phenylpropynoic acid thiazol-2-ylamide | 37469-36-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: phenylpropynoic acid thiazol-2-ylamide
• 英文别名: 3-phenyl-N-(1,3-thiazol-2-yl)prop-2-ynamide
• CAS: 37469-36-6
• 化学式: C₁₂H₈N₂OS
• 分子量: 228.274
• InChiKey: MTZBMSCIGGIMBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenylpropynoic acid thiazol-2-ylamide 在 sodium hydroxide 、 碘 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  2,5-Diarylisothiazolone: novel inhibitors of cytokine-induced cartilage destruction

  摘要：

  A series of 2,5-diarylisothiazolones is reported that inhibit the IL-lp-induced breakdown of bovine nasal septum cartilage in an organ culture assay. The synthesis and preliminary SAR of these compounds are described. These compounds represent a novel, nonpeptide lead series approach to the mediation of the chronic cartilage breakdown associated with arthritic disease. These compounds are relatively resistant to reductive metabolism by liver microsomal preparations and appear to inhibit cartilage breakdown by interfering with the proteolytic activation of matrix metalloproteinases. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00053-3
• 作为产物：
  描述：

  苯丙炔酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 phenylpropynoic acid thiazol-2-ylamide
  参考文献：
  名称：

  2,5-Diarylisothiazolone: novel inhibitors of cytokine-induced cartilage destruction

  摘要：

  A series of 2,5-diarylisothiazolones is reported that inhibit the IL-lp-induced breakdown of bovine nasal septum cartilage in an organ culture assay. The synthesis and preliminary SAR of these compounds are described. These compounds represent a novel, nonpeptide lead series approach to the mediation of the chronic cartilage breakdown associated with arthritic disease. These compounds are relatively resistant to reductive metabolism by liver microsomal preparations and appear to inhibit cartilage breakdown by interfering with the proteolytic activation of matrix metalloproteinases. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00053-3

文献信息

• Transition-metal and base-free thioannulation of propynamides with sodium sulfide and dichloromethane for the selective synthesis of 1,3-thiazin-4-ones and thiazolidine-4-ones
  作者：Sui-Qian Wang、Xiao-Wei Yan、Bo-Lun Hu、Xing-Guo Zhang

  DOI：10.1016/j.tet.2020.131021

  日期：2020.3

  A thioannulation of propynamides with sodium sulfide and CH2Cl2 in the absence of transition-metal and base has been established. This one-pot tandem reaction provides a facile and efficient method for the selective synthesis of 1,3-thiazide-4-ones or thiazolidine-4-ones through constructing both C–N and C–S bonds. The atom-economic reaction features mild conditions and good functional group tolerance

  已经建立了在不存在过渡金属和碱的情况下用硫化钠和CH 2 Cl 2进行丙炔酰胺的硫代环化反应。这一一锅串联反应为通过构建C–N和C–S键选择性合成1,3-噻嗪4-酮或噻唑烷4-酮提供了一种简便而有效的方法。原子经济反应具有温和的条件和良好的官能团耐受性，并使用廉价，安全和无味的硫源。
• Syntheses and Antimicrobial Activities of N-Heterocyclic-β-mercaptocinnamamides and Related Compounds
  作者：SHINSAKU MINAMI、MASATSUGU TOMITA、KAZUYO KAWAGUCHI

  DOI：10.1248/cpb.20.1716

  日期：——

  In order to obtain useful antimicrobial compounds, a number of N-heterocyclic-β-mercaptocinnamamides (IIIa-i) and related compounds were prepared. N-Heterocyclic phenylpropiolamides (I) were obtained by the reaction of heterocyclic amines with phenylpropioloyl chloride. The addition of thiourea to I gave the isothiuronium salts (II), which were converted into the mercapto compounds (III) with aqueous sodium hydroxide. In the reaction of 2-aminothiazole or 2-amino-4-methylthiazole with phenylpropioloyl chloride in the presence of triethylamine, thiazolo [3, 2-α] pyrimidines (V, VII and VIII) were given together with the expected amides (If and Ig). The hydrolysis of S-[2-(3-methyl-1-phenyl-5-pyrazolyl) carbamoyl-1-phenylvinyl]-isothiourea p-toluenesulfonate (IIe) with aqueous sodium hydroxide at 90° gave 6, 7-dihydro-1, 4-diphenyl-3-methyl-6-oxopyrazolo [3, 4-b] pyridine (IX) and a small amount of the mercapto compound (IIIe). Acyl migration from S to N was found in the acylthio derivatives of N-(2-thiazolyl)-(IIIf) and N-(4-methyl-2-thiazolyl)-β-mercaptocinnamamide (IIIg). Most of the compounds synthesized were considerably active in vitro against various gram-positive bacteria and fungi. However, only three of them were effective against Trichophyton in the in vivo tests.

  为了得到有用的抗菌化合物，制备了一系列 N-杂环-β-巯基肉桂酰胺（IIIa-i）及相关化合物。通过杂环胺与苯基丙炔酰氯的反应，得到了 N-杂环苯基丙炔酰胺（I）。向 I 中加入硫脲得到异硫脲盐（II），再用氢氧化钠水溶液将其转化为巯基化合物（III）。在三乙胺存在下，2-氨基噻唑或 2-氨基-4-甲基噻唑与苯基丙炔酰氯反应，得到了噻唑并[3, 2-α]嘧啶（V、VII 和 VIII）及预期的酰胺（If 和 Ig）。在 90°C 下用氢氧化钠水溶液水解 S-[2-(3-甲基-1-苯基-5-吡唑基)氨基甲酰-1-苯基乙烯基]-硫脲对甲苯磺酸盐（IIe），得到了 6, 7-二氢-1, 4-二苯基-3-甲基-6-氧代吡唑并[3, 4-b]吡啶（IX）及少量巯基化合物（IIIe）。在 N-(2-噻唑基)（IIIf）和 N-(4-甲基-2-噻唑基)-β-巯基肉桂酰胺（IIIg）的酰硫衍生物中，发生了酰基从硫向氮的迁移。所合成的大多数化合物对多种革兰氏阳性细菌和真菌的体外活性相当高。然而，在体内测试中，仅三种化合物对毛癣菌有效。