Methyl 4-[3-(4-butan-2-yloxy-3-methoxyphenyl)propanoylamino]benzoate | 1198186-99-0

• 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-[3-(4-butan-2-yloxy-3-methoxyphenyl)propanoylamino]benzoate
• CAS: 1198186-99-0
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: RIFQLTYMGBOSMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 4-[3-(4-butan-2-yloxy-3-methoxyphenyl)propanoylamino]benzoate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 C₂₁H₂₅NO₅
  参考文献：
  名称：

  Design, synthesis and preliminary biological evaluation of N-hydroxy-4-(3-phenylpropanamido)benzamide (HPPB) derivatives as novel histone deacetylase inhibitors

  摘要：

  A novel series of N-hydroxy-4-(3-phenylpropanamido)benzamide (HPPB) derivatives comprising N-hydroxybenzamide group as zinc-chelating moiety were designed, synthesized and evaluated for their ability to inhibit histone deacetylases. These compounds possessed inhibitory activity against the enzymes with IC50 values as low as 4.0 mu M. Among them, the thiophene substituted derivative 5j (IC50 = 0.3 mu M) and benzo[d][1,3]dioxole derivative 5t (IC50 = 0.4 mu M) exhibited good antiproliferative activity against the growth of human colon carcinoma cell line HCT116 and non-small cell lung cancer cell (NSCLC) line A549. In addition, they were found to potently induce cell-cycle arrest at G2 phase. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.010
• 作为产物：
  描述：

  methyl 4-(3-(4-hydroxy-3-methoxyphenyl)propanamido)benzoate 、 2-溴丁烷 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 Methyl 4-[3-(4-butan-2-yloxy-3-methoxyphenyl)propanoylamino]benzoate
  参考文献：
  名称：

  Design, synthesis and preliminary biological evaluation of N-hydroxy-4-(3-phenylpropanamido)benzamide (HPPB) derivatives as novel histone deacetylase inhibitors

  摘要：

  A novel series of N-hydroxy-4-(3-phenylpropanamido)benzamide (HPPB) derivatives comprising N-hydroxybenzamide group as zinc-chelating moiety were designed, synthesized and evaluated for their ability to inhibit histone deacetylases. These compounds possessed inhibitory activity against the enzymes with IC50 values as low as 4.0 mu M. Among them, the thiophene substituted derivative 5j (IC50 = 0.3 mu M) and benzo[d][1,3]dioxole derivative 5t (IC50 = 0.4 mu M) exhibited good antiproliferative activity against the growth of human colon carcinoma cell line HCT116 and non-small cell lung cancer cell (NSCLC) line A549. In addition, they were found to potently induce cell-cycle arrest at G2 phase. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.010

文献信息

• Design, synthesis and preliminary biological evaluation of N-hydroxy-4-(3-phenylpropanamido)benzamide (HPPB) derivatives as novel histone deacetylase inhibitors
  作者：Jie Jiao、Hao Fang、Xuejian Wang、Peng Guan、Yumei Yuan、Wenfang Xu

  DOI：10.1016/j.ejmech.2009.06.010

  日期：2009.11

  A novel series of N-hydroxy-4-(3-phenylpropanamido)benzamide (HPPB) derivatives comprising N-hydroxybenzamide group as zinc-chelating moiety were designed, synthesized and evaluated for their ability to inhibit histone deacetylases. These compounds possessed inhibitory activity against the enzymes with IC50 values as low as 4.0 mu M. Among them, the thiophene substituted derivative 5j (IC50 = 0.3 mu M) and benzo[d][1,3]dioxole derivative 5t (IC50 = 0.4 mu M) exhibited good antiproliferative activity against the growth of human colon carcinoma cell line HCT116 and non-small cell lung cancer cell (NSCLC) line A549. In addition, they were found to potently induce cell-cycle arrest at G2 phase. (C) 2009 Elsevier Masson SAS. All rights reserved.