Abstract
A strain-release-driven, cation-templated intramolecular nucleophilic addition of tethered alkoxides to prochiral cyclopropenes is described. Employment of chiral β- and γ-amino alkoxides allowed for highly diastereoselective assembly of a small series of enantiopure cyclopropane-fused oxazepanones. It was shown that the chiral center at C-4 plays a crucial role in controlling desymmetrization of the cyclopropenyl moiety, instigated by a profound potassium-templated effect. The preliminary biological activities of the new cyclopropane-fused medium heterocycles against Gram-positive bacteria, Gram-negative bacteria, mycobacteria, cancer cells, and fungus were evaluated.
Publication types
-
Research Support, N.I.H., Extramural
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Amino Alcohols / chemistry
-
Amino Alcohols / pharmacology*
-
Anti-Bacterial Agents / chemical synthesis
-
Anti-Bacterial Agents / chemistry
-
Anti-Bacterial Agents / pharmacology*
-
Antineoplastic Agents / chemical synthesis
-
Antineoplastic Agents / chemistry
-
Antineoplastic Agents / pharmacology*
-
Cell Proliferation / drug effects
-
Cycloaddition Reaction
-
Cyclopropanes / chemical synthesis
-
Cyclopropanes / chemistry
-
Cyclopropanes / pharmacology*
-
Drug Screening Assays, Antitumor
-
Fungi / drug effects
-
Gram-Negative Bacteria / drug effects
-
Gram-Positive Bacteria / drug effects
-
Microbial Sensitivity Tests
-
Molecular Structure
-
Neoplasms / drug therapy*
-
Neoplasms / pathology
-
Potassium / chemistry
-
Stereoisomerism
Substances
-
Amino Alcohols
-
Anti-Bacterial Agents
-
Antineoplastic Agents
-
Cyclopropanes
-
cyclopropene
-
cyclopropane
-
Potassium