5-{[(6-morpholin-4-ylpyridin-3-yl)amino]methyl}-1,3,4-oxadiazole-2-thiol | 1415835-20-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-{[(6-morpholin-4-ylpyridin-3-yl)amino]methyl}-1,3,4-oxadiazole-2-thiol
• 英文别名: 5-[[(6-Morpholino-3-pyridyl)amino]methyl]-1,3,4-oxadiazole-2-thiol；5-[[(6-morpholin-4-ylpyridin-3-yl)amino]methyl]-3H-1,3,4-oxadiazole-2-thione
• CAS: 1415835-20-9
• 化学式: C₁₂H₁₅N₅O₂S
• 分子量: 293.349
• InChiKey: HWVRHYIXRQDECX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N-苯基哌嗪 、 5-{[(6-morpholin-4-ylpyridin-3-yl)amino]methyl}-1,3,4-oxadiazole-2-thiol 以 二氯甲烷 为溶剂， 反应 3.0h， 以81%的产率得到5-{[(6-morpholin-4-ylpyridin-3-yl)amino]methyl}-3-[(4-phenylpiperazin-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione
  参考文献：
  名称：

  Antimicrobial and antiurease activities of newly synthesized morpholine derivatives containing an azole nucleus

  摘要：

  2-[6-(Morpholin-4-yl)pyridin-3-ylamino]acetohydrazide (4) was obtained starting from 6-morpholin-4-ylpyridin-3-amine (2) via the formation of ester (3) and then converted to the corresponding Schiff bases (5, 6) with the reaction with aromatic aldehydes. The carbothioamide (9), obtained from the reaction of hydrazide with phenylisothiocyanate, was converted to the corresponding 1,2,4-triazole (11) and 1,3,4-thiadiazole (12) derivatives by the treatment with NaOH or H2SO4, respectively. The cyclocondenzation of 9 with 4-chlorophenacyl bromide or ethyl bromoacetate produced the corresponding 1,3-thiazole (10) or 1,3-thiazolidine derivatives (13), respectively. Antimicrobial and antiurease activities of newly synthesized compounds were investigated. Some of them were found to be active on M. smegmatis, and they displayed activity toward C. albicans and S. cerevisiae in high concentration. Compound 10 proved to be the most potent showing an enzyme inhibition activity with an IC50 = 2.37 +/- A 0.19 mu M.

  DOI：

  10.1007/s00044-012-0318-1
• 作为产物：
  描述：

  3-氨基-6-吗啉基吡啶 在 一水合肼 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 21.0h， 生成 5-{[(6-morpholin-4-ylpyridin-3-yl)amino]methyl}-1,3,4-oxadiazole-2-thiol
  参考文献：
  名称：

  Antimicrobial and antiurease activities of newly synthesized morpholine derivatives containing an azole nucleus

  摘要：

  2-[6-(Morpholin-4-yl)pyridin-3-ylamino]acetohydrazide (4) was obtained starting from 6-morpholin-4-ylpyridin-3-amine (2) via the formation of ester (3) and then converted to the corresponding Schiff bases (5, 6) with the reaction with aromatic aldehydes. The carbothioamide (9), obtained from the reaction of hydrazide with phenylisothiocyanate, was converted to the corresponding 1,2,4-triazole (11) and 1,3,4-thiadiazole (12) derivatives by the treatment with NaOH or H2SO4, respectively. The cyclocondenzation of 9 with 4-chlorophenacyl bromide or ethyl bromoacetate produced the corresponding 1,3-thiazole (10) or 1,3-thiazolidine derivatives (13), respectively. Antimicrobial and antiurease activities of newly synthesized compounds were investigated. Some of them were found to be active on M. smegmatis, and they displayed activity toward C. albicans and S. cerevisiae in high concentration. Compound 10 proved to be the most potent showing an enzyme inhibition activity with an IC50 = 2.37 +/- A 0.19 mu M.

  DOI：

  10.1007/s00044-012-0318-1