Synthesis of some 4-arylidenamino-4H-1,2,4-triazole-3-thiols and their antituberculosis activity

Figures & data

Table I.  Some characteristics of compounds (2a–n).

Comp.	R1	R2	R3	R4	Yield (%)	Molecular Formula	Mol. Wt.	M.P. (°C)
2a	H	H	H	H	61	C14H12N4S2	300	181–182
2b	H	F	H	H	62	C14H11FN4S2	318	172–174
2c	H	Cl	H	H	56	C14H11ClN4S2	334	212–214
2d	H	CH3	H	H	58	C15H14N4S2	314	187–189
2e	H	OCH3	H	H	53	C15H14N4OS2	330	178–180
2f	H	CN	H	H	54	C15H11N5S2	325	225–226
2 g		O–CH2–O	H	H	55	C15H12N4O2S2	344	205–207
2 h	Cl	Cl	H	H	50	C14H10Cl2N4S2	368	208–210
2i	OH	OCH3	H	H	52	C15H14N4O2S2	346	202–204
2j	OH	OH	H	H	59	C14H12N4O2S2	332	193–194
2k	NO2	OH	H	H	61	C14H11N5O3S2	361	190–192
2 l	H	OCH3	O–CH2–C6H5	H	57	C22H20N4O2S2	436	198–200
2m	OCH3	OCH3	OCH3	H	63	C17H18N4O3S2	390	162–164
2n	H	N(CH3) 2	H	Cl	65	C16H16ClN5S2	377	224–226

Scheme 1 The general synthetic reaction.

Table II.  Antituberculosis activity of the compounds.

Compounds	Dose used (μg/mL)	% inhibition
2a	6.25	36
2b	6.25	60
2c	6.25	54
2d	6.25	49
2e	6.25	54
2f	6.25	58
2 g	6.25	57
2 h	6.25	55
2i	6.25	44
2j	6.25	69
2k	6.25	87
2 l	6.25	63
2m	6.25	43
2n	6.25	58
Rifampicin	0.25	98