2,2′-((1,4-Dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene))bis(quinoline-3-carboxylic acid)

Joanna Fedorowicz,Karol Gzella,Paulina Wiśniewska,Jarosław Sączewski

doi:10.3390/m1093

Joanna Fedorowicz, Karol Gzella + Show 2 more

Open Access

https://doi.org/10.3390/m1093

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Journal: Molbank	Publication Date: Nov 21, 2019
Citations: 1	License type: CC BY 4.0

Affiliation: Gdańsk Medical University

Abstract

The title compound, 2,2′-((1,4-dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene))bis(quinoline-3-carboxylic acid) was synthesized from isoxazolo[3,4-b]quinolin-3(1H)-one and dimethyl acetylenedicarboxylate (DMAD) via a double aza-Michael addition followed by [1,3]-H shifts. The product was characterized by infrared and nuclear magnetic resonance spectroscopy, as well as elemental analysis and high-resolution mass spectrometry (HRMS). The proposed reaction mechanism was rationalized by density functional theory (DFT) calculations.

Highlights

Isoxazol-3(2H)-one and isoxazol-5(2H)-one derivatives (Figure 1) represent an extensive class of heterocyclic ring systems found in natural products and building blocks employed in medicinal chemistry. They may be treated as useful tools in organic synthesis since they are small and easy to functionalize molecules that can be utilized to design novel bioactive compounds
Despite the molecular mechanism of antifungal action of isoxazol-5(2H)-ones such as TAN-950A [16] and drazoxolon [8,15] has not been established, it should be underlined that structurally similar antimicrobial oxazolidones such as posizolid, tedizolid, radezolid and linezolid or cycloserine serve as inhibitors of protein synthesis that prevent binding of N-formylmethionyl-tRNA to the ribosome. [33]
We have performed the reaction of isoxazolone 2 with dimethyl acetylenedicarboxylate (DMAD) in anhydrous methanol at room

Summary

Introduction

Isoxazol-3(2H)-one and isoxazol-5(2H)-one derivatives (Figure 1) represent an extensive class of heterocyclic ring systems found in natural products and building blocks employed in medicinal chemistry. It has been proven that these synthetic products exhibit antibacterial [1,2,3,4,5,6,7,8], antifungal [7,8,9,10,11,12,13,14,15,16], antitubercular [3], anticancer [3,6,17,18], antileucemic [5], antinflammatory [19,20,21], antiviral [22], anticonvulsant [1], antioxidant [2,7], and antiandrogenic [23,24] properties They may act as inhibitors of p38 MAP kinases [25], protein kinase C [26], and protein-tyrosine phosphatase 1B, which cause antiobesity effect [27,28]. Despite the molecular mechanism of antifungal action of isoxazol-5(2H)-ones such as TAN-950A [16] and drazoxolon [8,15] has not been established, it should be underlined that structurally similar antimicrobial oxazolidones such as posizolid, tedizolid, radezolid and linezolid or cycloserine serve as inhibitors of protein synthesis that prevent binding of N-formylmethionyl-tRNA to the ribosome. [33]

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Conclusion