3-isobutyl-6-methyluracil | 1804-01-9

• 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: 3-isobutyl-6-methyluracil
• 英文别名: 6-methyl-3-(2-methylpropyl)-1H-pyrimidine-2,4-dione
• CAS: 1804-01-9
• 化学式: C₉H₁₄N₂O₂
• 分子量: 182.222
• InChiKey: FMRWAKZUWFOTDM-UHFFFAOYSA-N

物化性质

• 熔点：
  199 °C
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  3-isobutyl-6-methyluracil 生成 3-(sec-Butyl)-6-methylpyrimidine-2,4(1H,3H)-dione, sodium salt
  参考文献：
  名称：

  SALIXOV, I. SH.;REZNIK, V. S.;SHVETSOV, YU. S.;PETROVA, V. V.;SHAGIDULLIN+, IZV. AN CCCP. CEP. XIM., 1986, N 5, 1173-1177

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲基尿嘧啶 、 碘代异丁烷 在 氢氧化钾 作用下， 生成 3-isobutyl-6-methyluracil 、 1-isobutyl-6-methyluracil
  参考文献：
  名称：

  Behrend; Bueckendorff, Justus Liebigs Annalen der Chemie, 1911, vol. 385, p. 316

  摘要：

  DOI：

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。
• Design, Synthesis, and Structure−Activity Relationships of 1-,3-,8-, and 9-Substituted-9-deazaxanthines at the Human A_2B Adenosine Receptor
  作者：Angelo Carotti、Maria Isabel Cadavid、Nuria B. Centeno、Cristina Esteve、Maria Isabel Loza、Ana Martinez、Rosa Nieto、Enrique Raviña、Ferran Sanz、Victor Segarra、Eddy Sotelo、Angela Stefanachi、Bernat Vidal

  DOI：10.1021/jm0506221

  日期：2006.1.1

  Over two hundred 1-, 3-, 8-, and 9-substituted-9-deazaxanthines were prepared and evaluated for their binding affinity at the recombinant human adenosine receptors, in particular at the hA(2B) and hA(2A) subtypes. Several ligands endowed with sub-micromolar to low nanomolar binding affinity at hA(2B) receptors, good selectivity over hA(2A) and hA(3), but a relatively poor selectivity over hA(1) were obtained. Good antagonistic potencies and efficacies, with pA(2) values close to the corresponding pK(i)s, were observed in functional assays in vitro performed on a selected series of compounds. 1,3-Dimethyl-8-phenoxy-(N-p-halogenophenyl)-acetamido-9-deazaxanthine derivatives appeared as the most interesting leads, some of them showing outstanding hA(2B) affinities, high selectivity over hA(2A) and hA(3), but low selectivity over hA(1). Structure-affinity relationships suggested that the binding potency at the hA(2B) receptor was mainly modulated by the steric (lipophilic) properties of the substituents at positions 1 and 3 and by the electronic and lipophilic characteristics of the substituents at position 8. A comparison among affinity and selectivity profiles of 9-deazaxanthines with the corresponding xanthines suggested some possible differences in their binding mode.
• Reaction of the sodium salts of some hydroxypyrimidines with ?,?-dihaloalkanes Communication 4. Synthesis of N-(?-haloalkyl)uracils
  作者：I. Sh. Salikhov、V. S. Reznik、Yu. S. Shvetsov、V. V. Petrova、R. R. Shagidullin

  DOI：10.1007/bf00955382

  日期：1986.5
• A2B ADENOSINE RECEPTOR ANTAGONISTS
  申请人：CV THERAPEUTICS, INC.

  公开号：EP1678181A2

  公开（公告）日：2006-07-12
• US7449473B2
  申请人：——

  公开号：US7449473B2

  公开（公告）日：2008-11-11