Synthesis, spectral analysis, antibacterial and antifungal activities of some 4,6-diaryl-4,5-dihydro-3-hydroxy-2[H]-indazole—a novel fused indazole derivative

Figures & data

Scheme 1. Synthetic pathway for the formation of 4,6-diaryl-4,5-diydro-3-hydroxy-2[H]-indazole

Table I.  Analytical data of compounds 25-32.

			Elemental analysis (%)
Compound	Yield (%)	m.p°C	C Found (calculated)	H Found (calculated)	N Found (calculated)	m/z (M^+.) Molecular formula
25	73	226	78.55 (78.59)	6.21 (6.25)	9.61 (9.65)	(291) C19H18N2O
26	70	230	78.88 (78.92)	6.59 (6.62)	9.17 (9.20)	(305) C20H20N2O
27	68	234	70.21 (70.26)	5.26 (5.28)	8.58 (8.62)	(326) C19H17Cl N2O
28	72	212	68.01 (68.05)	5.07 (5.11)	12.50 (12.53)	(336) C19H17N3O3
29	70	204	74.63 (74.98)	6.27 (6.29)	8.71 (8.74)	(321) C20H20N2O2
30	69	232	61.76 (61.80)	4.61 (4.64)	7.56 (7.59)	(370) C19H17BrN2O
31	60	225	78.89 (78.92)	6.59 (6.62)	9.17 (9.20)	(305) C20H20N2O
32	68	210	65.70 (65.74)	5.20 (5.24)	11.46 (11.50)	(366) C20H19N3O4

Table II.  In vitro profile of compounds 25-28 against test bacteria and fungi.

	Compound 25			Compound 26			Compound 27			Compound 28
Micro organisms	100 ppm	200 ppm	500 ppm	100 ppm	200 ppm	500 ppm	100 ppm	200 ppm	500 ppm	100 ppm	200 ppm	500 ppm
S. aureus	–	+	+++	–	+	+++	–	++	++++	–	++	+++
β-H.streptococcus	–	+	++	+	+	+++	–	+	+++	+	++	+++
V.cholerae	–	+	+++	+	++	+++	–	+	++++	–	++	+++
S. typhii	+	+	+++	+	+	+++	–	++	++++	+	++	++++
S. felxneri	–	+	+++	–	++	+++	+	+	++++	+	++	++++
E.coli	–	+	++	–	++	++	–	+	+++	–	++	+++
K.pneumonia	–	+	+++	+	++	+++	+	++	++++	+	++	++++
Pseudomonas	–	+	+++	+	+	+++	+	++	++++	+	++	++++
A.flavus	–	+	+++	–	+	+++	+	++	++++	+	++	++++
Mucor	+	+	++	–	+	+++	–	+	++++	+	++	++++
Rhizopus	–	+	+++	+	++	+++	–	++	++++	+	++	++++
M. gypsuem	–	+	+++	–	+	+++	+	++	++++	–	+++	++++

(–) = inactive, (+) = weakly active (12-16 mm), (+)(+) = moderately active (17-21 mm), (+)(+)(+) = strong active (22-29),(+)(+)(+)(+) = highly active (30-33). Ciprofloxacin (5μg/disc) was used as standard drug; whose zone of inhibition (mm) values for S. aureus, β-H.streptococcus, V.cholerae, S.typhii, S.felxneri, E.coli, K.pneumonia and Pseudomonas are 25, 28, 23, 22, 23, 24, 26 and 23 mm respectively. Fluconazole (100 units/disc) was used as a standard drug whose zone of inhibition (mm) values for A.flavus, Mucor, Rhizopus and M.gypsuem are 20 ± 0.5 zone of inhibition (mm) against all the tested fungi.

Table III.  In vitro profile of compounds 29-32 against test bacteria and fungi.

	Compound 29			Compound 30			Compound 31			Compound 32
Micro organisms	100 ppm	200 ppm	500 ppm	100 ppm	200 ppm	500 ppm	100 ppm	200 ppm	500 ppm	100 ppm	200 ppm	500 ppm
S. aureus	+	++	+++	–	++	+++	–	++	+++	–	++	++++
β-H.streptococcus	–	+	+++	–	+	+++	–	+	+++	+	++	++++
V.cholerae	–	+	+++	–	+	++++	–	+	++++	+	++	++++
S. typhii	–	++	++++	+	++	++++	+	++	++++	+	+	+++
S. felxneri	+	++	+++	–	++	+++	–	++	+++	+	++	+++
E.coli	+	++	+++	+	++	+++	+	+	+++	+	+	+++
K.pneumonia	–	+	+++	+	++	+++	+	+	+++	+	+	+++
Pseudomonas	+	+	++	+	+	+++	+	++	++	+	++	++++
A.flavus	+	+	+++	–	+	++	–	+	++	+	++	++++
Mucor	–	++	+++	–	++	+++	–	+	++	+	++	++++
Rhizopus	–	+	+++	+	++	+++	+	++	+++	+	+	++++
M. gypsuem	+	++	++++	+	++	+++	+	++	+++	+	++	++++

(–) = inactive, (+) = weakly active (12-16 mm), (+)(+) = moderately active (17-21 mm), (+)(+)(+) = strong active (22-29),(+)(+)(+)(+) = highly active (30-33). Ciprofloxacin (5μg/disc) was used as standard drug; whose zone of inhibition (mm) values for S. aureus, β-H.streptococcus, V.cholerae, S.typhii, S.felxneri, E.coli, K.pneumonia and Pseudomonas are 25, 28, 23, 22, 23, 24, 26 and 23 mm respectively. Fluconazole (100 units/disc) was used as a standard drug whose zone of inhibition (mm) values for A.flavus, Mucor, Rhizopus and M.gypsuem are 20 ± 0.5 zone of inhibition (mm) against all the tested fungi.

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

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

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

	Minimum Inhibitory Concentration (MIC) in μg/mL
Compound	S. felxneri	E.coli	K.pneumonia	Pseudomonas
25	50	200	50	25
26	50	200	50	25
27	12.5	100	12.5	12.5
28	12.5	100	12.5	12.5
29	50	12.5	50	100
30	50	12.5	50	200
31	50	50	100	200
32	200	50	100	12.5
Ciprofloxacin	25	25	50	25

Table VI.  In vitro antifungal activities (MIC) values for compounds 25-32.

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