N-[(2S)-2,3-epoxypropyl]-N-ethyltrifluoromethanesulfonamide | 259656-88-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-[(2S)-2,3-epoxypropyl]-N-ethyltrifluoromethanesulfonamide
• 英文别名: N-ethyl-1,1,1-trifluoro-N-[[(2S)-oxiran-2-yl]methyl]methanesulfonamide
• CAS: 259656-88-7
• 化学式: C₆H₁₀F₃NO₃S
• 分子量: 233.212
• InChiKey: QWTJXUCWCJMLQE-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(2S)-2,3-epoxypropyl]-N-ethyltrifluoromethanesulfonamide 在 10percent Pd/C 盐酸 、 氢气 、 红铝 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 72.0h， 生成 (2R,10R)-N¹-cyclopropylmethyl-N¹¹-2,10-dihydroxynorspermine tetrahydrochloride
  参考文献：
  名称：

  羟基化多胺类似物作为抗增殖剂的合成和评价。

  摘要：

  一种访问N（1）-环丙基甲基-N（11）-乙基去甲精胺（CPMENSPM）的新方法和（2R，10S）-N（1）-环丙基甲基-2,10-二羟基-N（11）-的首次合成描述了乙基去甲精胺[（2R，10S）-（HO）（2）CPMENSPM]。与N（1），N（11）-diethylnorspermine（DENSPM）或（2R，10R）-N（1），N（11）-相比，这两种多胺类似物均对L1210鼠白血病细胞的生长更具活性。处理96小时后，生成2,10-二羟基去甲精胺二乙基[（2R，10R）-（HO）（2）DENSPM]；在96小时时，该活性可与（2S，10S）-N（1），N（11）-二乙基-2,10-二羟基去甲精胺[（2S，10S）-（HO）（2）DENSPM]媲美。两种环丙基化合物都可以减少腐胺和亚精胺库，但效果不如DENSPM及其衍生物。仅CPMENSPM，而不是（2R，10S）-（HO）（2

  DOI：

  10.1021/jm000532q
• 作为产物：
  描述：

  N-[(4S)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl]-N-ethyltrifluoromethanesulfonamide 在 吡啶 、 盐酸 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 9.5h， 生成 N-[(2S)-2,3-epoxypropyl]-N-ethyltrifluoromethanesulfonamide
  参考文献：
  名称：

  Synthesis and Evaluation of Hydroxylated Polyamine Analogues as Antiproliferatives

  摘要：

  The synthesis of four hydroxylated polyamine analogues, (2R,10R)-N-1,N-11-diethyl-2,10-dihydroxynorspermine, droxynorspermine, (2S,10S)-N-1,N-11-diethyl-2,10-dihydroxynospermine, (3S, 12S)-N-1,N-14-diethyl-3, 12-dihydroyhomospermine, and (3R,12R)-N-1-N-14-diethyl-3,12-dihgrdroxyhomospermine, is described along with their impact on the growth and polyamine metabolism of L1210 murine leukemia cells. Four different synthetic approaches are set forth, two each for the hydroxylated norspermines and for the hydroxylated homospermines. The key step in the assembly of the norspermines was the coupling of either N-[2R)-2,3-epoxypropyl]-N-ethyl p-toluenesulfonamide or N-[(2S)-2, 3-epoxypropyl]-N-ethyl trifluoromethane sulfonamide to N,N'-dibenzyl-1,3-diaminopropane. The key step with homospermines employed alkylation of putrescine with (3S)-N-(benzyloxycarbonyl)-N-ethyl-3,4-epoxybutylamine or of N,N'-bis(mesitylenesulfonyl)-1,4-butanediamine with (2R)-2-benzyloxy-4-[N-(mesitylenesulfonyl], All of the hydroxylated analogues were active against L1210 cells with 96-h IC50 values of less than or equal to 2 mu M, and they also effectively reduced putrescine and spermidine, although the effect on spermine pools ranged from moderate to insignificant. Interestingly, the impact of the hydroxylated analogues an ornithine decarboxylase (ODC) was significantly less than that of unhydroxylated parent drug (e.g., (NN11)-N-1-diethylnorspermine [DENSPM]) at 1 mu M ; however, S-adenosylmethionine decarboxylase (AdoMetDC) depletion was nearly identical to what was observed in cells treated with parent drug. The most notable difference between the parent and hydroxylated analogues was seen with spermidine/spermine N-1-acetyltransferase (SSAT) upregulation in the DENSPM series. The hydroxylated analogues, especially (R,R)-(HO)(2)-DENSPM, were much less effective at upregulation than the parent DENSPM. Finally, a comparison of the toxicity of (RP)-(HO)(2)DENSPM with that of DENSPM at subchronic doses revealed that the neurological effects seen with DENSPM were now absent.

  DOI：

  10.1021/jm990375z

文献信息

• Synthesis and Evaluation of Hydroxylated Polyamine Analogues as Antiproliferatives
  作者：Raymond J. Bergeron、Ralf Müller、Guangfei Huang、James S. McManis、Samuel E. Algee、Hua Yao、William R. Weimar、Jan Wiegand

  DOI：10.1021/jm000532q

  日期：2001.7.1

  N(11)-diethyl-2,10-dihydroxynorspermine [(2S,10S)-(HO)(2)DENSPM] at 96 h. Both cyclopropyl compounds reduced putrescine and spermidine pools, but less effectively than did DENSPM and its derivatives. Only CPMENSPM, and not (2R,10S)-(HO)(2)CPMENSPM, lowered spermine pools. As with DENSPM and (2R,10R)-(HO)(2)DENSPM, both cyclopropyl analogues diminished ornithine decarboxylase and S-adenosylmethionine decarboxylase

  一种访问N（1）-环丙基甲基-N（11）-乙基去甲精胺（CPMENSPM）的新方法和（2R，10S）-N（1）-环丙基甲基-2,10-二羟基-N（11）-的首次合成描述了乙基去甲精胺[（2R，10S）-（HO）（2）CPMENSPM]。与N（1），N（11）-diethylnorspermine（DENSPM）或（2R，10R）-N（1），N（11）-相比，这两种多胺类似物均对L1210鼠白血病细胞的生长更具活性。处理96小时后，生成2,10-二羟基去甲精胺二乙基[（2R，10R）-（HO）（2）DENSPM]；在96小时时，该活性可与（2S，10S）-N（1），N（11）-二乙基-2,10-二羟基去甲精胺[（2S，10S）-（HO）（2）DENSPM]媲美。两种环丙基化合物都可以减少腐胺和亚精胺库，但效果不如DENSPM及其衍生物。仅CPMENSPM，而不是（2R，10S）-（HO）（2