2‐Amino‐2‐oxazolines, III: Synthesis, Structure, and Preliminary Pharmacological Evaluation of Cycloaddition Compounds with Unsaturated Carboxylic Esters

Abstract

The reaction of 5-substituted 2-amino-2-oxazolines with unsaturated carboxylic esters yielded 2,3,5,6-tetrahydro- and 2,3-dihydro-7H-oxazolo[3,2-a]pyrimidin-7-ones. The structure of these compounds was established by IR- and NMR-spectra and by X-ray crystallography. They were tested for anti-arrhythmic and hypocholesterolemic activities.

Simple and Expedient Access to Novel Fluorinated Thiazolo- and Oxazolo[3,2-a]pyrimidin-7-one Derivatives and Their Functionalization via Palladium-Catalyzed Reactions

“…Continuing our interest in the development of efficient methods for the synthesis of new fluorinated heterocyclic compounds with possible biological properties [41][42][43][44][45][46][47], we Classically, Thiazolo and oxazolo[3,2-a]pyrimidin-7-one derivatives have been synthesized by reactions of the corresponding 2-aminoazoles with a symmetric alkyne such as dialkyl acetylenedicarboxylates [28][29][30][31][32][33][34][35][36] (Figure 2a), or an asymmetric alkyne such as ethyl propiolate derivatives [37][38][39][40] (Figure 2b). However, despite their relevance, these procedures have several drawbacks such as a lack of generality, poor regioselectivity, the use of expensive reagents or less available reagents, as well as unsatisfactory yields.…”

Concentration-Dependent Orientational Changes of 2-Amino-2-thiazoline Molecule Adsorbed on Silver Nanocolloidal Surface Investigated by SERS and DFT

“…2-Amino-2-thiazoline (2ATH) molecules, containing the amidine group, are not only important heterocyclic compounds in synthetic organic chemistry but also are widely involved in enzyme-catalyzed biotransformation processes in biochemistry. The amidine moiety present in the molecule is known to occur naturally in numerous biologically active compounds, such as amino acids, drugs, and pesticides and is a versatile building block for cyclocondensation reactions . The 2ATH molecule can act as a potential inducer of reverse transformation of tumor cells, and this anticancer action mechanism depends on strong metal−ligand binding via the nitrogen atoms .…”

“…The amidine moiety present in the molecule is known to occur naturally in numerous biologically active compounds, such as amino acids, drugs, and pesticides 17 and is a versatile building block for cyclocondensation reactions. 18 The 2ATH molecule can act as a potential inducer of reverse transformation of tumor cells, and this anticancer action mechanism depends on strong metal-ligand binding via the nitrogen atoms. 19 It is an important constituent of many antihypertensive drugs 20 and is reported to act as an inhibitor of neuronal Na + channels.…”

DFT study and Monte Carlo simulation on proton transfers of 2‐amino‐2‐oxazoline, 2‐amino‐2‐thiazoline, and 2‐amino‐2‐imidazoline in the gas phase and in water

“…2‐Amino‐2‐oxazoline (AOZ), 2‐amino‐2‐thiazoline (ATZ), and 2‐amino‐2‐imidazoline (AIZ) are not only important heterocyclic compounds in synthetic chemistry and especially in medicinal chemistry, but also are widely involved in enzyme‐catalyzed biotransformation processes in biochemistry. Their amidine moiety occurs naturally in numerous biologically active compounds, such as amine acids, drugs, and pesticides,1–5 and is a versatile building block for cyclocondensation reactions leading to polycyclic compounds with a bridgehead nitrogen atom 6, 7. AOZ, ATZ, and AIZ may exist in two tautomeric forms (amino and imino).…”