4-(1-(acetylthio)methylthio)-1H-1,2,3-triazole | 140128-01-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(1-(acetylthio)methylthio)-1H-1,2,3-triazole
• 英文别名: (1H-1,2,3-triazol-4-yl)thiomethyl thioacetate；4-acetylthiomethylthio-1,2,3-triazole；Ethanethioic acid, S-[(1H-1,2,3-triazol-4-ylthio)methyl] ester；S-(2H-triazol-4-ylsulfanylmethyl) ethanethioate
• CAS: 140128-01-4
• 化学式: C₅H₇N₃OS₂
• 分子量: 189.262
• InChiKey: SHWXDEZMFCXAKD-UHFFFAOYSA-N

物化性质

• 沸点：
  355.0±22.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(1-(acetylthio)methylthio)-1H-1,2,3-triazole 在 sodium methylate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2H-triazol-4-ylsulfanylmethanethiol
  参考文献：
  名称：

  Practical Large-Scale Synthesis of Cefmatilen, A New Cephalosporin Antibiotic

  摘要：

  A practical large-scale process for the synthesis of cefmatilen hydrochloride hydrate (1), a new oral cephalosporin antibiotic, is described. Several impurities are isolated from a bulk drug and identified. Side reactions are discussed in order to prevent them. The conditions were optimized to control the formation of impurities. The process is amenable to a multikilogram-scale preparation. Several kilograms of compound 1 for clinical trials were successfully prepared by this process from the three starting materials (7-aminocephem hydrochloride 4, triethylammonium acetate 5, and triazole 7) on a pilot scale in overall yields of 61-65% (10-14% higher than those for the previous process).

  DOI：

  10.1021/op049920i
• 作为产物：
  描述：

  1H-1,2,3-Triazole-4-thiol, monosodium salt 、 Chloromethyl thiolacetate 、 N,N-二甲基甲酰胺 在 乙酸乙酯 、 水 、 碳酸氢钠 、 Sodium sulfate-III 、 正己烷 、 乙醚 作用下， 以 水 为溶剂， 反应 2.67h， 以to give 4-acetylthiomethylthio-1,2,3-triazole (38.9 g)的产率得到4-(1-(acetylthio)methylthio)-1H-1,2,3-triazole
  参考文献：
  名称：

  Thioalkylthio cephalosporin derivatives

  摘要：

  一种新的巯基烷基头孢菌素抗生素化合物，其化学式为I: ##STR1## 其中Acyl为C.sub.1-C.sub.12酰基；Het为含有一个或多个杂原子的选择性取代的单环杂芳基团；R.sup.1为单键或C.sub.1-C.sub.4烷基；R.sub.2为直链或支链C.sub.1-C.sub.4烷基；X为硫原子或亚砜基团；Y为氢原子或甲氧基团，或其药学上可接受的盐或氨基、羧基和/或羟基保护衍生物，以及包含该化合物的制剂和治疗细菌感染的方法。

  公开号：

  US05352792A1

文献信息

• Orally Active Cephalosporins. IV. Synthesis, Antibacterial Activity and Oral Absorption of 3-(1H-1,2,3-Triazol-4-yl)thiomethylthio-cephalosporins.
  作者：Masaharu KUME、Tadatoshi KUBOTA、Yasuo KIMURA、Hiromu NAKASHIMIZU、Kiyoshi MOTOKAWA

  DOI：10.1248/cpb.41.758

  日期：——

  The synthesis, antibacterial activity and oral absorption of 3-(1H-1, 2, 3, -trazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acids with various C-7 side chains (2) are described. The (1H-1, 2, 3-triazol-4-yl)thiomethylthio C-3 side chain was found to be an effective substituent for good oral absorption of cephalosporins with some C-7 side chains.

  介绍了具有不同 C-7 侧链 (2) 的 3-(1H-1,2,3,-三唑-4-基)硫代甲硫基-3-头孢-4-羧酸的合成、抗菌活性和口服吸收。研究发现，(1H-1, 2, 3-三唑-4-基)硫代甲硫基 C-3 侧链是具有某些 C-7 侧链的头孢菌素口服吸收良好的有效取代基。
• Thioalkylthio cephalosporin derivatives
  申请人：Shionogi & Co., Ltd.

  公开号：US05214037A1

  公开（公告）日：1993-05-25

  A novel thioalkylthio cephalosporin antibiotic compound of formula I: ##STR1## wherein Acyl is C.sub.1 -C.sub.12 acyl; Het is optionally substituted monocyclic heteroaromatic group containing one or more hetero atoms; R.sup.1 is a single bond or C.sub.1 -C.sub.4 alkylene; R.sub.2 is a straight or branched C.sub.1 -C.sub.4 alkylene; X is a sulfur atom or sulioxide group; and Y is a hydrogen atom or methoxy group, or a pharmaceutically acceptable salt or an amino-, carboxy- and/or hydroxy-protected derivative thereof, a formulation containing the same and a method for treating bacterial infections.

  化合物I的结构式为：##STR1## 其中Acyl为C.sub.1-C.sub.12酰基；Het为可选的含有一个或多个杂原子的单环杂芳基团；R.sup.1为单键或C.sub.1-C.sub.4烷基；R.sub.2为直链或支链C.sub.1-C.sub.4烷基；X为硫原子或亚砜基团；Y为氢原子或甲氧基，或其药学上可接受的盐或氨基、羧基和/或羟基保护衍生物，以及含有该化合物的制剂和治疗细菌感染的方法。
• Practical Large-Scale Synthesis of Cefmatilen, A New Cephalosporin Antibiotic
  作者：Tatsuya Kobayashi、Yoshiyuki Masui、Yoshihisa Goto、Yoji Kitaura、Taiku Mizutani、Isao Matsumura、Yoshihide Sugata、Yutaka Ide、Masami Takayama、Hisanori Takahashi、Akira Okuyama

  DOI：10.1021/op049920i

  日期：2004.9.1

  A practical large-scale process for the synthesis of cefmatilen hydrochloride hydrate (1), a new oral cephalosporin antibiotic, is described. Several impurities are isolated from a bulk drug and identified. Side reactions are discussed in order to prevent them. The conditions were optimized to control the formation of impurities. The process is amenable to a multikilogram-scale preparation. Several kilograms of compound 1 for clinical trials were successfully prepared by this process from the three starting materials (7-aminocephem hydrochloride 4, triethylammonium acetate 5, and triazole 7) on a pilot scale in overall yields of 61-65% (10-14% higher than those for the previous process).