5-[(1S,5R)-5-[(E,3S)-3-[tert-butyl(diphenyl)silyl]oxyoct-1-enyl]-4-oxocyclopent-2-en-1-yl]pentanoic acid | 1432425-62-1

• 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: 5-[(1S,5R)-5-[(E,3S)-3-[tert-butyl(diphenyl)silyl]oxyoct-1-enyl]-4-oxocyclopent-2-en-1-yl]pentanoic acid
• CAS: 1432425-62-1
• 化学式: C₃₄H₄₆O₄Si
• 分子量: 546.822
• InChiKey: PNQCUMKAYBDMQD-HDDKQZKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[(1S,5R)-5-[(E,3S)-3-[tert-butyl(diphenyl)silyl]oxyoct-1-enyl]-4-oxocyclopent-2-en-1-yl]pentanoic acid 在 氢氟酸 作用下， 以 水 、 乙腈 为溶剂， 反应 168.0h， 以68%的产率得到13-deoxy-Δ^10,12-2,3-dinor-prostaglandin J₁
  参考文献：
  名称：

  Synthesis and evaluation of 2,3-dinorprostaglandins: Dinor-PGD1 and 13-epi-dinor-PGD1 are peroxisome proliferator-activated receptor α/γ dual agonists

  摘要：

  2,3-Dinorprostaglandins (dinor-PGs) have been regarded as beta-oxidation products of arachidonic-acid-derived prostaglandins, but their biological activities in mammalian cells remain unclear. On the other hand, C18 polyunsaturated fatty acids (PUFAs), such as gamma-linolenic acid (GLA), have various biological activities, and dinor-PGs are speculated to be biosynthesized from GLA. Here, we synthesized dinor-PGs that may possibly be derived from GLA and examined their activities towards peroxisome proliferator-activated receptors (PPARs). Dinor-PGD(1) (1) and its epimer 13-epi-dinor-PGD(1) (epi-1) were found to be dual agonists for PPAR alpha/gamma, whereas PGD(2) derived from arachidonic acid is selective for PPAR gamma. Thus, GLA-derived dinor-PGs may have unique biological roles. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.024
• 作为产物：
  描述：

  科立内脂二醇 在 咪唑 、 4-二甲氨基吡啶 、 platinum(IV) oxide 、 sodium tetrahydroborate 、 copper(l) iodide 、 草酰氯 、 cerium(III) chloride heptahydrate 、 四丁基氟化铵 、 氢气 、 4-甲基苯磺酸吡啶 、 silica gel 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 戴斯-马丁氧化剂 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 76.17h， 生成 5-[(1S,5R)-5-[(E,3S)-3-[tert-butyl(diphenyl)silyl]oxyoct-1-enyl]-4-oxocyclopent-2-en-1-yl]pentanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of 2,3-dinorprostaglandins: Dinor-PGD1 and 13-epi-dinor-PGD1 are peroxisome proliferator-activated receptor α/γ dual agonists

  摘要：

  2,3-Dinorprostaglandins (dinor-PGs) have been regarded as beta-oxidation products of arachidonic-acid-derived prostaglandins, but their biological activities in mammalian cells remain unclear. On the other hand, C18 polyunsaturated fatty acids (PUFAs), such as gamma-linolenic acid (GLA), have various biological activities, and dinor-PGs are speculated to be biosynthesized from GLA. Here, we synthesized dinor-PGs that may possibly be derived from GLA and examined their activities towards peroxisome proliferator-activated receptors (PPARs). Dinor-PGD(1) (1) and its epimer 13-epi-dinor-PGD(1) (epi-1) were found to be dual agonists for PPAR alpha/gamma, whereas PGD(2) derived from arachidonic acid is selective for PPAR gamma. Thus, GLA-derived dinor-PGs may have unique biological roles. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.024

文献信息

• Synthesis and evaluation of 2,3-dinorprostaglandins: Dinor-PGD1 and 13-epi-dinor-PGD1 are peroxisome proliferator-activated receptor α/γ dual agonists
  作者：Ayato Sato、Kosuke Dodo、Makoto Makishima、Yuichi Hashimoto、Mikiko Sodeoka

  DOI：10.1016/j.bmcl.2013.03.024

  日期：2013.5

  2,3-Dinorprostaglandins (dinor-PGs) have been regarded as beta-oxidation products of arachidonic-acid-derived prostaglandins, but their biological activities in mammalian cells remain unclear. On the other hand, C18 polyunsaturated fatty acids (PUFAs), such as gamma-linolenic acid (GLA), have various biological activities, and dinor-PGs are speculated to be biosynthesized from GLA. Here, we synthesized dinor-PGs that may possibly be derived from GLA and examined their activities towards peroxisome proliferator-activated receptors (PPARs). Dinor-PGD(1) (1) and its epimer 13-epi-dinor-PGD(1) (epi-1) were found to be dual agonists for PPAR alpha/gamma, whereas PGD(2) derived from arachidonic acid is selective for PPAR gamma. Thus, GLA-derived dinor-PGs may have unique biological roles. (C) 2013 Elsevier Ltd. All rights reserved.