Synthesis and Biological Evaluation of Some Polysubstituted Fused
Pyrazoles as Possible Chemotherapeutic Agents.
Mohammed S. M. Al-Saadi
Division of Medicinal Chemistry, Faculty of Medicine, King Abdul-Aziz University,
P.O. Box 80205, Jeddah 21589, Saudi Arabia
Abstract
This work reports the synthetic strategies adopted to prepare a series of fused pyrazoles
substituted with different functionalities and other heterocyclic ring systems, with
anticipated chemotherapeutic activities. The key intermediate indazoline was synthesized
by cyclocondesation of 2-methyl-6-(thiophen-2-yl)methylene]cyclohexanone with 4hydrazinobenzenesulfonamide hydrochloride. The chemistry of the reactions employed in
the synthesis of the target compounds together with their chemical behaviour, are
discussed and the structures of the newly synthesized compounds were confirmed by the
IR and 1H-NMR spectral data. All the synthesized compounds showed weak anticancer
activity according to the protocol of the National cancer Institute (NCI), Maryland, USA.
Additionally, they showed weak antimicrobial activity against some bacteria and fungi.
NHNH2
O
SO2NH2
SO2NH2
SO2NH2
. HCl
N
Br2 / H2O
N
S
N
S
S
2
1
N
3
RNCO
R1NCS
SO2NHCONHR
SO2NHCSNHR1
N
O
N
N
N
S
S
S
CHO
+
R1 = 6: phenyl; 7: benzyl; 8: benzoyl
Scheme 1
R = 4: phenyl; 5: 1-naphthyl