(1R)-1-(5-tetrazolyl)ethylamine | 176894-59-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R)-1-(5-tetrazolyl)ethylamine
• 英文别名: (1R)-1-(1H-1,2,3,4-tetrazol-5-yl)ethan-1-amine；D-1-aminoethyltetrazole；(1R)-1-(2H-tetrazol-5-yl)ethanamine
• CAS: 176894-59-0
• 化学式: C₃H₇N₅
• 分子量: 113.122
• InChiKey: NDMDHZMRQFSFOZ-UWTATZPHSA-N

物化性质

• 熔点：
  268-270 °C (decomp)
• 沸点：
  283.9±42.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Z-谷安酸叔丁基酯 、 (1R)-1-(5-tetrazolyl)ethylamine 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 生成 (1R)-N-[N-(benzyloxycarbonyl)-α-tert-butyl-L-γ-glutamyl]-1-(5-tetrazolyl)ethylamine
  参考文献：
  名称：

  Carboxylic acid bioisosteres of γ-linked dipeptide analogues of the folate-based thymidylate synthase (TS) inhibitor, 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid (ICI 198583)

  摘要：

  Tetrazole carboxylic acid bioisosteres of gamma-linked dipeptide derivatives of 2-desamino-2-methyl-N-10-propargyl-5,8-dideazafolic acid (ICI 198583), a folate-based inhibitor of thymidylate synthase (TS), were synthesised by multistep routes starting from the appropriate pteroic acid analogue and Z-D-Ala or D-Glu. They exhibited excellent TS inhibitory activities which, however, were not accompanied by a parallel improvement in the L1210 cell growth inhibition.

  DOI：

  10.1016/0960-894x(96)00078-9
• 作为产物：
  描述：

  (1R)-N-(benzyloxycarbonyl)-1-(5-tetrazolyl)ethylamine 在 5%-palladium/activated carbon 、 氢气 作用下， 以74%的产率得到(1R)-1-(5-tetrazolyl)ethylamine
  参考文献：
  名称：

  作为新型丙氨酸消旋酶抑制剂的含 C 端 1-氨基乙基四唑的寡肽

  摘要：

  在接种患者样本的临床培养基中，选择性抑制共生菌对于准确诊断和有效治疗至关重要，因为它们可以掩盖病原菌的存在。研究了丙氨酸类似物 1-氨基乙基四唑作为潜在的丙氨酸消旋酶抑制剂。为了有效吸收和增强和选择性抗菌活性，通过固相肽偶联技术合成了包含二肽和寡肽的 C 端 1-氨基乙基四唑文库。对合成化合物的抗微生物活性的研究确定了几种临床适用的选择性抑制剂。这些能够区分密切相关的细菌，沙门氏菌和大肠杆菌，这在临床环境中很难区分。此外，

  DOI：

  10.3390/molecules25061315

文献信息

• Design and Synthesis of Cyclopenta[<i>g</i>]quinazoline-Based Antifolates as Inhibitors of Thymidylate Synthase and Potential Antitumor Agents^,
  作者：Vassilios Bavetsias、Jonathan H. Marriott、Camille Melin、Rosemary Kimbell、Zbigniew S. Matusiak、F. Thomas Boyle、Ann L. Jackman

  DOI：10.1021/jm991119p

  日期：2000.5.1

  Following the development of raltitrexed, the synthesis of nonpolyglutamatable inhibitors of TS that do not use the reduced folate carrier (RFC) for cellular entry should provide compounds which overcome mechanisms of resistance to folate-based inhibitors of TS that are associated with decreased/altered folylpolyglutamate synthetase (FPGS) expression and/or an impaired RFC. Examination of a computer graphics model of the humanized Escherichia coli TS enzyme with quinazoline inhibitors of TS, such as 1 bound in the active site of the enzyme, suggested that conformational restriction introduced by bridging the C9 with C7 to form a pentacycle may be beneficial for binding to TS. That led to the synthesis of a series of potent cyclopenta[g]quinazoline-based inhibitors of the enzyme in which the glutamyl residue associated with classical antifolates was replaced with a variety of glutamate-derived ligands; the most potent inhibitor being the L-Glu-gamma-D-GluT(alpha) derivative 7j. In the mouse L1210:1565 cell line (mutant RFC), the majority of these compounds had activity equal or only slightly greater compared with the parental L1210 cell line, indicating a reduced dependence on the RFC for cellular uptake in the L1210 cell line.
• Carboxylic acid bioisosteres of γ-linked dipeptide analogues of the folate-based thymidylate synthase (TS) inhibitor, 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid (ICI 198583)
  作者：Vassilios Bavetsias、Ann L. Jackman、Rosemary Kimbell、F. Thomas Boyle、Graham M.F. Bisset

  DOI：10.1016/0960-894x(96)00078-9

  日期：1996.3

  Tetrazole carboxylic acid bioisosteres of gamma-linked dipeptide derivatives of 2-desamino-2-methyl-N-10-propargyl-5,8-dideazafolic acid (ICI 198583), a folate-based inhibitor of thymidylate synthase (TS), were synthesised by multistep routes starting from the appropriate pteroic acid analogue and Z-D-Ala or D-Glu. They exhibited excellent TS inhibitory activities which, however, were not accompanied by a parallel improvement in the L1210 cell growth inhibition.
• C-Terminal 1-Aminoethyltetrazole-Containing Oligopeptides as Novel Alanine Racemase Inhibitors
  作者：Laszlo A. Kondacs、Sylvain Orenga、Rosaleen J. Anderson、Emma C.L. Marrs、John D. Perry、Mark Gray

  DOI：10.3390/molecules25061315

  日期：——

  coupling techniques. The investigation of the antimicrobial activity of the synthesised compounds identified several clinically applicable selective inhibitors. These enabled differentiation between the closely related bacteria, Salmonella and Escherichia coli, which can be difficult to discriminate between in a clinical setting. In addition, differentiation between enterococci and other Gram-positive cocci

  在接种患者样本的临床培养基中，选择性抑制共生菌对于准确诊断和有效治疗至关重要，因为它们可以掩盖病原菌的存在。研究了丙氨酸类似物 1-氨基乙基四唑作为潜在的丙氨酸消旋酶抑制剂。为了有效吸收和增强和选择性抗菌活性，通过固相肽偶联技术合成了包含二肽和寡肽的 C 端 1-氨基乙基四唑文库。对合成化合物的抗微生物活性的研究确定了几种临床适用的选择性抑制剂。这些能够区分密切相关的细菌，沙门氏菌和大肠杆菌，这在临床环境中很难区分。此外，