Abstract
A series of macrocyclic Schiff-bases and hexadecaazatricyclo-carboxamides has been prepared via the cyclocondensation of pyridine-2,6-dicarbonyl dichloride (1) or pyridine-2,6-dicarboxylic acid dihydrazide (3) or N,N-bis-[1- hydrazinyl-2-(substituted)]-pyridine-2,6-dicarboxamides (5a-d) with appropriate difunctional reagents. The coupling of 3 with tertacarboxylic acid dianhydride gave the macrocyclic tetraimidetetracarboxamides 6 and 7. Condensation of 5a-d with 3,3`-binaphthyl-dialdehyde yielded the corresponding macrocyclic hydrazones 8a-d, while compound 5a reacted with tertacarboxylic acid dianhydrides to give macrocyclic tetraimide octacarboxamide pyridine derivatives 9 and 10. The tricyclo-8,18-dimethyl ester derivative 12 was chemically synthesized, starting from the acid chloride 1 by coupling with L-lysine methyl ester. The tricyclo-8,18-dimethyl ester derivative 12 was treated with hydrazine hydrate to afford the corresponding hydrazide 13, which was condensed with aromatic aldehydes to afford tricyclo-bis-hydrazones 14a,b. The structure assignments of the new compounds are based on chemical and spectroscopic evidence. The biological activity screening tests showed that many of the obtained compounds exhibit high antimicrobial activity comparable to ampicillin and chloramphenicol which are used as reference compounds.
Keywords: Chiral macrocyclic, Schiff-bases and polycarboxamides, tricycle-bis-substituted pyridine, antimicrobial agents
Call for Papers in Thematic Issues
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
Photoswitches for Molecular Recognition
This Special Issue would cover the hot topics on synthesis and chemical and photophysical characterization of new photoswitchable derivatives and their applications on molecular recognition of metabolites and biological active compounds, both in physiological medium and in living cells. Photoswitches are compounds that can change their conformation or properties in ...read more
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
13