methyl 3-(1H-indol-1-ylsulfonyl)benzoate | 1609171-99-4

• 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-(1H-indol-1-ylsulfonyl)benzoate
• 英文别名: methyl 3-(indole-1-ylsulfonyl) benzoate
• CAS: 1609171-99-4
• 化学式: C₁₆H₁₃NO₄S
• 分子量: 315.35
• InChiKey: VPIKTXCQPHDPQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65.37
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3-(1H-indol-1-ylsulfonyl)benzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 3-(1H-indol-1-ylsulfonyl)benzaldehyde
  参考文献：
  名称：

  Azaindolylsulfonamides, with a More Selective Inhibitory Effect on Histone Deacetylase 6 Activity, Exhibit Antitumor Activity in Colorectal Cancer HCT116 Cells

  摘要：

  A series of indolylsulfonylcinnamic hydroxamates has been synthesized. Compound 12, (E)-3-(3-((1H-pyrrolo[2,3-b]pyridin-1-yl)sulfonyl)phenyl)-N-hydroxyacrylamide, which has a 7-azaindole core cap, was shown to have antiproliferative activity against KB, H460, PC3, HSC-3, HONE-1, A549, MCF-7, TSGH, MKN45, HT29, and HCT116 human cancer cell lines. Pharmacological studies indicated that 12 functions as a potent HDAC inhibitor with an IC50 value of 0.1 mu M. It is highly selective for histone deacetylase 6 (HDAC6) and is 60-fold more active than against HDAC1 and 223-fold more active than against HDAC2. It has a good pharmacokinetic profile with oral bioavailability of 33%. In in vivo efficacy evaluations in colorectal HCT116 xenografts, compound 12 suppresses tumor growth more effectively than SAHA (1, N-hydroxy-N'-phenyloctanediamide) and is therefore seen as a suitable candidate for further investigation.

  DOI：

  10.1021/jm401899x
• 作为产物：
  描述：

  吲哚 、 3-(氯磺酰基)苯甲酸甲酯 在 四丁基硫酸氢铵 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到methyl 3-(1H-indol-1-ylsulfonyl)benzoate
  参考文献：
  名称：

  Azaindolylsulfonamides, with a More Selective Inhibitory Effect on Histone Deacetylase 6 Activity, Exhibit Antitumor Activity in Colorectal Cancer HCT116 Cells

  摘要：

  A series of indolylsulfonylcinnamic hydroxamates has been synthesized. Compound 12, (E)-3-(3-((1H-pyrrolo[2,3-b]pyridin-1-yl)sulfonyl)phenyl)-N-hydroxyacrylamide, which has a 7-azaindole core cap, was shown to have antiproliferative activity against KB, H460, PC3, HSC-3, HONE-1, A549, MCF-7, TSGH, MKN45, HT29, and HCT116 human cancer cell lines. Pharmacological studies indicated that 12 functions as a potent HDAC inhibitor with an IC50 value of 0.1 mu M. It is highly selective for histone deacetylase 6 (HDAC6) and is 60-fold more active than against HDAC1 and 223-fold more active than against HDAC2. It has a good pharmacokinetic profile with oral bioavailability of 33%. In in vivo efficacy evaluations in colorectal HCT116 xenografts, compound 12 suppresses tumor growth more effectively than SAHA (1, N-hydroxy-N'-phenyloctanediamide) and is therefore seen as a suitable candidate for further investigation.

  DOI：

  10.1021/jm401899x

文献信息

• Design, synthesis, and antiviral activity of phenylalanine derivatives as HIV-1 capsid inhibitors
  作者：Jing Li、Xiangyi Jiang、Alexej Dick、Prem Prakash Sharma、Chin-Ho Chen、Brijesh Rathi、Dongwei Kang、Zhao Wang、Xiangkai Ji、Kuo-Hsiung Lee、Simon Cocklin、Xinyong Liu、Peng Zhan

  DOI：10.1016/j.bmc.2021.116414

  日期：2021.10