n-hexadecanoic acid [3-(2,5-dimethylbenzyloxy)-4-(N-methanesulfonyl-N-methylamino)phenyl]amide | 1357168-41-2

• 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: n-hexadecanoic acid [3-(2,5-dimethylbenzyloxy)-4-(N-methanesulfonyl-N-methylamino)phenyl]amide
• 英文别名: Hexadecanoic acid [3-(2,5-dimethyl-benzyloxy)-4-(methanesulfonyl-methyl-amino)-phenyl]-amide；N-[3-[(2,5-dimethylphenyl)methoxy]-4-[methyl(methylsulfonyl)amino]phenyl]hexadecanamide
• CAS: 1357168-41-2
• 化学式: C₃₃H₅₂N₂O₄S
• 分子量: 572.853
• InChiKey: FRPYEGLJZREFAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  40
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,5-二甲基苄氯 在 iron(III) chloride 、 水 、 sodium hydride 、 potassium carbonate 、 sodium hydroxide 、 锌 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 n-hexadecanoic acid [3-(2,5-dimethylbenzyloxy)-4-(N-methanesulfonyl-N-methylamino)phenyl]amide
  参考文献：
  名称：

  From COX-2 inhibitor nimesulide to potent anti-cancer agent: Synthesis, in vitro, in vivo and pharmacokinetic evaluation

  摘要：

  Cyclooxygenase-2 (COX-2) inhibitor nimesulide inhibits the proliferation of various types of cancer cells mainly via COX-2 independent mechanisms, which makes it a good lead compound for anti-cancer drug development. In the presented study, a series of new nimesulide analogs were synthesized based on the structure function analysis generated previously. Some of them displayed very potent anti-cancer activity with IC(50)s around 100 nM-200 nM to inhibit SKBR-3 breast cancer cell growth. CSUOH0901 (NSC751382) from the compound library also inhibits the growth of the 60 cancer cell lines used at National Cancer Institute Developmental therapeutics Program (NCIDTP) with IC(50)s around 100 nM-500 nM. Intraperitoneal injection with a dosage of 5 mg/kg/d of CSUOH0901 to nude mice suppresses HT29 colorectal xenograft growth. Pharmacokinetic studies demonstrate the good bioavailability of the compound. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.11.012

文献信息

• From COX-2 inhibitor nimesulide to potent anti-cancer agent: Synthesis, in vitro, in vivo and pharmacokinetic evaluation
  作者：Bo Zhong、Xiaohan Cai、Snigdha Chennamaneni、Xin Yi、Lili Liu、John J. Pink、Afshin Dowlati、Yan Xu、Aimin Zhou、Bin Su

  DOI：10.1016/j.ejmech.2011.11.012

  日期：2012.1

  Cyclooxygenase-2 (COX-2) inhibitor nimesulide inhibits the proliferation of various types of cancer cells mainly via COX-2 independent mechanisms, which makes it a good lead compound for anti-cancer drug development. In the presented study, a series of new nimesulide analogs were synthesized based on the structure function analysis generated previously. Some of them displayed very potent anti-cancer activity with IC(50)s around 100 nM-200 nM to inhibit SKBR-3 breast cancer cell growth. CSUOH0901 (NSC751382) from the compound library also inhibits the growth of the 60 cancer cell lines used at National Cancer Institute Developmental therapeutics Program (NCIDTP) with IC(50)s around 100 nM-500 nM. Intraperitoneal injection with a dosage of 5 mg/kg/d of CSUOH0901 to nude mice suppresses HT29 colorectal xenograft growth. Pharmacokinetic studies demonstrate the good bioavailability of the compound. Published by Elsevier Masson SAS.