Table A4.

Summary of classical rigid docking calculations of the derived analogues compound set over the CLK1 and Molecular Mechanics/Generalized Born Surface Area (MM/GBSA) calculations of the best posed analogue compounds. Lowercase letters represent the employed halogen group (a–g).

			CLK1
			1	2	3	4	5	6	7
Binding Energy	R0/R1	a	−7.5/−7.5	−8.8/−8.8	−6.4/−6.4	−6.8/−6.8	−6.2/−6.2	−6.4/−6.4	−6.9/−6.9
MM/GBSA			−29.8546	−34.1041	−15.2943	−26.7584	−25.8120	−27.7489	−24.0832
Binding Energy	R0/R1	b	−7.1/−7.1	−8.4/−8.4	−7/−7	−5.6/−5.6	−7.5/−7.5	−6.6/−6.6	−7.2/−7.2
MM/GBSA			−25.9089	−27.3711	−13.7919	−26.2326	−22.1539	−16.6984	−20.9149
Binding Energy	R0/R1	c	−7.6/−7.6	−9.1/−9.1	−7/−7	−7.3/−7.3	−6.4/−6.4	−6.6/−6.6	−6.4/−6.4
MM/GBSA				−34.0221	−16.2165	−24.6708	−29.4190	−25.8368	−20.9436
Binding Energy	R0/R1	d	−7.6/−7.6	−8.4/−8.4	−6.8/−6.8	−7.8/−7.8	−6.3/−6.3	−6.9/−6.9	−7/−7
MM/GBSA			−26.9398	−30.7361		−25.6581	−25.1797	−19.3712	−17.5727
Binding Energy	R0/R1	e	−6.8/−6.8	−8.9/−8.9	−6.9/−6.9	−7.5/−7.5	−5.9/−5.9	−7.1/−7.1	−7/−7
MM/GBSA			−30.0891		−16.2097	−28.3695	−28.0697	−27.0478	−17.4985
Binding Energy	R0/R1	f	−7.5/−7.5	−8.6/−8.6	−6.7/−6.7	−7.5/−7.5	−6.2/−6.2	−6.4/−6.4	−6.7/−6.7
MM/GBSA				−28.1471	−20.4786	−23.9274	−27.3596	−15.4231	−21.2829
Binding Energy	R0/R1	g	−7/−7	−8.9/−8.9	−6/−6	−7.4/−7.4	−6.8/−6.8	−6.4/−6.4	−6.8/−6.8
MM/GBSA			−30.3541	−33.9082	−16.3122	−25.0002		−30.7737	−25.4765

To avoid false positives, each docking calculation was performed twice (R0/R1). All energies values are kcal/mol.