AMF-26

• 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: AMF-26
• 英文别名: 2-methylcoprophilinamide；M-Copa；(2E,4E)-5-[(1S,2S,4aR,6R,7S,8S,8aS)-7-hydroxy-2,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-2-methyl-N-(pyridin-3-ylmethyl)penta-2,4-dienamide
• 化学式: C₂₅H₃₄N₂O₂
• 分子量: 394.557
• InChiKey: JQPHOWVAGGEOKI-VXBYPBBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  sorbyl bromide 在 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 tin(II) trifluoromethanesulfonate 、 四丙基高钌酸铵 、 (R)-1-methyl-2-(1-naphthylaminomethyl)pyrrolidine 、 2-甲基-6-硝基苯甲酸酐 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 二乙酸二丁基锡 、 N-甲基吗啉氧化物 、 lithium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 156.83h， 生成 AMF-26
  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

• OCTAHYDRONAPHTHALENE DERIVATIVE AND MEDICINE
  申请人：Nippon Shinyaku Co., Ltd.

  公开号：EP1702910A1

  公开（公告）日：2006-09-20

  It is an object of the invention to provide a novel octahydronaphthalene derivative with an activity of inhibiting ICAM-4 expression and a pharmaceutically acceptable salt thereof. The invention encompasses, for example, agents for suppressing ICAM-1, therapeutic agents for inflammatory diseases, therapeutic agents for rheumatoid arthritis, immunosuppressive agents, and agents for suppressing cell growth, comprising N-(pyridin-3-ylmethyl)-(2E,4E)-5-[(1S,2S,4aR,6R,7S,8S,8aS)-7-hydroxy-2,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-2-methylpenta-2,4-dienamide as an active ingredient.

  本发明的目的是提供一种具有抑制 ICAM-4 表达活性的新型八氢萘衍生物及其药学上可接受的盐。本发明包括例如抑制 ICAM-1 的制剂、炎症性疾病的治疗剂、类风湿性关节炎的治疗剂、免疫抑制剂和抑制细胞生长的制剂、包含 N-(吡啶-3-基甲基)-(2E,4E)-5-[(1S,2S,4aR,6R,7S,8S,8aS)-7-羟基-2,6,8-三甲基-1,2,4a,5,6,7,8,8a-八氢萘-1-基]-2-甲基戊-2,4-二酰胺作为活性成分。
• EP1702910
  申请人：——

  公开号：——

  公开（公告）日：——
• JP6143266
  申请人：——

  公开号：——

  公开（公告）日：——
• EP1702910A4
  申请人：——

  公开号：EP1702910A4

  公开（公告）日：2007-11-07
• Octahydronaphtalene derivative and medicine
  申请人：Yamada Naoyoshi

  公开号：US20070142539A1

  公开（公告）日：2007-06-21

  It is an object of the invention to provide a novel octahydronaphthalene derivative with an activity of inhibiting ICAM-4 expression and a pharmaceutically acceptable salt thereof. The invention encompasses, for example, agents for suppressing ICAM-1, therapeutic agents for inflammatory diseases, therapeutic agents for rheumatoid arthritis, immunosuppressive agents, and agents for suppressing cell growth, comprising N-(pyridin-3-ylmethyl)-(2E,4E)-5-[(1S,2S,4aR,6R,7S,8S,8aS)-7-hydroxy-2,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-2-methylpenta-2,4-dienamide as an active ingredient.