1-allyl-4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine | 181862-09-9

• 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-allyl-4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine
• 英文别名: 4,6-Dichloro-1-prop-2-enylpyrazolo[3,4-d]pyrimidine
• CAS: 181862-09-9
• 化学式: C₈H₆Cl₂N₄
• 分子量: 229.068
• InChiKey: CRXOCJGHCJYELC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：

  1-allyl-4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine 在 碘 、 甲烷 、 溶剂黄146 、 三乙胺 、 sodium iodide 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 62.17h， 生成 8-(iodomethyl)-6-methyl-1-(prop-2-enyl)-7,8-dihydro-1H-imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-one
  参考文献：
  名称：

  通过碘环化和[3 + 2]叠氮基环加成反应的分子内反应合成新型1,3,6-三唑嗪

  摘要：

  6-（烯基氨基）-1-烯丙基吡唑并[ 3,4- d ]嘧啶的选择性碘环化提供了1-烯丙基-8（9）-碘甲基咪唑并（pyrimido）[1,2- a ]吡唑并[4,3- e ]嘧啶，在75°C至80°C下与NaN 3进一步反应，得到一系列新型1,3,6-三唑嗪，与吡唑，嘧啶，咪唑（或嘧啶）和1,2 ，3-三唑环 通过分析，光谱（IR，1 H和13 C NMR，HPLC质量）和X射线衍射数据对合成的化合物进行结构表征。

  DOI：

  10.1002/jhet.4028
• 作为产物：
  描述：

  烯丙醇 、 4,6-二氯-1H-吡唑并[3,4-C]嘧啶 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以24.9%的产率得到1-allyl-4,6-dichloro-1H-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

文献信息

• 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.
• Synthesis of<scp>new‐type</scp>1,3,<scp>6‐triazocine</scp>via intramolecular reactions of iodocyclization and [3+2] azido cycloaddition
  作者：Ruslan I. Vaskevych、Alla I. Vaskevych、Eduard B. Rusanov、Oksana Ya. Mel'nyk、Mykhailo V. Vovk

  DOI：10.1002/jhet.4028

  日期：2020.8

  Selective iodocyclization of 6‐(alkenylamino)‐1‐allylpyrazolo[3,4‐d ]pyrimidines provided hydrogenated derivatives of 1‐allyl‐8(9)‐iodomethylimidazo(pyrimido)[1,2‐a ]pyrazolo[4,3‐e ]pyrimidines which were further reacted with NaN3 at 75°С to 80°С to give a series of new‐type 1,3,6‐triazocines annulated with the pyrazole, pyrimidine, imidazole (or pyrimidine), and 1,2,3‐triazole rings. The compounds

  6-（烯基氨基）-1-烯丙基吡唑并[ 3,4- d ]嘧啶的选择性碘环化提供了1-烯丙基-8（9）-碘甲基咪唑并（pyrimido）[1,2- a ]吡唑并[4,3- e ]嘧啶，在75°C至80°C下与NaN 3进一步反应，得到一系列新型1,3,6-三唑嗪，与吡唑，嘧啶，咪唑（或嘧啶）和1,2 ，3-三唑环 通过分析，光谱（IR，1 H和13 C NMR，HPLC质量）和X射线衍射数据对合成的化合物进行结构表征。