4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzonitrile | 1310494-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzonitrile
• 英文别名: 4-[4-[5-(5-Nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl]piperazin-1-yl]benzonitrile
• CAS: 1310494-13-3
• 化学式: C₁₇H₁₄N₆O₃S
• 分子量: 382.403
• InChiKey: XOUSMGRHKLCDBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzonitrile 在 盐酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 121.0h， 生成 1-(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazine hydrochloride
  参考文献：
  名称：

  Synthesis and antileishmanial activity of novel 5-(5-nitrofuran-2-y1)-1,3,4-thiadiazoles with piperazinyl-linked benzamidine substituents

  摘要：

  In order to optimize the antileishmanial activity of piperazinyl-linked 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazoles, we synthesized a series of 5-(5-nitrofuran-2-y1)-1,3,4-thiadiazoles with piperazinyl-linked benzamidine substituent as scaffold found in pentamidine related antiprotozoals. The structure of target compounds was confirmed by IR, H-1 NMR, C-13 NMR and Mass spectral data. All compounds were tested for in vitro activity against the promastigote and amastigote forms of Leishmania major. From the results, we found that the substitution on amidine nitrogen has profound role in the biological activity of these compounds. The 5-nitrofuran-2-yl-1,3,4-thiadiazoles having n-propyl, n-butyl and benzyl side chain on benzamidine (as in compounds 2d, 2e and 2g, respectively) showed very good activity in both forms of promastigote and amastigote. The most active compound was N-propyl-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl) benzamidine hydrochloride (2d) with IC50 value of 0.08 mu M in promastigote model. This compound showed a very low level of toxicity against macrophages (CC50 = 785 mu M), with the highest selectivity index (SI = 78.5) among the tested compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.053
• 作为产物：
  描述：

  5-(5-硝基-2-呋喃基)-1,3,4-噻二唑-2-基胺 在 盐酸 、 铜 、 potassium carbonate 、 sodium nitrite 作用下， 以 丁酮 为溶剂， 反应 8.0h， 生成 4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzonitrile
  参考文献：
  名称：

  Synthesis and antileishmanial activity of novel 5-(5-nitrofuran-2-y1)-1,3,4-thiadiazoles with piperazinyl-linked benzamidine substituents

  摘要：

  In order to optimize the antileishmanial activity of piperazinyl-linked 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazoles, we synthesized a series of 5-(5-nitrofuran-2-y1)-1,3,4-thiadiazoles with piperazinyl-linked benzamidine substituent as scaffold found in pentamidine related antiprotozoals. The structure of target compounds was confirmed by IR, H-1 NMR, C-13 NMR and Mass spectral data. All compounds were tested for in vitro activity against the promastigote and amastigote forms of Leishmania major. From the results, we found that the substitution on amidine nitrogen has profound role in the biological activity of these compounds. The 5-nitrofuran-2-yl-1,3,4-thiadiazoles having n-propyl, n-butyl and benzyl side chain on benzamidine (as in compounds 2d, 2e and 2g, respectively) showed very good activity in both forms of promastigote and amastigote. The most active compound was N-propyl-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl) benzamidine hydrochloride (2d) with IC50 value of 0.08 mu M in promastigote model. This compound showed a very low level of toxicity against macrophages (CC50 = 785 mu M), with the highest selectivity index (SI = 78.5) among the tested compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.053

文献信息

• Synthesis and antileishmanial activity of novel 5-(5-nitrofuran-2-y1)-1,3,4-thiadiazoles with piperazinyl-linked benzamidine substituents
  作者：Azar Tahghighi、Farzane Rezazade Marznaki、Farzad Kobarfard、Siavoush Dastmalchi、Javid Shahbazi Mojarrad、Sepideh Razmi、Sussan Kabudanian Ardestani、Saeed Emami、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2011.03.053

  日期：2011.6

  In order to optimize the antileishmanial activity of piperazinyl-linked 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazoles, we synthesized a series of 5-(5-nitrofuran-2-y1)-1,3,4-thiadiazoles with piperazinyl-linked benzamidine substituent as scaffold found in pentamidine related antiprotozoals. The structure of target compounds was confirmed by IR, H-1 NMR, C-13 NMR and Mass spectral data. All compounds were tested for in vitro activity against the promastigote and amastigote forms of Leishmania major. From the results, we found that the substitution on amidine nitrogen has profound role in the biological activity of these compounds. The 5-nitrofuran-2-yl-1,3,4-thiadiazoles having n-propyl, n-butyl and benzyl side chain on benzamidine (as in compounds 2d, 2e and 2g, respectively) showed very good activity in both forms of promastigote and amastigote. The most active compound was N-propyl-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl) benzamidine hydrochloride (2d) with IC50 value of 0.08 mu M in promastigote model. This compound showed a very low level of toxicity against macrophages (CC50 = 785 mu M), with the highest selectivity index (SI = 78.5) among the tested compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.