Drugs in tuberculosis and leprosy

Ramanathan, Meenakshi; Howell, Crystal K.; Sanders, James M.

doi:10.1016/bs.seda.2019.08.010

Cited by 3 publications

(1 citation statement)

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“…The chemistry of 4,5‐dihydroisoxazoles has gained increasing attention over the last decades due to their wide spectrum of biological activities. Remarkably, this versatile nucleus is also found in natural compounds like tricholomic acid, [1,2] acivicin, [3,4] and the well‐known and widely employed antibiotic cycloserine [5,6] . Among 4,5‐dihydroisoxazole derivatives, the 3‐halo‐4,5‐dihydroisoxazole (or 3‐halo‐Δ 2 ‐isoxazoline) core is the most appealing from a medicinal chemistry point of view.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Reactivity of 3‐Halo‐4,5‐dihydroisoxazoles: An Overview

Zana

Galbiati

2021

ChemistrySelect

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The 3‐halo‐4,5‐dihydroisoxazole moiety is an interesting emerging feature in medicinal and organic chemistry fields. The properties of this nucleus are intimately correlated with the nature of the halogen substituent, ranging from inertness to instability. In between, the 3‐bromo‐Δ2‐isoxazoline scaffold stands out as a handleable and easily affordable electrophilic warhead, able to react with nucleophilic active sites of different enzymes, determining inhibitory effects. However, the importance of 3‐bromo‐Δ2‐isoxazolines does not rely only upon their biological activity. In fact, they are valuable synthetic intermediates, presenting a peculiar reactivity spectrum that allows access to useful chemical functions, ranging from variously decorated dihydroisoxazoles to β‐hydroxynitriles, β‐hydroxyesters, and γ‐hydroxyamines. The synthesis of 3‐bromo‐Δ2‐isoxazolines is predominantly based on the 1,3‐dipolar cycloaddition, a pericyclic reaction accompanied by a remarkable regio‐ and stereo‐selectivity. Thus, this intermediate lends itself especially well to the production of complex molecules with regio‐ and stereo‐chemical requirements.

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Section: Introductionmentioning

confidence: 99%