1-[1-Prop-2-enyl-4-(prop-2-enylamino)pyrazolo[3,4-d]pyrimidin-6-yl]piperidin-4-one | 181862-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 1-[1-Prop-2-enyl-4-(prop-2-enylamino)pyrazolo[3,4-d]pyrimidin-6-yl]piperidin-4-one
• CAS: 181862-12-4
• 化学式: C₁₆H₂₀N₆O
• 分子量: 312.374
• InChiKey: MBTJALUSXCEPBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-氨基甲基二苯并环庚烷 、 1-[1-Prop-2-enyl-4-(prop-2-enylamino)pyrazolo[3,4-d]pyrimidin-6-yl]piperidin-4-one 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以97.4%的产率得到1-allyl-4-allylamino-6-{4-[(10,11-dihydro-5H-dibenzo[ a,d]cyclohepten-5-yl)methylamino]piperidino}pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  New Purines and Purine Analogs as Modulators of Multidrug Resistance

  摘要：

  A series of 36 purine and purine analog derivatives have been synthesized and tested for their ability to modulate multidrug resistance in vitro (P388/VCR-20 and KB-A1 cells) and in vivo (P388/VCR leukemia). Compounds were compared to S9788, a triazine derivative which has already shown some activity during phase 1 clinical trials and also a limiting cardiovascular side effect possibly linked to its calcium channel affinity. The fact that active compounds increase adriamycin accumulation in the resistant KB-A1 cells, and not in the sensitive KB-3-1 cells, suggests they act predominantly by inhibiting the P-glycoprotein-catalyzed efflux of cytotoxic agents. No direct relation was found between the affinity for the phenylalkylamine binding site of the calcium channel and in vitro sensitization of resistant cells. In vivo, when administered po in association with vincristine (0.25 mg/kg), five compounds (3, 4, 9, 25, and 26), of very differing calcium channel affinities (K-i from 5 to 560 nM), fully restored (T/V greater than or equal to 1.4) the sensitivity of P388/VCR leukemia to vincristine.

  DOI：

  10.1021/jm960361i
• 作为产物：
  描述：

  4,6-二氯-1H-吡唑并[3,4-C]嘧啶 在 盐酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 7.5h， 生成 1-[1-Prop-2-enyl-4-(prop-2-enylamino)pyrazolo[3,4-d]pyrimidin-6-yl]piperidin-4-one
  参考文献：
  名称：

  New Purines and Purine Analogs as Modulators of Multidrug Resistance

  摘要：

  A series of 36 purine and purine analog derivatives have been synthesized and tested for their ability to modulate multidrug resistance in vitro (P388/VCR-20 and KB-A1 cells) and in vivo (P388/VCR leukemia). Compounds were compared to S9788, a triazine derivative which has already shown some activity during phase 1 clinical trials and also a limiting cardiovascular side effect possibly linked to its calcium channel affinity. The fact that active compounds increase adriamycin accumulation in the resistant KB-A1 cells, and not in the sensitive KB-3-1 cells, suggests they act predominantly by inhibiting the P-glycoprotein-catalyzed efflux of cytotoxic agents. No direct relation was found between the affinity for the phenylalkylamine binding site of the calcium channel and in vitro sensitization of resistant cells. In vivo, when administered po in association with vincristine (0.25 mg/kg), five compounds (3, 4, 9, 25, and 26), of very differing calcium channel affinities (K-i from 5 to 560 nM), fully restored (T/V greater than or equal to 1.4) the sensitivity of P388/VCR leukemia to vincristine.

  DOI：

  10.1021/jm960361i