Synthesis of some new isoxazoline derivatives of chalconised indoline 2-one as a potential analgesic, antibacterial and anthelmimtic agents

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Date: January-March 2012
From: Journal of Young Pharmacists(Vol. 4, Issue 1)
Publisher: Medknow Publications and Media Pvt. Ltd.
Document Type: Report
Length: 1,995 words
Lexile Measure: 1560L

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Byline: P. Mondal, S. Jana, A. Balaji, R. Ramakrishna, L. Kanthal

A series of novel 1[5''-(2'''-substituted phenyl)-4'',5'''-dihydro isoxazole-3''-yl]-3-[(4 substituted phenyl)imino]1-3-dihydro-2H-indole-2-one were synthesized from different substituted chalconised indole-2,3-dione was prepared from the different chalconised Isatin. The structures of the compounds were elucidated by elemental and spectral (IR, [sup]1 H NMR, and MS) analysis. The synthesized compounds were screened for their analgesic activity by the acetic acid induced Writhing method and in vitro antimicrobial activity against the Gram-positive bacteria-Staphylococcus aureus and the Gram-negative bacteria-Pseudomonas auroginosa, Pseudomonas mirabilis, and E. coli by the cup plate agar diffusion method. Compounds 6a [sub]1 , 6a [sub]3 , 6b [sub]3 , and 6b [sub]2 were found to be active against bacteria. The compounds 6a [sub]1 , 6b [sub]3 , and 6a [sub]3 show a significant analgesic activity. Synthesized compounds also screened for anthelmintic activity against Pheretima posthuma. Compounds 6a [sub]1 , 6b [sub]1 , and 6b [sub]3 show significant anthelmintic activity.


Isatin and isoxazoline are biologically active, synthetically useful, and important heterocycles having a wide role in medicinal chemistry. Isatin is an endogenous compounds [sup][1] widely used as an antibacterial, [sup][2],[3] anti-inflammatory, [sup][4] antifungal agent. Isoxazolines are also reported [sup][5] to possess good antimicrobial, analgesic, anti-inflammatory activity. In view of the biological activities, some isatino isoxazoline derivatives and in continuation of our research work on synthesis of biologically active heterocyclic compounds, we investigated that the synthesis of some novel isoxazoline derivatives from chalconised isatin derivatives is synthesized and screened for their antibacterial activities against gm (+ve) and gm (-ve) bacteria, analgesic activity, and also anthelmintic activity. The structure of all compounds was established on the basis of spectral and elemental analysis. Almost all the isatino isoxazoline derivatives show very good antibacterial activities at 100 [micro]m/ml and analgesic activity [Scheme 1].


Materials and Methods

Melting points were recorded in open capillary tubes and are uncorrected. The IR spectra are recorded on a SHIMADZU-FT-IR spectrophotometer. The [sup]1 H NMR spectra were recorded on a Bruker-400 MHz spectrometer. Mass spectra were recorded in Maldi MS which shows a m / z peak at 465. Purity of the compounds was checked by the TLC. The characterizations of the synthesized compounds were given in [Table 1]. For antibacterial activity, the microbial strains are taken from Utkal University, Vani Vihar, Bhubneswer. The title compounds were prepared using the general synthetic strategy for the preparation of isoxazolin derivatives from the chalcones described as follows.{Table 1}

Preparation of 1[5 '' -(2 ''' -substituedphenyl)-4 '' ,5 ''' -dihydro isoxazole-3 ''' -yl]-3-[(4 substituted phenyl)imino]1-3 dihydro-2H-indole-2-one (6a [sub]1 -6a [sub]3 ), (6b [sub]1 -6b [sub]3 )

Compounds (isatinoid chalcones) of 0.1 m were dissolved in ethanol (Sol[sup] n - 1). Hydroxyl amine of 0.1 m was dissolved in ethanol (Sol[sup] n - 2) and 1 g of anhydrous sodium acetate was dissolved in 20 ml of glacial acetic acid (Sol[sup] n - 3). Then Sol[sup] n 1, 2, and 3 were taken in a RBF, and reflux the reaction mixture for about 6-8...

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Gale Document Number: GALE|A283801546