2-(3,4,5-trimethoxyphenyl)-5-methyloxazole-4-carboxylic acid | 1198279-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3,4,5-trimethoxyphenyl)-5-methyloxazole-4-carboxylic acid
• 英文别名: 5-methyl-2-(3,4,5-trimethoxyphenyl)oxazole-4-carboxylic acid；5-Methyl-2-(3,4,5-trimethoxyphenyl)-1,3-oxazole-4-carboxylic acid
• CAS: 1198279-82-1
• 化学式: C₁₄H₁₅NO₆
• 分子量: 293.276
• InChiKey: XDFFYRACPPSSCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  91
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(甲硫基)乙胺 、 2-(3,4,5-trimethoxyphenyl)-5-methyloxazole-4-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到2-(3,4,5-dimethoxyphenyl)-5-methyl-N-(2-(methylthio)ethyl)oxazole-4-carboxamide
  参考文献：
  名称：

  含硫的天然印度黄素衍生物可作为潜在的抗枯萎病菌的抗真菌剂。

  摘要：

  芳基-恶唑生物碱是重要的一类杂环天然产物，已被证明具有广泛的生物学功能。在我们研究天然产物中高活性化合物的过程中，已经合成并研究了具有典型芳基-恶唑单元的天然印度菊磷脂AD。因此，为了开发具有高度潜力的功能分子，设计并合成了一系列源自天然印度洋粉蛋白的新型含硫芳基-恶唑化合物，它们对四种常见的植物病原真菌（卵菌疫霉，子囊菌核盘菌）具有体外杀真菌活性。评估了菌核菌，氘核霉菌灰葡萄孢菌和担子菌根瘤菌（Rhizoctonia solani），结果表明化合物7b和7c在体外对担子菌R. solani具有良好的选择性和特异性。此外，体内抗真菌活性还表明化合物7b和7c可以保护蚕豆免受sol。R. solani感染，并且还研究了针对这些化合物的抗真菌作用的可能机理。

  DOI：

  10.1016/j.bmcl.2020.127245
• 作为产物：
  描述：

  2-(3,4,5,-trimethoxyphenyl)-4-carboxylmethyl-5-methyloxazole 在 lithium hydroxide monohydrate 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以96%的产率得到2-(3,4,5-trimethoxyphenyl)-5-methyloxazole-4-carboxylic acid
  参考文献：
  名称：

  Solution versus Fluorous versus Solid-Phase Synthesis of 2,5-Disubstituted 1,3-Azoles. Preliminary Antibacterial Activity Studies

  摘要：

  A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate alpha-amido-beta-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson's reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine With a fluorous tag in the ester moiety IS used as a starting material, the synthesis can be easily completed Without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a Suitable entry to the preparation of small libraries of these bioactive compounds. The prepared oxa(thia)zoles were assayed for their antibacterial activity, and several of them were active against Staphylococcus aureus.

  DOI：

  10.1021/jo9016265

文献信息

• Solution versus Fluorous versus Solid-Phase Synthesis of 2,5-Disubstituted 1,3-Azoles. Preliminary Antibacterial Activity Studies
  作者：Juan F. Sanz-Cervera、Raül Blasco、Julio Piera、Michael Cynamon、Ignacio Ibáñez、Marcelo Murguía、Santos Fustero

  DOI：10.1021/jo9016265

  日期：2009.12.4

  A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate alpha-amido-beta-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson's reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine With a fluorous tag in the ester moiety IS used as a starting material, the synthesis can be easily completed Without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a Suitable entry to the preparation of small libraries of these bioactive compounds. The prepared oxa(thia)zoles were assayed for their antibacterial activity, and several of them were active against Staphylococcus aureus.
• Sulfur-containing natural hinduchelins derivatives as potential antifungal agents against Rhizoctonia solani
  作者：Shaoyong Ke、Wei Fang、Wenbo Huang、Zhigang Zhang、Liqiao Shi、Zhongyi Wan、Kaimei Wang、Chunxia Cao、Daye Huang

  DOI：10.1016/j.bmcl.2020.127245

  日期：2020.7

  Aryl-oxazole alkaloids are an important class of heterocyclic natural products, and which has been demonstrated to exhibit broad biological functions. During the course of our research for highly active compounds from natural products, the natural hinduchelins A-D with typical aryl-oxazole unit have been synthesized and investigated. So, in order to develop highly potential functional molecules, a

  芳基-恶唑生物碱是重要的一类杂环天然产物，已被证明具有广泛的生物学功能。在我们研究天然产物中高活性化合物的过程中，已经合成并研究了具有典型芳基-恶唑单元的天然印度菊磷脂AD。因此，为了开发具有高度潜力的功能分子，设计并合成了一系列源自天然印度洋粉蛋白的新型含硫芳基-恶唑化合物，它们对四种常见的植物病原真菌（卵菌疫霉，子囊菌核盘菌）具有体外杀真菌活性。评估了菌核菌，氘核霉菌灰葡萄孢菌和担子菌根瘤菌（Rhizoctonia solani），结果表明化合物7b和7c在体外对担子菌R. solani具有良好的选择性和特异性。此外，体内抗真菌活性还表明化合物7b和7c可以保护蚕豆免受sol。R. solani感染，并且还研究了针对这些化合物的抗真菌作用的可能机理。