ethyl 3-(phenylsulfonyl)-1H-indole-2-carboxylate | 158561-81-0

• 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: ethyl 3-(phenylsulfonyl)-1H-indole-2-carboxylate
• 英文别名: 1H-Indole-2-carboxylic acid, 3-(phenylsulfonyl)-, ethyl ester；ethyl 3-(benzenesulfonyl)-1H-indole-2-carboxylate
• CAS: 158561-81-0
• 化学式: C₁₇H₁₅NO₄S
• 分子量: 329.376
• InChiKey: YZXUMFYPHQKYIU-UHFFFAOYSA-N

物化性质

• 熔点：
  148-149 °C
• 沸点：
  574.9±35.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(phenylsulfonyl)-1H-indole-2-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以100%的产率得到3-(phenylsulfonyl)-1H-indole-2-carbohydrazide
  参考文献：
  名称：

  Novel Indolyl Aryl Sulfones Active against HIV-1 Carrying NNRTI Resistance Mutations:  Synthesis and SAR Studies

  摘要：

  The potent anti-HIV-1 activities of L-737,126 (2) and PAS sulfones prompted us to design and test against HIV-1 in acutely infected MT-4 cells a number of novel 1- and 3-benzenesulfonylindoles. Indoles belonging to the 1-benzenesulfonyl series were found poorly or totally inactive. On the contrary, some of the 3-benzenesulfonyl derivatives turned out to be as potent as 2, being endowed with potencies in the low nanomolar concentration range. In particular, (2-methylphenyl)sulfonyl (72) and (3-methylphenyl)sulfonyl (73) derivatives showed EC50 values of 1 nM. Introduction of two methyl groups at positions 3 and 5 of the phenyl ring of 2 furnished derivatives (80 and 83) which showed very potent and selective anti-HIV-1 activity not only against the wt strain, but also against mutants carrying NNRTI-resistant mutations at positions 103 and 181 of the reverse transcriptase gene.

  DOI：

  10.1021/jm0211063
• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 4.8h， 生成 ethyl 3-(phenylsulfonyl)-1H-indole-2-carboxylate
  参考文献：
  名称：

  芳硫基吲哚，微管蛋白聚合的有效抑制剂。

  摘要：

  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。

  DOI：

  10.1021/jm049360d

文献信息

• InBr3-catalyzed sulfonation of indoles: a facile synthesis of 3-sulfonyl indoles
  作者：J.S. Yadav、B.V.S. Reddy、A.D. Krishna、T. Swamy

  DOI：10.1016/s0040-4039(03)01507-7

  日期：2003.8

  Indoles react smoothly with sulfonyl chlorides in the presence of a catalytic amount of indium tribromide at ambient temperature to afford the corresponding 3-arylsulfonyl indole derivatives in high yields with high regioselectivity.

  吲哚在环境温度下在催化量的三溴化铟存在下与磺酰氯平稳反应，以高收率和高区域选择性提供相应的3-芳基磺酰基吲哚衍生物。
• [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。
• [EN] PHOSPHOINDOLES AS HIV INHIBITORS<br/>[FR] PHOSPHOINDOLES UTILISÉS EN TANT QU'INHIBITEURS DU VIH
  申请人：IDENIX CAYMAN LTD

  公开号：WO2006054182A2

  公开（公告）日：2006-05-26

  (EN) 3-phosphoindole compounds for the treatment of retroviral infections, and particularly for HIV, are described. Also included are compositions comprising the 3-­phosphoindole derivatives alone or in combination with one or more other anti-retroviral agents, processes for their preparation, and methods of manufacturing a medicament incorporating these compounds.(FR) L'invention concerne des composés 3-phosphoindole utilisés pour le traitement d'infections rétrovirales, et en particulier du VIH. L'invention concerne des compositions comprenant les dérivés 3-phosphoindole seuls ou en combinaison avec un ou d'autres agents rétroviraux, leurs procédés de préparation, ainsi que procédés de fabrication d'un médicament comprenant lesdits composés.

  (FR) L'invention concerne des composés 3-phosphoindole utilisés pour le traitement d'infections rétrovirales, et en particulier du VIH. L'invention concerne des compositions comprenant les dérivés 3-phosphoindole seuls ou en combinaison avec un ou d'autres agents rétroviraux, leurs procédés de préparation, ainsi que procédés de fabrication d'un médicament comprenant lesdits composés.
• PHOSPHOINDOLES AS HIV INHIBITORS
  申请人：IDENIX Pharmaceuticals, Inc.

  公开号：EP1799696A2

  公开（公告）日：2007-06-27
• Novel Indolyl Aryl Sulfones Active against HIV-1 Carrying NNRTI Resistance Mutations:  Synthesis and SAR Studies
  作者：Romano Silvestri、Gabriella De Martino、Giuseppe La Regina、Marino Artico、Silvio Massa、Laura Vargiu、Massimo Mura、Anna Giulia Loi、Tiziana Marceddu、Paolo La Colla

  DOI：10.1021/jm0211063

  日期：2003.6.1

  The potent anti-HIV-1 activities of L-737,126 (2) and PAS sulfones prompted us to design and test against HIV-1 in acutely infected MT-4 cells a number of novel 1- and 3-benzenesulfonylindoles. Indoles belonging to the 1-benzenesulfonyl series were found poorly or totally inactive. On the contrary, some of the 3-benzenesulfonyl derivatives turned out to be as potent as 2, being endowed with potencies in the low nanomolar concentration range. In particular, (2-methylphenyl)sulfonyl (72) and (3-methylphenyl)sulfonyl (73) derivatives showed EC50 values of 1 nM. Introduction of two methyl groups at positions 3 and 5 of the phenyl ring of 2 furnished derivatives (80 and 83) which showed very potent and selective anti-HIV-1 activity not only against the wt strain, but also against mutants carrying NNRTI-resistant mutations at positions 103 and 181 of the reverse transcriptase gene.