且在Vero细胞的细胞毒性研究和健康人红细胞的溶血活性试验中显示出安全性。2-Arylimino-3-pyridin-thiazolineone衍生物不仅改善了clog P，而且在抑制表皮葡萄球菌和MRSA的生长中显示出强大的抗菌活性。特别是几种化合物（2f，2i，
• The 1,3-Diaminobenzene-Derived Aminophosphine Palladium Pincer Complex {C6H3[NHP(piperidinyl)2]2Pd(Cl)} - A Highly Active Suzuki-Miyaura Catalyst with Excellent Functional Group Tolerance
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1002/adsc.200900848

  日期：——

  The rapidly prepared 1,3‐diaminobenzene‐derived aminophosphine pincer complex C6H3[NHP(piperidinyl)2]2Pd(Cl)} (1) is an effective Suzuki catalyst with excellent functional group tolerance. Side‐product formations, such as homocoupling, debromation or protodeboration have only rarely been detected and if so, were in all cases below the 5% level. The presented reaction protocol is universally applicable

  快速制备的1,3-二氨基苯衍生的氨基膦钳形配合物C 6 H 3 [NHP（哌啶基）2 ] 2 Pd（Cl）}（1）是一种有效的Suzuki催化剂，具有出色的官能团耐受性。仅很少检测到副产物形成，例如均偶联，去溴化或原去硼，如果这样，在所有情况下均低于5％的水平。提出的反应方案是普遍适用的。实验观察表明，钯纳米颗粒的催化活性形式1。
• Bi-functional complexes and methods for making and using such complexes
  申请人：Gouliaev Alex Haahr

  公开号：US11225655B2

  公开（公告）日：2022-01-18

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.

  本发明涉及一种合成双功能复合物的方法，该复合物包括分子部分和识别分子部分的识别寡核苷酸部分。根据本发明的合成方法的一部分优选在一种或多种有机溶剂中进行，此时包含可选保护标签或寡核苷酸标识符的新生双功能复合物与固体支持物相连接，合成方法的另一部分优选在适合于将寡核苷酸标签酶加到溶液中的新生双功能复合物的条件下进行。
• Synthesis, in silico, in vitro evaluation of furanyl- and thiophenyl-3-phenyl-1H-indole-2-carbohydrazide derivatives as tubulin inhibitors and anticancer agents
  作者：Rungroj Saruengkhanphasit、Lukana Ngiwsara、Kriengsak Lirdprapamongkol、Jaruwan Chatwichien、Worawat Niwetmarin、Chatchakorn Eurtivong、Prasat Kittakoop、Jisnuson Svasti、Somsak Ruchirawat

  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。
• Identification of N-acylhydrazone derivatives as novel lactate dehydrogenase A inhibitors
  作者：Sebastiano Rupiani、Rosa Buonfiglio、Marcella Manerba、Lorenza Di Ianni、Marina Vettraino、Elisa Giacomini、Matteo Masetti、Federico Falchi、Giuseppina Di Stefano、Marinella Roberti、Maurizio Recanatini

  DOI：10.1016/j.ejmech.2015.06.028

  日期：2015.8

  Glycolysis is drastically increased in tumors and it is the main route to energy production with a minor use of oxidative phosphorylation. Among the key enzymes in the glycolytic process, LDH is emerging as one of the most interesting targets for the development of new inhibitors. In this context, in the present work, we carried out a virtual screening procedure followed by chemical modifications of the identified structures according to a "hit-to-lead" process. The effects of the new molecules were preliminary probed against purified human LDH-A. The compounds active at low micromolar level were additionally characterized for their activity on some cellular metabolic processes by using Raji human cell line. Within the series, 1 was considered the best candidate, and a more detailed characterization of its biological properties was performed. In Raji cells exposed to compound 1 we evidenced the occurrence of effects usually observed in cancer cells after LDH-A inhibition: reduced lactate production and NAD/NADH ratio, apoptosis. The flow cytometry analysis of treated cells also showed cell cycle changes compatible with effects exerted at the glycolytic level. Finally, in agreement with the data obtained with other inhibitors or by silencing LDH-A expression, compound 1 was found to increase Rail cells response to some commonly used chemotherapeutic agents. Taken together, all these finding are in support of the LDH-A inhibiting activity of compound 1. (C) 2015 Elsevier Masson SAS. All rights reserved.