5-allyl-6-methyl-2-phenyl-pyrimidin-4-ol | 255869-27-3

• 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: 5-allyl-6-methyl-2-phenyl-pyrimidin-4-ol
• 英文别名: 5-Allyl-6-methyl-2-phenylpyrimidin-4-ol；4-methyl-2-phenyl-5-prop-2-enyl-1H-pyrimidin-6-one
• CAS: 255869-27-3
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: YFZLXQQUPPACGT-UHFFFAOYSA-N

物化性质

• 沸点：
  348.7±35.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-allyl-6-methyl-2-phenyl-pyrimidin-4-ol 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 甲苯 为溶剂， 反应 102.0h， 生成 4-methyl-2-(4-methyl-2-phenyl-5,8-dihydro-pyrimido[4,5-b]azepin-9-yl)-pentanoic acid cyclohexylamide
  参考文献：
  名称：

  New Ugi-Smiles-Metathesis Strategy toward the Synthesis of Pyrimido Azepines

  摘要：

  A new strategy involving Ugi-Smiles coupling followed by ring-closure metathesis is described herein for the preparation of pyrimidine-fused heterocyclic scaffolds. The scope of this sequence is presented in relation with the heteroatom effect observed in the Ugi-Smiles coupling.

  DOI：

  10.1021/jo070706c
• 作为产物：
  描述：

  苄脒盐酸盐 、 2-乙酰基-4-戊酸乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以74%的产率得到5-allyl-6-methyl-2-phenyl-pyrimidin-4-ol
  参考文献：
  名称：

  New Ugi-Smiles-Metathesis Strategy toward the Synthesis of Pyrimido Azepines

  摘要：

  A new strategy involving Ugi-Smiles coupling followed by ring-closure metathesis is described herein for the preparation of pyrimidine-fused heterocyclic scaffolds. The scope of this sequence is presented in relation with the heteroatom effect observed in the Ugi-Smiles coupling.

  DOI：

  10.1021/jo070706c

文献信息

• [EN] NURR1:RXR ACTIVATING COMPOUNDS FOR SIMULTANEOUS TREATMENT OF SYMPTOMS AND PATHOLOGY OF PARKINSON'S DISEASE<br/>[FR] COMPOSÉS ACTIVANT NURR1:RXR POUR LE TRAITEMENT SIMULTANÉ DES SYMPTÔMES ET DE LA PATHOLOGIE DE LA MALADIE DE PARKINSON
  申请人：VASSILATIS DEMETRIOS K

  公开号：WO2017068070A1

  公开（公告）日：2017-04-27

  The invention provides a series of substituted aryl pyrimidine compounds and the use of these compounds as therapeutics to treat or prevent neurodegenerative disorders, including Parkinson's disease. Compounds of the invention are also able to treat the symptoms of such diseases and therefore represent a new treatment modality for ameliorating chronic and acute conditions. The compounds of the invention are capable of selectively potentiating the activity of the Nurr1:RXRα heterodimer, and are able to treat diseases or conditions associated with aberrant Nurr1:RXRα function. The invention further provides methods for treating neurodegenerative disorders by administration of Nurr1:RXRα activating agents.

  这项发明提供了一系列取代芳基嘧啶化合物，并利用这些化合物作为治疗剂来治疗或预防神经退行性疾病，包括帕金森病。该发明的化合物还能够治疗这些疾病的症状，因此代表了一种新的治疗方式，用于改善慢性和急性病症。该发明的化合物能够选择性地增强Nurr1:RXRα异源二聚体的活性，并能够治疗与异常Nurr1:RXRα功能相关的疾病或病症。该发明还提供了通过给予Nurr1:RXRα激活剂来治疗神经退行性疾病的方法。
• Fused pyrimidine systems: XVII. Arylsulfenylation of 5-allylpyrimidine-4(3H)-one derivatives. Synthesis of arylsulfanyl-substituted 5,6-dihydrofuro[2,3-d]- and 6,7-dihydro-5H-pyrano[2,3-d]pyrimidines
  作者：A. I. Vas’kevich、M. V. Vovk

  DOI：10.1134/s1070428017020221

  日期：2017.2

  5-Allylpyrimidine-4-ones react with arylsulfenyl chlorides in dichloromethane with the formation of 5-[(2-arylsulfanyl)-3-chloropropyl]-pyrimidine-4-ones that under the action of sodium acetate undergo cyclization into 6-arylsulfanyl-6,7-dihydro-5H-pyrano[2,3-d]pyrimidines. At performing similar reactions in nitromethane an intramolecular electrophilic cyclization occurs affording 6-[(arylsulfanyl)methyl]-5

  5-烯丙基嘧啶-4-酮与二氯甲烷中的芳基亚硫酰氯反应，生成5-[（2-芳基硫烷基）-3-氯丙基]-嘧啶-4-酮，在乙酸钠的作用下环化成6-芳基硫烷基- 6,7-二氢-5 H-吡喃并[2,3- d ]嘧啶。在硝基甲烷中进行类似反应时，发生分子内亲电环化，得到6-[[（芳基硫烷基）甲基] -5,6-二氢呋喃[2,3- d ]嘧啶。
• Nurr1:RXR activating compounds for simultaneous treatment of symptoms and pathology of Parkinson's disease
  申请人：Vassilatis Demetrios K.

  公开号：US10946019B2

  公开（公告）日：2021-03-16

  The invention provides a series of substituted aryl pyrimidine compounds and the use of these compounds as therapeutics to treat or prevent neurodegenerative disorders, including Parkinson's disease. Compounds of the invention are also able to treat the symptoms of such diseases and therefore represent a new treatment modality for ameliorating chronic and acute conditions. The compounds of the invention are capable of selectively potentiating the activity of the Nurr1:RXRα heterodimer, and are able to treat diseases or conditions associated with aberrant Nurr1:RXRα function. The invention further provides methods for treating neurodegenerative disorders by administration of Nurr1:RXRα activating agents.

  本发明提供了一系列取代芳基嘧啶化合物，并将这些化合物用作治疗或预防神经退行性疾病（包括帕金森病）的药物。本发明的化合物还能治疗此类疾病的症状，因此是一种改善慢性和急性疾病的新治疗方式。本发明的化合物能够选择性地增强Nurr1:RXRα异二聚体的活性，能够治疗与Nurr1:RXRα功能异常相关的疾病或病症。本发明进一步提供了通过施用 Nurr1:RXRα 激活剂治疗神经退行性疾病的方法。
• Discovery of selective PDE4B inhibitors
  作者：Kenji Naganuma、Akifumi Omura、Naomi Maekawara、Masahiro Saitoh、Naoto Ohkawa、Takashi Kubota、Hiromitsu Nagumo、Toshiyuki Kodama、Masayoshi Takemura、Yuji Ohtsuka、Junji Nakamura、Ryuichi Tsujita、Koh Kawasaki、Hirotsugu Yokoi、Masashi Kawanishi

  DOI：10.1016/j.bmcl.2009.04.121

  日期：2009.6

  In this study the first PDE4B selective inhibitor is described. Optimization of lead 2-arylpyrimidine derivatives afforded a series of potent PDE4B inhibitors with >100-fold selectivity over the PDE4D isozyme. With a good pharmacokinetic profile, a selected compound exhibited potent anti-inflammatory effects in vivo and showed less emesis compared with Cilomilast. (C) 2009 Elsevier Ltd. All rights reserved.
• NURR1:RXR ACTIVATING COMPOUNDS FOR SIMULTANEOUS TREATMENT OF SYMPTOMS AND PATHOLOGY OF PARKINSON'S DISEASE
  申请人：Vassilatis, Demetrios K.

  公开号：EP3365329B1

  公开（公告）日：2022-03-30