Tert-butyl-[4-(1,3-dithian-2-yl)-4-methylpentoxy]-dimethylsilane | 1380328-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: Tert-butyl-[4-(1,3-dithian-2-yl)-4-methylpentoxy]-dimethylsilane
• CAS: 1380328-06-2
• 化学式: C₁₆H₃₄OS₂Si
• 分子量: 334.663
• InChiKey: ALRJHVZJJIHZQK-UHFFFAOYSA-N

物化性质

• 沸点：
  373.9±22.0 °C(predicted)
• 密度：
  0.967±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Tert-butyl-[4-(1,3-dithian-2-yl)-4-methylpentoxy]-dimethylsilane 、 (R)-2-((2R,3R)-7-(3-(benzyloxy)phenyl)-3-((4-methoxybenzyl)oxy)heptan-2-yl)oxirane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S,4R)-1-[2-[5-[tert-butyl(dimethyl)silyl]oxy-2-methylpentan-2-yl]-1,3-dithian-2-yl]-4-[(4-methoxyphenyl)methoxy]-3-methyl-8-(3-phenylmethoxyphenyl)octan-2-ol
  参考文献：
  名称：

  JP6170908

  摘要：

  公开号：

文献信息

• Structure–Activity Studies on the Spiroketal Moiety of a Simplified Analogue of Debromoaplysiatoxin with Antiproliferative Activity
  作者：Masayuki Kikumori、Ryo C. Yanagita、Harukuni Tokuda、Nobutaka Suzuki、Hiroshi Nagai、Kiyotake Suenaga、Kazuhiro Irie

  DOI：10.1021/jm300566h

  日期：2012.6.14

  Aplog-1, a simplified analogue of tumor-promoting debromoaplysiatoxin, is antiproliferative but not tumor-promoting. Our recent study has suggested that local hydrophobicity around the spiroketal moiety is a crucial determinant for antiproliferative activity. To further clarify the structural features relevant to the activity, we synthesized two methyl derivatives of aplog-1, where a methyl group was installed at position 4 or 10 of the spiroketal moiety. 10-Methyl-aplog-1 (5) bound to the C1B domains of novel PKCs (delta, eta and theta) with subnanomolar K-i values, approximately 10-20 times stronger than aplog-1, and markedly inhibited the growth of many human cancer cell lines, while 4-methyl-aplog-1 (4) had levels of activity similar to those of aplog-1. Interestingly, 5 showed little tumor-promoting activity unlike the tumor promoter debromoaplysiatoxin. These results suggest that 5 is a potent PKC ligand without tumor-promoting activity and could be a therapeutic lead for the treatment of cancer, like bryostatins.