5-(1-adamantyl)-1,3,4-3H-thiadiazoline-2-thione | 1257344-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(1-adamantyl)-1,3,4-3H-thiadiazoline-2-thione
• 英文别名: 5-(Tricyclo[3.3.1.1~3,7~]dec-1-yl)-1,3,4-thiadiazole-2-thiol；5-(1-adamantyl)-3H-1,3,4-thiadiazole-2-thione
• CAS: 1257344-11-8
• 化学式: C₁₂H₁₆N₂S₂
• 分子量: 252.404
• InChiKey: QKINWJIDQWOLJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  81.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(1-adamantyl)-1,3,4-3H-thiadiazoline-2-thione 、 1-(氯甲基)-4-硝基苯 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以90%的产率得到2-(1-Adamantyl)-5-[(4-nitrophenyl)methylsulfanyl]-1,3,4-thiadiazole
  参考文献：
  名称：

  Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1,3,4-thiadiazole derivatives

  摘要：

  New 1-adamanyl-1,3,4-thiadiazole derivatives namely, 5-(1-adamantyl)-1,3,4-thiadiazoline-2-thione 3, 5-(1-adamantyl)-3-(benzyl- or 4-substituted benzyl)-1,3,4-thiadiazoline-2-thione 4a-d, 5-(1-adamantyl)-3-(4-substituted-1-piperazinylmethyl)-1,3,4-thiadiazoline-2-thiones 5a-c, 2-[5-(1-adamantyl)2-thioxo-1,3,4-thiadiazolin-3-yl]acetic acid 7, (+/-)-2-[5-(1-adamantyl)-2-thioxo-1,3,4-thiadiazolin-3-yl] propionic acid 9, 3-[5-(1-adamantyl)-2-thioxo-1,3,4-thiadiazolin-3-yl]propionic acid 11, N-[5-(1-adamantyl)-1,3,4-thiadiazol-2-yl]-N'-arylthioureas 15a-c and 5-(1-adamantyl)-1,3,4-thiadiazoline-2-one 16, were synthesized and tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 7, 9, 15b and 15c displayed marked activity against the tested Gram-positive bacteria, while compound 3 was highly active against the tested Gram-negative bacteria. Compounds 4b, 7 and 15c were weakly or moderately active against C albicans. In addition, the in vivo anti-inflammatory activity of the synthesized compounds was determined using the carrageenan-induced paw oedema method in rats. The propionic acid derivative 9 produced good dose-dependent anti-inflammatory activity. (C) 2010 Elsevier Masson SAS. All rights reserved,

  DOI：

  10.1016/j.ejmech.2010.08.007
• 作为产物：
  描述：

  二硫化碳 、 金刚烷-1-甲酰肼 在 potassium hydroxide 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以7.8 g的产率得到5-(1-adamantyl)-1,3,4-3H-thiadiazoline-2-thione
  参考文献：
  名称：

  Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1,3,4-thiadiazole derivatives

  摘要：

  New 1-adamanyl-1,3,4-thiadiazole derivatives namely, 5-(1-adamantyl)-1,3,4-thiadiazoline-2-thione 3, 5-(1-adamantyl)-3-(benzyl- or 4-substituted benzyl)-1,3,4-thiadiazoline-2-thione 4a-d, 5-(1-adamantyl)-3-(4-substituted-1-piperazinylmethyl)-1,3,4-thiadiazoline-2-thiones 5a-c, 2-[5-(1-adamantyl)2-thioxo-1,3,4-thiadiazolin-3-yl]acetic acid 7, (+/-)-2-[5-(1-adamantyl)-2-thioxo-1,3,4-thiadiazolin-3-yl] propionic acid 9, 3-[5-(1-adamantyl)-2-thioxo-1,3,4-thiadiazolin-3-yl]propionic acid 11, N-[5-(1-adamantyl)-1,3,4-thiadiazol-2-yl]-N'-arylthioureas 15a-c and 5-(1-adamantyl)-1,3,4-thiadiazoline-2-one 16, were synthesized and tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 7, 9, 15b and 15c displayed marked activity against the tested Gram-positive bacteria, while compound 3 was highly active against the tested Gram-negative bacteria. Compounds 4b, 7 and 15c were weakly or moderately active against C albicans. In addition, the in vivo anti-inflammatory activity of the synthesized compounds was determined using the carrageenan-induced paw oedema method in rats. The propionic acid derivative 9 produced good dose-dependent anti-inflammatory activity. (C) 2010 Elsevier Masson SAS. All rights reserved,

  DOI：

  10.1016/j.ejmech.2010.08.007

文献信息

• Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1,3,4-thiadiazole derivatives
  作者：Adnan A. Kadi、Ebtehal S. Al-Abdullah、Ihsan A. Shehata、Elsayed E. Habib、Tarek M. Ibrahim、Ali A. El-Emam

  DOI：10.1016/j.ejmech.2010.08.007

  日期：2010.11

  New 1-adamanyl-1,3,4-thiadiazole derivatives namely, 5-(1-adamantyl)-1,3,4-thiadiazoline-2-thione 3, 5-(1-adamantyl)-3-(benzyl- or 4-substituted benzyl)-1,3,4-thiadiazoline-2-thione 4a-d, 5-(1-adamantyl)-3-(4-substituted-1-piperazinylmethyl)-1,3,4-thiadiazoline-2-thiones 5a-c, 2-[5-(1-adamantyl)2-thioxo-1,3,4-thiadiazolin-3-yl]acetic acid 7, (+/-)-2-[5-(1-adamantyl)-2-thioxo-1,3,4-thiadiazolin-3-yl] propionic acid 9, 3-[5-(1-adamantyl)-2-thioxo-1,3,4-thiadiazolin-3-yl]propionic acid 11, N-[5-(1-adamantyl)-1,3,4-thiadiazol-2-yl]-N'-arylthioureas 15a-c and 5-(1-adamantyl)-1,3,4-thiadiazoline-2-one 16, were synthesized and tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 7, 9, 15b and 15c displayed marked activity against the tested Gram-positive bacteria, while compound 3 was highly active against the tested Gram-negative bacteria. Compounds 4b, 7 and 15c were weakly or moderately active against C albicans. In addition, the in vivo anti-inflammatory activity of the synthesized compounds was determined using the carrageenan-induced paw oedema method in rats. The propionic acid derivative 9 produced good dose-dependent anti-inflammatory activity. (C) 2010 Elsevier Masson SAS. All rights reserved,