methyl 8-hydroxy-5-octynoate | 85924-38-5

• 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 8-hydroxy-5-octynoate
• 英文别名: 8-hydroxy-oct-5-ynoic acid methyl ester；Methyl 8-hydroxyoct-5-ynoate
• CAS: 85924-38-5
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: PLHUQXLGDPCPPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 8-hydroxy-5-octynoate 在 dirhodium tetraacetate 咪唑 、 sodium tetrahydroborate 、 正丁基锂 、 jones reagent 、 cerium(III) chloride 、 copper(I) bromide dimethylsulfide complex 、 四溴化碳 、 草酸氯化物 、 四丁基氟化铵 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 、 苯 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Synthesis of ± 8- and 9-HETEs

  摘要：

  DOI：

  10.1016/s0040-4039(01)91141-4
• 作为产物：
  描述：

  5-氯戊炔 在 sodium hydroxide 、 正丁基锂 、 三氟化硼乙醚 作用下， 以 乙醚 、 乙醇 、 二甲基亚砜 为溶剂， 反应 20.08h， 生成 methyl 8-hydroxy-5-octynoate
  参考文献：
  名称：

  Total synthesis of (.+-.)-12-hydroxy-5,8,14-cis-10-trans-eicosatetraenoic acid (12-HETE)

  摘要：

  DOI：

  10.1021/jo00222a054

文献信息

• Synthesis of three potential inhibitors of leukotriene biosynthesis
  作者：Juerg R. Pfister、D. V. Krishna Murthy

  DOI：10.1021/jm00362a002

  日期：1983.8

  and 5,6-benzoarachidonic acid (3), potential substrate analogue inhibitors of leukotriene biosynthesis, are described. Two of these compounds (1 and 2) apparently stimulated, while 3 inhibited, the activity of lipoxygenase from intact human polymorphonuclear leukocytes in vitro when stimulated with Ca2+ and calcium ionophore A23187 in the presence of BSA and arachidonic acid.

  描述了7,7-二甲基-（1），10,10-二甲基-（2）和5,6-苯并花生四烯酸（3）的合成，这是白三烯生物合成的潜在底物类似物抑制剂。当在BSA和花生四烯酸存在下用Ca2 +和钙离子载体A23187刺激时，其中的两种化合物（1和2）在体外明显刺激了完整人多形核白细胞中脂氧合酶的活性。
• 12-HETrE analogs and methods of use thereof
  申请人：——

  公开号：US20020151734A1

  公开（公告）日：2002-10-17

  The present invention to 12-HETrE analogs which are agonists and antagonists of 12-HETrE. The compositions may be formulated in pharmaceutically acceptable formulations. The invention also includes methods and products for treating inflammatory conditions, neovascularization, tumor growth, cancer, ischemic cardiovascular diseases, and ocular conditions.

  本发明涉及12-HETrE类似物，其为12-HETrE的激动剂和拮抗剂。这些组合物可以制成药学上可接受的制剂。本发明还包括用于治疗炎症、新生血管形成、肿瘤生长、癌症、缺血性心血管疾病和眼部疾病的方法和产品。
• Design and synthesis of hydroxy-alkynoic acids and their methyl esters as novel activators of BK channels
  作者：Shivaputra Patil、Anna N. Bukiya、Wei Li、Alejandro M. Dopico、Duane Miller

  DOI：10.1016/j.bmcl.2008.03.080

  日期：2008.6

  Physiological and pharmacological agents that activate large conductance, voltage-, and calcium- gated potassium (BK) channels located in the smooth muscle are effective vasodilators. Thus, activators of smooth muscle BK channels may be potential therapeutic tools to treat cardiovascular disease associated with vasoconstriction and/or impaired dilation, such as cerebrovascular spasm and constriction. We previously showed that lithocholic acid (LC) and other cholane derivatives activated smooth muscle BK channels and, thus, caused endothelium-independent cerebral artery dilation. However, clinical use of these cholane derivatives could be limited by the actions of these steroids, such as elevation of intracellular calcium and induction of apoptosis. Using LC as template, we designed and synthesized a series of hydroxy-alkynoic acids and corresponding methyl esters, as putative, nonsteroid BK channel activators. Indeed, the newly synthesized compounds effectively and reversibly activated rat cerebrovascular myocyte BK channel at concentrations similar to those found effective with LC. Among all the novel compounds tested, C-10 hydroxy-alkynoic acid methyl ester appears to be the most effective activator of vascular myocyte BK channels. (c) 2008 Elsevier Ltd. All rights reserved.
• Palladium-mediated transannular cyclizations of medium-ring olefinic enolsilanes
  作者：Andrew S. Kende、Clara E. Mota Nelson、Sébastien Fuchs

  DOI：10.1016/j.tetlet.2005.09.125

  日期：2005.11

  Medium-ring olefinic ketone and lactone enolsilanes were subjected to palladium(II)-mediated cycloalkenylation conditions. Diverse bicyclic ring products were obtained in moderate to good yields. The effect of olefin geometry and ring size is discussed. (c) 2005 Elsevier Ltd. All rights reserved.
• Ethanoarachidonic acids. A new class of arachidonic acid cascade modulators. 1. Monoethano compounds
  作者：K. C. Nicolaou、N. A. Petasis、W. S. Li、T. Ladduwahetty、J. L. Randall、S. E. Webber、P. E. Hernandez

  DOI：10.1021/jo00174a061

  日期：1983.12