ethyl 3-nitro-1,2,4-triazolylacetate | 70965-24-1

• 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: ethyl 3-nitro-1,2,4-triazolylacetate
• 英文别名: ethyl 3-nitro-1,2,4-triazol-1-ylacetate；ethyl 2-(3-nitro-1H-1,2,4-triazol-1-yl)acetate；(3-nitro-[1,2,4]triazol-1-yl)-acetic acid ethyl ester；ethyl (3-nitro-1H-1,2,4-triazol-1-yl)acetate；ethyl 2-(3-nitro-1,2,4-triazol-1-yl)acetate
• CAS: 70965-24-1
• 化学式: C₆H₈N₄O₄
• mdl: MFCD00297199
• 分子量: 200.154
• InChiKey: IJKYMLBNYHCLIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-nitro-1,2,4-triazolylacetate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-硝基-1,2,4-三氮唑
  参考文献：
  名称：

  Terpigorev, A. N.; Shcherbinin, M. B.; Bazanov, A. G., Russian Journal of Organic Chemistry, 1982, vol. 18, p. 587 - 588

  摘要：

  DOI：
• 作为产物：
  描述：

  溴乙酸乙酯 、 3-硝基-1,2,4-三氮唑 在 乙醇 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 6.5h， 以68%的产率得到ethyl 3-nitro-1,2,4-triazolylacetate
  参考文献：
  名称：

  Scaffold Hopping and Optimization of Maleimide Based Porcupine Inhibitors

  摘要：

  Porcupine is an O-acyltransferase that regulates Wnt secretion. Inhibiting porcupine may block the Wnt pathway which is often dysregulated in various cancers. Consequently porcupine inhibitors are thought to be promising oncology therapeutics. A high throughput screen against porcupine revealed several potent hits that were confirmed to be Wnt pathway inhibitors in secondary assays. We developed a pharmacophore model and used the putative bioactive conformation of a xanthine inhibitor for scaffold hopping. The resulting maleimide scaffold was optimized to subnanomolar potency while retaining good physical druglike properties. A preclinical development candidate was selected for which extensive in vitro and in vivo profiling is reported.

  DOI：

  10.1021/acs.jmedchem.7b00662

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。
• Scaffold Hopping and Optimization of Maleimide Based Porcupine Inhibitors
  作者：Soo Yei Ho、Jenefer Alam、Duraiswamy Athisayamani Jeyaraj、Weiling Wang、Grace Ruiting Lin、Shi Hua Ang、Eldwin Sum Wai Tan、May Ann Lee、Zhiyuan Ke、Babita Madan、David M. Virshup、Li Jun Ding、Vithya Manoharan、Yun Shan Chew、Choon Bing Low、Vishal Pendharkar、Kanda Sangthongpitag、Jeffrey Hill、Thomas H. Keller、Anders Poulsen

  DOI：10.1021/acs.jmedchem.7b00662

  日期：2017.8.10

  Porcupine is an O-acyltransferase that regulates Wnt secretion. Inhibiting porcupine may block the Wnt pathway which is often dysregulated in various cancers. Consequently porcupine inhibitors are thought to be promising oncology therapeutics. A high throughput screen against porcupine revealed several potent hits that were confirmed to be Wnt pathway inhibitors in secondary assays. We developed a pharmacophore model and used the putative bioactive conformation of a xanthine inhibitor for scaffold hopping. The resulting maleimide scaffold was optimized to subnanomolar potency while retaining good physical druglike properties. A preclinical development candidate was selected for which extensive in vitro and in vivo profiling is reported.
• 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：——
• TERPIGOREV, A. N.;SHCHERBININ, M. B.;BAZANOV, A. G.;TSELINSKIJ, I. V., ZH. ORGAN. XIMII, 1982, 18, N 3, 676-677
  作者：TERPIGOREV, A. N.、SHCHERBININ, M. B.、BAZANOV, A. G.、TSELINSKIJ, I. V.

  DOI：——

  日期：——