Investigation of Antileishmanial Activities of Acridines Derivatives against Promastigotes and Amastigotes Form of Parasites Using Quantitative Structure Activity Relationship Analysis

Table 1

Chemical structure and antileishmanial activities of studied compounds (see Figure 8).

Number	R1	R2	R3	R4	R5	R6	R7
								PRO	AMA
1	H	NHCOCH3	H	H	H	NHCOCH3	H	−2.533	−0.653
2	H	NHCOC2H5	H	H	H	NHCOC2H5	H	−2.204	−0.886
3	H	NHCOC3H7	H	H	H	NHCOC3H7	H	−1.669	−1.107
4	H	NHCOph	H	H	H	NHCOPh	H	−0.634	−0.041
5	H	NHCO-p-PhCl	H	H	H	NHCO-p-PhCl	H	—	0.699
6	H	NHCO-p-PhF	H	H	H	NHCO-p-PhF	H	−0.230	1.523
7	H	NHCO-p-PhOMe	H	H	H	NHCO-p-PhOMe	H	−0.681	−0.041
8	H	NHCO-m,p-Ph(OMe)2	H	H	H	NHCO-m,p-Ph(OMe)2	H	−1.207	0.097
9	H	NHCOMe	H	H	H	NHCOph	H	−2.270	Tox
10	H	NHCOMe	H	H	H	NHCO-p-PhCl	H	−1.061	−0.462
11	H	NHCOMe	H	H	H	NHCO-p-PhF	H	−2.123	0.174
12	H	NHCOMe	H	H	H	NHCO-p-PhOMe	H	−1.939	Tox
13	H	NHCOMe	H	H	H	NHCO-m,p-Ph(OMe)2	H	—	−0.114
14	H	H	CH3	NH2	OMe	H	H	0.301	0.398
15	H	H	CH2OH	NH2	OMe	H	H	−0.732	−0.613
16	H	H	CH2Br	NH2	OMe	H	H	−0.556	−0.663
17	H	H	(CH2)2OCOOMe	NH2	OMe	H	H	−0.380	−0.114
18	H	H	(CH2)2OCO(CH2)2CH3	NH2	OMe	H	H	−0.491	−0.398
19	H	H	(CH2)2OCOCH2CH(CH3)2	NH2	OMe	H	H	−0.342	Tox
20	H	H	(CH2)2OCOPh	NH2	OMe	H	H	0.398	0.699
21	H	H	(CH2)2OCOPhF	NH2	OMe	H	H	−0.114	0.222
23	H	H	(CH2)2OCOPhOMe	NH2	OMe	H	H	−0.279	Tox
24	H	H	CH3	Cl	OMe	H	H	−0.041	−0.362
25	H	H	CH2OH	Cl	OMe	H	H	−2.262	−0.959
26	H	H	CH2Br	Cl	OMe	H	H	−1.703	−1.170
27	H	H	(CH2)2OCOOMe	Cl	OMe	H	H	−2.178	−1.877
28	H	H	(CH2)2OCO(CH2)2CH3	Cl	OMe	H	H	−1.707	−1.628
29	H	H	(CH2)2OCOCH2CH(CH3)2	Cl	OMe	H	H	−1.446	−1.561
30	H	H	(CH2)2OCOPh	Cl	OMe	H	H	−2.135	Tox
31	H	H	(CH2)2OCOPhF	Cl	OMe	H	H	−2.295	−1.645
32	H	H	(CH2)2OCOPhCl	Cl	OMe	H	H	−2.194	−2.191
33	H	H	(CH2)2OCOPhOMe	Cl	OMe	H	H	−2.098	−2.088
34	CH2NH2	H	H	H	H	H	H	−0.230	−0.531
35	CH2OH	H	H	H	H	H	H	Tox	−1.515
36	CH2NHCO(CH2)3Cl	H	H	H	H	H	H	−1.655	−1.427
37	CH2OCO(CH2)3Cl	H	H	H	H	H	H	−2.200	−2.185
38	CH2NHCOCH=CH2	H	H	H	H	H	H	−2.245	−0.833
39	CH2OCOCH=CH2	H	H	H	H	H	H	−1.464	—
40	CH2NHCOPh	H	H	H	H	H	H	−1.654	−1.121
41	CH2OCOPh	H	H	H	H	H	H	−1.885	Tox
42	CH2NHCO-p-PhF	H	H	H	H	H	H	−1.815	—
43	CH2OCO-p-PhF	H	H	H	H	H	H	−1.741	Tox
44	CH2NHCO-p-PhCl	H	H	H	H	H	H	Tox	−1.004
45	CH2OCO-p-PhCl	H	H	H	H	H	H	−1.790	−1.433
46	CH2NHCO-p-PhOMe	H	H	H	H	H	H	−1.513	−0.973
47	CH2OCO-p-PhOMe	H	H	H	H	H	H	−1.471	−0.869
48	CH2NHCO-p-PhNMe2	H	H	H	H	H	H	−1.539	−0.672
49	CH2OCO-p-PhNMe2	H	H	H	H	H	H	−1.819	Tox
50	CH2NH2	H	H	H	H	H	CH2NH2	−0.820	−0.531
51	CH2OH	H	H	H	H	H	CH2OH	Tox	0.222
52	CH2NHCO(CH2)3Cl	H	H	H	H	H	CH2NHCO(CH2)3Cl	−0.663	−0.813
54	CH2NHCOCH=CH2	H	H	H	H	H	CH2NHCOCHCH2	−1.061	Tox
56	CH2NHCOPh	H	H	H	H	H	CH2NHCOPh	−0.556	−1.236
57	CH2OCOPh	H	H	H	H	H	CH2OCOPh	Tox	−0.716
58	CH2NHCO-p-PhF	H	H	H	H	H	CH2NHCO-p-PhF	−0.756	−0.255
60	CH2NHCO-p-PhCl	H	H	H	H	H	CH2NHCO-p-PhCl	—	−1.562
62	CH2NHCO-p-PhOMe	H	H	H	H	H	CH2NHCO-p-PhOMe	−1.797	Tox
63	CH2OCO-p-PhOMe	H	H	H	H	H	CH2OCO-p-PhOMe	Tox	−1.825
64	CH2NHCO-p-PhNMe2	H	H	H	H	H	CH2NHCO-p-PhNMe2	−0.940	−0.724
65	CH2OCO-p-PhNMe2	H	H	H	H	H	CH2OCO-p-PhNMe2	Tox	−1.667

Toxic: toxicity observed on human macrophages at concentrations that did not display antileishmanial activity; -p-: para; -m-: meta; pIC₅₀ = −log (IC₅₀); pIC₅₀ AMA: antileishmanial activity against amastigotes parasite form; pIC₅₀ PRO: antileishmanial activity against promastigotes parasite form.