2-methyl-5-phenylpyrimidine-4,6-diol | 3602-98-0

• 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: 2-methyl-5-phenylpyrimidine-4,6-diol
• 英文别名: 2-methyl-5-phenyl-1H-pyrimidine-4,6-dione；2-methyl-5-phenyl-pyrimidine-4,6-diol；4-hydroxy-2-methyl-5-phenyl-1H-pyrimidin-6-one
• CAS: 3602-98-0
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: RRKXQQUNMRYPGF-UHFFFAOYSA-N

物化性质

• 熔点：
  >350 °C
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-5-phenylpyrimidine-4,6-diol 在 三氯氧磷 作用下， 以50%的产率得到4,6-dichloro-2-methyl-5-phenylpyrimidine
  参考文献：
  名称：

  4-Amino-5-aryl-6-arylethynylpyrimidines: Structure–activity relationships of non-nucleoside adenosine kinase inhibitors

  摘要：

  A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-yipyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.029
• 作为产物：
  描述：

  2-苯基丙二酰胺 、 乙酸乙酯 在 sodium ethanolate 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 2-methyl-5-phenylpyrimidine-4,6-diol
  参考文献：
  名称：

  [EN] FUSED PYRIMIDINES AS AKT INHIBITORS
  [FR] PYRIMIDINES CONDENSÉES EN TANT QU'INHIBITEURS D'AKT

  摘要：

  本发明涉及式(I)的化合物，其N-氧化物或互变异构体或立体异构体，或其盐，其中环B和与其融合的咪唑，R4、R6、R7、R10、m和n的含义如描述和权利要求中所给出，这些化合物是Pi3K/Akt途径的有效抑制剂，其生产过程及其作为药物的用途。

  公开号：

  WO2010091824A1

文献信息

• Heterocyclic Amplifiers of Phleomycin. VII. Phenyl-, Tolyl-, Phenoxy- and Benzyl-pyrimidines; also Some Carbocyclic Analogues
  作者：DJ Brown、BJ Cronin、S Lan、G Nardo

  DOI：10.1071/ch9850825

  日期：——

  Synthetic routes are described for 5-phenyl-, 5-p-chlorophenyl-, 2-p-tolyl-, 2- and 4-benzyl- and 4-phenoxy-pyrimidines, each bearing a sulfur-, nitrogen- or oxygen-linked basic side chain; also to analogous biphenyls and a diphenylmethane . These compounds were required for evaluation as amplifiers of phleomycin.

  本文介绍了 5-苯基、5-对氯苯基、2-对甲苯基、2-和 4-苄基以及 4-苯氧基嘧啶的合成路线，每种嘧啶都带有与硫、氮或氧相连的碱性侧链；还介绍了类似联苯和二苯基甲烷的合成路线。需要对这些化合物进行评估，以确定其是否可作为博来霉素的放大剂。
• FUSED PYRIMIDINES
  申请人：Beckers Barbara

  公开号：US20130310362A1

  公开（公告）日：2013-11-21

  The present invention relates to compounds of formula (I), a N-oxide or tautomer or stereoisomer thereof, or a salt thereof, wherein ring B and the imidazole to which it is fused, R4, R6, R7, R10, m and n have the meanings as given in the description and the claims, which are effective inhibitors of the Pi3K/Akt pathway, processes for their production and their use as pharmaceuticals.

  本发明涉及式(I)化合物，其为N-氧化物或其互变异构体或立体异构体或其盐，其中环B和它融合的咪唑环，R4、R6、R7、R10、m和n的含义如说明书和权利要求中所给出的，它们是有效的Pi3K/Akt途径抑制剂，其生产过程以及它们作为药物的用途。
• Cascade Wolff Rearrangement and Double <i>N</i>‐Acylation: A Cyclization of <i>α</i>‐Diazoketones with 2‐aminopyridines or 3‐aminopyrazoles to Synthesize Fused Pyrimidinediones
  作者：Jun‐Jie Ren、Jia‐Xin Zhou、Yanqin Song、An‐Xin Zhang、Lu‐Xin Zhao、Zun‐Yuan Zhao、Yan‐Ping Zhu、Wei Zhu

  DOI：10.1002/adsc.202300773

  日期：2023.12.5

  A cascade Wolff rearrangement and double N-acylation reaction has been developed for the synthesis of fused pyrimidinediones in one-pot under air. These reactions were performed with α-diazoketones and 2-aminopyridines or 3-aminopyrazoles under catalyst- and additive-free conditions. The protocol avoided traditional purification procedures, such as organic solvent extraction and column chromatography

  开发了级联 Wolff 重排和双N -酰化反应，用于在空气下一锅法合成稠合嘧啶二酮。这些反应是用α-重氮酮和2-氨基吡啶或3-氨基吡唑在无催化剂和添加剂的条件下进行的。该方案避免了传统的纯化程序，例如有机溶剂萃取和柱色谱。生物活性分子的合成和克级实验证明了该反应的潜在应用。
• FUSED PYRIMIDINES AS AKT INHIBITORS
  申请人：Bayer Intellectual Property GmbH

  公开号：EP2396331B1

  公开（公告）日：2013-10-16
• [EN] FUSED PYRIMIDINES AS AKT INHIBITORS<br/>[FR] PYRIMIDINES CONDENSÉES EN TANT QU'INHIBITEURS D'AKT
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2010091824A1

  公开（公告）日：2010-08-19

  The present invention relates to compounds of formula (I), a N-oxide or tautomer or stereoisomer thereof, or a salt thereof, wherein ring B and the imidazole to which it is fused, R4, R6, R7, R10, m and n have the meanings as given in the description and the claims, which are effective inhibitors of the Pi3K/Akt pathway, processes for their production and their use as pharmaceuticals.

  本发明涉及式(I)的化合物，其N-氧化物或互变异构体或立体异构体，或其盐，其中环B和与其融合的咪唑，R4、R6、R7、R10、m和n的含义如描述和权利要求中所给出，这些化合物是Pi3K/Akt途径的有效抑制剂，其生产过程及其作为药物的用途。