[(1S,4aS,5R,6S,8aS)-5-[(2-chloro-5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-5,6,8a-trimethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]methyl 6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate | 188477-72-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1S,4aS,5R,6S,8aS)-5-[(2-chloro-5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-5,6,8a-trimethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]methyl 6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 188477-72-7
• 化学式: C₃₃H₅₀ClNO₇
• 分子量: 608.216
• InChiKey: SUJLRGFRKUYUCY-HYVDHHNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1S,4aS,5R,6S,8aS)-5-[(2-chloro-5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-5,6,8a-trimethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]methyl 6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate 在 四(三苯基膦)钯 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.17h， 以16%的产率得到[(1S,4aS,5R,6S,8aS)-5-[(2-hydroxy-5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-5,6,8a-trimethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]methyl 6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
  参考文献：
  名称：

  研究水泡介导的蛋白质贩运的新工具：非基于放射性同位素的抗分泌试验中伊马醌类似物的合成和评估。

  摘要：

  已经制备了具有类似生物活性的海洋海绵状代谢产物伊利马醌的结构变体。通过新颖的，基于非放射性同位素的分泌测定法筛选了这些类似物以及相关的天然产物对高尔基体的影响。该测定法已鉴定出含有通用接头基团但仍保留天然产物的细胞活性的伊马醌的变体。这种功能性的ilimaquinone类似物将是研究细胞内蛋白运输的有价值的工具。

  DOI：

  10.1021/jo962292l
• 作为产物：
  描述：

  叔丁氧羰酰基6-氨基己酸 在 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 17.25h， 生成 [(1S,4aS,5R,6S,8aS)-5-[(2-chloro-5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-5,6,8a-trimethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]methyl 6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
  参考文献：
  名称：

  研究水泡介导的蛋白质贩运的新工具：非基于放射性同位素的抗分泌试验中伊马醌类似物的合成和评估。

  摘要：

  已经制备了具有类似生物活性的海洋海绵状代谢产物伊利马醌的结构变体。通过新颖的，基于非放射性同位素的分泌测定法筛选了这些类似物以及相关的天然产物对高尔基体的影响。该测定法已鉴定出含有通用接头基团但仍保留天然产物的细胞活性的伊马醌的变体。这种功能性的ilimaquinone类似物将是研究细胞内蛋白运输的有价值的工具。

  DOI：

  10.1021/jo962292l

文献信息

• Photoaffinity study of the cellular interactions of ilimaquinone
  作者：Heike S. Radeke、Marc L. Snapper

  DOI：10.1016/s0968-0896(98)00100-x

  日期：1998.8

  The marine sponge metabolite ilimaquinone (1) displays a broad range of biological activities. To better understand the effects of this natural product, a photoaffinity analogue was synthesized and used to probe the cellular interactions of ilimaquinone. Irradiation of photoaffinity probe 5 with liver cytosol in the presence and absence of excess competitive inhibitor 2 suggests that S-adenosylhomocysteinase is an important intracellular target of ilimaquinone. (C) 1998 Elsevier Science Ltd. All rights reserved.
• S -adenosylmethionine reverses ilimaquinone's vesiculation of the Golgi apparatus
  作者：Rebecca L Casaubon、Marc L Snapper

  DOI：10.1016/s0960-894x(00)00617-x

  日期：2001.1

  The marine sponge metabolite ilimaquinone has a wide range of biological activities, including vesiculation of the Golgi apparatus and interference with intracellular protein trafficking. Some of these activities may arise from ilimaquinone's influence on the activated methyl cycle. To visualize the morphological effects of ilimaquinone on the Golgi apparatus, NRK (normal rat kidney) cells were labeled with fluorescent wheat germ agglutinin and treated with ilimaquinone in the presence and absence of the methylating agent S-adenosylmethionine (SAMe). While ilimaquinone alone fragments the Golgi apparatus, the organelle remains intact when SAMe is included in the incubation mixture. This observation supports ilimaquinone's interaction with methylation enzymes as the cause of Golgi vesiculation. The examination of a fluorescently labeled ilimaquinone analogue in NRK cells suggests that the cellular interactions of ilimaquinone are not localized to the Golgi apparatus. (C) 2001 Published by Elsevier Science Ltd.
• New Tools for Studying Vesicular-Mediated Protein Trafficking:  Synthesis and Evaluation of Ilimaquinone Analogs in a Non-Radioisotope-Based Antisecretory Assay
  作者：Heike S. Radeke、Cheryl A. Digits、Steven D. Bruner、Marc L. Snapper

  DOI：10.1021/jo962292l

  日期：1997.5.1

  Structural variants of the marine sponge metabolite ilimaquinone, with comparable biological activity, have been prepared. These analogs, as well as related natural products, were screened for their effects on the Golgi apparatus through a novel, non-radioisotope-based secretion assay. The assay has identified a variant of ilimaquinone that contains a versatile linker group yet retains the natural

  已经制备了具有类似生物活性的海洋海绵状代谢产物伊利马醌的结构变体。通过新颖的，基于非放射性同位素的分泌测定法筛选了这些类似物以及相关的天然产物对高尔基体的影响。该测定法已鉴定出含有通用接头基团但仍保留天然产物的细胞活性的伊马醌的变体。这种功能性的ilimaquinone类似物将是研究细胞内蛋白运输的有价值的工具。