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Synthetic Approaches, Properties, and Applications of Acylals in Preparative and Medicinal Chemistry.

Synthetic Approaches, Properties, and Applications of Acylals in Preparative and Medicinal Chemistry.

Authors :
Keydel T
Link A
Source :
Molecules (Basel, Switzerland) [Molecules] 2024 Sep 19; Vol. 29 (18). Date of Electronic Publication: 2024 Sep 19.
Publication Year :
2024

Abstract

Diesters of geminal diols (R-CH(O-CO-R') <subscript>2</subscript> , RR'C(OCOR″) <subscript>2</subscript> , etc. with R = H, aryl or alkyl) are termed acylals according to IUPAC recommendations (Rule P-65.6.3.6 Acylals) if the acids involved are carboxylic acids. Similar condensation products can be obtained from various other acidic structures as well, but these related "non-classical acylals", as one might call them, differ in various aspects from classical acylals and will not be discussed in this article. Carboxylic acid diesters of geminal diols play a prominent role in organic chemistry, not only in their application as protective groups for aldehydes and ketones but also as precursors in the total synthesis of natural compounds and in a variety of organic reactions. What is more, acylals are useful as a key structural motif in clinically validated prodrug approaches. In this review, we summarise the syntheses and chemical properties of such classical acylals and show what potentially under-explored possibilities exist in the field of drug design, especially prodrugs, and classify this functional group in medicinal chemistry.

Details

Language :
English
ISSN :
1420-3049
Volume :
29
Issue :
18
Database :
MEDLINE
Journal :
Molecules (Basel, Switzerland)
Publication Type :
Academic Journal
Accession number :
39339447
Full Text :
https://doi.org/10.3390/molecules29184451