N-(4’-methoxyphenyl)-2-(2-oxo-5-(trifluoromethoxy)-indoline-3-ylidene)hydrazinecarbothioamide | 1084893-02-6

• 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: N-(4’-methoxyphenyl)-2-(2-oxo-5-(trifluoromethoxy)-indoline-3-ylidene)hydrazinecarbothioamide
• 英文别名: 5-trifluoromethoxy-1H-indole-2,3-dione 3-[N-(4-methoxyphenyl)thiosemicarbazone]；1-(5'-(trifluoromethoxy)isatin)-4-(4'-methoxyphenyl)-3-thiosemicarbazone；1-(4-methoxyphenyl)-3-[[2-oxo-5-(trifluoromethoxy)indol-3-yl]amino]thiourea
• CAS: 1084893-02-6
• 化学式: C₁₇H₁₃F₃N₄O₃S
• 分子量: 410.376
• InChiKey: NKVTWYIBTADJGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.98
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  吗啉 、 聚合甲醛 、 N-(4’-methoxyphenyl)-2-(2-oxo-5-(trifluoromethoxy)-indoline-3-ylidene)hydrazinecarbothioamide 以 乙醇 为溶剂， 反应 10.0h， 以90%的产率得到5-trifluoromethoxy-1-(morpholin-4-ylmethyl)-1H-indole-2,3-dione 3-[N-(4-methoxyphenyl)thiosemicarbazone]
  参考文献：
  名称：

  Synthesis and antituberculosis activity of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.08.050
• 作为产物：
  描述：

  4-甲氧基苯基 异硫氰酸酯 在 盐酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 N-(4’-methoxyphenyl)-2-(2-oxo-5-(trifluoromethoxy)-indoline-3-ylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  Pape, Veronika F.S.; Tóth, Szilárd; Füredi, András, European Journal of Medicinal Chemistry, 2016, vol. 117, p. 335 - 354

  摘要：

  DOI：

文献信息

• 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。
• [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。
• 5‐Fluoro/(trifluoromethoxy)‐2‐indolinone derivatives with anti‐interleukin‐1 activity
  作者：Özge Soylu‐Eter、Zekiye Şeyma Sevinçli、Betül Ersoy、Bahar Hasanusta、Uğur Gatfar、Nathan A. Lack、Burak Erman、Ahmet Gül、Hakan S. Orer、Nilgün Karalı

  DOI：10.1002/ardp.202300217

  日期：2023.12

  2-indolinone derivatives in preliminary studies to develop agents with anti-IL-1 activity. First, the putative efficacies and binding interactions of 2-indolinones were evaluated by docking studies. Second, previously synthesized 5-fluoro/(trifluoromethoxy)−1H-indole-2,3-dione 3-(4-phenylthiosemicarbazones) (compounds 47–69) which had the highest inhibitory effect in the screening were evaluated for inhibitory

  促炎细胞因子白介素-1 (IL-1) 驱动多种炎症性疾病的发病机制。最近的研究表明，2-吲哚酮可以调节细胞因子反应。因此，我们在初步研究中筛选了几种2-二氢吲哚酮衍生物，以开发具有抗IL-1活性的药物。首先，通过对接研究评估了 2-吲哚酮的假定功效和结合相互作用。其次，评估了先前合成的在筛选中具有最高抑制效果的5-氟/(三氟甲氧基)−1 H-吲哚-2,3-二酮3-(4-苯硫代缩氨基脲)（化合物47-69 ）的抑制效果。 IL-1 受体 (IL-1R)。选择化合物52 (IC 50 = 0.09 µM) 和65 (IC 50 = 0.07 µM) 作为先导化合物，用于随后合成新衍生物。设计、合成了新型5-氟/(三氟甲氧基)−1 H-吲哚-2,3-二酮3-(4-苯硫代缩氨基脲)（化合物70-116 ），并完成了体外研究。测试的化合物76 、 78 、 81 、 91 、 100 、 105和107在
• 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.
• Pape, Veronika F.S.; Tóth, Szilárd; Füredi, András, European Journal of Medicinal Chemistry, 2016, vol. 117, p. 335 - 354
  作者：Pape, Veronika F.S.、Tóth, Szilárd、Füredi, András、Szebényi, Kornélia、Lovrics, Anna、Szabó, Pál、Wiese, Michael、Szakács, Gergely

  DOI：——

  日期：——