4-(1H-1,2,4-三唑-1-基)-1-丁胺 | 100468-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(1H-1,2,4-三唑-1-基)-1-丁胺
• 中文别名: 4-(1H-1,2,4-三唑-1-基)丁烷-1-胺
• 英文名称: 4-[1,2,4]triazol-1-yl-butylamine
• 英文别名: 4-(1H-1,2,4-triazol-1-yl)butanamine；4-(1H-1,2,4-triazol-1-yl)butan-1-amine；4-(1H-1,2,4-triazol-1-yl)butylamine；1H-1,2,4-Triazole-1-butanamine；4-(1,2,4-triazol-1-yl)butan-1-amine
• CAS: 100468-21-1
• 化学式: C₆H₁₂N₄
• 分子量: 140.188
• InChiKey: CTGUMQCGJDHHNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氯-2-酰氯噻吩 、 4-(1H-1,2,4-三唑-1-基)-1-丁胺 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到5-chloro-N-[4-(1H-1,2,4-triazol-1-yl)butyl]-2-thiophenecarboxamide
  参考文献：
  名称：

  Thromboxane synthetase inhibitors and antihypertensive agents. 3. N-[(1H-imidazol-1-yl)alkyl]heteroaryl amides as potent enzyme inhibitors

  摘要：

  The title compounds were prepared as the heterocyclic analogues of thromboxane (TX) synthetase inhibitors and antihypertensive agents previously reported from our laboratories. These compounds were at least as active TX synthetase inhibitors as their benzene isosteres with the indole derivatives 50-55 having the most potent enzyme inhibiting activity measured to date in our laboratories. The best compound, 54, is more than 200-fold more potent than the standard, dazoxiben. In contrast, the antihypertensive activity of these series of compounds was no better than their benzene counterparts and is far lower than the isoindoledione derivatives prepared in a related series. The structure-activity relationship results from this study were similar to our previous observations and include the fact that the amide moiety effectively replaces a carboxylic acid for potent TX synthetase inhibition and that a four to six methylene unit separation (approximately 8.5 A) between amide and imidazole moieties achieves maximal activity.

  DOI：

  10.1021/jm00389a013
• 作为产物：
  描述：

  2-[4-(1H-1,2,4-triazol-1-yl)butyl]-1H-isoindol-1,3(2H)-dione 在 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4-(1H-1,2,4-三唑-1-基)-1-丁胺
  参考文献：
  名称：

  Discovery of a Highly Potent and Selective MYOF Inhibitor with Improved Water Solubility for the Treatment of Gastric Cancer

  摘要：

  DOI：

  10.1021/acs.jmedchem.3c01639

文献信息

• Thromboxane synthetase inhibitors and antihypertensive agents. 1. N-[(1H-imidazol-1-yl)alkyl]aryl amides and N-[(1H-1,2,4-triazol-1-yl)alkyl]aryl amides
  作者：William B. Wright、Jeffery B. Press、Peter S. Chan、Joseph W. Marsico、Margie F. Haug、Judy Lucas、Jess Tauber、Andrew S. Tomcufcik

  DOI：10.1021/jm00154a017

  日期：1986.4

  formation. The most interesting thromboxane synthetase inhibitors prepared were 4-chloro-, 4-(trifluoromethyl)-, and 4-bromobenzamide derivatives of (1H-imidazol-1-yl)alkylamines with C5-C8 alkyl chains separating the heterocycle from the amide moiety, while the most active antihypertensive agents were 3- or 4-chloro-, -bromo, or -(trifluoromethyl)benzamides with C3 alkyl chains. The best thromboxane

  制备标题化合物以研究其作为血栓烷合成酶抑制剂以及降压药的潜力。制备咪唑VIII和三唑X以检查芳族取代，链长和杂环取代对生物活性的影响。咪唑VIII和三唑X是不抑制前列环素形成的血栓烷合成酶抑制剂。制备的最有趣的血栓烷合成酶抑制剂是（1H-咪唑-1-基）烷基胺的4-氯-，4-（三氟甲基）-和4-溴苯甲酰胺衍生物，其C5-C8烷基链将杂环与酰胺部分分开，而最具活性的降压药是带有C3烷基链的3-或4-氯-，-溴或-（三氟甲基）苯甲酰胺。
• New antithrombotic 1-Phthalazinamines with Serotonin Antagonistic Properties
  作者：Matthias Johnsen、Klaus Rehse、Heinz Pertz、Johannes Peter Stasch、Erwin Bischoff

  DOI：10.1002/ardp.200300775

  日期：2003.12

  4‐arylalkyl‐1‐phthalazinamines (5—8) which we prepared and tested for antithrombotic properties. All compounds were assayed for their antiplatelet activity in the “Born test” with collagen as inducer of the aggregation. N‐[4‐(1H‐1, 2, 4‐triazol‐1‐yl)butyl]‐4‐phenyl‐1‐phthalazin‐amine (7 c) was the most potent compound, having an IC50 of 8 μM. When 5‐HT (Serotonin) was used to start aggregation the N‐(furan‐2‐yl‐met

  我们报告了 19 种 4- 芳基 - 和 4- 芳基烷基 - 1- 酞嗪胺 (5-8)，我们制备并测试了它们的抗血栓形成特性。在用胶原蛋白作为聚集诱导剂的“出生试验”中测定所有化合物的抗血小板活性。N- [4- (1H - 1, 2, 4- 三唑 - 1- 基) 丁基] -4 - 苯基 - 1- 酞嗪 - 胺 (7 c) 是最有效的化合物，IC50 为 8 μM。当使用 5-HT（5-羟色胺）开始聚集时，N-（呋喃-2-基-甲基）-4-苯基-1-邻苯二酚胺（8a）的 IC50 为 2 μM。体内效力非常显着。N- [5- (1H - 1, 2, 4- triazol - 1 - yl) pentyl] -4 - 苯基 - 1- 酞嗪胺 (7 d) 抑制小动脉血栓形成 12% (P <0.002) 和 7% (P < 0.01) 在使用我们的激光血栓形成模型测试的静脉中。对于化合物 8a，我们出人意料地发现了对
• The antitrypanosomal and antitubercular activity of some nitro(triazole/imidazole)-based aromatic amines
  作者：Maria V. Papadopoulou、William D. Bloomer、Howard S. Rosenzweig、Marcel Kaiser

  DOI：10.1016/j.ejmech.2017.07.060

  日期：2017.9

  were active against hypoxic Mtb with MIC values 2.89–9.18 μM. The present data support our previous observations that 2-nitroimidazole-based aromatic amines are selectively active against nonreplicating Mtb, while 3-nitrotriazole-based aromatic amines are potent antichagasic agents.

  合成了数量有限的新颖的3-硝基三唑和2-硝基咪唑连接的喹啉和喹唑啉，并筛选了其在体外抗胰锥虫和抗结核的活性以及在正常细胞中的细胞毒性。所有化合物均对克鲁斯氏锥虫具有活性，而除一种化合物外，其余所有化合物均对克氏杆菌具有活性或中度活性。罗得岛。但是，只有两种氯喹啉对克氏锥虫表现出令人满意的选择性指数（SI），并且只有其中一个对T.b表现出令人满意的SI 。罗得岛。所有测试的化合物对有氧Mtb的最低抑菌浓度（MIC）≥200μM。但是，基于2-硝基咪唑的类似物对缺氧的Mtb具有活性，MIC值为2.89–9.18μM。本数据支持我们以前的观察结果，即基于2-硝基咪唑的芳香胺对非复制型Mtb具有选择性活性，而基于3-硝基三唑的芳香胺则是有效的抗chachagasic剂。
• Novel 3-Nitro-1<i>H</i>-1,2,4-triazole-Based Aliphatic and Aromatic Amines as Anti-Chagasic Agents
  作者：Maria V. Papadopoulou、Bernadette Bourdin Trunz、William D. Bloomer、Caroline McKenzie、Shane R. Wilkinson、Chaiya Prasittichai、Reto Brun、Marcel Kaiser、Els Torreele

  DOI：10.1021/jm201215n

  日期：2011.12.8

  A series of novel 2-nitro-1H-imidazole- and 3-nitro-1H-1,2,4-triazole-based aromatic and aliphatic amines were screened for antitrypanosomal activity and mammalian cytotoxicity by the Drugs for Neglected Diseases initiative (DNDi). Out of 42 compounds tested, 18 3-nitro-1,2,4-triazoles and one 2-nitroimidazole displayed significant growth inhibitory properties against T. cruzi amastigotes (IC50 ranging from 40 nM to 1.97 mu M), without concomitant toxicity toward the host cells (L6 cells), having selectivity indices (SI) 44-1320. Most (16) of these active compounds were up to 33.8-fold more potent than the reference drug benznidazole, tested in parallel. Five novel 3-nitro-1,2,4-triazoles were active against bloodstream-form (BSF) T. b. rhodesiense trypomastigotes (IC50 at nM levels and SI 220-993). An NADH-dependent nitroreductase (TbNTR) plays a role in the antiparasitic activity because BSF T. b. brucei trypomastigotes with elevated TbNTR levels were hypersensitive to tested compounds. Therefore, a novel class of affordable 3-nitro-1,2,4-triazole-based compounds with antitrypanosomal activity has been identified.
• WRIGHT, W. B. ,, JR.;PRESS, J. B.;TOMCUFCIK, A. S.
  作者：WRIGHT, W. B. ,, JR.、PRESS, J. B.、TOMCUFCIK, A. S.

  DOI：——

  日期：——