methyl 4-amino-4-deoxy-10-methyl-10-(phenylsulfonyl)-8,10-dideazapteroate | 88393-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl 4-amino-4-deoxy-10-methyl-10-(phenylsulfonyl)-8,10-dideazapteroate
• CAS: 88393-11-7
• 化学式: C₂₄H₂₃N₅O₄S
• 分子量: 477.544
• InChiKey: MHLLNEUIJAAOFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  151.15
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  2,4-diamino-6-(bromomethyl)pyrido<3,2-d>pyrimidine 、 α-methyl-p-carbomethoxybenzyl phenyl sulfone 在 sodium hydride 作用下， 生成 methyl 4-amino-4-deoxy-10-methyl-10-(phenylsulfonyl)-8,10-dideazapteroate
  参考文献：
  名称：

  Synthesis and antifolate properties of 10-alkyl-8,10-dideazaminopterins

  摘要：

  The synthesis of 10-alkyl analogues of the potent antitumor agent 8,10-dideazaminopterin is described. Alkylation of appropriate alpha-alkyl homoterephthalate esters with 2,4-diamino-6-(bromomethyl)-8-deazapteridine afforded 10-alkyl-10-carboxy-4-amino-4-deoxy-8,10-dideazapteroic acid diesters. Ester cleavage and decarboxylation at C-10 were accomplished by heating with sodium cyanide in Me2SO at 170-180 degrees C to afford the 2,4-diamino-10-alkyl-8,10-dideazapteroic acids. The acids were coupled with diethyl glutamate, followed by saponification, to give the 10-alkyl-8,10-dideazaminopterins. The compounds were potent inhibitors of growth in folate-dependent bacteria, Streptococcus faecium and Lactobacillus casei. The 10-methyl and 10-ethyl analogues gave the highest percent increases in life span for mice infected with L1210 leukemia with ILS values of +203 and +235%, respectively.

  DOI：

  10.1021/jm00369a024