Crystal structure of isobutyl 3-(4-amino-2-oxo-1,3,5-triazin-1(2H)-yl) propanoate, C10H16N4O3

Abstract

Source of materialAllreactantare purchasedand used withoutfurther purification. In at ypical reaction 4-amino-1,3,5-triazin-2(1H)-one( 1.12 g, 10 mmol), isobutyl acrylate (2.2m l,15 mmol), and 0.06g boric acid (1 mmol)wereplacedintoaflask.Water (40 ml) was added andthe reaction mixture was stirred at 333 Kfor several hours. The progress of the reaction was monitored by thin-layer chromatography (TLC). The solvent was removed under reduced pressure.T hent he solidm aterial wasw ashedw ith ethyla cetate (40 ml) and the solution was filtered to afford the pure product. The purified product was dissolved in the mixture of ethyl alcohol and N,N-dimethylformamide (v/v =2/1).The resulting solution wasleft in air for afew days, yielding colourless crystals. Experimental detailsAllHatomswerepositionedgeometrically andallowed to ride on their parent atoms at distances of Csp 2 -H =0 .93 Åw ith U iso = 1.2U eq (parent atom), Csp 3 -H =0.97/0.98 Åwith U iso =1.5/1.2 U eq (parent atom)and N-H =0.86 Åwith U iso =1.2U eq (parent atom) [13,14]. DiscussionAmong various analogs of cytosine, the 5-azacytosine(5-azaC) analogs have attracted more attention than the normalcytosine or other analogs [1,2].For using as anti-cancer drugs, 5-azacytidine (AC)and 2'-deoxy-5-azacytidine (DAC), demonstrate their active in inhibition aflatoxin biosynthesis [3], the treatment of leukemia [4] and myelodysplastic syndrome (MDS) [5], acute myeloid leukemia (AML) [6], respectively.I na nti-viral range, HPMP-5-azaC,its cyclic formand ester prodrugs, all show remarkable activity againstvarious DNAviruses [7]. As analogsofHPMP-cytosine [8,9 ], they both have extinctf unctions anda nti-virus potential. As AC and DAC are unstable in water, further solutions are put forward, that is, saturation of the 5,6-double bond, which leads to 5,6-dihydro-5-azacytidine (DHAC)a nd 2'-deoxy-5,6-dihydro-5-azacytidine (DHDAC), formerone could inhibit RNA synthesis [10], while the later exhibits unique anti-HIV potential [11]. Beside their mainly applications in medical chemistry, they have shown distinctive lanthanides/actinides separation efficacy. Recently, report on the separation of uranium from multi-ion system has been discovered [12],broadening their scope to hazardous pollutants detection. Consequently, more effort and passion should be spend on the research of cytosine analogues. Herein we report the structure of isobutyl 3-(4-amino-2-oxo-1,3,5-triazin-1(2H)-yl)propanoate, also an cytosine analog. The bond lengths and angles in the title molecule (Fig.), are within normalranges. The N1-C1 and N1-C3 bond distances [1.4158(19) . Thepartial double bond character of the structure is presumed as aresult of the electron delocalization. Thedihedral angle formed by theheterocyclicringand theplane definedby N1/C4/C5 is 80.85°.The atoms C1, C2, C3, N1, N2 and N3 in the heterocyclic ring are slightly puckered, with an r.m.s. deviation of 0.093 Å. It should be noted that the hydrogen bonding interactions plays an important role in the crystal structure of the title comp...