methyl 4-(N,4-dimethyl-3-nitrophenylsulfonamido)benzoate | 1350916-05-0

• 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: methyl 4-(N,4-dimethyl-3-nitrophenylsulfonamido)benzoate
• 英文别名: Methyl 4-[methyl-(4-methyl-3-nitrophenyl)sulfonylamino]benzoate；methyl 4-[methyl-(4-methyl-3-nitrophenyl)sulfonylamino]benzoate
• CAS: 1350916-05-0
• 化学式: C₁₆H₁₆N₂O₆S
• 分子量: 364.379
• InChiKey: SYLLPINLEWCTLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-(N,4-dimethyl-3-nitrophenylsulfonamido)benzoate 在 tin(II) chloride dihdyrate 、 sodium hydride 、 苯硫酚 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 0.08h， 生成 methyl 1-hydroxy-6-(N-(4-(methoxycarbonyl)phenyl)-N-methylsulfamoyl)-1H-indole-2-carboxylate
  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
• 作为产物：
  描述：

  4-甲基-3-硝基苯磺酰氯 、 4-(甲氨基)苯甲酸甲酯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到methyl 4-(N,4-dimethyl-3-nitrophenylsulfonamido)benzoate
  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

• 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.