Recent Advances in the Synthesis of 1,3-Azoles

Abstract

The 1,3-azole motif is a common and integral feature of many clinical drugs. Due to their wide-ranging applications, the development of 1,3-azoles as therapeutic agents is an ongoing focus of medicinal chemists. This review highlights the recent approaches towards the assembly of 1,3-oxazole, 1,3-thiazole and 1,3-imidazole motifs.

Synthesis and Anticandidal Activity of New Imidazole-Chalcones

“…Antifungal azoles bind with nitrogen atoms to iron atoms of the heme group in the target protein and block fungal membrane ergosterol biosynthesis by inhibiting the demethylation of lanosterol to ergosterol and altering the fungal membrane structure and function [ 9 , 10 , 11 ]. The variability of azole nuclei is demonstrated in their present applications as pharmaceutical drugs used in the cure of bacterial, viral, and fungal infections, worm infestations, acid reflux, cancer, inflammations, and diabetes [ 12 ]. Imidazoles, the first group to be developed in azole antifungals also block the accumulation of methylated sterols, and disrupt the ergosterol biosynthesis, which is an essential component of the fungal cell wall.…”

Synthesis of Thiazoles Bearing Aryl Enamine/Aza‐enamine Side Chains: Effect of the π‐Conjugated Spacer Structure and Hydrogen Bonding on Photophysical Properties

“…A remarkable advantage for the development of new synthetic thiazoles is the numerous convenient methods for their construction, which provide different possibilities for peripheral derivatization [5] and allow the tuning of the optical properties of these compounds by varying their electronic nature with LUMO analyses, changes in electron density after S 0 → S 1v excitation and maps of electrostatic potential (MEPs) calculated by means of DFT have allowed us to estimate the particularities of the geometric and electronic structures of the ETZs and ATZs in the ground and excited states. The availability, synthetic simplicity, stability, large Stokes shifts and high sensitivity to the microenvironment (fluorosolvatochromic behaviour) make the obtained TZs a useful platform for the further design and synthesis of new effective compounds for applications in the field of fluorescence imaging.…”

“…The most well-known approach for forming the thiazole ring is the Hantzsch synthesis, in which primary thioamides or thioureas are treated with αhalocarbonyl compounds to afford various TZs in a single step. [5,6] This is an excellent method for functionalizing thiazole rings with primary, secondary and tertiary amine groups and different electron-donating and -accepting and also alkyl, aryl and >heteroaryl substituents. [3] An eloquent example of the excellent fluorescence of derivatives of this heterocycle depending on the structures of the attached substituents is represented by the recently published results of the synthesis and investigation of the photophysical properties of a series of 5-arylaminothiazoles, which show emission in the wide range of 460 to 610 nm and fluorescence quantum yields between 0.01 and 0.86.…”

“…A remarkable advantage for the development of new synthetic thiazoles is the numerous convenient methods for their construction, which provide different possibilities for peripheral derivatization and allow the tuning of the optical properties of these compounds by varying their electronic nature with electron‐donor and ‐acceptor groups as well as the length and nature of their conjugated systems. The most well‐known approach for forming the thiazole ring is the Hantzsch synthesis, in which primary thioamides or thioureas are treated with α‐halocarbonyl compounds to afford various TZs in a single step , . This is an excellent method for functionalizing thiazole rings with primary, secondary and tertiary amine groups and different electron‐donating and ‐accepting and also alkyl, aryl and >heteroaryl substituents …”

Design, synthesis, and evaluation of novel 2-phenylpropionic acid derivatives as dual COX inhibitory-antibacterial agents

“…Azole compounds are electron-rich nitrogen heterocycles, playing an extremely essential role in medicinal area. Hence, they have been gained a special attention 13 . Due to their heteroatomic ring system and electron-rich property, azole-based compounds can easily interact with the enzymes and receptors in organisms as a result of coordination bonds, hydrogen bonds, ion-dipole, cation-p, p-p stacking and hydrophobic effect as well as van der Waals force, etc., thereby exhibiting various bioactivities 14 .…”