6-氯-9-环丙基-9H-嘌呤 | 6627-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 6-氯-9-环丙基-9H-嘌呤
• 英文名称: 6-chloro-9-cyclopropyl-9H-purine
• 英文别名: 6-chloro-9-cyclopropyl-9H-purine；6-chloro-9-cyclopropylpurine
• CAS: 6627-30-1
• 化学式: C₈H₇ClN₄
• mdl: MFCD09756814
• 分子量: 194.623
• InChiKey: PSQPMAOEUNCGBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-氯-9-环丙基-9H-嘌呤 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 15.25h， 生成 N-Cyclopropyl-N-(9-cyclopropyl-9H-purin-6-yl)-acetamide
  参考文献：
  名称：

  6-(Alkylamino)-9-alkylpurines. A New Class of Potential Antipsychotic Agents

  摘要：

  A series of 6-(alkylamino)-9-alkylpurines was synthesized and evaluated for the property of antagonizing the behavioral effects in animals of the dopamine agonist apomorphine. This model for identifying potential antipsychotic agents is based on the hypothesis that agents that antagonize apomorphine-induced aggressive behavior in rats and apomorphine-induced climbing in mice, but that do not block stereotyped behavior, could have an antipsychotic effect in humans without producing extrapyramidal side effects. The antiaggressive-behavior activity of lead compound 1 (6-(dimethylamino)-9-(3-phenylalaninamidobenzyl)-9H-purine) was improved 48-fold with 6-(cyclopropylamino)-9-(cyclopropylmethyl)-2-(trifluoromethyl)-9H-purine (80) (po ED50 of 2 mg/kg), which was obtained through an iterative sequence of structure-activity relationship studies that encompassed evaluation of the effects of structure variations at the purine 9-, 6-, and 2-positions. Potency was enhanced with a 9-cyclopropyl group, the duration of action was improved with the 6-(cyclopropylamino) substituent, potency was further enhanced with an N-formyl prodrug, and an agent with reduced cardiovascular effect emerged with the 2-trifluoromethyl purine 80. This potential antipsychotic agent was not developed further due to undesirable effects on the stomach.

  DOI：

  10.1021/jm960662s
• 作为产物：
  描述：

  原甲酸三乙酯 、 5-amino-6-chloro-4-cyclopropylaminopyrimidine 在 乙基磺酸 作用下， 反应 46.0h， 以80%的产率得到6-氯-9-环丙基-9H-嘌呤
  参考文献：
  名称：

  6-(Alkylamino)-9-alkylpurines. A New Class of Potential Antipsychotic Agents

  摘要：

  A series of 6-(alkylamino)-9-alkylpurines was synthesized and evaluated for the property of antagonizing the behavioral effects in animals of the dopamine agonist apomorphine. This model for identifying potential antipsychotic agents is based on the hypothesis that agents that antagonize apomorphine-induced aggressive behavior in rats and apomorphine-induced climbing in mice, but that do not block stereotyped behavior, could have an antipsychotic effect in humans without producing extrapyramidal side effects. The antiaggressive-behavior activity of lead compound 1 (6-(dimethylamino)-9-(3-phenylalaninamidobenzyl)-9H-purine) was improved 48-fold with 6-(cyclopropylamino)-9-(cyclopropylmethyl)-2-(trifluoromethyl)-9H-purine (80) (po ED50 of 2 mg/kg), which was obtained through an iterative sequence of structure-activity relationship studies that encompassed evaluation of the effects of structure variations at the purine 9-, 6-, and 2-positions. Potency was enhanced with a 9-cyclopropyl group, the duration of action was improved with the 6-(cyclopropylamino) substituent, potency was further enhanced with an N-formyl prodrug, and an agent with reduced cardiovascular effect emerged with the 2-trifluoromethyl purine 80. This potential antipsychotic agent was not developed further due to undesirable effects on the stomach.

  DOI：

  10.1021/jm960662s

文献信息

• [EN] NOVEL COMPOUNDS AND METHODS FOR INCREASING KLOTHO GENE EXPRESSION<br/>[FR] NOUVEAUX COMPOSÉS ET MÉTHODES PERMETTANT D'AUGMENTER L'EXPRESSION DU GÈNE KLOTHO
  申请人：KLOTHO THERAPEUTICS INC

  公开号：WO2022011171A1

  公开（公告）日：2022-01-13

  Novel compounds and compositions including the same and methods of manufacturing and using the same, particularly for increasing klotho gene expression, and more particularly for increasing circulating or soluble Klotho protein levels through increasing klotho gene expression.

  包括新化合物和组合物以及制造和使用这些化合物的方法，特别是用于增加克洛托基因表达，更具体地通过增加克洛托基因表达来增加循环或可溶性克洛托蛋白水平的小说化合物和组合物。
• [EN] HETEROCYCLIC COMPOUND AND APPLICATION THEREOF<br/>[FR] COMPOSÉ HÉTÉROCYCLIQUE ET SON APPLICATION<br/>[ZH] 一种杂环化合物及其应用
  申请人：[en]SHENZHEN CHIPSCREEN BIOSCIENCES CO., LTD.;[zh]深圳微芯生物科技股份有限公司

  公开号：WO2022242743A1

  公开（公告）日：2022-11-24

  提供了一种具有式(I)所示结构的杂环化合物。实验结果表明，通过选择特定的修饰基团，所述杂环化合物作为TRβ激动剂相比于现有技术活性具有显著的提高并具有更高的TRβ选择性，可用于治疗和/或预防由甲状腺激素调节引起的疾病，并具有更低的副作用。
• 6-(Alkylamino)-9-alkylpurines. A New Class of Potential Antipsychotic Agents
  作者：James L. Kelley、R. Morris Bullock、Mark P. Krochmal、Ed W. McLean、James A. Linn、Micheal J. Durcan、Barrett R. Cooper

  DOI：10.1021/jm960662s

  日期：1997.9.1

  A series of 6-(alkylamino)-9-alkylpurines was synthesized and evaluated for the property of antagonizing the behavioral effects in animals of the dopamine agonist apomorphine. This model for identifying potential antipsychotic agents is based on the hypothesis that agents that antagonize apomorphine-induced aggressive behavior in rats and apomorphine-induced climbing in mice, but that do not block stereotyped behavior, could have an antipsychotic effect in humans without producing extrapyramidal side effects. The antiaggressive-behavior activity of lead compound 1 (6-(dimethylamino)-9-(3-phenylalaninamidobenzyl)-9H-purine) was improved 48-fold with 6-(cyclopropylamino)-9-(cyclopropylmethyl)-2-(trifluoromethyl)-9H-purine (80) (po ED50 of 2 mg/kg), which was obtained through an iterative sequence of structure-activity relationship studies that encompassed evaluation of the effects of structure variations at the purine 9-, 6-, and 2-positions. Potency was enhanced with a 9-cyclopropyl group, the duration of action was improved with the 6-(cyclopropylamino) substituent, potency was further enhanced with an N-formyl prodrug, and an agent with reduced cardiovascular effect emerged with the 2-trifluoromethyl purine 80. This potential antipsychotic agent was not developed further due to undesirable effects on the stomach.