5-(2-丙炔基磺酰基)-1,3,4-噻二唑-2-胺 | 53918-05-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 5-(2-丙炔基磺酰基)-1,3,4-噻二唑-2-胺
• 英文名称: 2-Amino-5-(2-propynylthio)-1,3,4-thiadiazol
• 英文别名: 2-amino-5-(2-propynyl)thio-1,3,4-thiadiazole；5-(prop-2-yn-1-ylsulfanyl)-1,3,4-thiadiazol-2-amine；5-(2-Propynylsulfanyl)-1,3,4-thiadiazol-2-ylamine；5-prop-2-ynylsulfanyl-1,3,4-thiadiazol-2-amine
• CAS: 53918-05-1
• 化学式: C₅H₅N₃S₂
• mdl: MFCD00175753
• 分子量: 171.247
• InChiKey: SJSZAQLZKIYESE-UHFFFAOYSA-N

物化性质

• 熔点：
  134-136°

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(2-丙炔基磺酰基)-1,3,4-噻二唑-2-胺 在 sodium carbonate 、 copper(l) chloride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 4.0h， 生成 [5-(4-Pyrrolidin-1-yl-but-2-ynylsulfanyl)-[1,3,4]thiadiazol-2-yl]-carbamic acid ethyl 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：

  3-氯丙炔 、 2-氨基-5-巯基-1,3,4-噻二唑 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以75%的产率得到5-(2-丙炔基磺酰基)-1,3,4-噻二唑-2-胺
  参考文献：
  名称：

  Jaeger, G.; Heitzer, H., Synthesis, 1981, # 9, p. 704 - 706

  摘要：

  DOI：

文献信息

• Heterocyclization of 2-(Propargylsulfanyl)-1,3-thiazole Derivatives by the Action of Halogens
  作者：N. M. Tarasova、D. G. Kim、O. S. El’tsov、T. S. Shtukina、A. E. Borisova

  DOI：10.1134/s1070428018030156

  日期：2018.3

  Reactions of 2-(propargylsulfanyl)-5-methyl-1,3,4-thiadiazole, N-[5-(propargylsulfanyl)-1,3,4-thiadiazol- 2-yl]benzamide, 2-(propargylsulfanyl)-1,3-benzothiazole, and 2-(propargylsulfanyl)-4,5-dihydro-1,3- thiazole with iodine involved annulation of the unsaturated substituent with formation of fused thiazole ring. 2(5)-(Propargylsulfanyl)-1,3,4-thiadiazole derivatives reacted with bromine to give

  2-（炔丙基硫烷基）-5-甲基-1,3,4-噻二唑，N- [5-（炔丙基硫烷基）-1,3,4-噻二唑-2-基]苯甲酰胺，2-（炔丙基硫烷基）-1的反应，3-苯并噻唑和2-（炔丙基硫烷基）-4，5-二氢-1，3-噻唑与碘的作用是使不饱和取代基环合并形成稠合的噻唑环。2（5）-（炔丙基硫烷基）-1,3,4-噻二唑衍生物与溴反应生成杂环化产物和三键溴加合物的混合物。2-（炔丙基硫烷基）-4，5-二氢-1，3-噻唑的溴化仅提供了三键的溴加成产物。
• Aglycone-focused randomization of 2-difluoromethylphenyl-type sialoside suicide substrates for neuraminidases
  作者：Hirokazu Kai、Hiroshi Hinou、Shin-Ichiro Nishimura

  DOI：10.1016/j.bmc.2012.02.001

  日期：2012.4

  potent inhibitor of neuraminidases, a hydrolase that is responsible for processing sialylated glycoconjugates, is a promising drug candidate for various infective diseases. The current study demonstrates that the use of an aglycone-focused library of 2-difluoromethylphenyl α-sialosides is an effective technique to find potent and selective mechanism-based labeling reagents for neuraminidases. The focused

  神经氨酸酶的选择性和有效抑制剂是负责处理唾液酸化糖缀合物的水解酶，是治疗各种感染性疾病的有希望的药物。目前的研究表明，使用以糖苷配基为中心的2-二氟甲基苯基α-唾液酸苷文库是一种有效的技术，可以找到针对神经氨酸酶的有效的，基于选择性机理的标记试剂。通过点击反应，由4-叠氮基-2-二氟甲基苯基唾液苷（2）和炔烃封端的化合物库构建了聚焦库。重点文库显示了两种神经氨酸酶，霍乱弧菌神经氨酸酶（VCNA）和人神经氨酸酶2（hNeu2），并为每种神经氨酸酶选择最有效的抑制剂。所选抑制剂的动力学分析表明，糖苷配基部分的修饰提高了K I值，相对于基本骨架而言，酶活性的t 1/2值几乎没有变化（2）。
• JAEGER, G.;HEITZER, H., SYNTHESIS, BRD, 1981, N 9, 704-706
  作者：JAEGER, G.、HEITZER, H.

  DOI：——

  日期：——
• MUHI-ELDEEN, ZUHAIR;AL-ZAHAWEI, SUHA KAHTTAN;HUSSEIN, FAHAD;SALMAN, SALMA+, EUR. J. MED. CHEM., 23,(1988) N 2, 133-137
  作者：MUHI-ELDEEN, ZUHAIR、AL-ZAHAWEI, SUHA KAHTTAN、HUSSEIN, FAHAD、SALMAN, SALMA+

  DOI：——

  日期：——
• 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.