5-benzyl-2,4-dichloro-pyrimidine | 82870-68-6

• 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-benzyl-2,4-dichloro-pyrimidine
• 英文别名: 5-Benzyl-2,4-dichlor-pyrimidin；5-benzyl-2,4-dichloropyrimidine
• CAS: 82870-68-6
• 化学式: C₁₁H₈Cl₂N₂
• 分子量: 239.104
• InChiKey: VFDYBLGZCHOWFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-benzyl-2,4-dichloro-pyrimidine 在 乙醇 、 硫酸 、 氨 、 水 作用下， 生成 4-氨基-5-苄基-2(1H)-嘧啶酮
  参考文献：
  名称：

  Goldberg, Bulletin de la Societe Chimique de France, 1951, p. 895,898

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-formyl-3-phenylpropionate 在 盐酸 、 sodium hydroxide 、 乙醇 、 三氯氧磷 作用下， 生成 5-benzyl-2,4-dichloro-pyrimidine
  参考文献：
  名称：

  Goldberg, Bulletin de la Societe Chimique de France, 1951, p. 895,898

  摘要：

  DOI：

文献信息

• Pyrimidine Acyclic Nucleotide Analogues with Aromatic Substituents in C-5 Position
  作者：Marcela Krečmerová、Antonín Holý、Milena Masojídková

  DOI：10.1135/cccc20070927

  日期：——

  NH₂-protected 5-phenylcytosine and its derivatives 2a-2d were treated with (2S)-2-[(trityloxy)methyl]oxirane (3) followed by etherification with diisopropyl [(tosyloxy)methyl]phosphonate (5) in the presence of sodium hydride. The intermediary phosphonate esters 6 were debenzoylated and subsequently transformed to free phosphonic acids, i.e. (S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-phenylcytosine (5-phenyl-HPMPC) derivatives (8a-8d) by the action of bromotrimethylsilane and subsequent hydrolysis. Deamination of these compounds with 3-methylbutyl nitrite afforded corresponding (S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-phenyluracil (5-phenyl-HPMPU) derivatives (9a-9d). R-Enantiomers 14 and 15 were prepared analogously starting from (2R)-2-[(trityloxy)methyl]oxirane. 5-Benzyl-, 5-[(1-naphthyl)methyl]- and 5-[(2-naphthyl)methyl]HPMPU (24a-24c) and -HPMPC (25a-25c) were synthesized from appropriate 5-arylmethyl-4-methoxypyrimidin-2(1H)-ones similarly as described for 5-phenyl derivatives. Antiviral activity was found for (S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-phenyluracil (9a) (HSV-1 and HSV-2) and (R)-1-[3-hydroxy2-(phosphonomethoxy)propyl]-5-phenylcytosine (14) (cytomegalovirus and varicella-zoster virus), both tested in cell cultures. Some of the 5-phenyluracil derivatives possessed inhibitory activity against thymidine phosphorylase from SD-lymphoma.

  NH₂保护的5-苯基胞嘧啶及其衍生物2a-2d与(2S)-2-[(三苄氧基)甲基]环氧乙烷(3)反应，随后在钠氢化物存在下与二异丙基[(对甲苯磺酰氧基)甲基]膦酸酯(5)醚化。中间体膦酸酯6被去苄酰化，随后转化为自由膦酸，即(5-苯基-HPMPC)衍生物8a-8d，通过溴三甲基硅烷的作用和随后的水解。这些化合物经过3-甲基丁基亚硝酸酯的去氨基化处理，得到相应的(5-苯基-HPMPU)衍生物9a-9d。类似地，从(2R)-2-[(三苄氧基)甲基]环氧乙烷开始，制备了R-对映体14和15。通过适当的5-芳基甲基-4-甲氧基嘧啶-2(1H)-酮合成了5-苄基、5-[(1-萘基)甲基]和5-[(2-萘基)甲基]HPMPU(24a-24c)和-HPMPC(25a-25c)，类似于5-苯基衍生物的合成方法。在细胞培养中测试后，发现(S)-1-[3-羟基-2-(膦甲氧基)丙基]-5-苯基尿嘧啶(9a) (HSV-1和HSV-2)和(R)-1-[3-羟基2-(膦甲氧基)丙基]-5-苯基胞嘧啶(14) (巨细胞病毒和水痘-带状疱疹病毒)具有抗病毒活性。一些5-苯基尿嘧啶衍生物对SD-淋巴瘤的胸苷磷酸酶具有抑制活性。
• Substituted pyrimidine derivatives, their preparation and their use in the treatment of neurodegenerative or neurological disorders of the central nervous system
  申请人：Krenitsky Pharmaceuticals, Inc.

  公开号：US06440965B1

  公开（公告）日：2002-08-27

  The present invention relates to novel derivatives of a series of substituted pyrimidines, to pharmaceutical compositions which contain them, to methods for their preparation and to their use in therapy, particularly in the treatment of neurodegenerative or other neurological disorders of the central and peripheral systems.

  本发明涉及一系列取代嘧啶的新衍生物，以及含有这些衍生物的制药组合物、其制备方法以及在治疗中的应用，特别是在治疗中枢和周围神经系统的神经退行性或其他神经系统疾病方面的应用。
• SUBSTITUTED N-(3-(PYRIMIDIN-4-YL)PHENYL)ACRYLAMIDE ANALOGS AS TYROSINE RECEPTOR KINASE BTK INHIBITORS
  申请人：Bearss David J.

  公开号：US20130059847A1

  公开（公告）日：2013-03-07

  In one aspect, the invention relates to substituted N-(3-(pyrimidin-4-yl)phenyl)acrylamide analogs, derivatives thereof, and related compounds, which are useful as inhibitors of the BTK kinase; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds and compositions to treat disorders associated with dysfunction of the BTK kinase. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在某个方面，本发明涉及取代的N-(3-(嘧啶-4-基)苯基)丙烯酰胺类似物、其衍生物和相关化合物，这些化合物可用作BTK激酶的抑制剂；制备这些化合物的合成方法；包含这些化合物的药物组合物；以及使用这些化合物和组合物治疗与BTK激酶功能障碍相关的疾病的方法。本摘要旨在作为特定领域搜索的扫描工具，不限制本发明。
• 4-substituted-2-chloro-5-benzylpyrimidine compounds
  申请人：NEPERA CHEMICAL CO INC

  公开号：US02687415A1

  公开（公告）日：1954-08-24
• SUBSTITUTED PYRIMIDINE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN THE TREATMENT OF NEURODEGENERATIVE OR NEUROLOGICAL DISORDERS OF THE CENTRAL NERVOUS SYSTEM
  申请人：Krenitsky Pharmaceutical Inc

  公开号：EP1025091A1

  公开（公告）日：2000-08-09