prostaglandin A₁ methyl ester | 16887-11-9

• 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: prostaglandin A₁ methyl ester
• 英文别名: Prostaglandin A1 methyl ester；methyl 7-[(1R,2S)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopent-3-en-1-yl]heptanoate
• CAS: 16887-11-9
• 化学式: C₂₁H₃₄O₄
• 分子量: 350.499
• InChiKey: YZBRCGCRYAHOHV-DQUZTPNMSA-N

物化性质

• 沸点：
  467.9±45.0 °C(predicted)
• 密度：
  1.046±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  prostaglandin A₁ methyl ester 在 双氧水 、 氯化铵 、 sodium hydroxide 、 锌 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 36.0h， 生成 甲基前列腺素E1
  参考文献：
  名称：

  合成前列腺素A1和E1甲基酯时的罐经济性

  摘要：

  运气：前列腺素调节广泛的生理过程，其某些衍生物被用作有效药物，但以前它们的制备需要许多步骤。通过使用最近开发的有机催化剂和涉及多个连续反应的实用一锅操作，可以在少量合成步骤中有效合成标题化合物。

  DOI：

  10.1002/anie.201209380
• 作为产物：
  描述：

  methyl 7-(3-hydroxy-2-nitro-5-((E)-3-oxooct-1-enyl)cyclopentyl)heptanoate 在 三乙烯二胺 、 aluminum oxide 、 N,N-二异丙基乙胺 、 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 90.5h， 生成 prostaglandin A₁ methyl ester
  参考文献：
  名称：

  合成前列腺素A1和E1甲基酯时的罐经济性

  摘要：

  运气：前列腺素调节广泛的生理过程，其某些衍生物被用作有效药物，但以前它们的制备需要许多步骤。通过使用最近开发的有机催化剂和涉及多个连续反应的实用一锅操作，可以在少量合成步骤中有效合成标题化合物。

  DOI：

  10.1002/anie.201209380

文献信息

• Chemical Implications for Antitumor and Antiviral Prostaglandins:  Reaction of Δ⁷-Prostaglandin A₁ and Prostaglandin A₁ Methyl Esters with Thiols
  作者：Masaaki Suzuki、Makoto Mori、Terutake Niwa、Ryu Hirata、Kyoji Furuta、Toshihisa Ishikawa、Ryoji Noyori

  DOI：10.1021/ja9628359

  日期：1997.3.1

  Prostaglandins (PGs) such as Delta(12)-PGJ(2) and Delta(7)-PGA(1) methyl ester that possess a cross-conjugated dienone unit exhibit unique antitumor and antiviral activities independent of intracellular cAMP levels. These compounds are transported reversibly into cultured cells and accumulate in nuclei via covalent interaction, eliciting growth inhibition. PGA(1) methyl ester, a simple cyclopentenone analog, is less potent. The unique cellular behavior of the dienone PGs correlates well with their chemical properties. The PGs react specifically with thiol nucleophiles such as glutathione. Michael addition of thiols to Delta(7)-PGA(1) methyl ester, an alkylidenecyclopentenone derivative, occurs facilely at the endocyclic C(11) position rather than at the C(7) position. This process is reversible, and in solution phase, the adducts are in equilibrium with considerable amounts of free PG and thiols. However, the reaction of this PG with Sephatose-bound thiols, regarded to be plausible mimics of protein thiols, is irreversible, and the resulting adducts are dissociated only by alkali treatment. On the other hand, PGA(1) methyl ester reacts with soluble or polymer-anchored thiols at lower rates than Delta(7)-PGA(1) methyl ester, but the resulting thiol adducts are substantially more stable than those of the dienone PGs. This tendency of the PGA(1) methyl ester causes its equilibrium to shift to the adduct formation. The reversibility of the Michael reaction of PGs with thiols is consistent with their intracellular behavior and biological activities. Since glutathione adducts of PGs have no antiproliferative activities for cancer cells, the intracellular free PGs are presumed to interact with target molecules to cause cell growth inhibition. The involvement of the ATP-dependent glutathione S-conjugate export pump (GS-X pump) in the efflux of PGs is discussed. Thus, the marked difference in potency of the dienone and enone PGs is explained by considering the combined kinetic and thermodynamic properties and the action of the GS-X pump.
• Pot Economy in the Synthesis of Prostaglandin A₁and E₁Methyl Esters
  作者：Yujiro Hayashi、Shigenobu Umemiya

  DOI：10.1002/anie.201209380

  日期：2013.3.18

  Pot luck: Prostaglandins regulate a broad range of physiological processes and some of their derivatives are used as effective drugs, but previously their preparation has required many steps. The title compounds were efficiently synthesized in a small number of synthetic steps by using a recently developed organocatalyst and practical, one‐pot operations involving several successive reactions.

  运气：前列腺素调节广泛的生理过程，其某些衍生物被用作有效药物，但以前它们的制备需要许多步骤。通过使用最近开发的有机催化剂和涉及多个连续反应的实用一锅操作，可以在少量合成步骤中有效合成标题化合物。