methyl 7-bromohept-5-ynoate | 41349-38-6

• 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: methyl 7-bromohept-5-ynoate
• 英文别名: methyl 7-bromo-5-heptynoate；7-Brom-hept-5-in-saeure-methylester；methyl 7-bromoheptynoate；7-bromo-hept-5-ynoic acid methyl ester；7-bromo-5-heptynoic acid methyl ester；Methyl-7-Bromo-5-heptynoate
• CAS: 41349-38-6
• 化学式: C₈H₁₁BrO₂
• 分子量: 219.078
• InChiKey: ORMJOYKCTLOKIS-UHFFFAOYSA-N

物化性质

• 沸点：
  150 °C(Press: 0.3 Torr)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 7-bromohept-5-ynoate 在 Lindlar's catalyst 、 对甲苯磺酸 lithium hydroxide 、 copper(l) iodide 、 正丁基锂 、 水 、 氢气 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 68.5h， 生成 10(S),11(R),12(R)-trihydroxyeicosa-5(Z),8(Z),14(Z)-trienoic acid
  参考文献：
  名称：

  Stereoselective synthesis of 10(S), 11(R), 12(R)-trihydroxyeicosa-5(Z), 8(Z), 14(Z)-trienoic acid from d-mannose

  摘要：

  A stereoselective synthesis of the title compound, from D-mannose using base induced double elimination of beta-alkoxy chloride as key step is described.

  DOI：

  10.1016/s0040-4039(00)77695-7
• 作为产物：
  描述：

  7-氯庚-2-炔-1-醇 在 吡啶 、 jones reagent 、 三溴化磷 、 potassium carbonate 、 PEG 400 作用下， 以 甲醇 、 四氯化碳 、 乙醚 、 水 、 丙酮 为溶剂， 反应 19.25h， 生成 methyl 7-bromohept-5-ynoate
  参考文献：
  名称：

  Theil, Fritz; Henning, Mechthild; Schick, Hans, Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 6, p. 917 - 922

  摘要：

  DOI：

文献信息

• 16-Ethers of 8-aza-9-dioxothia-11,12-seco-prostaglandins
  申请人：Merck & Co., Inc.

  公开号：US03991106A1

  公开（公告）日：1976-11-09

  The invention is concerned with novel 16-aryloxy-, 16-alkoxy-, 16-arylthio- and 16-alkylthio-8-aza-9-dioxothia-11,12-seco-prostaglandins and processes for their preparation. These novel compounds are useful as pharmaceuticals since they can be used in animals for estrus synchronization and treatment of infertility due to persistence of luteal function.

  这项发明涉及新颖的16-芳基氧基、16-烷氧基、16-芳基硫基和16-烷基硫基-8-氮杂-9-二氧硫-11,12-脱环前列腺素以及它们的制备方法。这些新颖化合物可用作药物，因为它们可用于动物的发情同步和由黄体功能持续引起的不孕症的治疗。
• Substituted phenoxy-tridecanoic acids
  申请人：Merck & Co., Inc.

  公开号：US04020177A1

  公开（公告）日：1977-04-26

  This invention relates to aryloxy-, and alkoxy-, arylthio-, and alkylthio-11,12-seco-prostaglandins and to processes for their manufacture. These compounds have prostaglandin-like activity and are particularly useful in fertility control such as for estrus synchronization in animals and postcoital contraceptive agents in humans.

  该发明涉及芳氧基、烷氧基、芳硫基和烷硫基11,12-脱环前列腺素及其制备方法。这些化合物具有类似前列腺素的活性，特别适用于生育控制，如动物的发情同步和人类的事后避孕药剂。
• Discovery of an 8-Aza-5-thiaProstaglandin E1 Analog as a Highly Selective EP4 Receptor Agonist
  作者：Tohru Kambe、Toru Maruyama、Atsushi Naganawa、Masaki Asada、Akiteru Seki、Takayuki Maruyama、Hisao Nakai、Masaaki Toda

  DOI：10.1248/cpb.59.1494

  日期：——

  For the purpose of discovering an orally available EP4 subtype-selective agonist, a series of 8-aza prostaglandin E1 (PGE1) analogs were synthesized and evaluated for their affinity for PGE2 receptor subtypes. Additionally, the structure–activity relationships of these compounds were studied. Among the tested compounds, the 8-aza PGE1 analog 6 and 8-aza-5-thiaPGE1 analog 12 had highly potent EP4 receptor affinity, good functional activity, and excellent subtype-selectivity. Furthermore, these analogs demonstrated good stability in human liver microsomes. As a result, we concluded that these two series of 8-aza PGE1 analogs could be promising chemical leads for an orally available EP4 subtype-selective agonist.

  为了发现一种口服可用的EP4亚型选择性激动剂，合成并评估了一系列8-氮原子前列腺素E1（PGE1）类似物对PGE2受体亚型的亲和力。此外，还研究了这些化合物的结构-活性关系。在测试的化合物中，8-氮PGE1类似物6和8-氮-5-硫PGE1类似物12对EP4受体具有高效的亲和力、良好的功能活性和优异的亚型选择性。此外，这些类似物在人体肝微粒体中表现出良好的稳定性。因此，我们得出结论，这两系列的8-氮PGE1类似物可能是口服可用的EP4亚型选择性激动剂的有前景的化学先导物。
• CoA-IT and PAF inhibitors
  申请人：SmithKline Beecham Corporation

  公开号：US05648373A1

  公开（公告）日：1997-07-15

  Coenzyme A-independent transacylase is required for the release of free arachidonic acid, and the production of arachidonic acid metabolites and platelet activation factor. Blocking of this enzyme inhibits the production of these inflammatory mediators and will be of therapeutic utility in a broad range of allergic and inflammatory diseases and disorders. Compounds are described herein which inhibit the action of CoA-IT and are therefore useful in the treatment of disease states caused thereby.

  无需辅酶A的转酰基酶在释放游离花生四烯酸、产生花生四烯酸代谢产物和血小板活化因子时起作用。阻断该酶会抑制这些炎症介质的产生，在广泛的过敏和炎症性疾病和障碍中具有治疗效用。本文描述的化合物可以抑制CoA-IT的作用，因此在治疗由此引起的疾病状态中是有用的。
• Synthesis of new secoprostaglandins as inducers of platelet aggregation.
  作者：TOSHIO TANAKA、KIYOSHI BANNAI、TAKESHI TORU、TAKEO OBA、NORIAKI OKAMURA、KENZO WATANABE、SEIZI KUROZUMI

  DOI：10.1248/cpb.30.51

  日期：——

  Two series of 8-acetyl-12-hydroxyalkadienoic acids and 14-hydroxy-9-oxoalkadienoic acids, which can be regarded as 11, 12-and 8, 12-secoprostaglandin E2, were synthesized and evaluated for biological activity on platelet function. Key members of each series, 11, 12-and 8, 12-seco-11-norprostaglandin E2, were found to induce platelet aggregation. This effect was inhibited by preincubation of PRP with prostaglandin I2 but was not inhibited by indomethacin.

  合成了两系列的8-乙酰基-12-羟基烯二烯酸和14-羟基-9-氧烯二烯酸，这些化合物可以视为11, 12-和8, 12-秒前列腺素E2，并评估了它们对血小板功能的生物活性。每个系列的关键成员，11, 12-和8, 12-秒-11-去羟基前列腺素E2，被发现能够诱导血小板聚集。该效应被前处理的血小板富血浆与前列腺素I2组合抑制，但并未被吲哚美辛抑制。