ethyl -6-amino-4-<(2-hydroxy-1-methyl-2-phenylethyl)amino>-5-nitropyridine-2-carbamate | 122293-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl -6-amino-4-<(2-hydroxy-1-methyl-2-phenylethyl)amino>-5-nitropyridine-2-carbamate
• 英文别名: N-[6-amino-4-[[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]azaniumyl]-5-nitropyridin-2-yl]-1-ethoxymethanimidate
• CAS: 122293-97-4
• 化学式: C₁₇H₂₁N₅O₅
• 分子量: 375.384
• InChiKey: MTFAZWAEQHVUAK-BONVTDFDSA-N

物化性质

• 沸点：
  536.2±50.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  155
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl -6-amino-4-<(2-hydroxy-1-methyl-2-phenylethyl)amino>-5-nitropyridine-2-carbamate 在 镍 吡啶 、 chromium(VI) oxide 、 氢气 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 (-)-(S)-N-(5-氨基-2-甲基-3-苯基-l,2-二氢吡啶并[3,4-b]吡嗪-7-基)氨基甲酸乙酯
  参考文献：
  名称：

  New anticancer agents: chiral isomers of ethyl 5-amino-1,2-dihydro-2-methyl-3-phenylpyrido[3,4-b]pyrazine-7-carbamate

  摘要：

  Racemic ethyl 5-amino-1,2-dihydro-2-methyl-3-phenylpyrido[3,4-b]pyrazine-7- carbamate (1a) has shown antitumor activity in a variety of in vivo experiments. The preparation of the R and S isomers gave compounds with significant differences in potency in several biological tests.

  DOI：

  10.1021/jm00129a012
• 作为产物：
  描述：

  去甲麻黄碱 、 (6-amino-4-chloro-5-nitropyridin-2-yl)carbamate 在 三乙胺 作用下， 以 乙醇 为溶剂， 以73%的产率得到ethyl -6-amino-4-<(2-hydroxy-1-methyl-2-phenylethyl)amino>-5-nitropyridine-2-carbamate
  参考文献：
  名称：

  New anticancer agents: chiral isomers of ethyl 5-amino-1,2-dihydro-2-methyl-3-phenylpyrido[3,4-b]pyrazine-7-carbamate

  摘要：

  Racemic ethyl 5-amino-1,2-dihydro-2-methyl-3-phenylpyrido[3,4-b]pyrazine-7- carbamate (1a) has shown antitumor activity in a variety of in vivo experiments. The preparation of the R and S isomers gave compounds with significant differences in potency in several biological tests.

  DOI：

  10.1021/jm00129a012

文献信息

• Antimitotic agents: structure-activity studies with some pyridine derivatives
  作者：Carroll Temple、Gregory A. Rener、William R. Waud、Patricia E. Noker

  DOI：10.1021/jm00098a014

  日期：1992.10

  n -2-yl] carbamate (8) and several related compounds. These compounds are precursors of the active ethyl pyrido[3,4-b]pyrazin-7-ylcarbamates (e.g., 4), which are potent antimitotic agents. In the 5-nitropyridine series overall biological activity was reduced by replacement of the oxime moiety with a keto or alcohol group and by replacement of the 1-methyl group of the side chain with hydrogen. Reduction

  观察到先前报道的乙基[6-氨基-4-[（1-甲基-2-苯基-2-氧代乙基）氨基] -5-硝基吡啶-2-基]氨基甲酸酯的肟在小鼠中的抗肿瘤活性（8）以及几种相关化合物。这些化合物是作为有效的抗有丝分裂剂的活性吡啶并[3，4-b]吡嗪-7-基氨基甲酸酯乙酯（例如4）的前体。在5-硝基吡啶系列中，通过用酮或醇基团取代肟部分和通过用氢取代侧链的1-甲基基团降低了总体生物活性。将在侧链中含有醇的5-硝基吡啶的硝基还原成相应的5-氨基吡啶可提高生物活性。初步研究表明，5-硝基吡啶肟作为抗有丝分裂剂的作用远不如吡啶并吡嗪有效，而且前者在体内显然没有转化为后者。抑制嘧啶核苷掺入DNA和RNA被认为是5-硝基吡啶肟的另一种可能的作用方式。
• New anticancer agents: chiral isomers of ethyl 5-amino-1,2-dihydro-2-methyl-3-phenylpyrido[3,4-b]pyrazine-7-carbamate
  作者：Carroll Temple、Gregory A. Rener

  DOI：10.1021/jm00129a012

  日期：1989.9

  Racemic ethyl 5-amino-1,2-dihydro-2-methyl-3-phenylpyrido[3,4-b]pyrazine-7- carbamate (1a) has shown antitumor activity in a variety of in vivo experiments. The preparation of the R and S isomers gave compounds with significant differences in potency in several biological tests.