3-氨基-6-(溴甲基)吡嗪-2-甲腈 | 61267-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 3-氨基-6-(溴甲基)吡嗪-2-甲腈
• 英文名称: 2-amino-5-bromomethylpyrazine-3-carbonitrile
• 英文别名: amino-2 bromomethyl-5 cyano-3 pyrazine；2-amino-5-bromomethyl-3-cyanopyrazine；3-Amino-6-(bromomethyl)pyrazine-2-carbonitrile
• CAS: 61267-55-8
• 化学式: C₆H₅BrN₄
• 分子量: 213.037
• InChiKey: TYFPZCNVBYVWIA-UHFFFAOYSA-N

物化性质

• 沸点：
  390.7±42.0 °C(Predicted)
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氨基-6-(溴甲基)吡嗪-2-甲腈 在 sodium 、 potassium carbonate 作用下， 反应 8.33h， 生成 diethyl N-(isonipecotinoyl)-L-glutamate
  参考文献：
  名称：

  Sekikawa, Isao; Takahashi, Yumiko, Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 807 - 809

  摘要：

  DOI：

文献信息

• Sturtz; Guillamot, European Journal of Medicinal Chemistry, 1984, vol. 19, # 3, p. 267 - 273
  作者：Sturtz、Guillamot

  DOI：——

  日期：——
• Synthesis and in Vitro Antifolate Activity of Rotationally Restricted Aminopterin and Methotrexate Analogues
  作者：Andre Rosowsky、Ronald A. Forsch、Joel E. Wright

  DOI：10.1021/jm040122s

  日期：2004.12.1

  Heretofore unknown analogues of aminopterin (AMT) and methotrexate (MTX) in which free rotation of the amide bond between the phenyl ring and amino acid side chain is prevented by a CH2 bridge were synthesized and tested for in vitro antifolate activity. The K-i of the AMT analogue (9) against human dihydrofolate reductase (DHFR) was 34 pM, whereas that of the MTX analogue (10) was 2100 pM. Both compounds were less potent than the parent drugs. However, although the difference between AMT and MTX was < 2-fold, the difference between 9 and 10 was 62-fold, suggesting that the effect of N-10-methyl substitution is amplified in the bridged compounds. The K-i values of 9 and 10 as inhibitors of [H-3]MTX influx into CCRF-CEM human leukemia cells via the reduced folate carrier (RFC) were 0.28 and 1.1 muM, respectively. The corresponding K-i and K-t values determined earlier for AMT and MTX were 5.4 and 4.7 muM, respectively. Thus, in contrast to its unfavorable effect on DHFR binding, the CH2 bridge increased RFC binding. In a 72 h growth assay with CCRF-CEM cells, the IC50 valuess of 9 and 10 were 5.1 and 140 nM, respectively, a 27-fold difference that was qualitatively consistent with the observed combination of weaker DHFR binding and stronger RFC binding. Although rotationally restricted inhibitors of other enzymes of folate pathway enzymes have been described previously, 9 and 10 are the first reported examples of DHFR inhibitors of this type.
• STURTZ, GEORGES LOUIS EDMOND;VOISIN, PATRICIA CECILE MARIE-LAURE
  作者：STURTZ, GEORGES LOUIS EDMOND、VOISIN, PATRICIA CECILE MARIE-LAURE

  DOI：——

  日期：——
• STURTZ, GEORGES;VOISIN-DACHEUX, PATRICIA;GUILLAMOT, GERARD, C. R. ACAD. SCI. SER. 2, 310,(1990) N, C. 739-742
  作者：STURTZ, GEORGES、VOISIN-DACHEUX, PATRICIA、GUILLAMOT, GERARD

  DOI：——

  日期：——
• STURTZ, G.;GUILLAMOT, G., EUR. J. MED. CHEM., 1984, 19, N 3, 267-273
  作者：STURTZ, G.、GUILLAMOT, G.

  DOI：——

  日期：——