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Abstract

SYNTHESIS AND IN VITRO ANTICANCER ACTIVITY OF NOVEL 5- [(1-BENZYL-1H-1,2,3-TRIAZOL-4-YL)METHYL]-3-METHYL-5HISOXAZOLO[ 5’,4’:5,6]PYRIDO[2,3-b]INDOLES

E. Rajanarendar*, P. Venkateshwarlu, S. Ramakrishna, K. Goverdhan Reddy, M. Nagi Reddy, Y.N. Reddy

ABSTRACT

Cancer is a deadly disease in the world today and causes more deaths
than any other disease. Inspite of the extensive efforts, the management
of human malignancies still contains a major challenge for
contemporary medicinal chemistry. There has been an urgent need for
development of more efficient anticancer agents with minimal side
effects. Neocryptolepine an alkaloid isolated from cryptolepis
sanguinoleta is found to display strong in vitro and in vivo cytotoxic
activities. In view of this, the present study was designed to synthesize
some novel derivatives of 1,2,3-triazolyl isoxazolo[5’,4’:5’,6] pyrido
[2,3-b] indoles which are bioisosteric with neocryptolepine derivatives. The synthesis of title
compounds was accomplished by condensation of 3,5-dimehtyl-4-nitroisoxazole with
different N-propargyl isatins, in ethanol in the presence of piperidine, followed by reductive
cyclization with iron powder in acetic acid, finally [2+3] cycloaddition of benzyl azide to
C=C in presence of saturated CuSO4 solution-Cu turnings in ethanol. The newly synthesized
compounds were screened for their in vitro anticancer activity by using MTT assay method.
The results indicate that these compounds have considerable in vitro anticancer activity. Out
of the eight derivatives, compound 5b and 5c have shown potential anticancer activity as
compared with the reference compound Cisplatin.

Keywords: 1,2,3-Triazolyl isoxazolo[5’,4’:5,6]pyrido[2,3-b]indoles, reductive cyclization, [2+3] cycloaddition, anticancer activity.


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