S-ethyl (2R,3S,4R,6E,8E)-3-hydroxy-2,4-dimethyldeca-6,8-dienethioate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: S-ethyl (2R,3S,4R,6E,8E)-3-hydroxy-2,4-dimethyldeca-6,8-dienethioate
• 英文别名: (2R,3S,4R,6E,8E)-S-ethyl 3-hydroxy-2,4-dimethyldeca-6,8-dienethioate
• 化学式: C₁₄H₂₄O₂S
• 分子量: 256.409
• InChiKey: WYZLADBSDVTCAJ-SLKRCTSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-ethyl (2R,3S,4R,6E,8E)-3-hydroxy-2,4-dimethyldeca-6,8-dienethioate 在 2,6-二甲基吡啶 、 四丙基高钌酸铵 、 氯化二乙基铝 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 35.16h， 生成 ethyl 2E-3-((3S,4S,4aS,5S,6S,7R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-(tert-butyldimethylsiloxy)-3,5,7-trimethylnaphthalen-4-yl)acrylate
  参考文献：
  名称：

  Total Synthesis of AMF-26, an Antitumor Agent for Inhibition of the Golgi System, Targeting ADP-Ribosylation Factor 1

  摘要：

  An effective method for the total synthesis of 1 (AMF-26), a potentially promising new anticancer drug that disrupts the Golgi system by inhibiting the ADP-ribosylation factor 1 (Arf1) activation, has been developed for the first time. The construction of the chiral linear precursor (a key to the synthesis) was achieved by the asymmetric aldol reaction followed by the computer-assisted predictive stereoselective intramolecular Diels-Alder reaction. The global antitumor activity of the totally synthetic 1 against a variety of human cancer cells was assessed using a panel of 39 human cancer cell lines (JFCR39), and it was shown that the synthetic 1 strongly inhibited the growth of several cancer cell lines at concentrations of less than 0.04 mu M. Biological assays of novel derivatives, 26 and 31, which have different side-chains at the C-4 positions in the Delta(1,2)-octalin backbone, disclosed the importance of the suitable structure of the side-chain containing conjugated multidouble bonds.

  DOI：

  10.1021/jm301695c
• 作为产物：
  描述：

  sorbyl bromide 在 lithium aluminium tetrahydride 、 tin(II) trifluoromethanesulfonate 、 四丙基高钌酸铵 、 (R)-1-methyl-2-(1-naphthylaminomethyl)pyrrolidine 、 sodium hexamethyldisilazane 、 二乙酸二丁基锡 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.75h， 生成 S-ethyl (2R,3S,4R,6E,8E)-3-hydroxy-2,4-dimethyldeca-6,8-dienethioate
  参考文献：
  名称：

  Total Synthesis of AMF-26, an Antitumor Agent for Inhibition of the Golgi System, Targeting ADP-Ribosylation Factor 1

  摘要：

  An effective method for the total synthesis of 1 (AMF-26), a potentially promising new anticancer drug that disrupts the Golgi system by inhibiting the ADP-ribosylation factor 1 (Arf1) activation, has been developed for the first time. The construction of the chiral linear precursor (a key to the synthesis) was achieved by the asymmetric aldol reaction followed by the computer-assisted predictive stereoselective intramolecular Diels-Alder reaction. The global antitumor activity of the totally synthetic 1 against a variety of human cancer cells was assessed using a panel of 39 human cancer cell lines (JFCR39), and it was shown that the synthetic 1 strongly inhibited the growth of several cancer cell lines at concentrations of less than 0.04 mu M. Biological assays of novel derivatives, 26 and 31, which have different side-chains at the C-4 positions in the Delta(1,2)-octalin backbone, disclosed the importance of the suitable structure of the side-chain containing conjugated multidouble bonds.

  DOI：

  10.1021/jm301695c

文献信息

• JP6143266
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] NOVEL COMPOUND, METHOD FOR PRODUCING SAME AND ANTITUMOR AGENT<br/>[FR] NOUVEAU COMPOSÉ, SON PROCÉDÉ DE PRODUCTION ET AGENT ANTITUMORAL
  申请人：UNIV TOKYO SCIENCE FOUNDATION

  公开号：WO2013151161A1

  公开（公告）日：2013-10-10

  　優れた細胞傷害性を有する新規化合物及び抗がん剤を提供する。また、該新規化合物を簡便に製造する方法を提供する。　下記式（１）～（４）で表される化合物及び該化合物を有効成分として含有する抗がん剤を提供する。式（１）～（４）中、Ｒ１～Ｒ９はアルキル基等を示し、Ｒ１０は－Ｃ（Ｏ）ＯＲｄ、－Ｃ（Ｏ）ＮＲｅＲｆ等の基を示し、Ｒｄ、Ｒｅ、Ｒｆはそれぞれ独立にアルキル基等を示す。但し、式（１）においてＲ１、Ｒ３、Ｒ６、Ｒ９がメチル基であり、Ｒ４、Ｒ５、Ｒ７、Ｒ８が水素原子であり、Ｒ２がヒドロキシ基であり、Ｒ１０がメチルエステル基等である場合を除く。
• Total Synthesis of AMF-26, an Antitumor Agent for Inhibition of the Golgi System, Targeting ADP-Ribosylation Factor 1
  作者：Isamu Shiina、Yuma Umezaki、Yoshimi Ohashi、Yuta Yamazaki、Shingo Dan、Takao Yamori

  DOI：10.1021/jm301695c

  日期：2013.1.10

  An effective method for the total synthesis of 1 (AMF-26), a potentially promising new anticancer drug that disrupts the Golgi system by inhibiting the ADP-ribosylation factor 1 (Arf1) activation, has been developed for the first time. The construction of the chiral linear precursor (a key to the synthesis) was achieved by the asymmetric aldol reaction followed by the computer-assisted predictive stereoselective intramolecular Diels-Alder reaction. The global antitumor activity of the totally synthetic 1 against a variety of human cancer cells was assessed using a panel of 39 human cancer cell lines (JFCR39), and it was shown that the synthetic 1 strongly inhibited the growth of several cancer cell lines at concentrations of less than 0.04 mu M. Biological assays of novel derivatives, 26 and 31, which have different side-chains at the C-4 positions in the Delta(1,2)-octalin backbone, disclosed the importance of the suitable structure of the side-chain containing conjugated multidouble bonds.