(2R)-2-amino-3-((1-(3-hydroxyphenyl)-1,2-diphenylethyl)sulfanyl)propanoic acid | 1394240-11-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2R)-2-amino-3-((1-(3-hydroxyphenyl)-1,2-diphenylethyl)sulfanyl)propanoic acid
• 英文别名: (2R)-2-amino-3-[1-(3-hydroxyphenyl)-1,2-diphenylethyl]sulfanylpropanoic acid
• CAS: 1394240-11-9
• 化学式: C₂₃H₂₃NO₃S
• 分子量: 393.507
• InChiKey: MAMGUVPVCXVLOC-BBQAJUCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苄基氯化镁 在 三氟化硼乙醚 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 (2R)-2-amino-3-((1-(3-hydroxyphenyl)-1,2-diphenylethyl)sulfanyl)propanoic acid
  参考文献：
  名称：

  Doing the methylene shuffle – Further insights into the inhibition of mitotic kinesin Eg5 with S-trityl l-cysteine

  摘要：

  S-Trityl L-cysteine (STLC) is an inhibitor of the mitotic kinesin Eg5 with potential as an antimitotic chemotherapeutic agent. We previously reported the crystal structure of the ligand protein complex, and now for the first time, have quantified the interactions using a molecular dynamics based approach. Based on these data, we have explored the SAR of the trityl head group using the methylene shuffle strategy to expand the occupation of one of the hydrophobic pockets. The most potent compounds exhibit strong (<100 nM) inhibition of Eg5 in the basal ATPase assay and inhibit growth in a variety of tumour-derived cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.034

文献信息

• Doing the methylene shuffle – Further insights into the inhibition of mitotic kinesin Eg5 with S-trityl l-cysteine
  作者：Murad N. Abualhasan、James A.D. Good、Kitiyaporn Wittayanarakul、Nahoum G. Anthony、Giacomo Berretta、Oliver Rath、Frank Kozielski、Oliver B. Sutcliffe、Simon P. Mackay

  DOI：10.1016/j.ejmech.2012.05.034

  日期：2012.8

  S-Trityl L-cysteine (STLC) is an inhibitor of the mitotic kinesin Eg5 with potential as an antimitotic chemotherapeutic agent. We previously reported the crystal structure of the ligand protein complex, and now for the first time, have quantified the interactions using a molecular dynamics based approach. Based on these data, we have explored the SAR of the trityl head group using the methylene shuffle strategy to expand the occupation of one of the hydrophobic pockets. The most potent compounds exhibit strong (<100 nM) inhibition of Eg5 in the basal ATPase assay and inhibit growth in a variety of tumour-derived cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.