7-(methoxymethoxy)-2-naphthalenyl trifluoromethanesulfonate | 287963-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-(methoxymethoxy)-2-naphthalenyl trifluoromethanesulfonate
• 英文别名: 7-methoxymethoxy-2-trifluoromethylsulfonyloxynaphthalene；[7-(Methoxymethoxy)naphthalen-2-yl] trifluoromethanesulfonate
• CAS: 287963-92-2
• 化学式: C₁₃H₁₁F₃O₅S
• 分子量: 336.289
• InChiKey: QKOXCAGWZRPVJO-UHFFFAOYSA-N

物化性质

• 沸点：
  416.5±45.0 °C(Predicted)
• 密度：
  1.450±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-(methoxymethoxy)-2-naphthalenyl trifluoromethanesulfonate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Design and synthesis of potent substrate-based inhibitors of the Trypanosoma cruzi dihydroorotate dehydrogenase

  摘要：

  Chagas disease, caused by the parasitic protozoan Trypanosoma cruzi, is the leading cause of heart disease in Latin America. T. cruzi dihydroorotate dehydrogenase (DHODH), which catalyzes the production of orotate, was demonstrated to be essential for T. cruzi survival, and thus has been considered as a potential drug target to combat Chagas disease. Here we report the design and synthesis of 75 compounds based on the orotate structure. A comprehensive structure-activity relationship (SAR) study revealed two 5-substituted orotate analogues (5u and 5v) that exhibit nPP values of several ten nanomolar level and a selectivity of more than 30,000-fold over human DHODH. The information presented here will be invaluable in the search for next-generation drug leads for Chagas disease. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.01.009
• 作为产物：
  描述：

  2,7-二羟基萘 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 7-(methoxymethoxy)-2-naphthalenyl trifluoromethanesulfonate
  参考文献：
  名称：

  新型4-2-（7-杂环甲氧基萘基-2-基甲氧基）乙基苯甲酸作为LTD（4）-拮抗剂的合成及药理评价。

  摘要：

  一组新的4- [2-（7-杂环甲氧基萘基-2-基甲氧基）乙基]苯甲酸已被合成，并在药理学上被评价为LTD（4）-拮抗剂。与我们的含喹啉铅分子相比，噻唑衍生物，尤其是4- [2- [7-（4-环丁基噻唑-2-基甲氧基）萘--2-基甲基-xy] et羟基]苯甲酸具有相当大的活​​性并改善了药代动力学特性证实了我们的化合物作为潜在的口服抗哮喘药的兴趣，并且至少在我们的一系列化合物中，4-烷基噻唑系统可以被认为是喹啉环的生物立体异构体。

  DOI：

  10.1016/s0223-5234(00)00142-2

文献信息

• New <i>N</i>-Arachidonoylserotonin Analogues with Potential “Dual” Mechanism of Action against Pain
  作者：Giorgio Ortar、Maria Grazia Cascio、Luciano De Petrocellis、Enrico Morera、Francesca Rossi、Aniello Schiano-Moriello、Marianna Nalli、Vito de Novellis、David F. Woodward、Sabatino Maione、Vincenzo Di Marzo

  DOI：10.1021/jm070678q

  日期：2007.12.27

  N-Arachidonoylserotonin (AA-5-HT, 1a) is an inhibitor of fatty acid amide hydrolase (FAAH) that acts also as an antagonist of transient receptor potential vanilloid-type 1 (TRPV1) channels and is analgesic in rodents. We modified the chemical structure of 1a with the aim of developing "hybrid" FAAH/TRPV1 blockers more potent than the parent compound or obtaining analogues with single activity at either of the two targets to study the mechanism of the analgesic action of 1a. Thirty-eight AA-5-HT analogues, containing a serotonin "head" bound to a variety of lipophilic moieties via amide, urea, or carbamate functionalities, were synthesized. Unlike 1a, most of the new compounds possessed activity at only one of the two considered targets. The amides 1b and 1c of alpha- and gamma-linolenic acid, however, showed "hybrid" activity similar to 1a. The carbarnate 3f (OMDM 106), although unable to antagonize TRPV1 receptors, was the most potent FAAH inhibitor in this study (IC50 = 0.5 mu M). Compounds 3f and 1m (OMDM129), which exhibited activity at only FAAH or TRPV1, respectively, were 10-fold less potent than 1a at preventing formal in-induced hyperalgesia in mice.
• Design and synthesis of potent substrate-based inhibitors of the Trypanosoma cruzi dihydroorotate dehydrogenase
  作者：Daniel Ken Inaoka、Maiko Iida、Satoshi Hashimoto、Toshiyuki Tabuchi、Takefumi Kuranaga、Emmanuel Oluwadare Balogun、Teruki Honma、Akiko Tanaka、Shigeharu Harada、Takeshi Nara、Kiyoshi Kita、Masayuki Inoue

  DOI：10.1016/j.bmc.2017.01.009

  日期：2017.2

  Chagas disease, caused by the parasitic protozoan Trypanosoma cruzi, is the leading cause of heart disease in Latin America. T. cruzi dihydroorotate dehydrogenase (DHODH), which catalyzes the production of orotate, was demonstrated to be essential for T. cruzi survival, and thus has been considered as a potential drug target to combat Chagas disease. Here we report the design and synthesis of 75 compounds based on the orotate structure. A comprehensive structure-activity relationship (SAR) study revealed two 5-substituted orotate analogues (5u and 5v) that exhibit nPP values of several ten nanomolar level and a selectivity of more than 30,000-fold over human DHODH. The information presented here will be invaluable in the search for next-generation drug leads for Chagas disease. (C) 2017 Elsevier Ltd. All rights reserved.
• Synthesis and pharmacological evaluation of new4-[2-(7-heterocyclemethoxynaftalen-2-ylmethoxy)ethyl]benzoic acidsas LTD4-antagonists
  作者：B Ballart

  DOI：10.1016/s0223-5234(00)00142-2

  日期：2000.4

  A group of new 4-[2-(7-heterocyclemethoxynaftalen-2-ylmethoxy)ethyl]benzoic acids have been synthesized and pharmacologically evaluated as LTD(4)-antagonists. Thiazole derivatives, especially 4-[2-[7-(4-cyclobutylthiazole-2-ylmethoxyl)naphthalen- 2-ylmetho-xy]et hyl]benzoic acid, present considerable activity and improved pharmacokinetic profiles in comparison with our quinoline containing lead molecule

  一组新的4- [2-（7-杂环甲氧基萘基-2-基甲氧基）乙基]苯甲酸已被合成，并在药理学上被评价为LTD（4）-拮抗剂。与我们的含喹啉铅分子相比，噻唑衍生物，尤其是4- [2- [7-（4-环丁基噻唑-2-基甲氧基）萘--2-基甲基-xy] et羟基]苯甲酸具有相当大的活​​性并改善了药代动力学特性证实了我们的化合物作为潜在的口服抗哮喘药的兴趣，并且至少在我们的一系列化合物中，4-烷基噻唑系统可以被认为是喹啉环的生物立体异构体。