Design, synthesis, characterization and in vitro antimicrobial evaluation of 4,6-diaryl-4,5-dihydro-2-phenyl-2H-indazol-3-ols

Figures & data

Scheme 1.  Reaction pathway for the synthesis of 4,5-Dihydro-2-phenyl-4,6-diaryl-2H-indazol-3-ols.

Table I.  Physical and analytical data of compounds 25–32.

Compound	Yield (%)	m.p.(°C)	Elemental analysis (%)			m/z (M^+.) Molecular formula
			C Found (calculated)	H Found (calculated)	N Found (calculated)
25	80	237	82.35 (82.39)	5.49 (5.53)	7.64 (7.69)	(364) C25H20N2O
26	75	242	82.47 (82.51)	5.82 (5.86)	7.36 (7.40)	(378) C26H22N2O
27	76	251	75.22 (75.28)	4.78 (4.80)	6.98 (7.02)	(398) C25H19Cl N2O
28	78	224	73.31 (73.34)	4.65 (4.68)	10.23 (10.26)	(409) C25H19N3O3
29	70	219	79.11 (79.16)	5.58 (5.62)	7.06 (7.10)	(394) C26H22N2O2
30	65	238	67.69 (67.73)	4.28 (4.32)	6.29 (6.32)	(443) C25H19BrN2O
31	60	239	82.46 (82.51)	5.81 (5.86)	7.36 (7.40)	(378) C26H22N2O
32	75	205	71.01 (71.06)	4.79 (4.82)	9.51 (9.56)	(439) C26H21N3O4

Table II.  In vitro antibacterial activities (MIC) values for compounds 25-32.

Compound	Minimum S.aureus	Inhibitory β-H.streptococcus	Concentration V.cholerae	(MIC) S. typhii	in μg/mL S. felxneri
25	200	100	100	–	200
26	6.25	12.5	200	100	200
27	–	200	12.5	12.5	100
28	100	100	25	25	100
29	12.5	6.25	100	200	200
30	200	–	100	200	25
31	100	200	50	100	50
32	100	50	–	12.5	12.5
Ciprofloxacin	25	50	50	50	25

Table III.  In vitro antifungal activities (MIC) values for compounds 25–32.

Compound	Minimum A.flavus	Inhibitory Mucor	Concentration Rhizopus	(MIC) in μg/mL M. gypsuem
25	200	100	200	100
26	12.5	–	12.5	–
27	100	25	200	25
28	100	50	100	25
29	12.5	200	12.5	200
30	100	50	100	12.5
31	25	200	25	100
32	25	25	12.5	6.25
Fluconazole	50	50	25	25