6-甲基-3-丙基尿嘧啶 | 7454-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-甲基-3-丙基尿嘧啶
• 英文名称: 6-methyl-3-propyluracil
• 英文别名: 6-methyl-3-propyl-1H-pyrimidine-2,4-dione；6-Methyl-3-propyl-1H-pyrimidin-2,4-dion；6-methyl-3-propyl-1,3-dihydropyrimidine-2,4-dione；3-propyl-6-methyluracil；6-Methyl-3-n-propyluracil；Uracil, 6-methyl-4-propyl-；6-methyl-3-propyl-1H-pyrimidine-2,4-dione
• CAS: 7454-99-1
• 化学式: C₈H₁₂N₂O₂
• 分子量: 168.195
• InChiKey: BBFJPUDLETXJCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-甲基-3-丙基尿嘧啶 在 sodium hydroxide 、 硫酸 、 硝酸 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 6-methyl-5-nitro-1,3-dipropyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Structure-Activity Relationships of Deazaxanthines: Analogs of Potent A1- and A2-Adenosine Receptor Antagonists

  摘要：

  A set of 22 9-deazaxanthines (pyrrolo[3,2-d]pyrimidine-2,4-diones) and three 7-deazaxanthines (pyrrolo[2,3-d] pyrimidine-2,4-diones) with various substituents in the 1-, 3-, 7- or 9-, and 8-positions was synthesized and investigated in A1 and A2a adenosine receptor binding assays at rat brain cortical membranes and rat brain striatal membranes, respectively. 9-Deazaxanthines showed structure-activity relationships that were similar to those of xanthines. They were about equipotent to the corresponding xanthines at A2a adenosine receptors. 9-Deazaxanthines were generally at least 2-3-fold more potent than xanthines at A1 receptors and therefore exhibited higher A1 selectivities compared to the xanthines. 1,3-Dimethyl-8-(2-naphthyl)-9-deazaxanthine (19e) showed high affinty (K-i = 26 nM) and selectivity for A1 adenosine receptors. A hydroxyl function at N7 of 9-deazaxanthines was unfavorable for A1 and A2a receptor binding. 7-Deazaxanthines were considerably less potent compared to xanthines and to 9-deazaxanthines at both receptor subtypes.

  DOI：

  10.1021/jm00036a019
• 作为产物：
  描述：

  丙脲 、 乙酰乙酸乙酯 在 盐酸 作用下， 以 乙醇 为溶剂， 以45%的产率得到6-甲基-3-丙基尿嘧啶
  参考文献：
  名称：

  Synthesis and Structure-Activity Relationships of Deazaxanthines: Analogs of Potent A1- and A2-Adenosine Receptor Antagonists

  摘要：

  A set of 22 9-deazaxanthines (pyrrolo[3,2-d]pyrimidine-2,4-diones) and three 7-deazaxanthines (pyrrolo[2,3-d] pyrimidine-2,4-diones) with various substituents in the 1-, 3-, 7- or 9-, and 8-positions was synthesized and investigated in A1 and A2a adenosine receptor binding assays at rat brain cortical membranes and rat brain striatal membranes, respectively. 9-Deazaxanthines showed structure-activity relationships that were similar to those of xanthines. They were about equipotent to the corresponding xanthines at A2a adenosine receptors. 9-Deazaxanthines were generally at least 2-3-fold more potent than xanthines at A1 receptors and therefore exhibited higher A1 selectivities compared to the xanthines. 1,3-Dimethyl-8-(2-naphthyl)-9-deazaxanthine (19e) showed high affinty (K-i = 26 nM) and selectivity for A1 adenosine receptors. A hydroxyl function at N7 of 9-deazaxanthines was unfavorable for A1 and A2a receptor binding. 7-Deazaxanthines were considerably less potent compared to xanthines and to 9-deazaxanthines at both receptor subtypes.

  DOI：

  10.1021/jm00036a019

文献信息

• A2B adenosine receptor antagonists
  申请人：Kalla Rao

  公开号：US20050119287A1

  公开（公告）日：2005-06-02

  Disclosed are novel compounds that are A 2B adenosine receptor antagonists having the following structure: wherein R 1 and R 2 are independently chosen from hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, and optionally substituted heteroaryl, and R 4 is an optionally substituted heteroaryl moiety. The compounds of the invention are useful for treating various disease states, including asthma, chronic obstructive pulmonary disorder, pulmonary inflammation, emphysema, diabetic disorders, inflammatory gastrointestinal tract disorders, immunological/inflammatory disorders, cardiovascular diseases, neurological disorders, and diseases related to angiogenesis.

  本发明涉及一种新的化合物，该化合物是A2B腺苷受体拮抗剂，其结构如下：其中R1和R2独立地选择自氢、可选择性取代的烷基、可选择性取代的环烷基、可选择性取代的芳基和可选择性取代的杂环芳基，而R4是可选择性取代的杂环芳基基团。本发明的化合物可用于治疗各种疾病状态，包括哮喘、慢性阻塞性肺疾病、肺部炎症、肺气肿、糖尿病性疾病、炎症性胃肠道疾病、免疫/炎症性疾病、心血管疾病、神经系统疾病和与血管生成相关的疾病。
• Pyrrolo[3,2-D] pyrimidines that are selective antagonists of A2badenosine receptors
  申请人：Wang Guoquan

  公开号：US20080125425A1

  公开（公告）日：2008-05-29

  The present invention provides compounds of the following formula and pharmaceutical compositions that are selective antagonists of A 2B adenosine receptors (ARs). These compounds and compositions are useful as pharmaceutical agents.

  本发明提供以下式子的化合物和药物组合物，它们是选择性A2B腺苷受体（ARs）拮抗剂。这些化合物和组合物可用作药物。
• PYRROLO[3,2-D]PYRIMIDINES THAT ARE SELECTIVE ANTAGONISTS OF A2B ADENOSINE RECEPTORS
  申请人：Wang Guoquan

  公开号：US20090082347A1

  公开（公告）日：2009-03-26

  The present invention provides compounds of the following formula and pharmaceutical compositions that are selective antagonists of A 2B adenosine receptors (ARs). These compounds and compositions are useful as pharmaceutical agents.

  本发明提供了以下化学式的化合物和药物组合物，它们是A2B腺苷受体（ARs）的选择性拮抗剂。这些化合物和组合物可用作药物剂。
• Substituted pyrrolo[3,2-d]pyrimidin-2,4-diones as A2b adenosine receptor antagonists
  申请人：CV Therapeutics, Inc.

  公开号：US07449473B2

  公开（公告）日：2008-11-11

  Disclosed are novel compounds that are A2B adenosine receptor antagonists having the following structure: wherein R1 and R2 are independently chosen from hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, and optionally substituted heteroaryl, and R4 is an optionally substituted heteroaryl moiety. The compounds of the invention are useful for treating various disease states, including asthma, chronic obstructive pulmonary disorder, pulmonary inflammation, emphysema, diabetic disorders, inflammatory gastrointestinal tract disorders, immunological/inflammatory disorders, cardiovascular diseases, neurological disorders, and diseases related to angiogenesis.

  本发明涉及新型化合物，其是A2B腺苷受体拮抗剂，具有以下结构：其中R1和R2分别选自氢、可选取取代基的烷基、可选取取代基的环烷基、可选取取代基的芳基和可选取取代基的杂环基，而R4是可选取取代基的杂环基团。本发明中的化合物可用于治疗多种疾病状态，包括哮喘、慢性阻塞性肺疾病、肺部炎症、肺气肿、糖尿病疾病、炎性胃肠道疾病、免疫/炎症性疾病、心血管疾病、神经系统疾病以及与血管生成相关的疾病。
• NOVEL PLEUROMUTILIN DERIVATIVES
  申请人：SmithKline Beecham p.l.c.

  公开号：EP1889845A1

  公开（公告）日：2008-02-20

  Pleuromutilin compounds of the formula (A) & (B) are of use in anti-bacterial therapy. in which: R1 is optionally substituted C(1-6)alkyl or C(3-6)cycloalkyl or optionally substituted heterocyclyl; R2 is vinyl or ethyl; R3 is H, OH or F, and R4 is H, or R3 is H and R4 is F, and R5 and R6 together form an oxo group; or R3 and R4 is each H, R5 is OH or H and R6 is H, or R5 is H and R6 is OH or H.

  式 (A) 和 (B) 的 Pleuromutilin 化合物可用于抗菌治疗。 其中 R1 是任选取代的 C(1-6)烷基或 C(3-6)环烷基或任选取代的杂环烷基； R2 是乙烯基或乙基； R3 是 H、OH 或 F，R4 是 H，或 R3 是 H，R4 是 F，R5 和 R6 共同形成一个氧代基团；或 R3 和 R4 均为 H，R5 为 OH 或 H，R6 为 H，或 R5 为 H，R6 为 OH 或 H。