Preparation of some pyrazoline derivatives and evaluation of their antifungal activities

Figures & data

Table 1.  Some characteristics of the compounds.

Compound	R1	R2	R3	X	Yield (%)	Molecular formula	Mol. weight	m.p. (°C)
A1	Cl	H	H	NH	78	C22H17ClN4O2S	436	232
A2	Cl	H	Cl	NH	75	C22H16Cl2N4O2S	470	167
A3	Cl	H	CH3	NH	72	C23H19ClN4O2S	450	132
A4	Cl	H	NO2	NH	76	C22H16ClN5O4S	483	165
A5	O-CH2-O		H	NH	69	C23H18N4O4S	446	189
A6	O-CH2-O		Cl	NH	79	C23H17ClN4O4S	480	160
A7	O-CH2-O		CH3	NH	71	C24H20N4O4S	460	186
A8	O-CH2-O		NO2	NH	70	C23H17N5O6S	491	161
A9	H	H	H	NH	74	C22H18N4O2S	402	163
A10	H	H	Cl	NH	70	C22H17ClN4O2S	436	247
A11	H	H	CH3	NH	62	C23H20N4O2S	416	180
A12	H	H	NO2	NH	75	C22H19N5O4S	449	181
A13	H	H	H	O	77	C22H17N3O3S	403	177
A14	H	H	Cl	O	71	C22H16ClN3O3S	437	182
A15	H	H	CH3	O	63	C23H19N3O3S	417	178
A16	Cl	H	Cl	O	80	C22H15Cl2N3O3S	471	162
A17	Cl	H	CH3	O	66	C23H18ClN3O3S	451	149
A18	O-CH2-O		H	O	81	C23H17N3O5S	447	165
A19	O-CH2-O		Cl	O	73	C23H16ClN3O5S	481	196
A20	O-CH2-O		CH3	O	70	C24H19N3O5S	461	156
A21	H	H	H	S	68	C22H17N3O2S2	419	125
A22	Cl	H	H	S	76	C22H16ClN3O2S2	453	138
A23	O-CH2-O		H	S	81	C23H17N3O4S2	463	144

Table 2.  Anticandidal evaluation of 1-[(benzazole-2-yl)thioacetyl]-3,5-diaryl-2-pyrazoline derivatives (MIC values in mg/mL).

Compound	Test substance
	A^a	B	C^a	D	E	F	G	H
A1	1	0.25	0.015	0.125	0.0625	0.25	0.015	0.125
A2	0.25	0.5	0.25	0.5	0.5	0.5	0.25	0.5
A3	2	0.5	2	2	2	2	2	2
A4	1	0.25	0.25	0.5	0.5	0.5	0.5	0.5
A5	1	0.125	0.015	0.125	0.0625	0.015	0.125	0.125
A6	0.5	0.125	0.007	0.031	0.031	0.015	0.031	0.125
A7	0.5	0.5	0.0625	0.125	0.015	0.031	0.125	0.25
A8	0.0625	1	0.25	0.5	0.5	0.25	0.25	0.5
A9	0.5	0.5	0.5	0.5	0.5	1	0.5	0.5
A10	1	0.0625	0.5	0.5	0.5	0.5	0.0625	0.5
A11	1	1	0.25	0.5	0.5	1	0.25	0.5
A12	2	1	1	0.5	1	0.5	0.5	0.25
A13	0.5	2	0.5	0.5	1	0.5	0.125	0.5
A14	1	0.5	0.5	1	1	0.5	0.25	1
A15	2	0.5	0.5	1	1	1	0.5	0.5
A16	2	0.125	2	2	2	2	2	2
A17	2	0.5	2	2	1	1	2	1
A18	1	0.003	0.015	0.125	0.0625	0.125	0.125	0.25
A19	0.5	0.125	0.031	0.125	0.015	0.015	0.015	0.125
A20	2	0.5	0.015	0.125	0.125	0.0625	0.031	0.25
A21	1	0.0625	0.25	0.25	0.125	0.125	0.25	0.125
A22	0.5	0.0625	0.125	0.125	0.015	0.0625	0.0625	0.125
A23	1	0.0625	0.007	0.0625	0.0625	0.015	0.0625	0.125
Ketoconazole	0.0625	0.0625	0.031	0.007	0.003	0.125	0.5	0.032

Note. A, Candida albicans (clinical isolate); B, Candida albicans (ATCC 90028); C, Candida glabrata (clinical isolate); D, Candida utilis (NRRL Y-900); E, Candida tropicalis (NRRL Y-12968); F, Candida krusei (NRRL Y-7179); G, Candida parapsilosis (NRRL Y-12696); H, Candida albicans (NRRL Y-12983).

^aClinical isolates were obtained from the Department of Microbiology, Faculty of Medicine, Osmangazi University, Eskisehir, Turkey.

Scheme 1.  General synthesis reaction (see Table 1 for A1–23, R₁, R₂, R₃, X details).