3-(5-methylthiophen-2-yl)propiolic acid | 1343396-45-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-(5-methylthiophen-2-yl)propiolic acid
• 英文别名: (5-Methyl-thiophen-2-YL)-propynoic acid；3-(5-methylthiophen-2-yl)prop-2-ynoic acid
• CAS: 1343396-45-1
• 化学式: C₈H₆O₂S
• 分子量: 166.2
• InChiKey: SIMRSCHSYOCVSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(5-methylthiophen-2-yl)propiolic acid 在 18-冠醚-6 、 caesium carbonate 、 联硼酸频那醇酯 作用下， 以 甲苯 为溶剂， 反应 22.5h， 以76%的产率得到
  参考文献：
  名称：

  通过无过渡金属的α硼化-原脱硼化序列对炔酸进行半还原

  摘要：

  已经开发了一种通过α-硼化和随后的原脱硼机理半还原炔酸的方法。不含过渡金属的方案是通过原位产生的羧酸酯部分活化双（频哪醇）二硼来生成的，从而生成芳基丙烯酸。我们的研究表明，羧酸根阴离子具有前所未有的双重作用，它涉及二硼试剂的活化以及在α-硼化反应中的直接作用。

  DOI：

  10.1016/j.tet.2019.02.030

文献信息

• Copper-mediated trifluoromethylation of propiolic acids: facile synthesis of α-trifluoromethyl ketones
  作者：Zhengbiao He、Rui Zhang、Mingyou Hu、Lingchun Li、Chuanfa Ni、Jinbo Hu

  DOI：10.1039/c3sc51613j

  日期：——

  Copper-mediated decarboxylative trifluoromethylation provides a new protocol for the efficient preparation of α-trifluoromethyl ketones from propiolic acids. It was found that water is involved as a reactant in the reaction, which is significantly different from the previously reported decarboxylative fluoroalkylation reactions.

  铜介导的脱羧三氟甲基化反应提供了一种新方法，可高效制备来自丙炔酸的α-三氟甲基酮。研究发现，水作为反应物参与其中，这与先前报道的脱羧氟代烷基化反应有显著差异。
• Synthesis and in silico screening of a library of β-carboline-containing compounds
  作者：Kay M Brummond、John R Goodell、Matthew G LaPorte、Lirong Wang、Xiang-Qun Xie

  DOI：10.3762/bjoc.8.117

  日期：——

  The synthesis of a library of tetrahydro-β-carboline-containing compounds in milligram quantities is described. Among the unique heterocyclic frameworks are twelve tetrahydroindolizinoindoles, six tetrahydrocyclobutanindoloquinolizinones and three tetrahydrocyclopentenoneindolizinoindolones. These compounds were selected from a virtual combinatorial library of 11,478 compounds. Physical chemical properties were calculated and most of them are in accordance with Lipinski’s rules. Virtual docking and ligand-based target evaluations were performed for the β-carboline library compounds and selected synthetic intermediates to assess the therapeutic potential of these small organic molecules. These compounds have been deposited into the NIH Molecular Repository (MLSMR) and may target proteins such as histone deacetylase 4, endothelial nitric oxide synthase, 5-hydroxytryptamine receptor 6 and mitogen-activated protein kinase 1. These in silico screening results aim to add value to the β-carboline library of compounds for those interested in probes of these targets.

  描述了以毫克为单位合成含有四氢-β-咔啉结构的化合物库。这些独特的杂环骨架中包括十二个四氢吲哚咔啉吲哚、六个四氢环丁基哌哆啉酮和三个四氢环戊酮吲哚咔啉酮。这些化合物是从一组包含11,478种化合物的虚拟组合库中选择出来的。计算了物理化学性质，大多数符合Lipinski的规则。对β-咔啉化合物库和选定的合成中间体进行了虚拟对接和基于配体的靶标评估，以评估这些小有机分子的治疗潜力。这些化合物已存入NIH分子库（MLSMR），可能靶向蛋白如组蛋白去乙酰化酶4、内皮一氧化氮合酶、5-羟色胺受体6和丝裂原活化蛋白激酶1。这些体外筛选结果旨在为对这些靶标探针感兴趣的人增加β-咔啉化合物库的价值。
• Small molecule inhibitors of the nuclear translocation of androgen receptor for the treatment of castration-resistant prostate cancer
  申请人：University of Pittsburgh—Of the Commonwealth System of Higher Education

  公开号：US10980806B2

  公开（公告）日：2021-04-20

  A compound, or a pharmaceutically acceptable salt or ester thereof, according to formula I: R20—(Z)b—(Y)c—(R21)a—(X)d—R22—R23 wherein R20 is aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, alkoxy, aryloxy, a thio-containing group, or a seleno-containing group; Z is alkanediyl, substituted alkanediyl, cycloalkanediyl, or substituted cycloalkanediyl; Y is S, O, S(═O), —S(═O)(═O)—, or NR10, wherein R10 is H or alkyl; R21 is alkanediyl, substituted alkanediyl, cycloalkanediyl, substituted cycloalkanediyl, alkadienyl, substituted alkadienyl, cycloalkenediyl, substituted cycloalkenediyl, alkatrienyl, substituted alkatrienyl; X is —C(═O)—, —S(═O)(═O)—, or —N(H)C(═O)—; R22 includes at least one divalent amino radical; R23 is aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, alkoxy, aryloxy, a thio-containing group, or a seleno-containing group; a, b, c, and d independently are 0 or 1.

  一种符合式 I 的化合物或其药学上可接受的盐或酯： R20-(Z)b-(Y)c-(R21)a-(X)d-R22-R23 其中 R20 是芳基、取代的芳基、杂芳基、取代的杂芳基、环烷基、取代的环烷基、杂环烷基、取代的杂环烷基、烷氧基、芳氧基、含硫基的基团或含硒基的基团；Z 是烷二基、取代的烷二基、环烷二基或取代的环烷二基； Y 是 S、O、S(═O)、-S(═O)(═O)- 或 NR10，其中 R10 是 H 或烷基；R21是烷二基、取代的烷二基、环烷二基、取代的环烷二基、烷二烯基、取代的烷二烯基、环烷二基、取代的环烷二基、烷三烯基、取代的烷三烯基；X是-C(═O)-、-S(═O)(═O)-或-N(H)C(═O)-；R22 包括至少一个二价氨基； R23 是芳基、取代的芳基、杂芳基、取代的杂芳基、环烷基、取代的环烷基、杂环烷基、取代的杂环烷基、烷氧基、芳氧基、含硫醚基团或含硒基团；a、b、c 和 d 独立地为 0 或 1。
• SMALL MOLECULE INHIBITOR OF THE NUCLEAR TRANSLOCATION OF ANDROGEN RECEPTOR FOR THE TREATMENT OF CASTRATION-RESISTANT PROSTATE CANCER
  申请人：University of Pittsburgh- Of the Commonwealth System of Higher Education

  公开号：EP3433239A1

  公开（公告）日：2019-01-30
• SMALL MOLECULE INHIBITORS OF THE NUCLEAR TRANSLOCATION OF ANDROGEN RECEPTOR FOR THE TREATMENT OF CASTRATION-RESISTANT PROSTATE CANCER
  申请人：University of Pittsburgh - Of the Commonwealth System of Higher Education

  公开号：US20190022093A1

  公开（公告）日：2019-01-24

  A compound, or a pharmaceutically acceptable salt or ester thereof, according to formula I: R 20 -(Z) b -(Y) c —(R 21 ) a —(X) d —R 22 —R 23 wherein R 20 is aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, alkoxy, aryloxy, a thio-containing group, or a seleno-containing group; Z is alkanediyl, substituted alkanediyl, cycloalkanediyl, or substituted cycloalkanediyl; Y is S, O, S(═O), —S(═O)(═O)—, or NR 10 , wherein R 10 is H or alkyl; R 21 is alkanediyl, substituted alkanediyl, cycloalkanediyl, substituted cycloalkanediyl, alkadienyl, substituted alkadienyl, cycloalkenediyl, substituted cycloalkenediyl, alkatrienyl, substituted alkatrienyl; X is —C(═O)—, —S(═O)(═O)—, or —N(H)C(═O)—; R 22 includes at least one divalent amino radical; R 23 is aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, alkoxy, aryloxy, a thio-containing group, or a seleno-containing group; a, b, c, and d independently are 0 or 1.