ethyl 5-chloro-3-methylbenzofuran-2-carboxylate | 119138-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: ethyl 5-chloro-3-methylbenzofuran-2-carboxylate
• 英文别名: ethyl 5-chloro-3-methyl-1-benzofuran-2-carboxylate
• CAS: 119138-73-7
• 化学式: C₁₂H₁₁ClO₃
• 分子量: 238.671
• InChiKey: JFVQSPWXZJLDHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-chloro-3-methylbenzofuran-2-carboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到5-氯-3-甲基-1-苯并呋喃-2-羧酸
  参考文献：
  名称：

  Convenient Synthesis of Some 3-Phenyl-1-benzofuran-2-carboxylic Acid Derivatives as New Potential Inhibitors of CLC-Kb Channels

  摘要：

  Improved experimental conditions were carried out for the preparation in high yields of some 3-phenyl-1-benzofuran-2-carboxylic acids, potent inhibitors of C1C-K chloride channels. A one-pot condensation-cyclization was set up starting from different 2-hydroxybenzophenones whose reactivity was significantly affected from the electronic properties of their substituents.

  DOI：

  10.3987/com-10-12070
• 作为产物：
  描述：

  2-(4-氯苯氧基)-3-氧代丁酸乙酯 在 PPA 作用下， 反应 2.0h， 以61.5%的产率得到ethyl 5-chloro-3-methylbenzofuran-2-carboxylate
  参考文献：
  名称：

  Selective heteronuclear NOE enhancements in benzoheterocycles. Effect of ring size on indirect three-spin effects

  摘要：

  对五种4-甲基香豆素、六种4-甲基-2(1H)-喹诺酮以及九种3-甲基苯并[b]呋喃（其中包括六种新化合物）的80 MHz 1H NMR和20 MHz 13C NMR谱进行了全面归属。在低功率预饱和甲基质子后，测量了同核1H{1H} NOE和选择性异核13C{1H} NOE。在适当的13C-1H-{1H}三自旋体系中发现了间接的负异核NOE增强，并且发现其幅度依赖于环的大小。首次描述了非质子化碳上的间接异核NOE增强的实例。

  DOI：

  10.1002/mrc.1260260615

文献信息

• Efficient synthesis of chiral benzofuryl β-amino alcohols via a catalytic asymmetric Henry reaction
  作者：Wei Chen、Zhao-Hui Zhou、Hong-Bin Chen

  DOI：10.1039/c6ob02569b

  日期：——

  Chiral β-amino alcohol ligands were found effective for the copper(II)-catalyzed asymmetric Henry reaction of benzofuran-2-carbaldehydes with nitromethane, which led to the formation of (S)-enriched benzofuryl β-nitro alcohols with satisfactory enantioselectivities (up to 98% ee). Using this catalytic protocol, bioactive (S)-benzofuryl β-amino alcohols could be conveniently prepared in short steps

  手性β氨基醇配体小号被发现有效地用于铜（II）催化苯并呋喃-2- carbaldehydes与硝基甲烷，而导致的（形成的不对称Henry反应小号）富集的苯并呋喃基β硝基醇与对映选择性令人满意（高达98％ee）。使用该催化方案，可以在短时间内方便地制备生物活性（S）-苯并呋喃基β-氨基醇。
• Discovery and Development of a Series of Pyrazolo[3,4-<i>d</i>]pyridazinone Compounds as the Novel Covalent Fibroblast Growth Factor Receptor Inhibitors by the Rational Drug Design
  作者：Yulan Wang、Yang Dai、Xiaowei Wu、Fei Li、Bo Liu、Chunpu Li、Qiufeng Liu、Yuanyang Zhou、Bao Wang、Mingrui Zhu、Rongrong Cui、Xiaoqin Tan、Zhaoping Xiong、Jia Liu、Minjia Tan、Yechun Xu、Meiyu Geng、Hualiang Jiang、Hong Liu、Jing Ai、Mingyue Zheng

  DOI：10.1021/acs.jmedchem.9b00510

  日期：2019.8.22

  which showed a highly selective and potent FGFR inhibition profile. Pharmacokinetic assessment, protein kinase profiling, and hERG inhibition evaluation were also conducted, and they confirmed the value of 15 as a lead for further investigation. Overall, this study exemplifies the importance of the integrative use of computational methods and experimental techniques in drug discovery.

  成纤维细胞生长因子受体（FGFRs）的改变在许多癌症的进展和发展中起着关键作用，这使FGFRs在癌症治疗中成为有吸引力的靶标。在本研究中，基于新设计的FGFR靶标特异性评分功能，通过虚拟筛选鉴定了一种新型FGFR抑制剂。然后，通过将分子对接和代谢位点预测与一系列体外评估和X射线共晶结构确定相结合来进行先导性最优化，从而产生共价FGFR抑制剂15，该抑制剂表现出高度的选择性和强大的FGFR抑制谱。还进行了药代动力学评估，蛋白激酶分析和hERG抑制评估，他们确定15的值可作为进一步研究的线索。全面的，
• 5-MEMBERED HETEROCYCLE FUSED WITH [3,4-D]PYRIDAZINONE, AND MANUFACTURING METHOD, PHARMACEUTICAL COMPOSITION, AND APPLICATION THEREOF
  申请人：Shanghai Institute of Materia Medica, Chinese Academy of Sciences

  公开号：EP3470415A1

  公开（公告）日：2019-04-17

  The present invention provides a compound comprising a 5-membered heterocycle fused with a pyridazinone, wherein the compound is used as an FGFR kinase inhibitor, and a manufacturing method and application thereof. The invention specifically provides a compound as represented by formula (I). Various radicals are as defined in the specification. The compound provided by the invention effectively inhibits an activity of an FGFR kinase, and can be used to manufacture a pharmaceutical product for treating a disease related to the activity of the FGFR kinase.

  本发明提供了一种化合物，该化合物包括与吡啶并嗪酮融合的5-成员杂环，其中该化合物用作FGFR激酶抑制剂，以及其制备方法和应用。该发明具体提供了一种由式（I）表示的化合物。各种基团如规范中所定义。本发明提供的化合物有效抑制FGFR激酶的活性，并可用于制造用于治疗与FGFR激酶活性相关的疾病的药物产品。
• [EN] PROTEIN KINASE C AGONISTS<br/>[FR] AGONISTES DE PROTÉINE KINASE C
  申请人：GILEAD SCIENCES INC

  公开号：WO2020176505A1

  公开（公告）日：2020-09-03

  The present disclosure relates generally to certain diacylglycerol lactone compounds, pharmaceutical compositions comprising said compounds, and methods of making and using said compounds and pharmaceutical compositions. The compounds and compositions disclosed herein may be used for the treatment or prevention of diseases, disorders, or infections modifiable by protein kinase C (PKC) agonists, such as HIV.

  本公开涉及某些二酰基甘油内酯化合物，包括该化合物的药物组合物，以及制备和使用该化合物和药物组合物的方法。本文所披露的化合物和组合物可用于治疗或预防可通过蛋白激酶C（PKC）激动剂调节的疾病、疾病或感染，如艾滋病。
• .alpha.-adrenergic receptor antagonists
  申请人：SmithKline Beecham Corporation

  公开号：US04978660A1

  公开（公告）日：1990-12-18

  .alpha.-adrenoceptor antagonists having the formula: ##STR1## which are useful to produce .alpha.-adrenoceptor antagonism, pharmaceutical compositions including these antagonists, and methods of using these antagonists to produce .alpha.-adrenoceptor antagonism in mannals.

  具有以下结构式的α-肾上腺素受体拮抗剂：##STR1##，用于产生α-肾上腺素受体拮抗作用，包括这些拮抗剂的药物组合物，以及使用这些拮抗剂在哺乳动物中产生α-肾上腺素受体拮抗作用的方法。