New Bioactive Aromatic Heterocyclic Macromolecules with Monosaccharide Core

Year 2022, Volume: 9 Issue: 3, 889 - 900, 31.08.2022

Israa İ Mahmood , Salih Salman , Luma Abd

https://doi.org/10.18596/jotcsa.1098055

Abstract

1,1,2-trimethyl-1H-benzo[e]indole is an important heterocyclic compound, its available in reasonable price and can easily modified to make a good intermediate for other derivatives. That is quite enough reasons to use as starting material for a new series of compounds with other biomolecules such as monosaccharides after simple modification. The target molecules show biological activity. So, the current work is aiming to improve the activity and the properties of the benzo indole by attaching with a naturally occurring, and biodegradable compounds represented by 2-deoxy-2-amino -d-glucose and 6-deoxy-6-amino-d-glucose to synthesis both mono and di-saccharides derivatives of benzo indole. Two steps synthesis were used for mono-saccharide derivatives and three steps for di-saccharide derivatives, the first is the functionalization of 1,1,2-trimethyl-1H-benzo[e]indole [1] via the reaction with POCl3 to produce 2-(1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene) malonaldehyde [2] with two aldehydes reaction centers, while in the second step the latter was coupled with sugar via amino groups to get the two monosaccharide derivatives [3,5], while the disaccharides molecules [4,6] taken one more step with harder conditions to overcome the steric hindrance at the other reaction center. The purity and characterization of the target molecules was confirmed using spectroscopy methods including 1H NMR and 13 NMR. The synthesized compound shows a good biological activity as antibacterial antifungal.

Keywords

Vilsmeier-Haack, Schiff bases, malonaldehyde, Fisher projection, Howarth formula, steric hindrance, biomolecules, biological activity

Thanks

The researches acknowledge and thankful to the University of Diyala, and the faculty of Sciences for submitting the entire requirements to do this re­search.

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