5-苄基-2-硫氧代-2,3-二氢嘧啶-4(1h)-酮 | 25912-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-苄基-2-硫氧代-2,3-二氢嘧啶-4(1h)-酮
• 英文名称: 5-benzyl-2-thiouracil
• 英文别名: 5-benzyl-2-tioxo-2,3-dihydro-pyrimidine-4(1H)-one；4(1H)-Pyrimidinone, 2,3-dihydro-5-(phenylmethyl)-2-thioxo-；5-benzyl-2-sulfanylidene-1H-pyrimidin-4-one
• CAS: 25912-36-1
• 化学式: C₁₁H₁₀N₂OS
• 分子量: 218.279
• InChiKey: IQONBPISLRWNJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  5-苄基-2-硫氧代-2,3-二氢嘧啶-4(1h)-酮 在 氨 、 溶剂黄146 、 牛血清白蛋白 、 氯乙酸 作用下， 以 甲醇 为溶剂， 反应 54.58h， 生成 5-苄基-1-(2-羟基乙氧基甲基)尿嘧啶
  参考文献：
  名称：

  Inhibition of uridine phosphorylase: synthesis and structure-activity relationships of aryl-substituted 5-benzyluracils and 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils.

  摘要：

  A series of 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils were synthesized and tested for inhibition of murine liver uridine phosphorylase (UrdPase). Inhibitors of UrdPase are reported to enhance the chemotherapeutic utility of 5-fluoro-2'-deoxyuridine and 5-fluorouracil and to ameliorate zidovudine-induced anemia in animal models. We prepared a series of 5-aryl-substituted analogues of 5-benzylacyclouridine (BAU), a good inhibitor of UrdPase (IC50 of 0.46 mu M), to develop a compound with enhanced potency and improved pharmacokinetics. The first phase of structure-activity relationship studies on a series of 32 aryl-substituted 5-benzyluracils found several 5-(3-alkoxybenzyl) analogues of 5-benzyluracil with enhanced potency. The acyclovir side chain, the (2-hydroxyethoxy)methyl group, was substituted on the more potent aryl-substituted 5-benzyluracils. The two most potent compounds, 10y (3-propoxy) and 10dd (3-sec-butoxy), were inhibitors of UrdPase with IC(50)s of 0.047 and 0.027 mu M, respectively. Six compounds were tested in vivo for effects on steady-state concentrations of circulating uridine in rats. Plasma uridine levels were elevated 3-9-fold by compound levels that ranged from 8 to 50 mu M.

  DOI：

  10.1021/jm00019a015
• 作为产物：
  描述：

  3-苯丙酸乙酯 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 乙二醇二甲醚 、 mineral oil 为溶剂， 反应 35.0h， 生成 5-苄基-2-硫氧代-2,3-二氢嘧啶-4(1h)-酮
  参考文献：
  名称：

  Heterocyclic derivative and pharmaceutical composition comprising the same

  摘要：

  本发明提供了具有P2X3和/或P2X2/3受体拮抗作用的新化合物。具有P2X3和/或P2X2/3受体拮抗作用的药物组合物包括式(I)的化合物：其中环A是取代或未取代的5至7成员环烷烃，取代或未取代的5至7成员环烯烃等；C是碳原子；-X-是-N(R16)-等；R16是氢、取代或未取代的烷基等；R7是取代或未取代的5-或6-成员杂芳基，取代或未取代的6至10成员芳基；Q1和Q2分别是碳原子或氮原子；-L-是-O-、-S-等；R6是取代或未取代的环烷基，取代或未取代的环烯基等；R2是氢、羟基等，或其药学上可接受的盐或溶剂化合物。

  公开号：

  US09212130B2

文献信息

• New Facile Synthesis of 2-Alkylthiopyrimidin-4(3H)-ones by Tandem Aza-Wittig Reaction Starting from the Baylis–Hillman Adducts
  作者：Ming-Wu Ding、Jun Xiong、Xiao Wei

  DOI：10.1055/s-0036-1588947

  日期：——

  Iminophosphoranes reacted with CS2 at –5 °C to produce the isothiocyanates, which were treated with primary amine to give thioureas in 73–91% yields. The subsequent reaction of thioureas with alkyl bromides in the presence of solid K2CO3 produced 2-alkylthiopyrimidin-4(3H)-ones in 68–88% yield via tandem intramolecular cyclization–isomerization–S-alkylation.

  亚氨基正膦与 CS 2在 –5 °C 下反应生成异硫氰酸酯，用伯胺处理异硫氰酸酯，得到硫脲，收率 73–91%。随后，硫脲与烷基溴在固体 K 2 CO 3存在下反应，通过串联分子内环化-异构化-S-烷基化生成2-烷硫基嘧啶-4(3 H )-酮，产率 68-88%。
• [EN] PYRIMIDINONE COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] COMPOSES DE PYRIMIDINONE ET COMPOSITIONS PHARMACEUTIQUES LES RENFERMANT
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1999024420A1

  公开（公告）日：1999-05-20

  (EN) A group of novel pyrimidone compounds are inhibitors of the enzyme LDL PLA2 and therefore of use in treating atherosclerosis.(FR) L'invention concerne un groupe de nouveaux composés de pyrimidinone qui sont des inhibiteurs de l'enzyme LDL PLA2 et qui s'utilisent donc pour le traitement de l'athérosclérose.

  一组新型嘧啶酮化合物是LDL PLA2酶的抑制剂，因此可用于治疗动脉粥样硬化。
• Pyrimidinone compounds and pharmaceutical compositions containing them
  申请人：——

  公开号：US20020120139A1

  公开（公告）日：2002-08-29

  A group of novel pyrimidone compounds are inhibitors of the enzyme LDL PLA2 and therefore of use in treating atherosclerosis.

  一组新型嘧啶酮化合物是LDL PLA2酶的抑制剂，因此可用于治疗动脉粥样硬化。
• Positive working photosensitive material
  申请人：AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.À R.L.

  公开号：US10976662B2

  公开（公告）日：2021-04-13

  The present application for patent relates to a light-sensitive positive working photosensitive composition especially useful for imaging thick films using a composition which gives very good film uniformity and promotes a good process latitude against feature pattern collapse in patterns created upon imaging and developing of these films.

  本专利申请涉及一种感光性正片工作感光组合物，特别适用于厚膜成像，该组合物可提供非常好的胶片均匀性，并在这些胶片成像和显影过程中，促进良好的加工纬度，防止图案特征崩溃。
• NOVEL HETEROCYCLIC DERIVATIVES AND PHARMACEUTICAL COMPOSITION CONTAINING SAME
  申请人：Shionogi & Co., Ltd.

  公开号：EP2604260B1

  公开（公告）日：2017-05-10