5-trifluoromethoxy-1H-indole-2,3-dione 3-[N-(4-methylphenyl)thiosemicarbazone] | 1084893-01-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-trifluoromethoxy-1H-indole-2,3-dione 3-[N-(4-methylphenyl)thiosemicarbazone]
• 英文别名: 1-(5'-(trifluoromethoxy)isatin)-4-(4'-methylphenyl)-3-thiosemicarbazone；1-(4-methylphenyl)-3-[[2-oxo-5-(trifluoromethoxy)indol-3-yl]amino]thiourea
• CAS: 1084893-01-5
• 化学式: C₁₇H₁₃F₃N₄O₂S
• 分子量: 394.377
• InChiKey: PSPGSCAGVIUMOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.75
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-trifluoromethoxy-1H-indole-2,3-dione 3-[N-(4-methylphenyl)thiosemicarbazone] 、 2'-溴-4-氯苯乙酮 以92%的产率得到(3Z)-5-(trifluoromethoxy)-1H-indole-2,3-dione-3-{[(2Z)-4-(4-chlorophenyl)-3-(4-methylphenyl)-1,3-thiazol-2(3H)-ylidene]hydrazone}
  参考文献：
  名称：

  某些新型isatin-3-hydrazonothiazolines的合成，生物学评估和对接研究

  摘要：

  豆腐脲酶活性部位中化合物6i的推定结合方式。

  DOI：

  10.1039/c6ra10043k
• 作为产物：
  描述：

  5-三氟甲氧基吲哚-2,3-二酮 、 4-4-甲苯基-3-胺基硫脲 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 5-trifluoromethoxy-1H-indole-2,3-dione 3-[N-(4-methylphenyl)thiosemicarbazone]
  参考文献：
  名称：

  某些新型isatin-3-hydrazonothiazolines的合成，生物学评估和对接研究

  摘要：

  豆腐脲酶活性部位中化合物6i的推定结合方式。

  DOI：

  10.1039/c6ra10043k

文献信息

• [EN] THIOSEMICARBAZONES WITH MDR1 - INVERSE ACTIVITY<br/>[FR] THIOSEMICARBAZONES À ACTIVITÉ ANTI-MDR1
  申请人：US HEALTH

  公开号：WO2012033601A1

  公开（公告）日：2012-03-15

  Disclosed herein are drug compounds that have MDR-inverse activity and thus are effective against multidrug-resistant cells. Exemplary compounds disclosed herein have the structure;Formula (I). Examples of the disclosed compounds have been found to have, inter alia, efficacy in directly treating multidrug resistant cells, rendering multidrug resistant cells susceptible to other chemotherapeutics and in some instances reversing multidrug resistance.

  本文披露了具有MDR逆转活性的药物化合物，因此对多药耐药细胞有效。本文披露的示例化合物具有下列结构；公式（I）。已发现披露的化合物的示例具有直接治疗多药耐药细胞的功效，使多药耐药细胞对其他化疗药物敏感，并在某些情况下逆转多药耐药。
• Synthesis and antituberculosis activity of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives
  作者：Özlen Güzel、Nilgün Karalı、Aydın Salman

  DOI：10.1016/j.bmc.2008.08.050

  日期：2008.10

  New series of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazones 3a-t, 1-methyl-5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazones 4a-y and 5-trifluoromethoxy-1-morpholinomethyl-1H-indole-2,3-dione 3-thiosemicarbazones 5a-m were synthesized. The structures of the synthesized compounds were confirmed by spectral data and elemental analysis. The new 5-methyl/trifluoromethoxy-1H-indole-2,3-dione derivatives, along with previously synthesized 5-methyl-1H-indole-2,3-dione 3-thiosemicarbazones 6a-1, were evaluated for in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv. 5-Methyl-1H-indole-2,3-dione 3-thiosemicarbazones (3b, 3d, 3f, 6c, 6d, and 6f), 5-trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazones (3q-s) and 5-trifluoromethoxy-1-morpholinomethyl-1H-indole-2,3-dione 3-thiosemicarbazones (5e and 5j-1) were found to be the most potent inhibitors of M. tuberculosis growth described in this study. (C) 2008 Elsevier Ltd. All rights reserved.
• [EN] 5-FLUORO/5-TRIFLUOROMETHOXY-1H-INDOLE-2,3-DIONE 3-(4-PHENYLTHIOSEMICARBAZONE) DERIVATIVES AS INTERLEUKIN 1 (IL-1) ANTAGONISTS AND ANTI-PYRETIC AND/OR ANTI-INFLAMMATORY AGENTS FOR USE IN TREATING E.G. BEHÇET'S DISEASE<br/>[FR] DÉRIVÉS DE 5-FLUORO/5-TRIFLUOROMÉTHOXY-1H-INDOLE-2,3-DIONE 3-(4-PHÉNYLTHIOSEMICARBAZONE) UTILISÉS EN TANT QU'ANTAGONISTES DE L'INTERLEUKINE 1 (IL-1) ET AGENTS ANTIPYRÉTIQUES ET/OU ANTI-INFLAMMATOIRES DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT, PAR EXEMPLE, DE LA MALADIE DE BEHÇET
  申请人：ISTANBUL UNIV

  公开号：WO2021162650A1

  公开（公告）日：2021-08-19

  The present invention provides 5-fluoro/5-trifluoromethoxy-lH- indole-2,3-dione 3-(4-phenylthiosemicarbazone) derivatives of formula (IV) as interleukin 1 (IL-1) antagonists and anti-pyretic and/or anti-inflammatory agents for use in a method of treatment of Behçet's disease, atherosclerosis, diabetes, gout or Alzheimer's disease. The present invention also provides a process for the preparation of such compounds, as well as intermediates of such a process of formula (III) The present description discloses the synthesis and characterisation of exemplary intermediates and final compounds as well as pharmacological data thereof (e.g. pages 70 to 93; examples 1 to 6; tables 1 to 9; figure pages 1/11 to 11/11; figures 1 to 20). Exemplary compounds are e.g.: • l-methyl-5-fluoro-lH-indole-2,3-dione 3-[4-(4- trifluoromethylphenyl)thiosemicarbazone] (4E9-2), • l-methyl-5-fluoro-lH-indole-2,3-dione 3-[4-(4- trifluoromethoxyphenyl)thiosemicarbazone] (4E10-2). l-ethyl-5-fluoro-lH-indole-2,3-dione 3-[4-(4-trifluoromethylphenyl) thiosemicarbazone] (4E9-3),. -5-fluoro-lH-indole-2,3-dione 3-[4-(4-trifluoromethoxy phenyl) thiosemicarbazone] (4E10-3) and. l-benzyl-5-fluoro-lH-indole-2,3-dione 3-[4-(4-trifluoromethylphenyl) thiosemicarbazone] (4E9-4).
• Synthesis, biological evaluation and docking studies of some novel isatin-3-hydrazonothiazolines
  作者：Maqbool Ahmad、Humayun Pervez、Sumera Zaib、Muhammad Yaqub、Muhammad Moazzam Naseer、Shafi Ullah Khan、Jamshed Iqbal

  DOI：10.1039/c6ra10043k

  日期：——

  The putative binding mode of compound 6i in the active site of Jack bean urease.

  豆腐脲酶活性部位中化合物6i的推定结合方式。