Synthesis and antimicrobial activity of new 1,2,4-triazole and 1,3,4-thiadiazole derivatives

Figures & data

Table I.  Physicochemical data of [1(2H)-Phthalazinone-2-yl]acetyl/propanoylthiosemicarbazide derivatives (6a–l).

Comp.	n	R	(Cryst. Sol)	mp	Yield (%)
6a	1	Phenyl	Ethanol	207–209	75
6b	1	Benzyl	Methanol	208	55
6c	1	Phenethyl	Methanol	225	50
6d	1	4-Chlorophenyl	Methanol	237	65
6e	1	4-Methoxyphenyl	Methanol	223–224	60
6f	1	4-Methylphenyl	Methanol	210	65
6g	2	Phenyl	Methanol	205	60
6h	2	Benzyl	Methanol	209,5	45
6i	2	Phenethyl	Ethanol	196–197	40
6j	2	4-Chlorophenyl	Ethanol	186	55
6k	2	4-Methoxyphenyl	Ethanol	201	50
6l	2	4-Methylphenyl	Ethanol	208	55

Table II.  Physicochemical data for the title compounds (7a–l, 8a–l).

Comp.	n	R	Cryst. Sol	Yield (%)	Mp (°C)
7a	1	Phenyl	Methanol	65	238–240
7b	1	Benzyl	Ethanol	45	230–231
7c	1	Phenethyl	Methanol	40	231–233
7d	1	4-Chlorophenyl	Ethanol	50	239–240
7e	1	4-Methoxyphenyl	2-Propanol	45	210–211
7f	1	4-Methylphenyl	Ethanol	55	>300
7g	2	Phenyl	Ethanol-Water	60	168–170
7h	2	Benzyl	Ethanol	40	193–194
7i	2	Phenethyl	Methanol	42	216–217
7j	2	4-Chlorophenyl	Methanol	50	228–229
7k	2	4-Methoxyphenyl	Ethanol	55	225
7l	2	4-Methylphenyl	Methanol	55	239–241
8a	1	Phenyl	Ethanol	60	228–231
8b	1	Benzyl	Ethanol	55	170–171
8c	1	Phenethyl	Methanol	50	175–176
8d	1	4-Chlorophenyl	Ethanol-Water	45	273
8e	1	4-Methoxyphenyl	Ethanol-Water	50	207
8f	1	4-Methylphenyl	Ethanol	55	223
8g	2	Phenyl	Ethanol	60	202–203
8h	2	Benzyl	Acetone-P.Ether	55	165–166
8i	2	Phenethyl	Ethanol	45	161
8j	2	4-Chlorophenyl	Toluene	50	225–226
8k	2	4-Methoxyphenyl	Ethanol	55	183–184
8l	2	4-Methylphenyl	Methanol	55	184–185

Scheme 1 Synthetic route for the title compounds.

Table III.  Minimum inhibitory concentrations (MICs, μg/mL) for the title compounds.

	Staphylococcus aureus	Bacillus subtilis	Escherichia coli	Pseudomonas aeruginosa	Candida albicans	Candida parapsilosis
Compounds	ATCC 25923	ATCC 6633	ATCC 25922	ATCC 27853	ATCC 10231	ATCC 90018
7a	512	512	256	256	512	512
7b	512	32	256	256	128	64
7c	256	256	128	256	32	32
7d	512	64	256	256	512	512
7e	512	32	256	256	512	512
7f	512	64	256	256	512	512
7g	512	64	256	256	512	256
7h	512	64	256	256	64	64
7i	512	32	256	256	256	32
7j	512	64	256	256	512	512
7k	512	64	256	256	64	32
7l	512	64	256	256	512	512
8a	512	16	128	256	512	64
8b	128	32	128	256	128	64
8c	256	64	128	256	32	32
8d	256	256	128	512	32	32
8e	256	256	128	512	32	32
8f	512	256	128	512	128	32
8g	128	32	256	256	128	16
8h	256	128	256	256	512	128
8i	512	32	256	256	32	64
8j	512	128	256	512	128	64
8k	512	32	256	256	128	64
8l	512	32	256	256	128	16
Ampicillin	4	8	4	–	–	–
Fluconazole	–	–	–	–	8	0.25