7-allyl-2, 6-dichloro-7H-purine | 181862-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 7-allyl-2, 6-dichloro-7H-purine
• 英文别名: 2,6-Dichloro-7-prop-2-enylpurine
• CAS: 181862-39-5
• 化学式: C₈H₆Cl₂N₄
• 分子量: 229.068
• InChiKey: ZCGZBGAONKSIOY-UHFFFAOYSA-N

物化性质

• 沸点：
  328.577±52.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.558±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-allyl-2, 6-dichloro-7H-purine 在 potassium iodide 作用下， 以 乙醇 为溶剂， 反应 25.5h， 生成 2-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]-N,7-bis(prop-2-enyl)purin-6-amine
  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：

  3-溴丙烯 、 2,6-二氯嘌呤 在 甲基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 16.5h， 以74%的产率得到7-allyl-2, 6-dichloro-7H-purine
  参考文献：
  名称：

  Direct, Regioselective N-Alkylation of 1,3-Azoles

  摘要：

  Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numerous examples are provided, on varying 1,3-azole scaffolds, with yields ranging from 25 to 95%.

  DOI：

  10.1021/acs.orglett.5b02994

文献信息

• Direct, Regioselective <i>N</i>-Alkylation of 1,3-Azoles
  作者：Shuai Chen、Russell F. Graceffa、Alessandro A. Boezio

  DOI：10.1021/acs.orglett.5b02994

  日期：2016.1.4

  Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numerous examples are provided, on varying 1,3-azole scaffolds, with yields ranging from 25 to 95%.
• New Purines and Purine Analogs as Modulators of Multidrug Resistance
  作者：Alain Dhainaut、Gilbert Regnier、Andre Tizot、Alain Pierre、Stephane Leonce、Nicolas Guilbaud、Laurence Kraus-Berthier、Ghanem Atassi

  DOI：10.1021/jm960361i

  日期：1996.1.1

  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.