Synthesis and blood glucose lowering activity of some novel benzenesulfonylthiourea derivatives substituted with 4-aryl-1-oxophthalazin-2(1H)yl-ones

Figures & data

Figure 1. Structure of biologically active agent of benzenesulfonylthiourea’s as blood glucose lowering and rationally designed template for targeted compound.

Scheme 1. Reagents and conditions: (a) anhydrous AlCl₃, room temperature; (b) absolute alcohol, reflux; (c) isothiocyanate, K₂CO₃, dry acetone, reflux 24–72 h. 1a, 2a, 2f, 2j, 2o: Ar = Phenyl; 1b, 2b, 2g, 2k, 2p: Ar = 4-Methylphenyl 2a–2e:R₁ = –CH₂C₆H₅; 1c, 2c, 2h, 2l: Ar = 4-Chlorophenyl; 1d, 2d, 2i, 2m, 2q: Ar = 4-Chloro-3-methylphenyl; 1e, 2e, 2n, 2k: Ar = 2-Chloro-5-methyl; 2f–2i: R₁ = –C₃H₇; 2j–2n: R₁ = –C₄H₉; 2o–2q: R₁ = –C₆H₁₁.

Table 1. Antihyperglycemic activity of SU derivatives (2a–q) and the standard drug gliclazide in glucose-fed (3g/kg) hyperglycemic normal rats.

Treatment	Dose per kg b.w. (mg)	% Activity	Significance
2a	20	4.79	p < 0.05
2b	20	8.57	p < 0.05
2c	20	4.61	p > 0.05
2d	20	6.22	p < 0.05
2e	20	11.66	p > 0.05
2f	20	16.0	p < 0.05
2g	20	9.05	p < 0.05
2h	20	11.44	p < 0.05
2i	20	3.27	p > 0.05
2j	20	1.0	p < 0.05
2k	20	1.92	p < 0.05
2l	20	8.40	p > 0.05
2m	20	17.53	p < 0.01
2n	20	9.25	p > 0.05
2o	20	11.09	p < 0.05
2p	20	3.18	p > 0.05
2q	20	12.18	p > 0.05
Gliclazide	20	35.0	p < 0.01