2-Substituted pyridine, quinoline, isoquinoline, bipyridine, and 1,10-phenanthroline analogues of benzylic acetates undergo SmI(2)-promoted coupling with aldehydes and ketones to afford (2-hydroxyalkyl)heteroaromatics. [reaction: see text]
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http://dx.doi.org/10.1021/ol050944z | DOI Listing |
ACS Omega
January 2025
Department of Chemistry and Biochemistry, Warren Center for Drug Discovery, The University of Notre Dame, 305 McCourtney Hall, Notre Dame, Indiana 46556, United States.
Selective inhibition of glucose regulated protein 94 (Grp94), the most structurally unique isoform of heat shock protein 90 (Hsp90), has been implicated in the treatment of various disease states, including primary open-angle glaucoma and metastatic cancer. In this study, nine analogues were designed and synthesized by conformationally restricting , a second generation Grp94-selective inhibitor. Conformational constraints were applied to restrict the rotatable bonds and to bias the benzyl moiety into the Grp94 site 1 pocket as well as to reduce the entropic penalty paid upon binding.
View Article and Find Full Text PDFChemMedChem
January 2025
China Pharmaceutical University, Medicinal Chemistry, Tongjiaxiang 24#, 210009, Nanjing, CHINA.
Presented herein is the chemical construction of unprecedented 3,4-trans-3,6-anhydro hexofuranose frameworks. The disfavored 3,6-anhydro hexofuranosides were effectively established by Pd-catalyzed debenzylative intramolecular acetalation for the first time. The critical roles of benzyl protection and Pd as catalyst were demonstrated.
View Article and Find Full Text PDFCarbohydr Res
January 2025
Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Thiruvananthapuram, 695019, Kerala, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India. Electronic address:
The synthesis of 2-hydroxy analogues of castanospermine from two new iminooctitols via Mitsunobu cyclization is described. The iminooctitols were derived from the dihydroxylation of an allyl alcohol intermediate, obtained by adding vinylmagnesium bromide to the C6-aldehyde of a protected 1-deoxynojirimycin. An orthogonally protected hemiacetal with silyl group at the C6-hydroxy position and remaining as benzyl ethers, synthesized in four steps from d-glucose, served as a building block in the synthesis of the 1-deoxynojirimycin intermediate.
View Article and Find Full Text PDFOrganometallics
January 2025
Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, United Kingdom.
Cyclopentadienyl anions ([Cp]) are pervasive ligands in coordination chemistry. In contrast, heavy-element derivatives of these ligands, particularly those that feature arsenic, are not as well developed. In this work, a new arsenic-based heterocycle with a structure analogous to [Cp] is presented.
View Article and Find Full Text PDFRSC Adv
January 2025
The Organic Chemistry Research Laboratory (OCRL), Department of Chemistry, Faculty of Science, University of Zanjan Zanjan 45371-38791 Iran
In recent research, quinoline and indole structures have gained recognition for their significant clinical relevance and effectiveness. These compounds are known for their wide-ranging pharmacological effects, which include anticancer, antibacterial, antifungal, antiviral, and anti-inflammatory properties. Researchers have successfully implemented a variety of innovative synthetic strategies, leading to the creation of numerous compounds that display fascinating biological activities in diverse fields.
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