AI Article Synopsis
- Stereoselective synthesis of thieno analogues of bioactive alkaloids was achieved in five steps using enantiopure 2-aminoadipic acid as a source of chirality and nitrogen.
- Key steps included π-cationic cyclization of chiral 6-oxopipecolinic acids into pure keto-lactams and their regioselective and diastereoselective reduction.
- A notable Friedel-Crafts cyclization produced unexpected enamides and enamidones with trifluoromethyl groups, and a mechanism explaining their formation was discussed.
Article Abstract
The stereoselective synthesis of -thieno analogues of the phenanthroquinolizidine bioactive alkaloids (-)-Cryptopleurine and (-)-(15)-Hydroxycryptopleurine was achieved in five steps starting from easily available enantiopure ()-2-aminoadipic acid used as chiral pool and nitrogen atom source. During these investigations, both π-cationic cyclization of chiral -thienylmethyl-6-oxopipecolinic acids into pure ()-keto-lactams and theirs regioselective and diastereoselective reduction, considered as key steps of this sequence, were studied. Of particular interest, the Friedel-Crafts cyclization using (CFCO)O/BF·EtO show that near the expected keto-lactams, enamides and enamidones containing trifluoromethyl residue were isolated. A mechanism leading to the latter products with high synthetic potential was discussed.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7111795 | PMC |
| http://dx.doi.org/10.1016/j.tet.2016.04.047 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
4-Alkyl-4-thieno[2',3':4,5]pyrrolo[2,3-]quinoxaline Derivatives as New Heterocyclic Analogues of Indolo[2,3-]quinoxalines: Synthesis and Antitubercular Activity.
Int J Mol Sci
January 2025
Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Street, 22, Ekaterinburg 620137, Russia.
The synthetic approach based on a sequence of Buchwald-Hartwig cross-coupling and annulation through intramolecular oxidative cyclodehydrogenation has been used for the construction of novel 4-alkyl-4-thieno[2',3':4,5]pyrrolo[2,3-]quinoxaline derivatives. For the first time, these polycyclic compounds were evaluated for antimycobacterial activity, including extensively drug-resistant strains. A reasonable bacteriostatic effect against HRv was demonstrated.
View Article and Find Full Text PDFAdvances in structural identification of some thieno[2,3-d]pyrimidine scaffolds as antitumor molecules: Synthetic approaches and control programmed cancer cell death potential.
Bioorg Chem
January 2025
Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Cairo University, Cairo 11562, Egypt. Electronic address:
Thieno[2,3-d]pyrimidine fragment is not only bioistostere to quinazoline ring but also to purines which exist in nucleic acids responsible for several key biological processes of the living cells, thus it is of a great interest for many researchers. Thieno[2,3-d]pyrimidine ring has become an important scaffold for different compounds with versatile pharmacological activities including anticancer. These compounds exert their anticancer activity through variant mechanisms of action; one of these is the induction of different programmed cell death types as apoptosis and necroptosis which is an effective approach for cancer treatment.
View Article and Find Full Text PDFThe AMPK allosteric activator MK-8722 improves the histology and spliceopathy in myotonic dystrophy type 1 (DM1) skeletal muscle.
FASEB J
December 2024
Department of Cellular and Molecular Medicine, Faculty of Medicine, University of Ottawa, Ottawa, Ontario, Canada.
Multiple signaling pathways have been reported to be altered in Myotonic Dystrophy type 1 (DM1) skeletal muscle, contributing to pathogenicity. In particular, previous work established that AMPK signaling, a key sensor of energy metabolism, is repressed in DM1 mouse muscle and that activating AMPK through exercise and/or with pharmacological activators is beneficial for the DM1 muscle phenotype. Here, we explored the effects of a newer, more specific allosteric AMPK activator acting directly on AMPK.
View Article and Find Full Text PDFMechanisms of Action Underlying Conductance-Modifying Positive Allosteric Modulators of the NMDA Receptor.
Mol Pharmacol
November 2024
Departments of Pharmacology and Chemical Biology, Emory School of Medicine (E.Z.U., R.E.P., S.F.T.) and Chemistry (S.P., R.G.F., N.S.A., L.J., D.C.L.), Emory University, Atlanta, Georgia
N-methyl-D-aspartate receptors (NMDARs) are ionotropic glutamate receptors that mediate a slow, Ca-permeable component of excitatory neurotransmission. Modulation of NMDAR function has the potential for disease modification as NMDAR dysfunction has been implicated in neurodevelopment, neuropsychiatric, neurologic, and neurodegenerative disorders. We recently described the thieno[2,3-day]pyrimidin-4-one (EU1622) class of positive allosteric modulators, including several potent and efficacious analogs.
View Article and Find Full Text PDFComplement factor B inhibitor LNP023 mediates the effect and mechanism of AMPK/mTOR on autophagy and oxidative stress in lupus nephritis.
Kaohsiung J Med Sci
November 2024
Department of Nephrology, The Second Affiliated Hospital of University of South China, Hengyang, China.
This study investigated the impact of LNP023 on the AMPK/mTOR signaling pathway in lupus nephritis (LN) and its effects on autophagy and oxidative stress. A mouse model of LN was established, and renal injury was confirmed by assessing various LN markers, including antinuclear antibody, ds-DNA, anti-Sm antibody, and others. Mice were treated with LNP023, the AMPK activator AICAR, or the AMPK inhibitor dorsomorphin.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!