3-(1,4-dioxo-5-sulfamoyl-1,4-dihydronaphthalen-2-ylamino)cyclohexanecarboxylic acid | 1529793-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(1,4-dioxo-5-sulfamoyl-1,4-dihydronaphthalen-2-ylamino)cyclohexanecarboxylic acid
• 英文别名: 3-[(1,4-Dioxo-5-sulfamoylnaphthalen-2-yl)amino]cyclohexane-1-carboxylic acid；3-[(1,4-dioxo-5-sulfamoylnaphthalen-2-yl)amino]cyclohexane-1-carboxylic acid
• CAS: 1529793-15-4
• 化学式: C₁₇H₁₈N₂O₆S
• 分子量: 378.406
• InChiKey: GZTXFXISXWOBIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  143.63
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1-萘磺酰胺 在 chromium(VI) oxide 、 copper(II) acetate monohydrate 作用下， 以 水 、 溶剂黄146 、 三氟乙酸 为溶剂， 反应 0.3h， 生成 3-(1,4-dioxo-5-sulfamoyl-1,4-dihydronaphthalen-2-ylamino)cyclohexanecarboxylic acid
  参考文献：
  名称：

  Regioselective one-pot C–N coupling of substituted naphthoquinones: selective intramolecular ring fusion of sulfonamides

  摘要：

  The first one-pot copper-catalyzed highly regioselective C - N bond formation between aryl/alkyl amines and sulfonamide-substituted naphthoquinones was accomplished. Facile chemoselective routes obtained diverse ring-opening 6-amino/anilino-naphthalen-dione-1-sulfonamides and ring-fused 6-amino/aniline5H-naphth[1,8-cd]isothiazol-5-one,1,1 -dioxides with great functional group tolerance. Regiochemistry was confirmed by 1D- and 2D-NMRs. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.041

文献信息

• Discovery of an Orally Selective Inhibitor of Signal Transducer and Activator of Transcription 3 Using Advanced Multiple Ligand Simultaneous Docking
  作者：Wenying Yu、Chenglong Li、Wenda Zhang、Yuanzheng Xia、Shanshan Li、Jia-yuh Lin、Keqin Yu、Mu Liu、Lei Yang、Jianguang Luo、Yijun Chen、Hongbin Sun、Lingyi Kong

  DOI：10.1021/acs.jmedchem.6b01489

  日期：2017.4.13

  Targeting signal transducer and activator of transcription 3 (STAT3) is a potential anticancer strategy. However, STAT3 inhibitors with good selectivity and bioavailability are rare. The aim of this study was to discover selective direct STAT3 inhibitors with good druglikeness. By the advanced multiple ligand simultaneous docking (AMLSD) method, compound 9 was designed as an orally bioavailable STAT3 inhibitor that presented superior druggability and selectivity compared with other representative STAT3 inhibitors. 9 directly and selectively inhibited the pY705 site of STAT3 with an affinity (K-i) of 440 nM. The IC50 of 9 for MDA-MB-231 breast cancer cells was 184-fold lower than its IC50 for MCF-10A normal breast epithelial cells. 9 in vivo induced significant antitumor responses (better than gefitinib), and its therapeutic index should be over 100, indicating good safety of 9.
• Regioselective one-pot C–N coupling of substituted naphthoquinones: selective intramolecular ring fusion of sulfonamides
  作者：Wenying Yu、Chenglong Li

  DOI：10.1016/j.tet.2013.11.041

  日期：2014.1

  The first one-pot copper-catalyzed highly regioselective C - N bond formation between aryl/alkyl amines and sulfonamide-substituted naphthoquinones was accomplished. Facile chemoselective routes obtained diverse ring-opening 6-amino/anilino-naphthalen-dione-1-sulfonamides and ring-fused 6-amino/aniline5H-naphth[1,8-cd]isothiazol-5-one,1,1 -dioxides with great functional group tolerance. Regiochemistry was confirmed by 1D- and 2D-NMRs. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.