2-chloro-6-allylamino-9-allylpurine | 157838-41-0

• 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: 2-chloro-6-allylamino-9-allylpurine
• 英文别名: 2-chloro-N,9-bis(prop-2-enyl)purin-6-amine
• CAS: 157838-41-0
• 化学式: C₁₁H₁₂ClN₅
• 分子量: 249.703
• InChiKey: HTLKAEBCRRUTGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-6-allylamino-9-allylpurine 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 1-[9-Prop-2-enyl-6-(prop-2-enylamino)purin-2-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
• 作为产物：
  描述：

  2,6-二氯嘌呤 在 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 1.5h， 生成 2-chloro-6-allylamino-9-allylpurine
  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

• Bicyclic pyrimidines
  申请人：Adir Et Compagnie

  公开号：US05508277A1

  公开（公告）日：1996-04-16

  Novel bicyclic pyrimidine compounds for use as drugs and having formula (I). Said novel compounds and physiologically tolerable salts thereof may be used in therapeutics, particularly for suppressing tumour cell resistance to antineoplastic agents. ##STR1##

  新型双环嘧啶化合物可用作药物，具有公式（I）。这些新型化合物及其生理耐受性盐可用于治疗，特别是用于抑制肿瘤细胞对抗肿瘤药物的抵抗力。## STR1 ##
• NOUVEAUX COMPOSES BICYCLIQUES DE PYRIMIDINE, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES LES RENFERMANT
  申请人：ADIR ET COMPAGNIE

  公开号：EP0673376A1

  公开（公告）日：1995-09-27
• COMPOSES BICYCLIQUES DE PYRIMIDINE, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES LES RENFERMANT
  申请人：ADIR ET COMPAGNIE

  公开号：EP0673376B1

  公开（公告）日：1996-05-22
• US5508277A
  申请人：——

  公开号：US5508277A

  公开（公告）日：1996-04-16
• [EN] NOVEL BICYCLIC PYRIMIDINE COMPOUNDS, METHOD FOR PREPARING SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAID COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES BICYCLIQUES DE PYRIMIDINE, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES LES RENFERMANT
  申请人：——

  公开号：WO1994013668A1

  公开（公告）日：1994-06-23

  [EN] Novel bicyclic pyrimidine compounds for use as drugs and having formula (I). Said novel compounds and physiologically tolerable salts thereof may be used in therapeutics, particularly for suppressing tumour cell resistance to antineoplastic agents.
  [FR] Nouveaux composés bicyclique de pyrimidine utilisables comme médicaments et répondant à la formule (I). Ces nouveaux composés et leurs sels physiologiquement tolérables peuvent être utilisés en thérapeutique, notamment pour supprimer la résistance des cellules tumorales aux agents anti-cancéreux.