A series of 1,2,3-triazolylsterols was prepared from pregnenolone through reductive amination and copper(I)-catalyzed azide-alkyne cycloaddition (click chemistry). The newly generated stereocenter of the key propargylamino intermediate provided a mixture of diastereomers which were separated chromatographically, and the configuration of the R isomer was determined by X-ray crystallography. Ten triazolyl sterols were prepared, and the products and intermediates were screened in vitro against different parasites, with some compounds presenting IC50 values in the low micromolar range against Leishmania donovani.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.steroids.2013.10.010 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Recent Developments in Azetidinone-Azole Conjugates: Emerging Antimicrobial Potentials.
Med Chem
January 2025
Department of Pharmaceutical Chemistry, MM College of Pharmacy, Maharishi Markandeshwar (Deemed to be University), Mullana, Ambala 133207, India.
The emergence of multidrug-resistant microbial strains poses a significant challenge to global public health. In response, researchers have been exploring innovative antimicrobial agents with enhanced efficacy and novel mechanisms of action. One promising approach involves the synthesis of hybrid molecules combining azetidinone and azole moieties, capitalizing on the respective antimicrobial properties of both structural elements.
View Article and Find Full Text PDFDevelopment of coumarin-inspired bifunctional hybrids as a new class of anti-Alzheimer's agents with potent efficacy.
RSC Med Chem
December 2024
Department of Pharmaceutical Sciences, Guru Nanak Dev University Amritsar Punjab 143005 India
Considering the multifactorial and complex nature of Alzheimer's disease and the requirement of an optimum multifunctional anti-Alzheimer's agent, a series of triazole tethered coumarin-eugenol hybrid molecules was designed as potential multifunctional anti-Alzheimer's agents using donepezil and a template. The designed hybrid molecules were synthesized a click chemistry approach and preliminarily screened for cholinesterase and Aβ aggregation inhibition. Among them, AS15 emerged as a selective inhibitor of AChE (IC = 0.
View Article and Find Full Text PDFRing-in-Ring Assembly Facilitates the Synthesis of a [12]Cycloparaphenylene ABC-Type [3]Catenane.
Angew Chem Int Ed Engl
January 2025
Henan University, Colleg of Chemistry and Molecular Sciences, Jingmin, 475004, Kaifeng, CHINA.
Cycloparaphenylenes (CPPs) represent a significant challenge for the synthesis of mechanically interlocked architectures, because they lack heteroatoms, which precludes traditional active and passive template methods. To circumvent this problem and explore the fundamental and functional properties of CPP rotaxanes and catenanes, researches have resorted to unusual non-covalent and even to labor-intensive covalent template approaches. Herein, we report a ring-in-ring non-covalent template strategy that makes use of the surprisingly strong non-covalent inclusion of crown ethers into suitably sized CPPs.
View Article and Find Full Text PDFSite-Specific Molecular Engineering of Nanobody-Glucoside Conjugates for Enhanced Brain Tumor Targeting.
Bioconjug Chem
January 2025
Guangdong Provincial Key Laboratory of Advanced Biomaterials, Department of Biomedical Engineering, Southern University of Science and Technology, Shenzhen, Guangdong 518055, China.
Nanobodies play an increasingly prominent role in cancer imaging and therapy. However, their efficacy is often constrained by inadequate tumor penetration and rapid clearance from the bloodstream, particularly in brain tumors due to the intractable blood-brain barrier (BBB). Glycosylation is a favorable strategy for modulating the biological functions of nanobodies, including permeability and pharmacokinetics, but it also leads to heterogeneous glycan structures, which affect the targeting ability, stability, and quality of nanobodies.
View Article and Find Full Text PDFBackground: Intrathecally (IT) delivered antisense oligonucleotides (ASOs) are promising therapies that can reduce tau pathology in Alzheimer's Disease (AD). However, current plasma and CSF sampling methods to estimate brain tissue exposure of ASOs are inherently limited, hampering ASO clinical developmental plans. We developed the PET tracer [F]BIO-687, which binds ASO conjugates (ASO-Tz) in vivo, allowing us to image ASO distribution in a living brain using "pretargeted" imaging.
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!