1-isobutyl-3-methyl-7-(naphthalene-1-ylmethyl)-1,5-dihydropteridine-2,4,6(3H)-trione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 1-isobutyl-3-methyl-7-(naphthalene-1-ylmethyl)-1,5-dihydropteridine-2,4,6(3H)-trione
• 英文别名: 3-methyl-1-(2-methylpropyl)-7-(naphthalen-1-ylmethyl)-5H-pteridine-2,4,6-trione
• 化学式: C₂₂H₂₂N₄O₃
• 分子量: 390.442
• InChiKey: BTUSRASQSIYIRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-isobutyl-3-methyl-7-(naphthalene-1-ylmethyl)-1,5-dihydropteridine-2,4,6(3H)-trione 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 6-((3-hydroxypropyl)thio)-1-isobutyl-3-methyl-7-(naphthalen-1-ylmethyl)pteridine-2,4-(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of Pteridine Dione and Trione Monocarboxylate Transporter 1 Inhibitors

  摘要：

  Novel substituted pteridine-derived inhibitors of monocarboxylate transporter 1 (MCT1), an emerging target for cancer therapy, are reported. The activity of these compounds as inhibitors of lactate transport was confirmed using a (14)C-lactate transport assay, and their potency against MCT1-expressing human tumor cells was established using MTT assays. The four most potent compounds showed substantial anticancer activity (EC50 37-150 nM) vs MCT1-expressing human Raji lymphoma cells.

  DOI：

  10.1021/jm500640x
• 作为产物：
  描述：

  6-氯-3-甲基尿嘧啶 在 硫酸 、 硝酸 、 sodium carbonate 、 potassium carbonate 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 锌 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 56.67h， 生成 1-isobutyl-3-methyl-7-(naphthalene-1-ylmethyl)-1,5-dihydropteridine-2,4,6(3H)-trione
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of Pteridine Dione and Trione Monocarboxylate Transporter 1 Inhibitors

  摘要：

  Novel substituted pteridine-derived inhibitors of monocarboxylate transporter 1 (MCT1), an emerging target for cancer therapy, are reported. The activity of these compounds as inhibitors of lactate transport was confirmed using a (14)C-lactate transport assay, and their potency against MCT1-expressing human tumor cells was established using MTT assays. The four most potent compounds showed substantial anticancer activity (EC50 37-150 nM) vs MCT1-expressing human Raji lymphoma cells.

  DOI：

  10.1021/jm500640x

文献信息

• Synthesis and Structure–Activity Relationships of Pteridine Dione and Trione Monocarboxylate Transporter 1 Inhibitors
  作者：Hui Wang、Chunying Yang、Joanne R. Doherty、William R. Roush、John L. Cleveland、Thomas D. Bannister

  DOI：10.1021/jm500640x

  日期：2014.9.11

  Novel substituted pteridine-derived inhibitors of monocarboxylate transporter 1 (MCT1), an emerging target for cancer therapy, are reported. The activity of these compounds as inhibitors of lactate transport was confirmed using a (14)C-lactate transport assay, and their potency against MCT1-expressing human tumor cells was established using MTT assays. The four most potent compounds showed substantial anticancer activity (EC50 37-150 nM) vs MCT1-expressing human Raji lymphoma cells.