methyl 3-(phenylthio)-1H-indole-2-carboxylate | 116757-24-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 3-(phenylthio)-1H-indole-2-carboxylate
• 英文别名: methyl 3-(phenylsulfanyl)-1H-indole-2-carboxylate；methyl 3-phenylsulfanyl-1H-indole-2-carboxylate
• CAS: 116757-24-5
• 化学式: C₁₆H₁₃NO₂S
• mdl: MFCD14280820
• 分子量: 283.351
• InChiKey: ZFFZRQNMJVPVBG-UHFFFAOYSA-N

物化性质

• 溶解度：
  0.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(phenylthio)-1H-indole-2-carboxylate 在 硫代水杨酸 作用下， 以 三氟乙酸 为溶剂， 反应 0.25h， 以91%的产率得到吲哚-2-羧酸甲酯
  参考文献：
  名称：

  Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides

  摘要：

  Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction. We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring. In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched. Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides. This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.

  DOI：

  10.1021/jo00100a045
• 作为产物：
  描述：

  吲哚-2-羧酸 在 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 24.0h， 生成 methyl 3-(phenylthio)-1H-indole-2-carboxylate
  参考文献：
  名称：

  5-Chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase

  摘要：

  A series of highly potent, structurally novel, non-nucleoside RT inhibitors has been described. Low nanomolar concentrations of 5-chloro-3-(phenylsulfonyl)-indole-2-carboxamide (1) inhibit the HIV-1 RT enzyme in vitro and HTLVIIIb viral spread in MT-4 human T-lymphoid cells. Good oral bioavailability was observed in rhesus monkeys upon oral dosing of 1 as a suspension in methocel. When compared to other non-nucleoside inhibitors (e.g. 15-18), 1 possesses improved inhibitory potency with respect to the wild-type RT, as well as the K103N and Y181C mutant enzymes. Additional studies within this class of inhibitors are in progress.

  DOI：

  10.1021/jm00061a022

文献信息

• 3-substituted indole antiproliferative angiogenesis inhibitors
  申请人：——

  公开号：US20020091148A1

  公开（公告）日：2002-07-11

  3-Substituted indole carbohydrazides having the formula 1 are useful for inhibiting angiogenesis and cell proliferation. Also disclosed are compositions which inhibit angiogenesis and cell proliferation and methods of inhibiting angiogenesis and cancer in a mammal.

  具有下式的3-取代吲哚羰肼对抑制血管生成和细胞增殖具有用处。还揭示了抑制血管生成和细胞增殖的组合物以及抑制哺乳动物中的血管生成和癌症的方法。
• [EN] ARYLTHIOINDOLE TUBULIN POLYMERIZATION INHIBITORS AND METHODS OF TREATING OR PREVENTING CANCER USING SAME<br/>[FR] INHIBITEURS DE LA POLYMERISATION DE LA TUBULINE DE TYPE ARYLTHIOINDOLE, ET PROCEDES POUR TRAITER OU PREVENIR UN CANCER AU MOYEN DE CES INHIBITEURS
  申请人：HUMAN SERVICES GOVERNMENT OF T

  公开号：WO2006041961A1

  公开（公告）日：2006-04-20

  The present invention features arylthioindole compounds, pharmaceutical compositions of arylthioindole compounds and methods of treating a patient suffering from cancer or inflammatory, cardiac, or helminthic diseases, the method comprising administering to a patient one or more arylthioindole compounds of the invention.

  本发明涉及芳基硫代吲哚化合物，芳基硫代吲哚化合物的药物组合物以及治疗患有癌症或炎症、心脏病或寄生虫病的患者的方法，该方法包括向患者施用本发明的一种或多种芳基硫代吲哚化合物。
• Iodine-promoted selective 3-selanylation and 3-sulfenylation of indoles with dichalcogenides under mild conditions
  作者：Su-Qin Chen、Qian-Mei Wang、Ping-Chuan Xu、Shao-Peng Ge、Ping Zhong、Xiao-Hong Zhang

  DOI：10.1080/10426507.2014.999068

  日期：2016.1.2

  GRAPHICAL ABSTRACT Abstract A simple method was developed for the synthesis of 3-chalcogen indoles via iodine-promoted direct 3-selanyl- and 3-sulfenylation of indoles with dichalcogenides. The reaction was carried out smoothly in EtOH under air at room temperature, selectively giving a series of 3-chalcogen indoles bearing different functional groups in good to excellent yields. The procedure has

  图形摘要 摘要 开发了一种通过碘促进的吲哚与二硫属元素化物直接 3- 硒基和 3- 磺基化合成 3- 硫属元素吲哚的简单方法。该反应在室温下在 EtOH 中顺利进行，选择性地得到一系列带有不同官能团的 3-硫族吲哚，收率良好至极好。该工艺具有环境友好、操作简便、底物范围广、反应条件温和等优点。
• A New Synthesis of 3-Arylthioindoles
  作者：Joseph G. Atkinson、Pierre Hamel、Yves Girard

  DOI：10.1055/s-1988-27615

  日期：——

  The reaction of the anions of indoles with diaryl disulfides in dimethylformamide at room temperature gives the 3-arylthioindoles in 59-91% yield.

  在室温下，吲哚的阴离子与二芳基二硫化物在二甲基甲酰胺中反应生成 3-芳硫基吲哚，产率为 59-91%。
• Arylthioindoles, Potent Inhibitors of Tubulin Polymerization
  作者：Gabriella De Martino、Giuseppe La Regina、Antonio Coluccia、Michael C. Edler、Maria Chiara Barbera、Andrea Brancale、Elizabeth Wilcox、Ernest Hamel、Marino Artico、Romano Silvestri

  DOI：10.1021/jm049360d

  日期：2004.12.1

  Several arylthioindoles had excellent activity as inhibitors both of tubulin polymerization and of the growth of MCF-7 human breast carcinoma cells. Methyl 3-[(3,4,5-trimethoxyphenyl)thio]-5-methoxy-1H-indole-2-carboxylate (21), the most potent derivative, showed IC(50) = 2.0 microM, 1.6 times more active than colchicine and about as active as combretastatin A-4 (CSA4). Compound 21 inhibited the growth

  几种芳基硫代吲哚作为微管蛋白聚合和MCF-7人乳腺癌细胞生长的抑制剂均具有出色的活性。最有效的衍生物3-[（3,4,5-三甲氧基苯基）硫代] -5-甲氧基-1H-吲哚-2-羧酸甲酯（21）的IC（50）= 2.0 microM，活性是其1.6倍秋水仙碱，其活性与康维他汀A-4（CSA4）差不多。化合物21在IC（50）= 13 nM时抑制了MCF-7细胞的生长。秋水仙碱和CSA4与这些细胞分别具有13 nM和17 nM IC（50）值。