Synthesis and Evaluation of Some New Thiazolidin-4-One Derivatives as Potential Antimicrobial Agents

Table 1

Spectral and analytical data of the title compounds (7a-l).

Compound	R	Molecular formula	Mol. wt.	Yield (%)	MP (°C)	Elemental analysis Calcd./(found)			IR (KBr, cm^−1)
						C	H	N
7a	–H	C17H15N6O2S3	432	72	96–98	47.21 (47.14)	3.73 (3.80)	19.43 (19.38)	3334 (NH), 2465 (S–H), 1742, 1728 (both C=O), 1620 (C=N str.), 1591 (C=C str.), 1349 (C–N), 688 (C–S–C str.)
7b	2-OH–	C17H16N6O3S3	448	65	195-194	45.52 (45.44)	3.60 (3.65)	18.74 (18.82)	3292 (Ph–OH Str.), 3234 (NH), 2460 (S–H), 1720, 1700 (both C=O), 1628 (C=N str.), 1598 (C=C str.), 1351 (C–N), 689 (C–S–C str.)
7c	4-Cl–	C17H15N6O2S2Cl	467	65	120–122	43.72 (43.67)	3.24 (3.28)	18.00 (18.07)	3290 (NH), 2458 (S–H), 1720, 1695 (both C=O), 1622 (C=N), 1600 (C=C str.), 1350 (C–N), 760 (C–Cl), 690 (C–S–C str.)
7d	3-NO2–	C17H15N7O4S2	477	68	208–210	42.76 (42.71)	3.17 (3.22)	20.53 (20.57)	3360 (NH), 2444 (S–H), 1700, 1689 (both C=O), 1610 (C=N str.), 1523 (–NO2 str), 1352 (C–N), 709 (C–S–C str.).
7e	2-NO2–	C17H15N7O4S2	477	70	210–212	42.76 (42.68)	3.17 (3.15)	20.53 (20.60)	3172 (NH), 2527 (S–H), 1740, 1700 (both C=O str.), 1610 (C=N str.), 1588 (C=C str.), 1520 (–NO2 str.), 1349 (C–N), 704 (C–S–C str.)
7f	4-OH–	C17H16N6O3S3	448	70	117–120	45.52 (45.42)	3.60 (3.66)	18.74 (18.78)	3295 (Ph–OH Str.), 3199 (NH), 2435 (S–H), 1738, 1709 (both C=O), 1636 (C=N str.), 1585 (C=C str.), 1350 (C–N), 672 (C–S–C str.)
7g	4-(CH3)2N–	C19H21N7O2S3	475	60	200–202	47.98 (47.94)	4.45 (4.54)	20.61 (20.65)	3380–3290 (bs, NH), 2460 (S–H), 1720, 1680 (both C=O), 1610 (C=N), 1588 (C=C str.), 1335 (C–N), 692 (C–S–C str.).
7h	3,4,5-(OCH3)3–	C20H22N6O5S3	522	57	174–176	45.96 (45.92)	4.24 (4.29)	16.08 (16.13)	3272 (NH), 2394 (S–H), 1718–1673 (both C=O), 1646 (C=N str.), 1588 (C=C str.), 1351 (C–N), 1150 (C–O–C), 689 (C–S–C str.)
7i	4-OCH3–	C18H18N6O3S3	462	40	130–132	46.74 (46.70)	3.92 (3.96)	18.17 (18.21)	3370–3250 (bs, NH), 2403 (S–H), 1715, 1690 (both C=O), 1620 (C=N), 1585 (C=C str.), 1340 (C–N), 1145 (C–O–C), 680 (C–S–C str.)
7j	4-Br–	C17H15N6O2S3Br	511	70	188–190	39.93 (39.89)	2.96 (3.00)	16.43 (16.48)	3175 (NH), 2366 (S–H), 1738, 1690 (both C=O str.), 1605 (C=N str.), 1578 (C=C str.), 1518 (–NO2 str.), 1349 (C–N), 701 (C–S–C str.). 512 (C–Br),
7k	4-CH3–	C18H18N6O2S3	446	50	204–206	48.41 (48.36)	4.06 (4.10)	18.82 (18.86)	3395–3260 (bs, NH), 2400 (S–H), 1715–1695 (both C=O), 1610 (C=N), 1581 (C=C str.), 1348 (C–N), 695 (C–S–C str.)
7l	4-F–	C17H15N6O2S3F	450	55	180–182	45.32 (45.27)	3.36 (3.41)	18.65 (18.69)	3385–3280 (bs, NH), 2430 (S–H), 1725–1695 (both C=O), 1618 (C=N), 1588 (C=C str.), 1348 (C–N), 1235 (C–F), 688 (C–S–C str.)