N-<5-(2-propynyl)-thio-1,3,4-thiadiazol-2-yl>-2-allylcarbamate | 141992-64-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-<5-(2-propynyl)-thio-1,3,4-thiadiazol-2-yl>-2-allylcarbamate
• 英文别名: prop-2-enyl N-(5-prop-2-ynylsulfanyl-1,3,4-thiadiazol-2-yl)carbamate
• CAS: 141992-64-5
• 化学式: C₉H₉N₃O₂S₂
• 分子量: 255.321
• InChiKey: OBBOTLXDEPSWCI-UHFFFAOYSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2,6,6-四甲基哌啶 、 聚合甲醛 、 N-<5-(2-propynyl)-thio-1,3,4-thiadiazol-2-yl>-2-allylcarbamate 在 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以76%的产率得到{5-[4-(2,2,6,6-Tetramethyl-piperidin-1-yl)-but-2-ynylsulfanyl]-[1,3,4]thiadiazol-2-yl}-carbamic acid allyl ester
  参考文献：
  名称：

  Synthesis and antimicrobial activity of N-[5-(4-t-amino-2-butynyl)thio-1,3,4-thiadiazol-2-yl]-2-carbamates

  摘要：

  Three series of 5-thio-1,3,4-thiadiazole carbamates containing alkynyl, aminoalkynyl, alkenyl or alkyl thio substituents have been synthesized as potential antimicrobial agents. The influence of both the alkynyl linkage and the various terminal nitrogen heterocyclic moieties on antimicrobial activity was assessed utilizing representative Gram-positive, Gram-negative and fungal species. Mannich base analogs containing a 2-ethyl carbamate group and a nitrogen heterocyclic of limited bulk provided the broadest spectrum of antimicrobial activity. The thiadiazole carbamates containing a 5-alkylthio substituent were consistently active against the Pseudomonas and Candida organisms studied. It is concluded that an acetylenic linkage is not an absolute requirement for potent antimicrobial activity in this molecular series, and that the binding sites of the organisms tested exhibit a steric requirement for lipophilic, but non-bulky, amine-containing heterocycles on Mannich base analogs.

  DOI：

  10.1016/0223-5234(92)90096-j
• 作为产物：
  描述：

  氯甲酸烯丙酯 、 5-(2-丙炔基磺酰基)-1,3,4-噻二唑-2-胺 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以65%的产率得到N-<5-(2-propynyl)-thio-1,3,4-thiadiazol-2-yl>-2-allylcarbamate
  参考文献：
  名称：

  Synthesis and antimicrobial activity of N-[5-(4-t-amino-2-butynyl)thio-1,3,4-thiadiazol-2-yl]-2-carbamates

  摘要：

  Three series of 5-thio-1,3,4-thiadiazole carbamates containing alkynyl, aminoalkynyl, alkenyl or alkyl thio substituents have been synthesized as potential antimicrobial agents. The influence of both the alkynyl linkage and the various terminal nitrogen heterocyclic moieties on antimicrobial activity was assessed utilizing representative Gram-positive, Gram-negative and fungal species. Mannich base analogs containing a 2-ethyl carbamate group and a nitrogen heterocyclic of limited bulk provided the broadest spectrum of antimicrobial activity. The thiadiazole carbamates containing a 5-alkylthio substituent were consistently active against the Pseudomonas and Candida organisms studied. It is concluded that an acetylenic linkage is not an absolute requirement for potent antimicrobial activity in this molecular series, and that the binding sites of the organisms tested exhibit a steric requirement for lipophilic, but non-bulky, amine-containing heterocycles on Mannich base analogs.

  DOI：

  10.1016/0223-5234(92)90096-j

文献信息

• Synthesis and antimicrobial activity of N-[5-(4-t-amino-2-butynyl)thio-1,3,4-thiadiazol-2-yl]-2-carbamates
  作者：ME Zuhair、A Abu-Al-Teman、FA Hussein、SR Salman、D Al-Dujaili、VF Roche

  DOI：10.1016/0223-5234(92)90096-j

  日期：1992.3

  Three series of 5-thio-1,3,4-thiadiazole carbamates containing alkynyl, aminoalkynyl, alkenyl or alkyl thio substituents have been synthesized as potential antimicrobial agents. The influence of both the alkynyl linkage and the various terminal nitrogen heterocyclic moieties on antimicrobial activity was assessed utilizing representative Gram-positive, Gram-negative and fungal species. Mannich base analogs containing a 2-ethyl carbamate group and a nitrogen heterocyclic of limited bulk provided the broadest spectrum of antimicrobial activity. The thiadiazole carbamates containing a 5-alkylthio substituent were consistently active against the Pseudomonas and Candida organisms studied. It is concluded that an acetylenic linkage is not an absolute requirement for potent antimicrobial activity in this molecular series, and that the binding sites of the organisms tested exhibit a steric requirement for lipophilic, but non-bulky, amine-containing heterocycles on Mannich base analogs.