Synthesis, Structure Analysis, and Antitumor Activity of (R)‐2,4‐Dioxo‐5‐fluoro‐1‐[1‐(methoxycarbonyl) Ethylaminocarbonylmethyl]‐1,2,3,4‐tetrahydropyrimidine

A new dipeptide compound, (R)-2,4-dioxo-5-fluoro-1-[1-(methoxycarbonyl) ethylaminocarbonylmethyl]-1,2,3, 4-tetrahydropyrimidine (5-FUAPM), has been synthesized and identified by means of elemental analysis, IR, 1H NMR and 13C NMR spectra. The single crystal of compound 5-FUAPM·DMF was also obtained and characterized by DSC-TGA techniques. The crystal belongs to orthorhombic space group P2121 21 with the cell parameters: a=0.4740(7) nm, b=1.923(3) nm, c=1.9229 nm, α=β=γ=90°, V=1.753 nm3, Z=4, Dc=1.312 g/cm3, Mr=346.32, F(000) =728 and μ=0.111 mm−1. The final R and wR are 0.1378 and 0.2862, respectively. The result of the biological test showed that the compound 5-FUAPM has certain antitumor activities.

[1]  Yan Hu,et al.  Preparation and photoluminescence properties of ZnO/amorphous-BaTiO3 thin-films by sol–gel process , 2006 .

[2]  Mao‐Lin Hu,et al.  LaIII complexes of uracil-1-acetic acid, [La(phen)X3]n, X = uracil-1-acetate (UA) and 5-fluorouracil-1-acetate (5-FUA), two 2D coordination polymer, structural and thermal studies , 2006 .

[3]  Mao‐Lin Hu,et al.  The first Pb–O bond, a novel 2D coordination polymer, [Pb(5-FUOAc)2]n, 5-FUOAc = 5-fluorouracil-1-acetate , 2006 .

[4]  S. Price,et al.  A new polymorph of 5-fluorouracil found following computational crystal structure predictions. , 2005, Journal of the American Chemical Society.

[5]  Jui-Lung Chien,et al.  In Vitro Simulation of Solid-Solid Dehydration, Rehydration, and Solidification of Trehalose Dihydrate Using Thermal and Vibrational Spectroscopic Techniques , 2003, Pharmaceutical Research.

[6]  P. Wang,et al.  Synthesis and cytotoxicity of 5-fluorouracil/diazeniumdiolate conjugates. , 2003, Bioorganic & medicinal chemistry.

[7]  Qiang Xu,et al.  5-Fluorouracil-cisplatin adducts with potential antitumor activity. , 2003, Journal of inorganic biochemistry.

[8]  Shun-Li Wang,et al.  Hydration-induced proton transfer in the solid state of norfloxacin. , 2002, Journal of pharmaceutical sciences.

[9]  Z. Lin,et al.  A novel kind of antitumour drugs using sulfonamide as parent compound. , 2001, European journal of medicinal chemistry.

[10]  Z. Yamaizumi,et al.  Synthesis of a novel dioxane nucleoside having two bases, 2(R)-(5-fluorouracil-1-yl)-5(R)-hydroxymethyl-3(R)-(uracil-1-yl)-1,4-dioxane and its 2(S)-isomer, from uridine , 1997 .

[11]  K. R. Barnard,et al.  Mononuclear and Binuclear Molybdenum(V) Complexes of the Ligand N,N‘-Dimethyl-N,N‘-bis(2-mercaptophenyl)ethylenediamine: Geometric Isomers , 1997 .

[12]  D. Scudiero,et al.  New colorimetric cytotoxicity assay for anticancer-drug screening. , 1990, Journal of the National Cancer Institute.

[13]  T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. , 1983, Journal of immunological methods.