(2-ethoxycarbonyl-3-methoxybenzyl)triphenylphosphonium chloride | 110202-78-3

• 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: (2-ethoxycarbonyl-3-methoxybenzyl)triphenylphosphonium chloride
• 英文别名: 2-ethoxycarbonyl-3-methoxybenzyltriphenylphosphonium chloride；(2-Ethoxycarbonyl-3-methoxyphenyl)methyl-triphenylphosphanium;chloride
• CAS: 110202-78-3
• 化学式: C₂₉H₂₈O₃P*Cl
• 分子量: 490.966
• InChiKey: WHGYKYPAKBMXTJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-ethoxycarbonyl-3-methoxybenzyl)triphenylphosphonium chloride 在 platinum on activated charcoal 氢气 、 三溴化硼 、 lithium hexamethyldisilazane 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 氢化白果酸
  参考文献：
  名称：

  Prostaglandin Synthetase Inhibitors from the African Medicinal PlantOzoroa mucronata

  摘要：

  从O. mucronata中分离出了两种前列腺素合酶抑制剂——酚酸。通过光谱法确定了这些抑制剂的结构。报道了通过定向金属化合成这两种物质的高效方法。

  DOI：

  10.1246/cl.1987.1101
• 作为产物：
  描述：

  ethyl 6-(chloromethyl)-2-methoxybenzoate 、 三苯基膦 生成 (2-ethoxycarbonyl-3-methoxybenzyl)triphenylphosphonium chloride
  参考文献：
  名称：

  Prostaglandin Synthetase Inhibitors from the African Medicinal PlantOzoroa mucronata

  摘要：

  从O. mucronata中分离出了两种前列腺素合酶抑制剂——酚酸。通过光谱法确定了这些抑制剂的结构。报道了通过定向金属化合成这两种物质的高效方法。

  DOI：

  10.1246/cl.1987.1101

文献信息

• Syntheses of anacardic acids and ginkgoic acid
  作者：Yoshiro Yamagiwa、Kinji Ohashi、Yoshitaka Sakamota、Shinji Hirakawa、Tadao Kamikawa、Isao Kubo

  DOI：10.1016/s0040-4020(01)81629-x

  日期：——

  Syntheses of two anacardic acids [6-pentadecyl- and 6-(10-pentadecenyl) salicylic acid], inhibitors of prostaglandin synthetase and of the growth of certain insects, and ginkgoic acid via directive metallation is reported.

  据报导，合成了两种漆树酸[6-十五烷基和6-（10-十五碳烯基）水杨酸]，前列腺素合成酶的抑制剂和某些昆虫的生长，以及通过定向金属化作用生成的银杏酸。
• Synthetic studies of thiazoline and thiazolidine-containing natural products — 1. Phosphorus pentachloride-mediated thiazoline construction reaction
  作者：Akira Ino、Akira Murabayashi

  DOI：10.1016/s0040-4020(99)00582-7

  日期：1999.8

  Phosphorus pentachloride effectively mediates the cyclization of N-acylcysteamine derivatives giving rise to thiazoline rings. Using this method, sterically hindered thiazoline analogs could be constructed and thus segment A (the left half) of micacocidin, a unique antimycoplasma antibiotic, was synthesized efficiently.

  五氯化磷可有效​​介导N-酰基半胱胺衍生物的环化反应，产生噻唑啉环。使用这种方法，可以构建空间受阻的噻唑啉类似物，从而有效合成了micacocidin的A段（左半部分），一种独特的抗支原体抗生素。
• Total synthesis of the antimycoplasma antibiotic micacocidin
  作者：Akira Ino、Yasushi Hasegawa、Akira Murabayashi

  DOI：10.1016/s0040-4039(98)00518-8

  日期：1998.5

  A total synthesis of the antimycoplasma antibiotic micacocidin (1) is described. Construction of sterically hindered thiazoline 12 was achieved by a phosphorus pentachloride-mediated cyclization reaction of S-protected aryloylcysteine 11, and compound 1 with desired chirality at C-10 was favorably obtained from diastereomeric mixture 30 through formation of the Zn complex 31. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Anacardic acid derivatives as inhibitors of glyceraldehyde-3-phosphate dehydrogenase from Trypanosoma cruzi
  作者：Junia M. Pereira、Richele P. Severino、Paulo C. Vieira、João B. Fernandes、M. Fátima G.F. da Silva、Aderson Zottis、Adriano D. Andricopulo、Glaucius Oliva、Arlene G. Corrêa

  DOI：10.1016/j.bmc.2008.08.057

  日期：2008.10

  Chagas' disease, a parasitic infection caused by the flagellate protozoan Trypanosoma cruzi, is a major public health problem affecting millions of individuals in Latin America. On the basis of the essential role in the life cycle of T. cruzi, the glycolytic enzyme glyceraldehyde-3-phosphate dehydrogenase (GAPDH) has been considered an attractive target for the development of novel antitrypanosomatid agents. In the present work, we describe the inhibitory effects of a small library of natural and synthetic anacardic acid derivatives against the target enzyme. The most potent inhibitors, 6-n-pentadecyl-(1) and 6-n-dodecylsalicilic acids (10e), have IC50 values of 28 and 55 mu M, respectively. The inhibition was not reversed or prevented by the addition of Triton X-100, indicating that aggregate-based inhibition did not occur. In addition, detailed mechanistic characterization of the effects of these compounds on the T. cruzi GAPDH-catalyzed reaction showed clear noncompetitive inhibition with respect to both substrate and cofactor. (C) 2008 Elsevier Ltd. All rights reserved.