6-氯-1-(苯基甲基)-2,4(1H,3H)-嘧啶二酮 | 124218-96-8

• 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: 6-氯-1-(苯基甲基)-2,4(1H,3H)-嘧啶二酮
• 中文别名: 3-羟基-2-{[3-羟基-2,2-二(羟甲基)丙氧基]甲基}-2-[(辛基桥氧基)甲基]丙基癸酸酯
• 英文名称: 1-benzyl-6-chlorouracil
• 英文别名: 1-benzyl-6-chloropyrimidine-2,4(1H,3H)-dione；1-benzyl-6-chloropyrimidine-2,4-dione
• CAS: 124218-96-8
• 化学式: C₁₁H₉ClN₂O₂
• 分子量: 236.658
• InChiKey: ASQJYDTXWTWENK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 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：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-氯-1-(苯基甲基)-2,4(1H,3H)-嘧啶二酮 在 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 1-benzyl-6-methylamino-5-formylaminouracil
  参考文献：
  名称：

  Youssif, Shaker, Journal of Chemical Research, 2004, # 5, p. 341 - 343

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氯尿嘧啶 、 氯化苄 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以45%的产率得到6-氯-1-(苯基甲基)-2,4(1H,3H)-嘧啶二酮
  参考文献：
  名称：

  下一代葡萄糖-1-磷酸胸苷转移酶 (RmlA) 抑制剂：指导未来设计的扩展 SAR 研究

  摘要：

  L-鼠李糖单糖是细菌细胞壁的重要组成部分。L-鼠李糖生物合成途径的第一步是由1-磷酸葡萄糖胸苷转移酶 (RmlA) 催化，该酶将 1-磷酸葡萄糖 (Glu-1-P) 与脱氧胸苷三磷酸 (dTTP) 缩合生成 dTDP- d-葡萄糖. 除了发生催化该反应的活性位点外，RmlA 还具有对其功能很重要的变构位点。在之前的报告的基础上，SAR 研究进一步探索了变构位点，从而发现了非常有效的铜绿假单胞菌RmlA 抑制剂。C6-NH 2处的修饰抑制剂的嘧啶二酮核心结构被耐受。铜绿假单胞菌RmlA 与新型类似物的复合物的 X 射线晶体学分析表明，C6-氨基烷基取代基可用于将可修饰的胺定位在变构袋外。这开辟了将铁载体与这类抑制剂联系起来的可能性，目的是提高细菌细胞壁的通透性。

  DOI：

  10.1016/j.bmc.2021.116477

文献信息

• Synthesis and Anti-HIV-1 and Anti-HCMV Activity of 1-Substituted 3-(3,5-Dimethylbenzyl)uracil Derivatives
  作者：Tokumi Maruyama、Shigetada Kozai、Yosuke Demizu、Myriam Witvrouw、Christophe Pannecouque、Jan Balzarini、Robert Snoecks、Graciella Andrei、Erik De Clercq

  DOI：10.1248/cpb.54.325

  日期：——

  3-(3,5-Dimethylbenzyl)uracil (3) was treated with alkyl halides in the presence of alkali to give 1-substituted congeners. Condensation of 3 with alcohols using the Mitsunobu reaction was also employed as an alternative method. The anti-HIV-1 activity of 1-substituted analogues of 3-(3,5-dimethylbenzyl)uracil was evaluated according to previously established procedures. It appeared that the nitrogen

  在碱存在下用烷基卤处理3-（3,5-二甲基苄基）尿嘧啶（3），得到1-取代的同类物。使用Mitsunobu反应将3与醇缩合也用作替代方法。根据先前建立的程序评估3-（3,5-二甲基苄基）尿嘧啶的1-取代类似物的抗HIV-1活性。看来1-氰甲基的氮对于抗HIV-1活性是重要的，表明与HIV-1逆转录酶的氨基酸残基相互作用。1-芳基甲基衍生物也显示出良好的抗HIV-1活性。并且2-和4-吡啶甲基衍生物的特别好。这些结果已通过Docking Studies使用“ Glide配体对接工作”程序进行了确认，
• Improved procedures for the syntheses of pyrido- and pyrrolo(2,3-d) pyrimidines, and ribosides thereof.
  作者：Tsuneo ITOH、Raphael G. MELIK-OHANJANIAN、Ichiro ISHIKAWA、Norio KAWAHARA、Yoshihisa MIZUNO、Yoshio HONMA、Motoo HOZUMI、Haruo OGURA

  DOI：10.1248/cpb.37.3184

  日期：——

  Pyrido[2, 3-d]pyrimidines were obtained by treatment of 6-allylaminouracils with PdCl2 at 60 °C, under which conditions the yields of the products were improved to a considerable extent as compared with our previously reported reaction. Pyrrolo[2, 3-d]pyrimidines were prepared under the above conditions from 6-(N-allyl-N-methylamino)uracils which were substituted with a methyl group at 6-NH of uracil. In addition, pyrido- and pyrrolo[2, 3-d]pyrimidine nucleosides were prepared from 6-(substituted allyl- or N-allyl-N-methylamino)uridines by adaptation of the above method. That is, the presence or absence of a substituent on the 6-amino group influences the size of ring formed. We proposed plausible pathways to explain why products having different ring sizes were formed.

  Pyrido[2, 3-d]嘧啶类化合物是通过将6-烯丙基氨基尿嘧啶与PdCl2在60°C下反应得到的，在这种条件下，产品的产率与我们之前报告的反应相比显著提高。根据上述条件，从6-(N-烯丙基-N-甲基氨基)尿嘧啶（其在尿嘧啶的6-NH位点上有甲基取代）制备了吡咯[2, 3-d]嘧啶类化合物。此外，通过调整上述方法，从6-(取代的烯丙基或N-烯丙基-N-甲基氨基)尿苷中制备了吡啶和吡咯[2, 3-d]嘧啶类核苷。也就是说，6-氨基基团上取代基的有无影响形成的环的大小。我们提出了合理的路径来解释为什么产生了不同环大小的产品。
• Isolation of New Chlorinated Regioisomers of Mono N-Substituted Uracil Derivatives and Synthesis of 3-Substituted 8-Phenylpyrimido[5,4-e]-1,2,4-triazine-5,7(6H,8H)-diones
  作者：Tomohisa Nagamatsu、Hirofumi Yamasaki、Fumio Yoneda

  DOI：10.3987/com-93-s146

  日期：——

  A variety of fervenulin type products, 3-substituted 8-phenylpyrimido[5,4-e]-1,2,4-triazine-5,7(6H,8H)-diones (18a-i), were synthesized by nitrosative or nitrative cyclization of the aldehyde hydrazones (17a-i) derived from 6-(1-methylhydrazino)-1-phenyluracil (16) with aliphatic as well as aromatic aldehydes. The compound (16) was prepared by the reaction of 6-chloro-1-phenyluracil (8) with methylhydrazine. In addition, not only the precursor of 16, 6-chloro-1-phenyluracil (8), but also other new chlorinated regioisomers of mono N-substituted pyrimidine (9) and uracil (14) were isolated and characterized by the reductive dechlorination of them.
• Ishikawa, Ichiro; Itoh, Tsuneo; Melik-Ohanjanian, Raphael G., Heterocycles, 1990, vol. 31, # 9, p. 1641 - 1646
  作者：Ishikawa, Ichiro、Itoh, Tsuneo、Melik-Ohanjanian, Raphael G.、Takayanagi, Hiroaki、Mizuno, Yoshihisa、et al.

  DOI：——

  日期：——
• Synthesis of new derivatives of 5-(3,4-dihydro-2Н-pyrrol-5-yl)-pyrimidine
  作者：S. P. Gasparyan、M. V. Alexanyan、G. K. Arutyunyan、S. L. Kocharov、A. H. Martirosyan、R. A. Tamazyan、A. G. Ayvazyan、H. A. Panosyan、G. G. Danagulyan

  DOI：10.1134/s1070428016110166

  日期：2016.11

  By one-stage condensation of 6-(arylamino)pyrimidine-2,4(1De,3De)-diones with pyrrolidin-2-one new potential antiviral compounds were obtained, analogs of pyrrolinylpyrimidine containing structural fragments of known drugs AZT and HEPT used in treating HIV-infections.