N-[3-[[(2-羟基-1-萘基)亚甲基]氨基]苯基]-α-甲基苯乙酰胺 | 1105698-15-4

• 物质功能分类: 生物化工 - 抑制剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-[3-[[(2-羟基-1-萘基)亚甲基]氨基]苯基]-α-甲基苯乙酰胺
• 英文名称: salermide
• 英文别名: N-{3-[(2-Hydroxy-naphthalen-1-ylmethylene)-amino]-phenyl}-2-phenyl-propionamide；N-[3-[(2-hydroxynaphthalen-1-yl)methylideneamino]phenyl]-2-phenylpropanamide
• CAS: 1105698-15-4
• 化学式: C₂₆H₂₂N₂O₂
• 分子量: 394.473
• InChiKey: HQSSEGBEYORUBY-UHFFFAOYSA-N

物化性质

• 沸点：
  666.7±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：>10mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P273,P280
• 危险性描述：
  H317,H412

反应信息

• 作为产物：
  描述：

  (R/S)-N-(3-aminophenyl)-2-phenylpropanamide 、 2-羟基-1-萘甲醛 在 溶剂黄146 作用下， 以 乙醇 、 苯 为溶剂， 以84%的产率得到N-[3-[[(2-羟基-1-萘基)亚甲基]氨基]苯基]-α-甲基苯乙酰胺
  参考文献：
  名称：

  Discovery of Salermide-Related Sirtuin Inhibitors: Binding Mode Studies and Antiproliferative Effects in Cancer Cells Including Cancer Stem Cells

  摘要：

  Chemical changes performed on 1a (sirtinol) led to a series of SIRT1/2 inhibitors, in some cases more potent than la mainly against SIRT1. Tested in human leukemia U937 cells, the benzamide and anilide derivatives 1b, 1c, 2b, and 2c as well as the 4-(2-phenylpropyl)thioanalogue 4c showed huge apoptosis induction, while some sulfinyl and sulfonyl derivatives (5b, 5c, and 6a-c) were highly efficient in granulocytic differentiation. When assayed in human leukemia MOLT4 as well as in human breast MDA-MB-231 and colon RKO cancer cell lines, the anilide 2b (salermide) and the phenylpropylthio analogue 4b emerged as the most potent antiproliferative agents. Tested on colorectal carcinoma and glioblastoma multiforme cancer stem cells (CSCs) from patients, 2b was particularly potent against colorectal carcinoma CSCs, while 4b, 6a, and the SIRT2-selective inhibitor AGK-2 showed the highest effect against glioblastoma multiforme CSCs. Such compounds will be further explored for their broad-spectrum anticancer properties.

  DOI：

  10.1021/jm3011614