(4E,7R)-(+)-7-methoxytetradec-4-enoic acid | 936445-79-3

• 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: (4E,7R)-(+)-7-methoxytetradec-4-enoic acid
• 英文别名: (R)-Lyngbic acid；(7R,4E)-Methoxytetradecenoic Acid；(E,7R)-7-methoxytetradec-4-enoic acid
• CAS: 936445-79-3
• 化学式: C₁₅H₂₈O₃
• 分子量: 256.386
• InChiKey: DHIPOEWPWSLXNL-RCQQVGEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (4E,7R)-(+)-7-methoxytetradec-4-enoic acid 在 氢氧化钾 、 2-chloro-1,3-dimethyl-2-imidazolium PF₆ 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 35.0h， 生成
  参考文献：
  名称：

  Total synthesis of malyngamide X and its 7′S-epi isomer

  摘要：

  Stereoselective syntheses of malyngamide X (1) and its 7'(S)-epimer are described. A Lewis acid (Et2AlCl) mediated anti-aldol reaction was employed to generate the stereocenters C-7 and C-8. The route is convergent and provides a convenient access to the synthesis of structural variants of malyngamide X. Stereochemistry at C-7' in the molecules of natural and synthetic 1, and 7'(S)-epi 1 was confirmed by NMR chiral solvation experiments. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.035
• 作为产物：
  描述：

  (R)-1,2-epoxynonane 在 chromium(VI) oxide 、 正丁基锂 、 硫酸 、 氨 、 lithium 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二甲基亚砜 、 丙酮 、 叔丁醇 为溶剂， 反应 11.0h， 生成 (4E,7R)-(+)-7-methoxytetradec-4-enoic acid
  参考文献：
  名称：

  Total synthesis of malyngamide X and its 7′S-epi isomer

  摘要：

  Stereoselective syntheses of malyngamide X (1) and its 7'(S)-epimer are described. A Lewis acid (Et2AlCl) mediated anti-aldol reaction was employed to generate the stereocenters C-7 and C-8. The route is convergent and provides a convenient access to the synthesis of structural variants of malyngamide X. Stereochemistry at C-7' in the molecules of natural and synthetic 1, and 7'(S)-epi 1 was confirmed by NMR chiral solvation experiments. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.035

文献信息

• Synthesis and evaluation of hermitamides A and B as human voltage-gated sodium channel blockers
  作者：Eliseu O. De Oliveira、Kristin M. Graf、Manoj K. Patel、Aparna Baheti、Hye-Sik Kong、Linda H. MacArthur、Sivanesan Dakshanamurthy、Kan Wang、Milton L. Brown、Mikell Paige

  DOI：10.1016/j.bmc.2011.05.043

  日期：2011.7

  hermitamides are ligands for the human voltage-gated sodium channel (hNaV) based on their structural similarity to the jamaicamides. Herein, we describe the nonracemic total synthesis of hermitamides A and B and their epimers. We report the ability of the hermitamides to displace [3H]-BTX at 10 μM more potently than phenytoin, a clinically used sodium channel blocker. We also present a potential binding mode

  Hermitamides A 和 B 是从巴布亚新几内亚海洋蓝藻Lyngbya majuscula 的集合中分离出来的脂肽。我们假设 Hermitamides 是人类电压门控钠通道 (hNa V ) 的配体，这是基于它们与牙买加酰胺的结构相似性。在此，我们描述了hermitamides A 和B 及其差向异构体的非外消旋全合成。我们报告了 Hermitamides比苯妥英（一种临床使用的钠通道阻滞剂）更有效地置换 10 μM 的[ 3 H]-BTX的能力。我们还在BTX 结合位点和电生理学中展示了 ( S )-hermitamide B的潜在结合模式，表明这些化合物是 hNav1.2 电压门控钠通道的有效阻滞剂。
• NA CHANNELS, DISEASE, AND RELATED ASSAYS AND COMPOSITIONS
  申请人：Brown Milton L.

  公开号：US20110230442A1

  公开（公告）日：2011-09-22

  Disclosed are molecules and their synthesis, for use in blocking gated ion channels such as voltage-gated sodium channels (VGSCs) and prostate voltage sodium channels (PVSCs). These inhibitors have superior blocking efficacy, for instance in displacing the radioligand [ 3 H]-Batrachotoxin-B ([ 3 H]-BTX-B) that binds to site 2 of a VGSC. The molecules of the invention comprise a moiety which increases the binding affinity of molecules for the protein binding site in prostate cancer cells (PCs), and which is also fluorescent. In one embodiment the invention molecules are an inhibition system that can be used to target over-abundant or hyperactive VGSCs selectively in pain, epilepsy or prostate cancer, inhibiting the proliferation of PCs. The fluorescent moiety also facilitates screening, tracking, and pharmacodynamic studies of the drug in a biological system both in vitro and in vivo.

  本发明涉及分子及其合成，用于阻断门控离子通道，例如电压门控钠通道（VGSC）和前列腺电压钠通道（PVSC）。这些抑制剂具有卓越的阻断效力，例如在取代结合到VGSC的位点2的放射性配体[3H]-Batrachotoxin-B ([3H]-BTX-B)方面。本发明的分子包括一个基团，增加分子对前列腺癌细胞（PC）中蛋白质结合位点的结合亲和力，并且也是荧光的。在一种实施方式中，本发明的分子是一种抑制系统，可用于选择性地靶向过度丰富或过度活跃的VGSC，从而抑制疼痛、癫痫或前列腺癌的PC的增殖。荧光基团还有助于在体外和体内生物系统中筛选、跟踪和药效学研究药物。
• An Improved Asymmetric Synthesis of Malyngamide U and Its 2′-Epimer
  作者：Jian-Peng Feng、Zi-Fa Shi、Yang Li、Jun-Tao Zhang、Xian-Liang Qi、Jie Chen、Xiao-Ping Cao

  DOI：10.1021/jo800876u

  日期：2008.9.1

  An accelerated and improved asymmetric synthesis of malyngamide U (1) and its 2'-epimer (2'-epi-1) was accomplished from readily available n-hexanal, ethanolamine and (R)-(-)-carvone. The key steps involved a Johnson-Claisen rearrangement in the synthesis of an unsaturated carboxylic acid 4 and an aldol reaction in the construction of the skeleton of I and 2'-epi-1. There are 13 steps in the synthesis, with a 2.7% overall yield for 1 and a 0.4% yield for 2'-epi-1.
• Novel malyngamide structural analogs: synthesis and biological evaluation
  作者：G. Venkateswar Reddy、T. Vijaya Kumar、B. Siva、K. Suresh Babu、P. V. Srinivas、Irum Sehar、A. K. Saxena、J. Madhusudana Rao

  DOI：10.1007/s00044-013-0466-y

  日期：2013.10

  In the course of our search for new anticancer agents, a series of novel malyngamide derivatives were synthesized by sharpless asymmetric epoxidation, followed by Julia-Kocinski olefination reactions as key reaction sequence. Anticancer activities of all these derivatives were screened against IMR-32, SF-295, SKNSH, HeLa, Colon-502713, SW-620, and Hop-62 cell lines for the first time.
• The enantioselective synthesis and biological evaluation of chimeric promysalin analogs facilitated by diverted total synthesis
  作者：Kyle W Knouse、William M Wuest

  DOI：10.1038/ja.2016.4

  日期：2016.4