甲基4-氟-1-苯并噻吩-2-羧酸酯 | 220180-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 甲基4-氟-1-苯并噻吩-2-羧酸酯
• 中文别名: 4-吡啶甲腈,3-氨基-5-(羟甲基)-2-甲基-；4-氟苯并[B]噻吩-2-羧酸甲酯
• 英文名称: methyl 4-fluorobenzo[b]thiophene-2-carboxylate
• 英文别名: methyl 4-fluoro-1-benzothiophene-2-carboxylate；4-fluoro-benzo[b]thiophene-2-carboxylic acid methyl ester；4-fluoro-benzo[b]thiophene-2-carboxlic acid methyl ester
• CAS: 220180-55-2
• 化学式: C₁₀H₇FO₂S
• mdl: MFCD06200964
• 分子量: 210.229
• InChiKey: SPZLAMSTAIFDBN-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98°
• 沸点：
  308.3±22.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  甲基4-氟-1-苯并噻吩-2-羧酸酯 在 喹啉 、 铜 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 4-氟苯并噻吩
  参考文献：
  名称：

  Design and development of cyclometalated ruthenium complexes containing thiophenyl-pyridine ligand for dye-sensitized solar cells

  摘要：

  Two new cyclometalated ruthenium sensitizers NC102 (1) and NC103 (2), where the two NCS- ligands of the N3 analog were replaced with the 2-thiophen-2-yl-pyridine and 2-benzo[b]thiophen-2-yl-pyridine ligands, respectively, were designed and synthesized for dye-sensitized solar cell applications. The effects of these two ligands on the photophysical behavior of ruthenium complexes were investigated by their optical, electrochemical, and photovoltaic properties. The sensitizer NC103 (2) with the fluoride substitution in the ligand exhibited the best cell performance with a short-circuit current (J(sc)) of 9.45 mA/cm(2), an open-circuit voltage (V-oc) of 630 mV, and a fill factor (FF) of 0.71, giving an overall power conversion efficiency of (eta) 4.22% under simulated AM 1.5 irradiation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.07.014
• 作为产物：
  描述：

  1,3-二氟苯 在 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 甲基4-氟-1-苯并噻吩-2-羧酸酯
  参考文献：
  名称：

  4-Substituted (benzo[b]thiophene-2-carbonyl)guanidines as novel Na+/H+ exchanger isoform-1 (NHE-1) inhibitors

  摘要：

  A series of 4-substituted (benzo[b]thiophene-2-carbonyl)guanidines was synthesized and evaluated for the NHE-1 inhibitory activity and cardioprotective efficacy both in vitro and in vivo. Several analogs exhibited a strong inhibition on NHE-1, and which was generally well correlated with their cardioprotective efficacy. Especially the 4-nitro 20 and cyano 50 compounds excellently improved the cardiac function and reduced infarct size against ischemia/reperfusion injury. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.046

文献信息

• Urokinase inhibitors
  申请人：Eisai Co., Ltd.

  公开号：US05340833A1

  公开（公告）日：1994-08-23

  Disclosed are benzothiophene and thienothiophene derivatives useful for inhibiting urokinase activity.

  揭示了对抑制尿激酶活性有用的苯并噻吩和噻吩噻吩衍生物。
• COLD MENTHOL RECEPTOR-1 ANTAGONISTS
  申请人：Colburn Raymond W.

  公开号：US20120053347A1

  公开（公告）日：2012-03-01

  The invention is directed to TRPM8 antagonists of Formula (I). More specifically, the present invention relates to certain novel compounds, methods for preparing compounds, compositions, intermediates and derivatives thereof and methods for treating TRPM8-mediated disorders. Pharmaceutical and veterinary compositions and methods of treating pain and various other disease states or conditions using compounds of the invention are also described.

  这项发明涉及式(I)的TRPM8拮抗剂。更具体地，本发明涉及某些新颖化合物，制备化合物的方法，组合物，中间体及其衍生物，以及治疗TRPM8介导的疾病的方法。还描述了使用本发明化合物治疗疼痛和各种其他疾病状态或病情的药用和兽医组合物及治疗方法。
• Discovery of fluorescent coumarin-benzo[b]thiophene 1, 1-dioxide conjugates as mitochondria-targeting antitumor STAT3 inhibitors
  作者：Guiping Cai、Wenying Yu、Dongmei Song、Wenda Zhang、Jianpeng Guo、Jiawen Zhu、Yuhao Ren、Lingyi Kong

  DOI：10.1016/j.ejmech.2019.04.024

  日期：2019.7

  STAT3 has been extensively studied as a potential antitumor target. Though studies on regulating STAT3 mainly focus on the inhibition of STAT3 phosphorylation at Tyr705 residue, the phosphorylation at Ser727 residue of STAT3 protein is also closely associated with the mitochondrial import of STAT3 protein. N, N-diethyl-7-aminocoumarin is a fluorescent mitochondria-targeting probe. In this study, a

  STAT3已被广泛研究为潜在的抗肿瘤靶标。尽管关于调节STAT3的研究主要集中在抑制Tyr705残基上的STAT3磷酸化，但是STAT3蛋白的Ser727残基上的磷酸化也与STAT3蛋白的线粒体导入密切相关。N，N-二乙基-7-氨基香豆素是一种荧光的线粒体靶向探针。在这项研究中，通过将N，N-二乙基-7-氨基香豆素荧光团与苯并[ b ]噻吩1，1-二氧化物部分相连，开发了一系列STAT3抑制剂。所有设计的化合物均显示出对癌细胞有效的抗增殖活性。代表性化合物7a主要通过荧光可见的线粒体中积累。化合物7a在Tyr705和Ser727残基均抑制STAT3磷酸化。化合物7a抑制STAT3磷酸化，而对STAT1，JAK2，Src和Erk1 / 2的磷酸化水平没有影响，表明化合物7a具有良好的选择性。此外，化合物7a下调STAT3靶基因Bcl-2和Cyclin D1的表达，增加ROS的产生并显着降低线
• Enantioselective Synthesis of Five-Membered-Ring Atropisomers with a Chiral Rh(III) Complex
  作者：Saad Shaaban、Houhua Li、Felix Otte、Carsten Strohmann、Andrey P. Antonchick、Herbert Waldmann

  DOI：10.1021/acs.orglett.0c03355

  日期：2020.12.4

  chemistry, and efficient methods for their synthesis are in high demand. This applies in particular to atropisomers derived from five-membered aromatic rings because their lower barrier for rotation among the biaryl axis limits their asymmetric synthesis. We report here an enantioselective C–H functionalization method using our chiral RhJasCp complex for the synthesis of the biaryl atropisomer types that

  轴向手性阻转异构化合物广泛用于不对称催化和药物化学中，对合成的有效方法有很高的要求。这尤其适用于衍生自五元芳族环的阻转异构体，因为它们在联芳基轴之间旋转的较低阻挡层限制了它们的不对称合成。我们在这里报告了一种手性Rh Jas Cp络合物的对映选择性CH功能化方法，用于合成可从三个不同的五元环杂环中获得的联芳基阻转异构体类型。
• 2-Heteroarylcarboxylic acid amides
  申请人：Hendrix Martin

  公开号：US20050119325A1

  公开（公告）日：2005-06-02

  The invention relates to novel 2-heteroarylcarboxamides, processes for their preparation, and their use for producing medicaments for the treatment and/or prophylaxis of diseases and for improving perception, concentration, learning and/or memory.

  本发明涉及新型2-杂环芳基甲酰胺、其制备方法以及用于制备治疗和/或预防疾病以及改善感知、注意力、学习和/或记忆的药物的用途。