2-(4-n-pentyl-1H-1,2,3-triazol-1-yl)acetic acid | 1393720-42-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(4-n-pentyl-1H-1,2,3-triazol-1-yl)acetic acid
• 英文别名: 2-(4-Pentyl-1h-1,2,3-triazol-1-yl)acetic acid；2-(4-pentyltriazol-1-yl)acetic acid
• CAS: 1393720-42-7
• 化学式: C₉H₁₅N₃O₂
• 分子量: 197.237
• InChiKey: MOGIMNSSSHJCJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-n-pentyl-1H-1,2,3-triazol-1-yl)acetic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 48.0h， 生成 3-[(4-pentyl-1-1,2,3-triazol-1-yl)methyl]-1-phenyl-1,5,6,7-tetrahydro-4H-indazol-4-one
  参考文献：
  名称：

  1,2,3-Triazole-Containing 1,5,6,7-Tetrahydro-4H-indazol-4-ones and 6,7-Dihydrobenzo[d]isoxazol-4(5H)-ones: Synthesis and Biological Activity

  摘要：

  摘要 通过 2-[(1H-1,2,3-三唑-1-基)乙酰基]环己烷-1,3-二酮分别与苯肼（4-氟苯肼）或羟胺环缩合合成了含三唑的 1,5,6,7- 四氢-4H-吲唑-4-酮和 6,7- 二氢苯并[d]异恶唑-4(5H)-酮。通过 1H、13C、19F NMR 光谱法和元素分析数据证实了所获化合物的结构和组成。在体外研究了所获系列化合物对人肝癌细胞 HepG2、乳腺腺癌细胞 MCF-7 和喉癌细胞 Hep2 的细胞毒性和细胞抑制活性。

  DOI：

  10.1134/s1070363223020068
• 作为产物：
  描述：

  ethyl 2-(4-pentyl-1H-1,2,3-triazol-1-yl)acetate 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以96%的产率得到2-(4-n-pentyl-1H-1,2,3-triazol-1-yl)acetic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators

  摘要：

  New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.007

文献信息

• Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators
  作者：Mohamad Sabbah、Fanny Fontaine、Lucie Grand、Mohamed Boukraa、Mohamed L. Efrit、Alain Doutheau、Laurent Soulère、Yves Queneau

  DOI：10.1016/j.bmc.2012.06.007

  日期：2012.8

  New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists. (C) 2012 Elsevier Ltd. All rights reserved.
• 1,2,3-Triazole-Containing 1,5,6,7-Tetrahydro-4H-indazol-4-ones and 6,7-Dihydrobenzo[d]isoxazol-4(5H)-ones: Synthesis and Biological Activity
  作者：T. S. Khlebniсova、V. G. Zinovich、Yu. A. Piven、A. V. Baranovsky、F. A. Lakhvich、R. E. Trifonov、Yu. A. Golubeva、L. S. Klyushova、E. V. Lider

  DOI：10.1134/s1070363223020068

  日期：2023.2

  Triazole-containing 1,5,6,7-tetrahydro-4H-indazol-4-ones and 6,7-dihydrobenzo[d]isoxazol-4(5H)-ones were synthesized by cyclocondensation of 2-[(1H-1,2,3-triazol-1-yl)acetyl]cyclohexane-1,3-diones with phenylhydrazine (4-fluorophenylhydrazine) or hydroxylamine, respectively. Structure and composition of the obtained compounds were confirmed by ¹H, ¹³C, ¹⁹F NMR spectroscopy methods and by data of elemental analysis. Cytotoxic and cytostatic activities of the series of obtained compounds were investigated in vitro against human hepatocellular carcinoma cells HepG2, mammary adenocarcinoma cells MCF-7, and laryngeal cancer cells Hep2.

  摘要 通过 2-[(1H-1,2,3-三唑-1-基)乙酰基]环己烷-1,3-二酮分别与苯肼（4-氟苯肼）或羟胺环缩合合成了含三唑的 1,5,6,7- 四氢-4H-吲唑-4-酮和 6,7- 二氢苯并[d]异恶唑-4(5H)-酮。通过 1H、13C、19F NMR 光谱法和元素分析数据证实了所获化合物的结构和组成。在体外研究了所获系列化合物对人肝癌细胞 HepG2、乳腺腺癌细胞 MCF-7 和喉癌细胞 Hep2 的细胞毒性和细胞抑制活性。