Synthesis, Antimicrobial Studies, and Molecular Docking Simulation of Novel Pyran, Pyrazole, and Pyranopyrazole Derivatives

Table 1

In vitro antimicrobial activity of compounds 2a–d, 3a–d, and 4a–h (inhibition zone in mm)^a.

Compounds		Antimicrobial activity
		Bacterial species (G^+)				Bacterial species (G^−)
		Bacillus subtilis		Staphylococcus aureus		Escherichia coli		Pseudomonas aeruginosa
		IZ	RA%	IZ	RA%	IZ	RA%	IZ	RA%
Control: DMSO		0.0	0.0	0.0	0.0	0.0	0.0	0.0	0.0
Standard	Chloramphenicol	25	100	40	100	29	100	30	100
2a		21	84	16	40	15	51.7	—	—
2b		19	76	38	95	20	68.9	—	—
2c		21	84	12	30	29	100	25	83.3
2d		29	116	30	75	33	113.8	35	116.7
3a		27	108	30	75	29	100	29	96.7
3b		16	64	35	87.5	31	106.9	27	90
3c		15	60	30	75	28	96.6	29	96.7
3d		32	128	40	100	30	103.4	30	100
4a		25	100	30	75	15	51.7	—	—
4b		33	132	46	115	27	93.1	30	100
4c		28	112	35	87.5	21	72.4	27	90
4d		25	100	32	80	20	68.9	30	100
4e		20	80	32	80	29	100	32	106.7
4f		25	100	26	65	32	110.3	30	100
4g		21	84	31	77.5	30	103.4	30	100
4h		30	120	30	75	25	86.2	25	83.3

^aG⁺ = Gram positive; G⁻ = Gram negative; R.A. = relative activity; RA = ; IZ: inhibition zone diameter (mm/mg sample).