Molecular Modeling Studies of Some Uracil and New Deoxyuridine Derivatives

Table 1

Ground and excited states’ computed reactivity indices values in a.u. of (a) 5-FU, (b) uracil, (c) TU, and (d) DTU in different media.

(a)

Calculated parameters	Vacuum		O		EtOH		DMSO
		−0.0326	−0.0724	−0.0332	−0.0747	−0.0332	−0.0442	−0.0333	−0.0443
	−0.2772	−0.2676	−0.2819	−0.2686	−0.2818	−0.2418	−0.2819	−0.2418
−μ	0.155	0.170	0.158	0.172	0.158	0.143	0.158	0.143
	0.245	0.195	0.249	0.194	0.249	0.198	0.249	0.198
	4.089	5.124	4.022	5.155	4.023	5.060	4.022	5.062

Units: Hartree and Hartree⁻¹ for .

(b)

Calculated parameters	Vacuum		O		EtOH		DMSO
		−0.0251	−0.0625	−0.0298	−0.0651	−0.0295	−0.0649	−0.2977	−0.0650
	−0.2660	−0.2682	−0.2746	−0.2688	−0.2742	−0.2688	−0.2745	−0.2688
−	0.146	0.165	0.152	0.167	0.152	0.167	0.152	0.167
	0.241	0.206	0.245	0.204	0.245	0.204	0.245	0.204
	4.152	4.863	4.085	4.907	4.086	4.904	4.086	4.902

(c)

Calculated parameters	Vacuum		O		EtOH		DMSO
		−0.7711	−0.08705	−0.08759	−0.08860	−0.08709	−0.08853	−0.08743	−0.08858
	−0.21387	−0.23176	−0.22459	−0.22965	−0.22408	−0.22975	−0.22443	−0.22969
−	0.146	0.159	0.156	0.159	0.156	0.59	0.156	0.159
	0.137	0.145	0.137	0.141	0.137	0.141	0.137	0.141
	7.312	6.910	7.300	7.087	7.300	7.081	7.300	7.087

(d)

Calculated parameters	Vacuum		O		EtOH		DMSO
		−0.9777	−0.0927	−0.1035	−0.0947	−0.1033	−0.0946	−0.1035	−0.0947
	−0.2186	−0.2354	−0.2772	−0.2342	−0.2268	−0.2342	−0.2270	−0.2342
−	0.158	0.164	0.165	0.161	0.161	0.164	0.165	0.165
	0.121	0.143	0.124	0.139	0.124	0.140	0.124	0.140
	8.267	7.010	8.088	7.171	8.900	7.163	8.092	7.169

(e)

Calculated parameters	U124 X=OH. R=OCCH3 (I); aminodeoxyuridine		U124 X=OH. R=H (II); deoxyuridine		U124 X=F. R=H (III); uridine		Amino-FU (IV); 5-FU-amino acid; ester conjugate
		−0.02308	−0.05903	−0.01683	−0.05338	−0.02104	−0.05322	−0.03273
	−0.26161	−0.26023	−0.25667	−0.25404	−0.25764	−0.25585	−0.26791
−	0.142	0.160	0.137	0.154	0.139	0.155	0.150
	0.239	0.201	0.240	0.201	0.237	0.203	0.235
	4.192	4.970	4.169	4.983	4.227	4.935	4.242