5-benzylpyrimidine-4,6-diol | 562102-89-0

• 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: 5-benzylpyrimidine-4,6-diol
• 英文别名: 5-benzyl-1H-pyrimidine-4,6-dione；5-benzyl-4-hydroxy-1H-pyrimidin-6-one
• CAS: 562102-89-0
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: CJYWRFDJJXEDIN-UHFFFAOYSA-N

物化性质

• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 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：

  5-benzylpyrimidine-4,6-diol 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 [4-(5-benzyl-6-chloropyrimidin-4-ylethynyl)phenyl]dimethylamine
  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：

  醋酸甲脒 、 苄基丙二酸二乙酯 在 sodium methylate 、 盐酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 26.0h， 生成 5-benzylpyrimidine-4,6-diol
  参考文献：
  名称：

  [EN] PYRIMIDINE DERIVATIVES AND USE THEREOF AS AGRICULTURAL AND HORTICULTURAL FUNGICIDES
  [FR] DERIVES DE PYRIMIDINE ET UTILISATION DE CEUX-CI COMME FONGICIDES AGRICOLES ET HORTICOLES

  摘要：

  一种农业园艺杀菌剂，其特征在于含有苯基嘧啶衍生物，其化学式为（I），其中R1至R6和Q如描述中所定义。

  公开号：

  WO2005079798A1

文献信息

• [EN] PYRIMIDINE DERIVATIVES AND USE THEREOF AS AGRICULTURAL AND HORTICULTURAL FUNGICIDES<br/>[FR] DERIVES DE PYRIMIDINE ET UTILISATION DE CEUX-CI COMME FONGICIDES AGRICOLES ET HORTICOLES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2005079798A1

  公开（公告）日：2005-09-01

  An agrohorticultural fungicide characterized by containing benzylpyrimidine derivatives represented by the formula (I) wherein R1 to R6 and Q are as defined in the description.

  一种农业园艺杀菌剂，其特征在于含有苯基嘧啶衍生物，其化学式为（I），其中R1至R6和Q如描述中所定义。
• Nucleic Acid Component Analogues: Synthesis of 2′-Deoxynucleosides from 5-Substituted-4- Hydroxy-6(1H)-Pyrimidinones
  作者：Ahmed F. Khattab、Ahmed E.-S. Abdel Megied、Erik B. Pedersen

  DOI：10.1081/ncn-120018626

  日期：2003.4

  2'-deoxynucleosides 7a-c, the pure alpha- and beta-anomers were separated and deprotected with sodium methoxide in methanol to give 1-(2'-deoxy-alpha-D-pentafuranosyl)-4-hydroxy-5-substituted-6(1H)-pyrimidinones 10a,b and 13a and their corresponding beta-anomers 11a,b and 13b.

  使用三甲基甲硅烷基磺酸盐作为催化剂，将甲硅烷基化的嘧啶5a-c与2-脱氧-3,5-二-O-甲苯甲酰基-D-戊呋喃糖苷甲基缩合，得到2'-脱氧核苷7a-c，纯的α-分离β-端基异构体并用甲醇钠在甲醇中脱保护，得到1-（2'-脱氧-α-D-戊呋喃糖基）-4-羟基-5-取代-6（1H）-嘧啶酮10a，b和13a及其衍生物相应的β-端基异构体11a，b和13b。
• Pyrimidine derivatives and use thereof as agricultural and horticultural fungicides
  申请人：Ito Mashito

  公开号：US20070167421A1

  公开（公告）日：2007-07-19

  This invention relates to an agrohorticultural fungicide containing benzylpyrimidine derivatives represented by the formula wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are as defined in the disclosure.

  本发明涉及一种农业园艺用杀菌剂，其包含由以下式表示的苯基嘧啶衍生物：其中R1、R2、R3、R4、R5和R6如说明书所定义。
• Design, Synthesis, and Structure−Activity Relationship of 6-Alkynylpyrimidines as Potent Adenosine Kinase Inhibitors
  作者：Arthur Gomtsyan、Stanley Didomenico、Chih-Hung Lee、Mark A. Matulenko、Ki Kim、Elizabeth A. Kowaluk、Carol T. Wismer、Joe Mikusa、Haixia Yu、Kathy Kohlhaas、Michael F. Jarvis、Shripad S. Bhagwat

  DOI：10.1021/jm020049a

  日期：2002.8.1

  Adenosine (ADO) is an extracellular signaling molecule within the central and peripheral nervous system. Its concentration is increased at sites of tissue injury and inflammation. One of the mechanisms by which antinociceptive and antiinflammatory effects of ADO can be enhanced consists of inhibition of adenosine kinase (AK), the primary metabolic enzyme for ADO. Novel nonnucleoside AK inhibitors based on 4-amino-6-alkynylpyrimidines were prepared, and the importance of the length of the linker at the 5-position for high affinity AK inhibition was demonstrated. Compounds with 2- and 3-atom linkers were the most potent AK inhibitors. Optimization of their physicochemical properties led to 31a and 37a that effectively reduced pain and inflammation in animal models.
• PYRIMIDINE DERIVATIVES AND USE THEREOF AS AGRICULTURAL AND HORTICULTURAL FUNGICIDES
  申请人：Bayer CropScience AG

  公开号：EP1718305A1

  公开（公告）日：2006-11-08