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Biocatalytic Synthesis of Homochiral 2-Hydroxy-4-butyrolactone Derivatives by Tandem Aldol Addition and Carbonyl Reduction.
ACS Catal
April 2023
Dept. of Biological Chemistry, Institute for Advanced Chemistry of Catalonia, IQAC-CSIC, Jordi Girona 18-26, 08034 Barcelona, Spain.
Chiral 2-hydroxy acids and 2-hydroxy-4-butyrolactone derivatives are structural motifs often found in fine and commodity chemicals. Here, we report a tandem biocatalytic stereodivergent route for the preparation of these compounds using three stereoselective aldolases and two stereocomplementary ketoreductases using simple and achiral starting materials. The strategy comprises (i) aldol addition reaction of 2-oxoacids to aldehydes using two aldolases from , 3-methyl-2-oxobutanoate hydroxymethyltransferase (KPHMT ), 2-keto-3-deoxy-l-rhamnonate aldolase (YfaU ), and --hydroxybenzylidene pyruvate hydratase-aldolase from (HBPA ) and (ii) subsequent 2-oxogroup reduction of the aldol adduct by ketopantoate reductase from (KPR ) and a Δ-piperidine-2-carboxylate/Δ-pyrroline-2-carboxylate reductase from pv.
View Article and Find Full Text PDFSynthesis of Stereoenriched Piperidines via Chemo-Enzymatic Dearomatization of Activated Pyridines.
J Am Chem Soc
November 2022
Department of Chemistry, University of Manchester, Manchester Institute of Biotechnology, 131 Princess Street, Manchester M1 7DN, United Kingdom.
The development of efficient and sustainable methods for the synthesis of nitrogen heterocycles is an important goal for the chemical industry. In particular, substituted chiral piperidines are prominent targets due to their prevalence in medicinally relevant compounds and their precursors. A potential biocatalytic approach to the synthesis of this privileged scaffold would be the asymmetric dearomatization of readily assembled activated pyridines.
View Article and Find Full Text PDFIsoquinolone derivatives as lysophosphatidic acid receptor 5 (LPA5) antagonists: Investigation of structure-activity relationships, ADME properties and analgesic effects.
Eur J Med Chem
December 2022
Research Triangle Institute, Research Triangle Park, NC, 27709, USA. Electronic address:
Blockade of lysophosphatidic acid receptor 5 (LPA5) by a recently reported antagonist AS2717638 (2) attenuated inflammatory and neuropathic pains, although it showed moderate in vivo efficacy and its structure-activity relationships and the ADME properties are little studied. We therefore designed and synthesized a series of isoquinolone derivatives and evaluated their potency in LPA5 calcium mobilization and cAMP assays. Our results show that substituted phenyl groups or bicyclic aromatic rings such as benzothiophenes or benzofurans are tolerated at the 2-position, 4-substituted piperidines are favored at the 4-position, and methoxy groups at the 6- and 7-positions are essential for activity.
View Article and Find Full Text PDFApplications of Isosteres of Piperazine in the Design of Biologically Active Compounds: Part 2.
J Agric Food Chem
September 2022
Syngenta Crop Protection Research, Schaffhauserstrasse, CH-4332 Stein, Switzerland.
Applications of piperazine and homopiperazine in drug design are well-established, and these heterocycles have found use as both scaffolding and terminal elements and also as a means of introducing a water-solubilizing element into a molecule. In the accompanying review (10.1021/acs.
View Article and Find Full Text PDFSynthesis, Characterisation and Docking Studies of Thioxoquinoline Derivatives as Potential Anti-Alzheimer Agents.
Curr Drug Discov Technol
November 2022
Department of Pharmaceutical Chemistry, P.E. S's Rajaram, and Tarabai Bandekar, College of Pharmacy, Farmagudi, Ponda, Goa, 403 401, India.
Background: Alzheimer's Disease (AD) is related to the total loss of presynaptic neurotransmitters of the cholinergic system in regions of the brain related to memory. Approximately 15% of the population beyond the age of 65 years are suffering from dementia due to AD and the rate is rising exponentially with age.
Objective: The objective of this research was the synthesis of a series of 1-(4-substituted-2- thioxoquinolin-1(2H)-yl)-2-substituted ethanoneV (a-c(1-4)) by undergoing acetylation at the nitrogen of 4-hydroxyquinolin-2-(1H)-one and replacing its oxygen atom with sulphur moiety via the process of thionation.
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