12 research outputs found
Morpholine as a privileged structure: A review on the medicinal chemistry and pharmacological activity of morpholine containing bioactive molecules
Morpholine is a heterocycle featured in numerous approved and
experimental drugs as well as bioactive molecules. It is often employed
in the field of medicinal chemistry for its advantageous
physicochemical, biological, and metabolic properties, as well as its
facile synthetic routes. The morpholine ring is a versatile and readily
accessible synthetic building block, it is easily introduced as an amine
reagent or can be built according to a variety of available synthetic
methodologies. This versatile scaffold, appropriately substituted,
possesses a wide range of biological activities. There are many examples
of molecular targets of morpholine bioactive in which the significant
contribution of the morpholine moiety has been demonstrated; it is an
integral component of the pharmacophore for certain enzyme active-site
inhibitors whereas it bestows selective affinity for a wide range of
receptors. A large body of in vivo studies has demonstrated morpholine's
potential to not only increase potency but also provide compounds with
desirable drug-like properties and improved pharamacokinetics. In this
review we describe the medicinal chemistry/pharmacological activity of
morpholine derivatives on various therapeutically related molecular
targets, attempting to highlight the importance of the morpholine ring
in drug design and development as well as to justify its classification
as a privileged structure
A Bio-Guided Screening for Antioxidant, Anti-Inflammatory and Hypolipidemic Potential Supported by Non-Targeted Metabolomic Analysis of Crepis spp.
This study was designed to evaluate the chemical fingerprints and the antioxidant, anti-inflammatory and hypolipidemic activity of selected Crepis species collected in Greece, namely, C. commutata, C. dioscoridis, C. foetida, C. heldreichiana, C. incana, C. rubra, and Phitosia crocifolia (formerly known as Crepis crocifolia). For the phytochemical analyses, sample measurements were carried out by using nuclear magnetic resonance (NMR) spectroscopy and liquid chromatography coupled with mass spectrometry (LC-MS). Τhe extracts were evaluated both in vitro (radical scavenging activity: DPPH assay and total phenolic content: Folin–Ciocalteu) and in vivo (paw edema reduction and hypolipidemic activity: experimental mouse protocols). Among the tested extracts, C. incana presented the highest gallic acid equivalents (GAE) (0.0834 mg/mL) and the highest antioxidant activity (IC50 = 0.07 mg/mL) in vitro, as well as the highest anti-inflammatory activity with 32% edema reduction in vivo. Moreover, in the hypolipidemic protocol, the same extract increased plasma total antioxidant capacity (TAC) by 48.7%, and decreased cholesterol (41.3%) as well as triglycerides (37.2%). According to fractionation of the extract and the phytochemical results, this biological effect may be associated with the rich phenolic composition; caffeoyl tartaric acid derivatives (cichoric and caftaric acid) are regarded as the most prominent bioactive specialized metabolites. The present study contributes to the knowledge regarding the phytochemical and pharmacological profile of Crepis spp