(3-硝基-1H-1,2,4-噻唑-1-基)乙酸 | 116419-36-4

• 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
• 中文名称: (3-硝基-1H-1,2,4-噻唑-1-基)乙酸
• 中文别名: 2-(3-硝基-1,2,4-三唑-1-基)乙酸；(3-硝基-[1,2,4]三唑-1-基)-乙酸；(3-硝基-1H-1,2,4-三唑-1-基)乙酸
• 英文名称: (3-nitro-1,2,4-triazol-1-yl)acetic acid
• 英文别名: 2-(3-nitro-1H-1,2,4-triazol-1-yl)acetic acid；(3-nitro-1H-1,2,4-triazol-1-yl)acetic acid；2-(3-nitro-1,2,4-triazol-1-yl)acetic acid
• CAS: 116419-36-4
• 化学式: C₄H₄N₄O₄
• mdl: MFCD00297307
• 分子量: 172.1
• InChiKey: JNJSKDYVVRMEPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (3-硝基-1H-1,2,4-噻唑-1-基)乙酸 在 氯化亚砜 作用下， 反应 4.0h， 生成 (3-Nitro-[1,2,4]triazol-1-yl)-acetyl chloride
  参考文献：
  名称：

  五元 C-硝基杂环的水解动力学：吡唑、咪唑、1,2,4-三唑和异恶唑衍生物

  摘要：

  五元杂环的单和二硝基衍生物（即吡唑、咪唑、1,2,4-三唑和异恶唑）的碱性水解伴随着硝基以亚硝酸根阴离子的形式被消除。通过极谱法和光度法研究了水解动力学。实验确定的水解速率常数取决于杂环的性质。根据计算出的反应热力学参数（ΔG≠、ΔH≠、ΔS≠），提出了所研究化合物水解转化的可能机制。

  DOI：

  10.1007/s11172-006-0195-1
• 作为产物：
  描述：

  ethyl 3-nitro-1,2,4-triazolylacetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以94%的产率得到(3-硝基-1H-1,2,4-噻唑-1-基)乙酸
  参考文献：
  名称：

  放疗中仿生化学和光谱学评估3-硝基1,1,2,4-三唑的N1-和N2-取代的衍生物对缺氧细胞的放射增敏潜力：替代效果显着不同

  摘要：

  对3-硝基-1,2,4-三唑（3-NTR）的N1-和N2-衍生物进行了非生物评估方法，包括仿生，化学和光谱学方法，以进行放射增敏。因此，建议3-NTR的N1-衍生物比N2-衍生物对体内低氧细胞更有希望的放射增敏剂。

  DOI：

  10.1016/s0040-4020(01)85460-0

文献信息

• Biomimetic chemical, and spectroscopic evaluations for the radiosensitizing potential of N1- and N2-substituted derivatives of 3-Nitro-1,2,4-Triazole toward hypoxic cells in the radiotherapy: Remarkably different substitution effect
  作者：Yoshimitsu Nagao、Shigeki Sano、Masahito Ochiai、Eiichi Fujita

  DOI：10.1016/s0040-4020(01)85460-0

  日期：1990.1

  evaluation methods involving biomimetic, chemical, and spectroscopic procedures for the radio-sensitizing potential. Consequently, the N1-derivatives of 3-NTR were suggested to be more promising radiosensitizers to hypoxic cells in vivo than the N2-derivatives.

  对3-硝基-1,2,4-三唑（3-NTR）的N1-和N2-衍生物进行了非生物评估方法，包括仿生，化学和光谱学方法，以进行放射增敏。因此，建议3-NTR的N1-衍生物比N2-衍生物对体内低氧细胞更有希望的放射增敏剂。
• Preparation and evaluation of a 99mTcN–PNP complex of sanazole analogue for detecting tumor hypoxia
  作者：Anupam Mathur、Madhava B. Mallia、Sharmila Banerjee、H.D. Sarma、M.R.A. Pillai

  DOI：10.1016/j.bmcl.2012.12.079

  日期：2013.3

  A sanazole derivative, having a favorable single electron reduction potential (SERP) value compared to that of misonidazole, was synthesized and radiolabeled with [(TcN)-Tc-99m(PNP)] precursor to evaluate its potential as a hypoxia imaging agent. The complex, which was lipophilic, could be prepared in good yields and challenging studies with cysteine showed stability of the complex against trans-chelation. However, despite being lipophilic as well as possessing favorable SERP value, biodistribution studies of this complex in fibrosarcoma tumor bearing Swiss mice showed low uptake in tumor. This observation is possibly attributed to fast clearance of the complex from blood, whereby the complex spends insufficient time in tumor to get reduced and trapped. Though uptake in tumor was low, slow clearance of activity from tumor suggests reduction and trapping of the complex in hypoxic cells. The present Tc-99m-complex demonstrated acceptable values of tumor to blood (TBR) and tumor to muscle (TMR) ratios. However, low uptake in tumor which may not be indicative of the actual hypoxic status of the tumor, limit the utility of the complex to detect tumor hypoxia. (c) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and properties of 1-dinitromethyl-3-R-1,2,4-triazoles
  作者：T. P. Kofman、A. E. Trubitsyn、I. V. Dmitrienko、E. Yu. Glazkova、I. V. Tselinskii

  DOI：10.1134/s1070428007050193

  日期：2007.5

  Reductive denitration of 1-trinitromethyl-3-R-1,2,4-triazoles by KI or NH2OH followed by the treatment of the formed 1-dinitromethyl-3-R-1,2,4-triazoles salts with sulfuric acid yielded dinitromethyl compounds (R = H, N-3, Cl, NO2), sufficiently strong CH-acids (pK(a) 1.37-0.12) whose typical reactions are similar to those of gem-dinitrocompounds from the aliphatic series. The spectral data and the analysis of correlation relations between pK(a) of 1-dinitromethyl-3-R-1,2,4-triazoles and the substituent constants confirm that their structure is analogous to that of the majority of compounds belonging to the mentioned series.
• NAGAO, YOSHIMITSU;SANO, SHIGEKI;OCHIAI, MASAHITO;FUJITA, EIICHI, TETRAHEDRON, 46,(1990) N, C. 3211-3232
  作者：NAGAO, YOSHIMITSU、SANO, SHIGEKI、OCHIAI, MASAHITO、FUJITA, EIICHI

  DOI：——

  日期：——
• WO2023/189602
  申请人：——

  公开号：——

  公开（公告）日：——