(4-Methoxyphenyl)-[1-(3,4,5-trimethoxyphenyl)tetrazol-5-yl]methanone | 1268445-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-Methoxyphenyl)-[1-(3,4,5-trimethoxyphenyl)tetrazol-5-yl]methanone
• 英文别名: (4-methoxyphenyl)-[1-(3,4,5-trimethoxyphenyl)tetrazol-5-yl]methanone
• CAS: 1268445-66-4
• 化学式: C₁₈H₁₈N₄O₅
• 分子量: 370.365
• InChiKey: NALJSIVFFPLRAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-(3,4,5-trimethoxy)phenylformamide 在 叠氮基三甲基硅烷 、 10% palladium on activated carbon 、 氢气 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 104.0h， 生成 (4-Methoxyphenyl)-[1-(3,4,5-trimethoxyphenyl)tetrazol-5-yl]methanone
  参考文献：
  名称：

  A Practical Synthesis of 5-Aroyl-1-aryltetrazoles Using an Ugi-Like 4-Component Reaction Followed by a Biomimetic Transamination

  摘要：

  多组分反应（MCRs）及其后续转化是快速有效合成具有潜在药理学意义的分子骨架的迷人工具。我们对制备新型的5-芳酰基-1-芳基四唑产生了兴趣，原因有二：（1）这些结构在当前文献所描述的方法下仍被视为难以获得的具有挑战性的结构；（2）α-酮基四唑框架可能被认为是一种潜在的查尔酮连接子生物电子等排体。本工作中描述了一种新颖、简单、高效且通用的此类化合物的合成方法。

  DOI：

  10.1055/s-0030-1258273

文献信息

• Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation
  作者：Ornella Mesenzani、Alberto Massarotti、Mariateresa Giustiniano、Tracey Pirali、Valentina Bevilacqua、Antonio Caldarelli、Pierluigi Canonico、Giovanni Sorba、Ettore Novellino、Armando A. Genazzani、Gian Cesare Tron

  DOI：10.1016/j.bmcl.2010.11.113

  日期：2011.1

  In the chalcone scaffold, it is thought that the double bond is an important structural linker but it is likely not essential for the interaction with tubulin. Yet, it may be a potential site of metabolic degradation and interaction with biological nucleophiles. In this letter, we have replaced this olefinic portion of chalcones with two metabolically stable and chemically inert heterocyclic rings, namely triazole or tetrazole. Yet, our biologic data suggest that, unlike in other antitubulinic structures, the olephinic ring might not be merely a structural linker. (C) 2010 Elsevier Ltd. All rights reserved.
• A Practical Synthesis of 5-Aroyl-1-aryltetrazoles Using an Ugi-Like 4-Component Reaction Followed by a Biomimetic Transamination
  作者：Gian Tron、Mariateresa Giustiniano、Tracey Pirali、Alberto Massarotti、Beatrice Biletta、Ettore Novellino、Pietro Campiglia、Giovanni Sorba

  DOI：10.1055/s-0030-1258273

  日期：2010.12

  Multicomponent reactions (MCRs), followed by subsequent transformations, are fascinating tools for the rapid and effective synthesis of molecular scaffolds with potential pharmacological relevance. We became interested in the preparation of novel 5-aroyl-1-aryltetrazoles as (1) they still represent challenging structures not easily accessible through the methods described in literature, and (2) the α-ketotetrazolic framework may be considered as a potential bioisostere of the enonic linker of chalcones. In the present work, a novel, simple, effective and general synthesis for this class of compounds is described.

  多组分反应（MCRs）及其后续转化是快速有效合成具有潜在药理学意义的分子骨架的迷人工具。我们对制备新型的5-芳酰基-1-芳基四唑产生了兴趣，原因有二：（1）这些结构在当前文献所描述的方法下仍被视为难以获得的具有挑战性的结构；（2）α-酮基四唑框架可能被认为是一种潜在的查尔酮连接子生物电子等排体。本工作中描述了一种新颖、简单、高效且通用的此类化合物的合成方法。