3-(苯磺酰基)-1H-吲哚-2-甲酰胺 | 540740-84-9

• 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
• 中文名称: 3-(苯磺酰基)-1H-吲哚-2-甲酰胺
• 英文名称: 1H-Indole-2-carboxamide, 3-(phenylsulfonyl)-
• 英文别名: 3-(benzenesulfonyl)-1H-indole-2-carboxamide
• CAS: 540740-84-9
• 化学式: C₁₅H₁₂N₂O₃S
• 分子量: 300.338
• InChiKey: FZZBOGZHKTXPHC-UHFFFAOYSA-N

物化性质

• 熔点：
  226-227 °C
• 沸点：
  612.8±40.0 °C(Predicted)
• 密度：
  1.437±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 在 ammonium hydroxide 、 三氟化硼乙醚 、 氯化铵 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 5.5h， 生成 3-(苯磺酰基)-1H-吲哚-2-甲酰胺
  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

文献信息

• 3-ARYLTHIOINDOLE-2-CARBOXAMIDE DERIVATIVES AND ANALOGS THEREOF AS INHIBITORS OF CASEIN KINASE I
  申请人：METZ Arthur William

  公开号：US20070142454A1

  公开（公告）日：2007-06-21

  The present invention relates to methods for treating a patient suffering from a disease or disorder of the central nervous system associated with the disturbance of the human circadian clock that are ameliorated by inhibition of casein kinase Iε activity such as, for example, mood disorders including major depressive disorder, bipolar I disorder and bipolar II disorder, and sleep disorders including circadian rhythm sleep disorders such as, for example, shift work sleep disorder, jet lag syndrome, advanced sleep phase syndrome and delayed sleep phase syndrome, comprising administering to said patient a therapeutically effective amount of a compound of formula I. its stereoisomer, enantiomer, racemate, tautomer or pharmaceutically acceptable salt thereof,

  本发明涉及一种治疗中枢神经系统疾病或障碍的方法，该疾病或障碍与人类昼夜节律紊乱有关，该方法通过抑制酪蛋白激酶Iε活性来改善，例如情绪障碍，包括重度抑郁障碍、双相I型障碍和双相II型障碍，以及睡眠障碍，包括昼夜节律睡眠障碍，例如轮班工作睡眠障碍、时差综合症、睡眠相位提前综合症和睡眠相位延后综合症，包括向该患者施用公式I化合物的治疗有效量，其立体异构体、对映异构体、外消旋体、互变异构体或其药学上可接受的盐。
• Phenylindoles for the treatment of HIV
  申请人：LaColla Paulo

  公开号：US20070293668A1

  公开（公告）日：2007-12-20

  The invention as disclosed herein is a method and composition for the treatment of HIV in humans and other host animals, that includes the administration of an effective HIV treatment amount of a phenylindole as described herein or a pharmaceutically acceptable salt or prodrug thereof, optionally in a pharmaceutically acceptable carrier. The compounds of this invention either possess antiviral (i.e., anti-HIV) activity, or are metabolized to a compound that exhibits such activity.

  本发明公开了一种用于治疗人类和其他宿主动物HIV的方法和组合物，包括给予所述的苯基吲哚或其药学上可接受的盐或前药的有效HIV治疗剂量，可选地在药学上可接受的载体中。本发明的化合物具有抗病毒（即抗HIV）活性，或代谢为表现出这种活性的化合物。
• US8008340B2
  申请人：——

  公开号：US8008340B2

  公开（公告）日：2011-08-30
• [EN] 3-ARYLTHIOINDOLE-2-CARBOXAMIDE DERIVATIVES AND ANALOGS THEREOF AS INHIBITORS OF CASEIN KINASE Ie<br/>[FR] DÉRIVÉS DES 3-ARYLTHIOINDOLE-2-CARBOXAMIDES ET ANALOGUES DE CEUX-CI EN TANT QU'INHIBITEURS DE LA CASÉINE KINASE Ie
  申请人：AVENTIS PHARMA INC

  公开号：WO2006023590A1

  公开（公告）日：2006-03-02

  The present invention relates to methods for treating a patient suffering from diseases or disorders of the central nervous system associated with the disturbance of the human circadian clock that are ameliorated by inhibition of casein kinase Iϵ activity such as , for example, mood disorders including major depressive disorder, bipolar I disorder and bipolar II disorder, and sleep disorders including circadian rhythm sleep disorders such as, for example, shift work sleep disorder, jet lag syndrome, advanced sleep phase syndrome and delayed sleep phase syndrome, with 3-arylthioindole-2-carboxamides, 5-substituted-3-arylthioindole-2-carboxamides and related analogues.
• 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.