1-hydroxy-6-(N-methyl-N-phenylsulfamoyl)-1H-indole-2-carboxylic acid | 1303571-04-1

• 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: 1-hydroxy-6-(N-methyl-N-phenylsulfamoyl)-1H-indole-2-carboxylic acid
• 英文别名: 1-hydroxy-6-[N-methyl-N-phenylsulfamoyl]-1H-indol-2-carboxylic acid；1-Hydroxy-6-[methyl(phenyl)sulfamoyl]indole-2-carboxylic acid
• CAS: 1303571-04-1
• 化学式: C₁₆H₁₄N₂O₅S
• 分子量: 346.364
• InChiKey: UECBZSJONLAMBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲基-3-硝基苯磺酰氯 在 sodium hypophosphite monohydrate 、 palladium 10% on activated carbon 、 水 、 sodium hydride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.0h， 生成 1-hydroxy-6-(N-methyl-N-phenylsulfamoyl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of sulfonamide-containing N-hydroxyindole-2-carboxylates as inhibitors of human lactate dehydrogenase-isoform 5

  摘要：

  N-Hydroxyindole-2-carboxylates possessing sulfonamide-substituents at either position 5 or 6 were designed and synthesized. The inhibitory activities of these compounds against isoforms 1 and 5 of human lactate dehydrogenase were analysed, and K-i values of the most efficient inhibitors were determined by standard enzyme kinetic studies. Some of these compounds displayed state-of-the-art inhibitory potencies against isoform 5 (K-i values as low as 5.6 mu M) and behaved as competitive inhibitors versus both the substrate and the cofactor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.031

文献信息

• [EN] COMPOUNDS INHIBITORS OF ENZYME LACTATE DEHYDROGENASE (LDH) AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS D'ENZYME LACTATE DÉSHYDROGÉNASE (LDH) ET COMPOSITIONS PHARMACEUTIQUES CONTENANT CES COMPOSÉS
  申请人：UNIV PISA

  公开号：WO2011054525A1

  公开（公告）日：2011-05-12

  The present invention concerns compounds, some of which are novel, and their pharmaceutical applications. The compounds of the invention inhibit the enzyme lactate dehydrogenase (LDH) involved both in the metabolic process of hypoxic tumour cells, and in the process used by parasitic protozoa that cause malaria to obtain most of the energy they need.

  这项发明涉及化合物，其中一些是新颖的，以及它们的药用应用。该发明的化合物抑制乳酸脱氢酶（LDH）酶，该酶参与低氧肿瘤细胞的代谢过程，以及疟疾引起的寄生原虫利用获取所需大部分能量的过程。
• COMPOUNDS INHIBITORS OF ENZYME LACTATE DEHYDROGENASE (LDH) AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE COMPOUNDS
  申请人：Universita Di Pisa

  公开号：EP2499114A1

  公开（公告）日：2012-09-19
• LDH INHIBITORS AS TREATMENT FOR FIBROSIS AND FIBROTIC-RELATED DISORDERS
  申请人：Kottmann Robert M.

  公开号：US20150335674A1

  公开（公告）日：2015-11-26

  One aspect of the disclosure relates to methods of treating a fibrotic condition in an individual. The methods include administering to an individual having a fibrotic condition an effective amount of a lactic dehydrogenase (LDH) inhibitor, wherein the fibrotic condition involves an internal organ or tissue, or ocular tissue, and said administering is effective to treat the fibrotic condition. Methods of administration and pharmaceutical compositions and systems for practicing such methods are also disclosed.
• US9750761B2
  申请人：——

  公开号：US9750761B2

  公开（公告）日：2017-09-05
• Synthesis of sulfonamide-containing N-hydroxyindole-2-carboxylates as inhibitors of human lactate dehydrogenase-isoform 5
  作者：Carlotta Granchi、Sarabindu Roy、Marco Mottinelli、Elisa Nardini、Fabio Campinoti、Tiziano Tuccinardi、Mario Lanza、Laura Betti、Gino Giannaccini、Antonio Lucacchini、Adriano Martinelli、Marco Macchia、Filippo Minutolo

  DOI：10.1016/j.bmcl.2011.10.031

  日期：2011.12

  N-Hydroxyindole-2-carboxylates possessing sulfonamide-substituents at either position 5 or 6 were designed and synthesized. The inhibitory activities of these compounds against isoforms 1 and 5 of human lactate dehydrogenase were analysed, and K-i values of the most efficient inhibitors were determined by standard enzyme kinetic studies. Some of these compounds displayed state-of-the-art inhibitory potencies against isoform 5 (K-i values as low as 5.6 mu M) and behaved as competitive inhibitors versus both the substrate and the cofactor. (C) 2011 Elsevier Ltd. All rights reserved.