4',6'-Diamino-4,4,6-trimethyl-3,4-dihydro-[1,5']bipyrimidinyl-2-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4',6'-Diamino-4,4,6-trimethyl-3,4-dihydro-[1,5']bipyrimidinyl-2-thione
• 化学式: C₁₁H₁₆N₆S
• 分子量: 264.354
• InChiKey: BIYIAUYQQCLWEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  93.09
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-isothiocyanato-4-methylpentan-2-one 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 128.0h， 生成 4',6'-Diamino-4,4,6-trimethyl-3,4-dihydro-[1,5']bipyrimidinyl-2-thione
  参考文献：
  名称：

  摘要：

  4,5-Dimethyl-1,2-phenylenediamine and 4-chloro-1,2-phenylenediamine react with 4-isothiocyanato-4-methylpentan-2-one (15) to give compounds (3a) and (3b), respectively. 3,4-Diaminobenzoic acid reacts similarly with (15) to give a mixture of compounds, possibly (2a) and (2b), which could be cyclized at pH similar to5 to compound (3c). 3,4-Diaminopyridine reacted with (15) in DMF to give compounds (5) and (6), whereas condensation of 5,6-diaminopyrimidine and 4,5,6-triaminopyrimidine sulfate under similar conditions gave compounds (8a) and (8b), respectively. Compounds (8a) and (8b) at pH similar to4 gave a mixture of compounds (9a), (10a) and (9b), (10b), respectively. Condensation of 4,5-diamino-6-hydroxy-2-mercaptopyrimidine, 4,5-diamino-2,6-dimercaptopyrimidine and 5,6-diamino-1,3-dimethyluracil hydrate with (15) gave corresponding mercaptopyrimidines (12a), (12b) and (14), respectively. The evaluation of (3a-c), (8a,b), (12a,b) and (14) aganist a small panel of six cancer cell lines, consisting of prostate (DU145), colon (HT29), melanoma (LOX), breast (MCF, MCF7/ADR), ovarian (OVCAR3) and CNS (U251) is reported. The most active was compound (8b), against colon (HT29) (44.2 muM). Anti-inflammatory and analgesic activity is also reported.

  DOI：

  10.1071/ch00141

文献信息

• ——
  作者：Sham M. Sondhi、Monika Johar、Shefali Rajvanshi、Sunanda G. Dastidar、Rakesh Shukla、Ram Raghubir、J. William Lown

  DOI：10.1071/ch00141

  日期：——

  4,5-Dimethyl-1,2-phenylenediamine and 4-chloro-1,2-phenylenediamine react with 4-isothiocyanato-4-methylpentan-2-one (15) to give compounds (3a) and (3b), respectively. 3,4-Diaminobenzoic acid reacts similarly with (15) to give a mixture of compounds, possibly (2a) and (2b), which could be cyclized at pH similar to5 to compound (3c). 3,4-Diaminopyridine reacted with (15) in DMF to give compounds (5) and (6), whereas condensation of 5,6-diaminopyrimidine and 4,5,6-triaminopyrimidine sulfate under similar conditions gave compounds (8a) and (8b), respectively. Compounds (8a) and (8b) at pH similar to4 gave a mixture of compounds (9a), (10a) and (9b), (10b), respectively. Condensation of 4,5-diamino-6-hydroxy-2-mercaptopyrimidine, 4,5-diamino-2,6-dimercaptopyrimidine and 5,6-diamino-1,3-dimethyluracil hydrate with (15) gave corresponding mercaptopyrimidines (12a), (12b) and (14), respectively. The evaluation of (3a-c), (8a,b), (12a,b) and (14) aganist a small panel of six cancer cell lines, consisting of prostate (DU145), colon (HT29), melanoma (LOX), breast (MCF, MCF7/ADR), ovarian (OVCAR3) and CNS (U251) is reported. The most active was compound (8b), against colon (HT29) (44.2 muM). Anti-inflammatory and analgesic activity is also reported.