Methyl 3-(diethylsulfamoyl)benzoate | 445298-39-5

• 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 3-(diethylsulfamoyl)benzoate
• CAS: 445298-39-5
• 化学式: C₁₂H₁₇NO₄S
• mdl: MFCD20141886
• 分子量: 271.337
• InChiKey: DDNMQVZPLKLILK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3-(diethylsulfamoyl)benzoate 在 溶剂黄146 、 肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.5h， 生成 (E)-3-(2-(4-chloro-7-hydroxy-2,3-dihydro-1H-inden-1-ylidene)hydrazinecarbonyl)-N,N-diethylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis and biological evaluation of novel (E)-N′-(2,3-dihydro-1H-inden-1-ylidene) benzohydrazides as potent LSD1 inhibitors

  摘要：

  Lysine specific demethylase 1 (LSD1) plays an important role in regulating histone lysine methylation at residues K4 and K9 on histone H3 and is recognized as an attractive therapeutic target in multiple malignancies. In this study, a series of novel (E)-N'-(2,3-dihydro-1H-inden-1-ylidene) benzohydrazides were synthesized and biologically evaluated for their potential LSD1 inhibitory effect. Among them, compounds 5a and 5n showed the most potent LSD1 inhibitory activity with IC50 values of 1.4 and 1.7 nM, respectively, which were about 10 times more potent compared with (E)-N-(1-(5-chloro-2-hydroxyphenyl) ethylidene)-3-(morpholinosulf-only) benzohydrazide (J. Med. Chem. 2013, 56, 9496-9508; as reference compound). Compounds 5a and 5n also exhibited marked anti-proliferation activities against cancer cell lines that highly expressed LSD1. These results suggest that these optimized compounds might be served as promising LSD1 inhibitors against cancer, which merit further study. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2015.06.054
• 作为产物：
  描述：

  3-氯磺酰基苯甲酸 在 硫酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 Methyl 3-(diethylsulfamoyl)benzoate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel (E)-N′-(2,3-dihydro-1H-inden-1-ylidene) benzohydrazides as potent LSD1 inhibitors

  摘要：

  Lysine specific demethylase 1 (LSD1) plays an important role in regulating histone lysine methylation at residues K4 and K9 on histone H3 and is recognized as an attractive therapeutic target in multiple malignancies. In this study, a series of novel (E)-N'-(2,3-dihydro-1H-inden-1-ylidene) benzohydrazides were synthesized and biologically evaluated for their potential LSD1 inhibitory effect. Among them, compounds 5a and 5n showed the most potent LSD1 inhibitory activity with IC50 values of 1.4 and 1.7 nM, respectively, which were about 10 times more potent compared with (E)-N-(1-(5-chloro-2-hydroxyphenyl) ethylidene)-3-(morpholinosulf-only) benzohydrazide (J. Med. Chem. 2013, 56, 9496-9508; as reference compound). Compounds 5a and 5n also exhibited marked anti-proliferation activities against cancer cell lines that highly expressed LSD1. These results suggest that these optimized compounds might be served as promising LSD1 inhibitors against cancer, which merit further study. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2015.06.054

文献信息

• COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATING OR PREVENTING PNEUMOVIRUS INFECTION AND ASSOCIATED DISEASES
  申请人：Rys David J.

  公开号：US20110305666A1

  公开（公告）日：2011-12-15

  Compounds, compositions and methods are provided for the prophylaxis and treatment of infections caused by viruses of the Pneumovirinae subfamily of Paramyxoviridae and diseases associated with such infections.
• US8119672B2
  申请人：——

  公开号：US8119672B2

  公开（公告）日：2012-02-21
• US9321739B2
  申请人：——

  公开号：US9321739B2

  公开（公告）日：2016-04-26
• Synthesis and biological evaluation of novel (E)-N′-(2,3-dihydro-1H-inden-1-ylidene) benzohydrazides as potent LSD1 inhibitors
  作者：Yang Zhou、Yan Li、Wen-Jing Wang、Pu Xiang、Xin-Mei Luo、Li Yang、Sheng-Yong Yang、Ying-Lan Zhao

  DOI：10.1016/j.bmcl.2015.06.054

  日期：2016.9

  Lysine specific demethylase 1 (LSD1) plays an important role in regulating histone lysine methylation at residues K4 and K9 on histone H3 and is recognized as an attractive therapeutic target in multiple malignancies. In this study, a series of novel (E)-N'-(2,3-dihydro-1H-inden-1-ylidene) benzohydrazides were synthesized and biologically evaluated for their potential LSD1 inhibitory effect. Among them, compounds 5a and 5n showed the most potent LSD1 inhibitory activity with IC50 values of 1.4 and 1.7 nM, respectively, which were about 10 times more potent compared with (E)-N-(1-(5-chloro-2-hydroxyphenyl) ethylidene)-3-(morpholinosulf-only) benzohydrazide (J. Med. Chem. 2013, 56, 9496-9508; as reference compound). Compounds 5a and 5n also exhibited marked anti-proliferation activities against cancer cell lines that highly expressed LSD1. These results suggest that these optimized compounds might be served as promising LSD1 inhibitors against cancer, which merit further study. (C) 2016 Published by Elsevier Ltd.