1,3-diallyl-6-amino-5-nitrosouracil | 102284-73-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,3-diallyl-6-amino-5-nitrosouracil
• 英文别名: 6-amino-5-nitroso-1,3-di-2-propenyl-2,4(1H,3H)-pyrimidinedione；1,3-diallyl-5-nitroso-6-aminouracil；Uracil, 1,3-diallyl-6-amino-5-nitroso-；6-amino-5-nitroso-1,3-bis(prop-2-enyl)pyrimidine-2,4-dione
• CAS: 102284-73-1
• 化学式: C₁₀H₁₂N₄O₃
• 分子量: 236.23
• InChiKey: HSAZTSOJSHRTLL-UHFFFAOYSA-N

物化性质

• 沸点：
  308.9±52.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  96.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-diallyl-6-amino-5-nitrosouracil 在 ammonium hydroxide 、 sodium dithionite 作用下， 以 水 为溶剂， 反应 1.0h， 生成 1,3-diallyl-6-amino-5-formamidouracil
  参考文献：
  名称：

  Analogs of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors

  摘要：

  A variety of analogues of caffeine and theophylline in which the 1-,3-, and 7-methyl substituents have been replaced with n-propyl, allyl, propargyl, and isobutyl and, in a few cases, with chloroethyl, hydroxyethyl, or benzyl were assessed for potency and selectivity as antagonists at A1- and A2-adenosine receptors in brain tissue. Caffeine and theophylline are nonselective for these receptors. Nearly all of the 22 analogues of caffeine are more potent than caffeine itself at adenosine receptors. Replacement of the 1-methyl moiety with n-propyl, allyl, or propargyl substituent has little effect on potency at the A1 receptor while enhancing potency about 7- to 10-fold at the A2 receptor. 3,7-Di-methyl-1-propylxanthine is only slightly (1.4-fold) more potent than caffeine at the A1 receptor while being 10-fold more potent at the A2 receptor. 1,3-Di-n-propyl-7-methylxanthine is also selective for the A2 receptor, being 8-fold more potent than caffeine at the A1 receptor and 40-fold more potent at the A2 receptor. A number of other caffeine analogues including 3,7-dimethyl-1-n-propylxanthine, 7-allyl-1,3-dimethylxanthine, and 1,3-dimethyl-7-propargylxanthine are also somewhat selective for the A2 receptor. The most potent caffeine analogue was 1,3-di-n-propyl-7-propargylxanthine, which was about 100-fold more potent than caffeine at both A1 and A2 receptors. The 10 theophylline analogues were relatively nonselective except for the 1-ethyl analogue and the 1,3-diallyl analogue, which were selective for the A2 receptor, and the 1,3-di-n-propyl, 1,3-diisobutyl, and 1,3-dibenzyl analogues, which were somewhat selective for the A1 receptor. 1,3-Di-n-propylxanthine was 20-fold more potent than theophylline at the A1 receptor and 5-fold more potent at the A2 receptor.

  DOI：

  10.1021/jm00157a035
• 作为产物：
  描述：

  6-氨基-1,3-二-2-丙烯-1-基-2,4(1H,3H)-嘧啶二酮 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 以87%的产率得到1,3-diallyl-6-amino-5-nitrosouracil
  参考文献：
  名称：

  8-substituted xanthines as selective adenosine receptor agents

  摘要：

  具有一般结构（I）的黄嘌呤衍生物，包括（R）和（S）对映体及其外消旋混合物，以及其药用盐，其中R.sub.1和R.sub.2分别独立地为（C.sub.1-C.sub.4）低碳基或（C.sub.2-C.sub.4）低碳烯基，Z为（II）或（III）或（IV），其中R.sub.3为氢，（C.sub.1-C.sub.3）低碳基，硝基，氨基，羟基，氟，溴或氯，R.sub.4为（C.sub.1-C.sub.4）低碳基，n为1或2，这些衍生物在腺苷受体上具有选择性作用，并且在一般上作为腺苷拮抗剂被揭示。从体外研究中已知，由于这种选择性，可以区分特定的生理效应，并且体外腺苷受体活性与体内腺苷受体活性相关。基于本文披露的化合物的选择性结合活性，可以制备所述化合物的药物制剂，这将增强某些生理效应，同时最小化其他效应，例如降低血压而不降低心率。

  公开号：

  US05734052A1

文献信息

• Xanthine derivatives as adenosine A1 receptor antagonists
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05840729A1

  公开（公告）日：1998-11-24

  A method of attenuating a cognitive deficit in a patient in need thereof comprising administering to the patient a xanthine derivative.

  一种减轻患者认知缺陷的方法，包括向患者施用黄嘌呤衍生物。
• Selective adenosine receptor agents
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05047534A1

  公开（公告）日：1991-09-10

  Xanthine derivative which act selectively at adenosine receptors and which act in general as adenosine antagonists are disclosed. From in vitro studies it is known that specific physiological effects can be distinguished as a result of this selectively and that adenosine receptor activity in vitro correlates with adenosine receptor activity in vivo. Pharmaceutical preparations of the subject compounds can be prepared on the basis of the selective binding activity of the compounds disclosed herein which will enhance certain physiological effects while minimizing others, such as decreasing blood pressure without decreasing heart rate.

  本发明揭示了在腺苷受体上选择性作用的黄嘌呤衍生物，通常作为腺苷拮抗剂。从体外研究中已知，由于这种选择性，可以区分特定的生理效应，并且体外的腺苷受体活性与体内的腺苷受体活性相关。根据本文披露的化合物的选择性结合活性，可以制备这些化合物的药物制剂，这将增强某些生理效应，同时最小化其他效应，例如降低血压而不降低心率。
• 8-substituted xanthines as selective adenosine receptor agents
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05734052A1

  公开（公告）日：1998-03-31

  Xanthine derivatives having general structure (I) including the (R) and (S) enantiomers and racemic mixtures thereof, and the pharmaceutically acceptable salts thereof, wherein R.sub.1 and R.sub.2 are each independently (C.sub.1 -C.sub.4)lower alkyl or (C.sub.2 -C.sub.4)lower alkenyl, Z is (II) or (III) or (IV) wherein R.sub.3 is hydrogen, (C.sub.1 -C.sub.3)lower alkyl, nitro, amino, hydroxy, fluoro, bromo or chloro, R.sub.4 is (C.sub.1 -C.sub.4)lower alkyl and n is 1 or 2 which act selectively at adenosine receptors and which act in general as adenosine antagonists are disclosed. From in vitro studies it is known that specific physiological effects can be distinguished as a result of this selectivity and that adenosine receptor activity in vitro correlates with adenosine receptor activity in vivo. Pharmaceutical preparations of the subject compounds can be prepared on the basis of the selective binding activity of the compounds disclosed herein which will enhance certain physiological effects while minimizing others, such as descreasing blood pressure without descreasing heart rate.

  具有一般结构（I）的黄嘌呤衍生物，包括（R）和（S）对映体及其外消旋混合物，以及其药用盐，其中R.sub.1和R.sub.2分别独立地为（C.sub.1-C.sub.4）低碳基或（C.sub.2-C.sub.4）低碳烯基，Z为（II）或（III）或（IV），其中R.sub.3为氢，（C.sub.1-C.sub.3）低碳基，硝基，氨基，羟基，氟，溴或氯，R.sub.4为（C.sub.1-C.sub.4）低碳基，n为1或2，这些衍生物在腺苷受体上具有选择性作用，并且在一般上作为腺苷拮抗剂被揭示。从体外研究中已知，由于这种选择性，可以区分特定的生理效应，并且体外腺苷受体活性与体内腺苷受体活性相关。基于本文披露的化合物的选择性结合活性，可以制备所述化合物的药物制剂，这将增强某些生理效应，同时最小化其他效应，例如降低血压而不降低心率。
• Dialkenyl derivatives of xanthine, pharmaceutical compositions and
  申请人：Warner-Lambert Company

  公开号：US04772607A1

  公开（公告）日：1988-09-20

  The present invention is various novel diallyl analogs of xanthine. Additionally, the invention is pharmaceutical compositions having as the active compound diallyl analogs of xanthines and methods of use therefor. Processes of preparation of diallyl analogs of xanthine are also the invention. The use of the analogs relates particularly to a desirable affinity at adenosine receptors, particularly the A.sub.1 receptor. The analogs are adenosine receptor antagonists. The analogs, thus, for example provide activity for use as a CNS stimultant cognition activator, antifibrillatory agent, and bronchodilator.

  本发明是关于黄嘌呤的多种新型二烯丙基类似物。此外，本发明还涉及以二烯丙基黄嘌呤为活性化合物的药物组合物及其使用方法。制备二烯丙基黄嘌呤的方法也是本发明的一部分。该类似物的使用特别涉及对腺苷受体的亲和力，特别是A.sub.1受体。该类似物是腺苷受体拮抗剂。因此，该类似物例如可用于作为中枢神经系统兴奋剂，认知激活剂，抗心颤药和支气管扩张剂的活性。
• ニトロソウラシルの製造方法
  申请人：——

  公开号：JP2004131414A

  公开（公告）日：2004-04-30

  【課題】従来技術における、最終生成物中に不純物が混入するという実用面での欠点を解消し、効率的な４−アミノ−１、３−ジアルキル−５−ニトロソウラシルの製造方法を提供する。【解決手段】酢酸滴下の時間を１．５時間以上とし、酢酸滴下時の温度を１１〜３９℃に制御して反応する。【効果】最終生成物中への不純物の混入を低下でき、４−アミノ−１、３−ジアルキル−５−ニトロソウラシルの効率的な工業的製造法を提供できる。【選択図】なし

  消除了传统技术中最终产品中存在杂质的实际缺点，并提供了一种生产 4-氨基-1,3-二烷基-5-亚硝基尿嘧啶的高效方法。提供了生产 4-氨基-1,3-二烷基-5-亚硝基尿嘧啶的方法。该反应是通过将醋酸滴加时间设定为 1.5 小时或以上，并将醋酸滴加时的温度控制在 11-39°C 进行的。通过减少最终产品中的杂质，可使 4-氨基-1,3-二烷基-5-亚硝基尿嘧啶的生产方法更有效。无。