3-(4-thioxo-1,3,5-triazinan-1-yl)propanoic acid | 84982-67-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪烷类
• 英文名称: 3-(4-thioxo-1,3,5-triazinan-1-yl)propanoic acid
• 英文别名: 3-(4-thioxo-1,3,5-triazinan-1-yl)propionic acid；3-(4-Sulfanylidene-1,3,5-triazinan-1-ium-1-yl)propanoate
• CAS: 84982-67-2
• 化学式: C₆H₁₁N₃O₂S
• 分子量: 189.238
• InChiKey: OHELLDVEWGGEHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  96.7
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3-(4-thioxo-1,3,5-triazinan-1-yl)propanoic acid 以 异丙醇 为溶剂， 反应 4.5h， 生成 diethylamine 3-(4-(methylthio)-3,6-dihydro-1,3,5-triazin-1(2H)-yl)propanoate hydroiodide
  参考文献：
  名称：

  Alkylation of cyclic mannich bases, derivatives of thiourea and simple amino acids

  摘要：

  Aminomethylation of thiourea with aqueous formaldehyde and simple amino acids (glycine, beta-alanine, gamma-aminobutyric acid) have resulted in the formation of (4-thioxo-1,3,5-triazinan-1-yl)-substituted acetic, propionic, and butyric acids, respectively. By alkylation of these compounds corresponding S-methyl and S-ethyl iodides were obtained, and by the action of tert-butylamine, the corresponding salts. The same salts were obtained by the reaction of amine exchange between 5-tert-butyl-1,3,5-triazinan-2-thione and these amino acids in water. As a result of neutralization of S-methyl iodides with tert-butylamine in 2-propanol or aqueous 2-propanol zwitterionic [4-(methyl-sulfanyl)-3,6-dihydro-1,3,5-triazin-1(2H)-yl] derivatives of these acids were isolated. From aqueous solutions of S-methyl iodides and tert-butylamine ion associates of the corresponding zwitter-ions and tert-butylammonium iodide have crystallized. The same associates have formed at treating S-methyl iodides with tert-butylamine or diethylamine in the absence of a solvent.

  DOI：

  10.1134/s1070363212020132
• 作为产物：
  描述：

  聚合甲醛 、 硫脲 、 β-丙氨酸 以 水 为溶剂， 以86.1%的产率得到3-(4-thioxo-1,3,5-triazinan-1-yl)propanoic acid
  参考文献：
  名称：

  Alkylation of cyclic mannich bases, derivatives of thiourea and simple amino acids

  摘要：

  Aminomethylation of thiourea with aqueous formaldehyde and simple amino acids (glycine, beta-alanine, gamma-aminobutyric acid) have resulted in the formation of (4-thioxo-1,3,5-triazinan-1-yl)-substituted acetic, propionic, and butyric acids, respectively. By alkylation of these compounds corresponding S-methyl and S-ethyl iodides were obtained, and by the action of tert-butylamine, the corresponding salts. The same salts were obtained by the reaction of amine exchange between 5-tert-butyl-1,3,5-triazinan-2-thione and these amino acids in water. As a result of neutralization of S-methyl iodides with tert-butylamine in 2-propanol or aqueous 2-propanol zwitterionic [4-(methyl-sulfanyl)-3,6-dihydro-1,3,5-triazin-1(2H)-yl] derivatives of these acids were isolated. From aqueous solutions of S-methyl iodides and tert-butylamine ion associates of the corresponding zwitter-ions and tert-butylammonium iodide have crystallized. The same associates have formed at treating S-methyl iodides with tert-butylamine or diethylamine in the absence of a solvent.

  DOI：

  10.1134/s1070363212020132

文献信息

• Synthesis of new cyclic derivatives of isothiourea, potential inhibitors of NO-synthases
  作者：N. N. Martinovich、V. V. Abzianidze、V. A. Kuznetsov、S. M. Ramsh

  DOI：10.1134/s1070363216040381

  日期：2016.4

  Nowadays active search for selective inhibitors of nitric oxide synthases (NOS) is going on. NOS inhibitors display a wide range of pharmacological properties [1–3]. Linear and cyclic derivatives of isothiourea have been suggested as promising selective NOS inhibitors [5–9]. They contain thioamidine fragment RNHC(SR)=NR which is isosteric to the guanidine group of L-arginine. Under the effect of the

  目前正在积极寻找一氧化氮合酶 (NOS) 的选择性抑制剂。NOS 抑制剂显示出广泛的药理特性 [1-3]。异硫脲的线性和环状衍生物已被认为是有前途的选择性 NOS 抑制剂 [5-9]。它们含有硫脒片段 RNHC(SR)=NR，它与 L-精氨酸的胍基团是等排的。在一氧化氮合酶和相应辅酶的作用下，L-精氨酸代谢成一氧化氮，因此是其主要的内源性来源 [10]。具有硫脒片段的化合物在竞争一氧化氮合酶的活性位点的一氧化氮的酶促合成中可能发挥L-精氨酸的竞争性拮抗剂的作用。直链异硫脲衍生物的制备方法，
• Alkylation of cyclic mannich bases, derivatives of thiourea and simple amino acids
  作者：Minyan Song、S. M. Ramsh、V. S. Fundamensky、S. Yu. Solov’eva、V. I. Zakharov

  DOI：10.1134/s1070363212020132

  日期：2012.2

  Aminomethylation of thiourea with aqueous formaldehyde and simple amino acids (glycine, beta-alanine, gamma-aminobutyric acid) have resulted in the formation of (4-thioxo-1,3,5-triazinan-1-yl)-substituted acetic, propionic, and butyric acids, respectively. By alkylation of these compounds corresponding S-methyl and S-ethyl iodides were obtained, and by the action of tert-butylamine, the corresponding salts. The same salts were obtained by the reaction of amine exchange between 5-tert-butyl-1,3,5-triazinan-2-thione and these amino acids in water. As a result of neutralization of S-methyl iodides with tert-butylamine in 2-propanol or aqueous 2-propanol zwitterionic [4-(methyl-sulfanyl)-3,6-dihydro-1,3,5-triazin-1(2H)-yl] derivatives of these acids were isolated. From aqueous solutions of S-methyl iodides and tert-butylamine ion associates of the corresponding zwitter-ions and tert-butylammonium iodide have crystallized. The same associates have formed at treating S-methyl iodides with tert-butylamine or diethylamine in the absence of a solvent.