Design, synthesis, spectral analysis and in vitro microbiological evaluation of 2-phenyl-3-(4,6-diarylpyrimidin-2-yl)thiazolidin-4-ones

Figures & data

Figure 1.  Synthetic compounds having the core structure with antituberculosis and antimicrobial activity.

Scheme 1.  Synthesis of nove 2-phenyl-3-(4,6-diarylpyrimidin-2-yl)thiazolidin-4-ones.

Table 1.  Physical and analytical data of 2-phenyl-3-(4,6-diarylpyrimidin-2-yl) thiazolidin-4-ones 23-33.

Entry	X	Y	Z	Yield (%)	m.p° C	Elemental analysis (%)			m/z (M+1)^+ Molecular formula
						C Found (calculated)	H Found (calculated)	N Found (calculated)
23	H	H	H	65	145	73.31	4.60	10.23	410
						(73.35)	(4.64)	(10.26)	C25H19N3OS
24	H	H	Cl	52	162	67.65	4.04	9.41	444
						(67.66)	(4.06)	(9.46)	C25H18Cl N3OS
25	H	Cl	H	49	130	67.62	4.01	9.44	444
						(67.66)	(4.06)	(9.46)	C25H18Cl N3OS
26	H	H	OCH3	60	110	71.03	4.72	9.51	440
						(71.08)	(4.78)	(9.56)	C26H21N3O2S
27	H	H	CH3	65	162	73.72	4.92	9.89	424
						(73.76)	(4.96)	(9.92)	C26H21N3OS
28	H	H	F	70	104	70.23	4.18	9.79	428
						(70.27)	(4.21)	(9.83)	C25H18FN3OS
29	Cl	H	H	65	114	67.64	4.01	9.41	444
						(67.66)	(4.05)	(9.46)	C25H18Cl N3OS
30	OCH3	H	H	58	137	71.02	4.72	9.55	440
						(71.08)	(4.78)	(9.56)	C26H21N3O2S
31	Cl	H	CH3	55	125	68.17	4.32	9.15	458
						(68.21)	(4.36)	(9.17)	C26H20ClN3OS
32	Cl	H	Cl	60	130	62.71	3.52	8.76	479
						(62.78)	(3.55)	(8.78)	C25H17Cl2N3OS
33	Cl	H	F	65	103	64.98	3.65	9.04	462
						(65.02)	(3.68)	(9.09)	C25H17ClFN3OS

Table 2.  In vitro antibacterial activity (MIC) values for compounds 23-33.

Compounds			Minimum	Inhibitory	Concentration	(MIC)	in μg/mL
	S.aureus	β-H streptococcus	V.cholerae	S.typhii	S.felxneri	E.coli	K.pneumonia	P.aeruginosa
23	200	100	100	50	100	50	100	200
24	100	200	50	50	100	100	200	100
25	50	-^a	50	100	-^a	-^a	100	50
26	50	6.25	25	6.25	25	6.25	12.5	25
27	25	12.5	12.5	12.5	6.25	12.5	6.25	12.5
28	50	-^a	25	50	-^a	-^a	50	100
29	200	100	100	100	200	200	50	50
30	25	25	50	50	100	12.5	25	12.5
31	12.5	25	12.5	6.25	6.25	25	25	6.25
32	6.25	50	50	12.5	100	12.5	200	50
33	12.5	100	50	12.5	100	12.5	100	100
Ciprofloxacin	25	50	25	50	50	25	50	12.5

^a No inhibition even at higher concentration i.e., at 200 μg/mL

Table 3.  In vitro antifungal activity (MIC) values for compounds 23-33

Compounds	Minimum	Inhibitory	Concentration	(MIC) in μg/mL
	A.flavus	Mucor	Rhizopus	M. gypsuem
23	-^a	100	200	-^a
24	200	25	25	200
25	100	12.5	50	200
26	50	200	-^a	100
27	100	12.5	200	200
28	50	50	100	50
29	200	25	25	200
30	100	-^a	-^a	50
31	12.5	50	6.25	100
32	6.25	12.5	25	12.5
33	12.5	6.25	12.5	25
Fluconazole	25	25	50	50

^a No inhibition even at higher concentration i.e., at 200 μg/mL