methyl 14-triphenylphosphonio-tetradeca-all-cis-5,8,11,trienoate iodide | 112638-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 14-triphenylphosphonio-tetradeca-all-cis-5,8,11,trienoate iodide
• 英文别名: methyl (5Z,8Z,11Z)-14-(triphenylphosphonio)tetradeca-5,8,11-trienoate；[(3Z,6Z,9Z)-14-methoxy-14-oxotetradeca-3,6,9-trienyl]-triphenylphosphanium;iodide
• CAS: 112638-50-3
• 化学式: C₃₃H₃₈O₂P*I
• 分子量: 624.542
• InChiKey: WBGCOCKRGBCFAX-AGNMJYADSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 14-triphenylphosphonio-tetradeca-all-cis-5,8,11,trienoate iodide 在 溴 、 sodium hexamethyldisilazane 、 三苯基膦 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 20-bromo-16,16-dimethyl-eicosa-5,8,11,14-all-cis-tetraenoic acid methyl ester
  参考文献：
  名称：

  The Synthesis of N-Vanillyl-arachidonoyl-amide (Arvanil) and its Analogs: An Improved Procedure for the Synthesis of the Key Synthon Methyl 14-Hydroxy-(all-cis)-5,8,11-tetradecatrienoate

  摘要：

  Several arvanil analogs were synthesized where the end n-pentyl chain was branched and carried substituents at the terminal end of the chain. A high yielding total synthesis of these analogs was developed from methyl hex-5-ynoate, which was converted to the synthon 6 in a facile five strip sequence (overall yield, 33%). The pharmacological profile of these novel analogs suggests that they may be acting through a novel site of action for anandamide (arachidonylethanolamide, AEA). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00877-2
• 作为产物：
  描述：

  花生四烯酸 在 咪唑 、 lead(IV) acetate 、 sodium tetrahydroborate 、 高氯酸 、 双氧水 、 碘 、 三苯基膦 、 环戊烯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 40.5h， 生成 methyl 14-triphenylphosphonio-tetradeca-all-cis-5,8,11,trienoate iodide
  参考文献：
  名称：

  Synthesis of three new dehydroarachidonic acid derivatives and their oxidation by soybean lipoxygenase

  摘要：

  DOI：

  10.1016/s0040-4039(00)96736-4

文献信息

• 9,11-cycloendoperoxide pro-drugs of prostaglandin analogues for treatment of ocular hypertension and glaucoma
  申请人：——

  公开号：US20040023954A1

  公开（公告）日：2004-02-05

  9,11-Cycloendoperoxide derivatives of biologically active prostaglandin analogs, and particularly of the ocular hypotensive drugs Bimatoprost, Latanaprost, Unoprostone, Travoprost and prostaglandin H 2 1-ethanolamide or of structurally closely related analogs, are pro-drugs which hydrolyze under physiological conditions to provide prostaglandin analogues that are capable of providing sustained ocular and other in vivo concentrations of the respective drugs. The compounds of the invention have the formula shown below where the variables have the meaning defined in the specification. 1

  9,11-环内过氧化物衍生物是生物活性前列腺素类似物，特别是眼压降药物比马前列素、拉坦前列素、尤诺前列素、曲普前列素和前列腺素H2-乙醇胺或结构上密切相关的类似物的前体药物，在生理条件下水解，提供能够提供相应药物持续眼部和其他体内浓度的前列腺素类似物。本发明的化合物具有下面所示的公式，其中变量的含义在说明书中定义。
• Novel eicosanoid analgesics
  申请人：——

  公开号：US20040122089A1

  公开（公告）日：2004-06-24

  Analogs of andandamide and arvanil have been found to act preferential at CB 1 and AR 1 receptors, and at receptors other than CB 1 and AR 1 . The analogs provide analgesic effects in vivo, and are useful in pain management. In addition, the analogs may be used as anti-proliferative/anti-tumor agents, vasodilators, and in other applications. Several of the anandamide and arvanil analogs are more potent than anandamide and arvanil.

  已发现与anandamide和arvanil类似物作用于CB1和AR1受体时具有优先性，并且还作用于非CB1和AR1受体。这些类似物在体内提供镇痛效果，并在疼痛管理中有用。此外，这些类似物还可以用作抗增殖/抗肿瘤剂、血管扩张剂以及其他应用。几种anandamide和arvanil类似物比anandamide和arvanil更有效。
• Stereoselective synthesis of 17,18-epoxy derivative of EPA and stereoisomers of isoleukotoxin diol by ring opening of TMS-substituted epoxide with dimsyl sodium
  作者：Yutaro Nanba、Riku Shinohara、Masao Morita、Yuichi Kobayashi

  DOI：10.1039/c7ob02291c

  日期：——

  corresponding mono mesylate was prepared and subjected to epoxide ring formation to afford 17(R),18(S)-EpETE stereoselectively. Similarly, a reaction of the anti epoxy alcohol derived from (R)-1-TMS-1-octen-3-ol with NaDMSO gave the anti form of 1-nonene-3,4-diol, which was converted to 12(S),13(R)-isoleukotoxin diol through Wittig reaction. 12(R),13(R)-Isoleukotoxin diol was synthesized in a similar manner

  TMS取代的环氧醇（及其衍生物）与二甲基钠（NaDMSO）反应生成1-烯烃-3,4-二醇，用于合成对映异构体富集的17（R），18（S）-EpETE和两个异白细胞毒素二醇的非对映异构体。在17（R），18（S）-EpETE的合成中，衍生自（R）-1-TMS-1-戊烯-3-醇的环氧醇的α-乙氧基乙基醚（EE）与NaDMSO反应生成得到单EE保护的1-己烯-3，4-二醇。将通过硼氢化/氧化获得的醛进行Wittig反应，得到单EE-保护的二醇。制备相应的甲磺酸酯并使其形成环环，得到17（R），18（S）-EpETE立体选择。类似地，（R）-1-TMS-1-辛烯-3-醇衍生的抗环氧醇与NaDMSO的反应得到1-壬烯-3,4-二醇的抗形式，其转化为12（S），13（R）-异uk毒素二醇通过Wittig反应。以类似的方式合成了12（R），13（R）-异豆毒素二醇。
• Potent Anandamide Analogs:  The Effect of Changing the Length and Branching of the End Pentyl Chain
  作者：William J. Ryan、W. Kenneth Banner、Jenny L. Wiley、Billy R. Martin、Raj K. Razdan

  DOI：10.1021/jm970212f

  日期：1997.10.1

  To examine the effect of changing the length and branching of the end pentyl chain (C5H11) of anandamide (AN), various analogs 1a-h and 2a-f were synthesized from either the known aldehyde ester 6a or from the alcohol 6b and tested for their pharmacological activity. A reproducible procedure was developed for the conversion of arachidonic acid to 6a or 6b in gram quantities (overall yield 15%). The appropriate tetraene esters 7 were prepared by carrying out a Wittig reaction, between 6a and the ylide generated from the phosphonium salt of the appropriate alkyl halide or between the ylide of 6d (prepared from 6a --> 6b --> 6c --> 6d) and the appropriate alkyl aldehydes. They were then hydrolyzed to the corresponding acids and transformed into AN analogs 1 via their acid chlorides then treated with excess ethanolamine. alpha-Alkylation of esters 7 gave compounds 8 which were hydrolyzed to the corresponding acids. These acids via their acid chlorides and subsequent treatment with excess fluoroethylamine gave the target compounds 2. In this way analogs 1e and 2a-c were synthesized from 6d while all the remaining analogs were prepared from 6a. In order to assess the optimal length of the alkyl terminus, analogs 1a-d were prepared and showed moderately high affinities (18-55 nM). However analogs 1a-c failed to produce significant pharmacological effects at doses up to 30 mg/kg. Analog 1d was found to be a weak partial agonist. The reason for the lack of activity in 1a-c is presently not clear. Like the THCs, the branching of the end pentyl chain in AN (1e-h) increased potency both in in vitro and in vivo activities; the dimethylheptyl (DMH) analog 1e was the most potent in the series. Similar alkyl substitutions were carried out in the fluoro-2-methylanandamide series (2a-f), and all of these analogs had high receptor affinities (1-14 nM), the DMH analog 2a being the most potent. With a few exceptions they showed robust pharmacological effects, and AN-like profiles, It was shown that the SAR of the end pentyl chain in AN is very similar to that of THCs. However, the magnitude of enhanced potency observed when the side chain of THC was changed from straight to branched was not observed when the end chain of AN was similarly changed.
• RING D-MODIFIED GIBBERELLIN COMPOUNDS, AND PREPARATION AND USE THEREOF
  申请人：THE AUSTRALIAN NATIONAL UNIVERSITY

  公开号：EP0777662B1

  公开（公告）日：2004-04-28