5,7-dichloro-1H-indole-2,3-dione 3-[N-(4-sulfamoylphenyl)thiosemicarbazone]

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,7-dichloro-1H-indole-2,3-dione 3-[N-(4-sulfamoylphenyl)thiosemicarbazone]
• 英文别名: 2-(5,7-dichloro-2-oxo-1,2-dihydro-3H-indole-3-yliden)-N-(4-sulphamoylphenyl)hydrazinecarbothioamide；1-[(5,7-dichloro-2-oxoindol-3-yl)amino]-3-(4-sulfamoylphenyl)thiourea
• 化学式: C₁₅H₁₁Cl₂N₅O₃S₂
• 分子量: 444.322
• InChiKey: ALRWEUNFASKTRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 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：
  0.0
• 拓扑面积：
  125.68
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-异硫氰基苯磺酰胺 在 硫酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 5,7-dichloro-1H-indole-2,3-dione 3-[N-(4-sulfamoylphenyl)thiosemicarbazone]
  参考文献：
  名称：

  Novel sulfonamide-containing 2-indolinones that selectively inhibit tumor-associated alpha carbonic anhydrases

  摘要：

  Human carbonic anhydrases IX and XII are upregulated in many tumors and form a novel target for new generation anticancer drugs. Here we report the synthesis of novel 2-indolinone derivatives with the sulfonamide group as a zinc binding moiety. Enzyme inhibition assays confirmed that the compounds showed selectivity against hCA IX and XII over the widely distributed off-targets hCA I and II. Molecular modelling studies were performed to suggest modes of binding for these compounds. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.05.029

文献信息

• [EN] N-[(AMINOSULFONYL)PHENYL]-2-(1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)-HYDRAZINECARBOTHIOAMIDE DERIVATIVES FOR TREATING CANCER AND IMMUNOLOGICAL DISORDERS<br/>[FR] DÉRIVÉS DE N-[(AMINOSULFONYL)PHÉNYL]-2-(1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDÈNE)-HYDRAZINECARBOTHIOAMIDE POUR LE TRAITEMENT DU CANCER ET DE TROUBLES IMMUNOLOGIQUES
  申请人：ISTANBUL UNIV REKTORLUGU

  公开号：WO2017099695A1

  公开（公告）日：2017-06-15

  N-[(aminosulfonyl)phenyl]-2-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)-hydrazinecarbothioamide derivatives of the following formula (III) for treating cancer and immunological disorders. R5, R6 and R7 are each independently selected from hydrogen and a sulfonamide group, provided that at least one of R5, R6 or R7 is a sulfonamide group. The substituents R1 to R4 are each independently either hydrogen or one of the substituents defined in the claims.
• Novel sulfonamide-containing 2-indolinones that selectively inhibit tumor-associated alpha carbonic anhydrases
  作者：Nilgün Karalı、Atilla Akdemir、Füsun Göktaş、Pınar Eraslan Elma、Andrea Angeli、Merih Kızılırmak、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2017.05.029

  日期：2017.7

  Human carbonic anhydrases IX and XII are upregulated in many tumors and form a novel target for new generation anticancer drugs. Here we report the synthesis of novel 2-indolinone derivatives with the sulfonamide group as a zinc binding moiety. Enzyme inhibition assays confirmed that the compounds showed selectivity against hCA IX and XII over the widely distributed off-targets hCA I and II. Molecular modelling studies were performed to suggest modes of binding for these compounds. (C) 2017 Elsevier Ltd. All rights reserved.