N1,N3-bis(prop-2-yne-1-yl)uracil

• 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: N1,N3-bis(prop-2-yne-1-yl)uracil
• 英文别名: N¹,N³-dipropargyl uracil；1,3-di(prop-2-yn-1-yl)pyrimidine-2,4(1H,3H)-dione；1,3-bis(prop-2-yn-1-yl)-2,4(1H,3H)-pyrimidinedione；1,3-Di(prop-2-ynyl)pyrimidine-2,4(1h,3h)-dione；1,3-bis(prop-2-ynyl)pyrimidine-2,4-dione
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: FSINDQWYPYDEIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N1,N3-bis(prop-2-yne-1-yl)uracil 在 copper(l) iodide 、 聚合甲醛 、 二环己胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以68%的产率得到1,3-di(buta-2,3-dien-1-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Regio and stereoselective catalytic five-component cascades of diverse heterocyclic bisallenes: tri-directional exploration of biochemical space

  摘要：

  We report protecting group free Pd(0) catalyzed cascade syntheses of molecular scaffolds built from heterocyclic bisallenes. These generate novel molecular architecture permitting tri-directional exploration of biochemical space. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.060
• 作为产物：
  描述：

  3-溴丙炔 、 尿嘧啶 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 18.0h， 以79%的产率得到N1,N3-bis(prop-2-yne-1-yl)uracil
  参考文献：
  名称：

  Synthesis of New 1,2,3-Triazole Derivatives of Uracil and Thymine with Potential Inhibitory Activity against Acidic Corrosion of Steels

  摘要：

  十个1,4-二取代的1,2,3-三氮唑从1-(叠氮甲基)苯、1-(叠氮甲基)-4-氟苯、1-(叠氮甲基)-4-氯苯、1-(叠氮甲基)-4-溴苯或1-(叠氮甲基)-4-碘苯中的一种（由叠氮化钠和相应的苄基卤在现场生成）以及二炔丙基尿嘧啶或二炔丙基胸腺嘧啶合成。对传统的点击化学确立了最佳实验条件。本文还介绍了这些化合物的部分腐蚀抑制性能，这些性能是通过电化学技术测定的。

  DOI：

  10.3390/molecules18044613

文献信息

• Synthesis of New 1,2,3-Triazole Derivatives of Uracil and Thymine with Potential Inhibitory Activity against Acidic Corrosion of Steels
  作者：Guillermo Negrón-Silva、Rodrigo González-Olvera、Deyanira Angeles-Beltrán、Nidia Maldonado-Carmona、Araceli Espinoza-Vázquez、Manuel Palomar-Pardavé、Mario Romero-Romo、Rosa Santillan

  DOI：10.3390/molecules18044613

  日期：——

  Ten 1,4-disubstituted 1,2,3-triazoles were synthesized from one of 1-(azido-methyl)benzene, 1-(azidomethyl)-4-fluorobenzene, 1-(azidomethyl)-4-chlorobenzene, 1-(azidomethyl)-4-bromobenzene or 1-(azidomethyl)-4-iodobenzene, generated in situ from sodium azide and the corresponding benzyl halide, and dipropargyl uracil or dipropargyl thymine. Optimal experimental conditions were established for the conventional click chemistry. The corrosion inhibiting properties of some of these compounds, which were determined by means of an electrochemical technique, are also presented.

  十个1,4-二取代的1,2,3-三氮唑从1-(叠氮甲基)苯、1-(叠氮甲基)-4-氟苯、1-(叠氮甲基)-4-氯苯、1-(叠氮甲基)-4-溴苯或1-(叠氮甲基)-4-碘苯中的一种（由叠氮化钠和相应的苄基卤在现场生成）以及二炔丙基尿嘧啶或二炔丙基胸腺嘧啶合成。对传统的点击化学确立了最佳实验条件。本文还介绍了这些化合物的部分腐蚀抑制性能，这些性能是通过电化学技术测定的。
• Synthesis and biological evaluations of mono‐ and bis‐ferrocene uracil derivatives
  作者：Senka Djaković、Ljubica Glavaš‐Obrovac、Jasmina Lapić、Silvija Maračić、Juraj Kirchofer、Marija Knežević、Marijana Jukić、Silvana Raić‐Malić

  DOI：10.1002/aoc.6052

  日期：2021.1

  uracil derivatives showed pronounced and selective cytostatic activities on colon adenocarcinoma (CaCo‐2) and Burkitt lymphoma (Raji) cells, with higher potency and selectivity than the reference drug 5‐fluorouracil. Generation of reactive oxygen species (ROS) in CaCo‐2 and Raji cells when treated with compounds 5b, 5e, and 6d was observed. Bis‐ferrocenyl 5‐chlorouracil 6c induced significant disruption

  合成了由（1,2a，3-三唑）桥联的单（3a - 3e和4a - 4e）和双二茂铁（5a - 5e和6a - 6e）共轭5取代的尿嘧啶衍生物。观察到二茂铁单元和二茂铁与三唑之间的间隔基对自由基清除能力的影响。双二茂铁基尿嘧啶衍生物比其单二茂铁基类似物具有更好的抗增殖活性。双二茂铁基甲基（5b）和卤素取代的（5e，6c和6d）尿嘧啶衍生物对结肠腺癌（CaCo-2）和Burkitt淋巴瘤（Raji）细胞具有明显的选择性细胞抑制活性，其效力和选择性均高于参考药物5-氟尿嘧啶。当用化合物5b，5e和6d处理时，在CaCo-2和Raji细胞中产生了活性氧（ROS）。双二茂铁基5-氯尿嘧啶6c引起线粒体膜电位的显着破坏，并伴随CaCo-2，Raji和急性淋巴细胞白血病（CCRF-CEM）细胞凋亡的激活，而6d引起线粒体功能障碍和CaCo-中的细胞凋亡诱导。 2和Raji细胞。6c的强抗增殖活性6d和6
• Synthesis of novel pyrimidine nucleoside analogues owning multiple bases/sugars and their glycosidase inhibitory activity
  作者：Ravi Kumar Thakur、Akansha Mishra、K.K.G. Ramakrishna、Rohit Mahar、Sanjeev K. Shukla、A.K. Srivastava、Rama P. Tripathi

  DOI：10.1016/j.tet.2014.09.078

  日期：2014.11

  A series of novel nucleoside analogues having dual bases (pyrimidine and triazole) and sugars have been synthesized by CuAAC reaction of azido sugars with propynylated pyrimidines. These compounds were evaluated for their in vitro α-glucosidase inhibitory activity. In this series, compounds 4b, 4d, 8a, 8b, 8c, 8e, 8g, 8h, and 8i exhibited very good inhibition of α-glucosidase enzyme. Nucleoside analogues

  通过叠氮基糖与丙炔基嘧啶的CuAAC反应合成了一系列具有双碱基（嘧啶和三唑）和糖的新型核苷类似物。评价这些化合物的体外α-葡糖苷酶抑制活性。在这个系列中，化合物4b，4d，8a，8b，8c，8e，8g，8h和8i表现出非常好的α-葡萄糖苷酶抑制作用。核苷类似物8a，4b，8h和8c 与标准药物阿卡波糖（53.4％）相当，分别显示出47.4％，41.8％，39.4％和34.6％的抑制作用。
• Cu–Al mixed oxide catalysts for azide–alkyne 1,3-cycloaddition in ethanol–water
  作者：R. González-Olvera、C. I. Urquiza-Castro、G. E. Negrón-Silva、D. Ángeles-Beltrán、L. Lomas-Romero、A. Gutiérrez-Carrillo、V. H. Lara、R. Santillan、J. A. Morales-Serna

  DOI：10.1039/c6ra10097j

  日期：——

  Cu(Al)O mixed oxide promotes the formation of 1,2,3-triazoles from an alkyne–azide cycloaddition reaction with excellent yields using an EtOH–H₂O mixture as the solvent under microwave heating.

  Cu(Al)O混合氧化物促进了在微波加热下使用EtOH-H₂O混合溶剂从炔烃-叠氮基环加成反应中高产率形成1,2,3-三唑的过程。
• Synthesis of novel 1H-1,2,3-triazole tethered C-5 substituted uracil–isatin conjugates and their cytotoxic evaluation
  作者：Kewal Kumar、Sunil Sagar、Luke Esau、Mandeep Kaur、Vipan Kumar

  DOI：10.1016/j.ejmech.2012.10.008

  日期：2012.12

  The present manuscript describes the synthesis of uracil isatin hybrids via azide-alkyne cycloadditions and their cytotoxic evaluation against three human cancer cell lines viz. HeLa (cervix), MCF-7 (breast) and DU145 (prostate) using MIT assay. The evaluation studies revealed the dependence of cytotoxicity on C-5 substituents of both uracil and isatin as well as the alkyl chain length with compounds 6g and 6k showing IC50 values 18.21 and 13.90 mu M respectively against DU145 cell lines. Most of the synthesized conjugates exhibited considerable selectivity against MCF-7 and DU145 cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.