1-<15-(3-iodophenyl)pentadecanoyl>-2-acetyl-3-O-trityl-rac-glycerol | 121269-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-<15-(3-iodophenyl)pentadecanoyl>-2-acetyl-3-O-trityl-rac-glycerol
• 英文别名: 1-[15-(3-iodophenyl)pentadecanoyl]-2-acetyl-3-O-trityl-rac-glycerol；1-[15-(m-iodophenyl)pentadecanoyl]-2-acetyl-3-O-trityl-rac-glycerol；(2-acetyloxy-3-trityloxypropyl) 15-(3-iodophenyl)pentadecanoate
• CAS: 121269-76-9
• 化学式: C₄₅H₅₅IO₅
• 分子量: 802.833
• InChiKey: XOJVRGFYICTYCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  51
• 可旋转键数：
  26
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-<15-(3-iodophenyl)pentadecanoyl>-2-acetyl-3-O-trityl-rac-glycerol 在 硼酸 、 silica gel 作用下， 以 Petroleum ether 为溶剂， 以74%的产率得到1-[15-(m-iodophenyl)pentadecanoyl]-2-acetyl-rac-glycerol
  参考文献：
  名称：

  Iodoaryl analogs of dioctanoylglycerol and 1-oleoyl-2-acetylglycerol as probes for protein kinase C

  摘要：

  Analogues of dioctanoylglycerol (diC8) and 1-oleoyl-2-acetylglycerol (OAG) containing an iodoaryl group have been synthesized and shown to compete with [3H]phorbol dibutyrate [( ([3H]PDBu) for binding to protein kinase C in a crude rat brain preparation. Phorbol diesters have been shown to bind specifically to protein kinase C and the PDBu receptor has been copurified with protein kinase C activity. All three diacylglycerol analogues were comparable to OAG in binding affinity. In an assay of protein kinase C activation, the diC8 analogue was more active than the OAG analogues, thus demonstrating greater structural specificity under the conditions of this assay.

  DOI：

  10.1021/jm00129a014
• 作为产物：
  描述：

  methyl 15-(3-nitrophenyl)pentadec-12-enoate 在 palladium on activated charcoal 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 氢气 、 碘 、 N,N'-二环己基碳二亚胺 、 potassium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 乙酸乙酯 、 苯 为溶剂， 反应 14.75h， 生成 1-<15-(3-iodophenyl)pentadecanoyl>-2-acetyl-3-O-trityl-rac-glycerol
  参考文献：
  名称：

  Iodoaryl analogs of dioctanoylglycerol and 1-oleoyl-2-acetylglycerol as probes for protein kinase C

  摘要：

  Analogues of dioctanoylglycerol (diC8) and 1-oleoyl-2-acetylglycerol (OAG) containing an iodoaryl group have been synthesized and shown to compete with [3H]phorbol dibutyrate [( ([3H]PDBu) for binding to protein kinase C in a crude rat brain preparation. Phorbol diesters have been shown to bind specifically to protein kinase C and the PDBu receptor has been copurified with protein kinase C activity. All three diacylglycerol analogues were comparable to OAG in binding affinity. In an assay of protein kinase C activation, the diC8 analogue was more active than the OAG analogues, thus demonstrating greater structural specificity under the conditions of this assay.

  DOI：

  10.1021/jm00129a014

文献信息

• Radioiodinated diacylglycerol analogues and methods of use
  申请人：The University of Michigan

  公开号：US04925649A1

  公开（公告）日：1990-05-15

  Novel iodinated and radioiodinated 1,2-diacylglycerol analogues are biological reagents for studying the effect of diacylglycerols in the activation of protein kinase C. This calcium-requiring enzyme may be involved in tumor promotion by phorbol diesters and related compounds. Iodinated and radioiodinated 1,2-diacylglycerol analogues, in accordance with the invention, are useful as imaging agents, such as radiopaques and radiopharmaceuticals, and have the general formula: ##STR1## The triglycerol backbone structure is 1,2-disubstituted with one position being occupied by an iodine-containing substituent, preferably an amino-substituted-2,4,6-triiodophenyl aliphatic chain, such as iopanoic acid, or by a monoiodiphenyl aliphatic chain, such as (m-iodophenyl)propanoic acid. The other position may be substituted with saturated and unsaturated long and short aliphatic chains.

  新型碘化和放射碘化的1,2-二酰基甘油类似物是用于研究二酰基甘油在激活蛋白激酶C中的作用的生物试剂。这种需要钙离子的酶可能参与了佛波酯和相关化合物的肿瘤促进作用。根据本发明，碘化和放射碘化的1,2-二酰基甘油类似物可用作成像剂，如放射性造影剂和放射性药物，其通式如下：##STR1## 三酰甘油骨架结构被1,2-二取代，其中一个位置被含碘取代基占据，优选为氨基取代的2,4,6-三碘苯基脂肪链，如碘丙酸或单碘苯基脂肪链，如（m-碘苯基）丙酸。另一个位置可以被饱和和不饱和的长短脂肪链取代。
• COUNSELL, RAYMOND E.;STAWN, LAURIE
  作者：COUNSELL, RAYMOND E.、STAWN, LAURIE

  DOI：——

  日期：——
• US4925649A
  申请人：——

  公开号：US4925649A

  公开（公告）日：1990-05-15