Antimicrobial activities of some synthesized macrocyclic pentaazapyridine and dipeptide pyridine derivatives

Abstract

A series of tetracarboxamide Schiff base and macrocyclic pentaazapyridines has been prepared from 3,5-bis(N-(1-hydrazinyl-1-oxo-3-phenylpropan-2-yl))pyridine carboxamide 4 as starting material, which was synthesized from 3,5-dinicotinic acid 1. Treatment of 4 with 1,4-diaminobutane, 1,6-diaminohexane or cycloalkanone derivatives gave the corresponding macrocyclic tetracarboxamides 5a and 5b, and cycloalkyl Schiff bases 6a-6c, respectively. Treatment of 4 with acetophenone or acetylpyridine derivatives gave the corresponding Schiff bases 7a-7e and 8a-8c, respectively. Carboxylic acid hydrazide 4 was treated with acid anhydrides in glacial acetic acid to afford the corresponding diimide tetracarboxamides 9-11, respectively. The structures of newly synthesized compounds are established by physical and spectral data evidences. Some of the synthesized compounds were screened as antimicrobial agents.

Heteroaryl Rings in Peptide Macrocycles

“…Cyclization of dipeptides 1220 and 1221 or tetrapeptides 1223 and 1224 with different diamino linkers ( 1238a – e ) afforded the corresponding series of cyclic tri- or pentapeptide esters 1240 and 1239 , respectively (Scheme ). − …”

Chiral Pyridine-3,5-bis- (L-phenylalaninyl-L-leucinyl) Schiff Base Peptides as Potential Anticancer Agents: Design, Synthesis, and Molecular Docking Studies Targeting Lactate Dehydrogenase-A

“…In the present investigation and as a continuation of our previous work [31][32][33][34][35][36][37][38] in peptide and heterocyclic chemistry, chiral N3,N5-bis[(l-phenylalaninyl-l-leucinyl) substituted aryl or heterocyclic Schiff base]pyridine candidates were successfully designed, synthesized, and plausibly characterized by analytical techniques including IR, nuclear magnetic resonance (NMR), and mass spectroscopy evidences. In addition, their cytotoxicity effects on MCF-7 cancer cell lines, in vivo and in vitro inhibition of p53 ubiquitination, and lactate dehydrogenase-A were demonstrated in detail.…”

Synthesis, antimicrobial activity, and ion transportation investigation of four new [1 + 1] condensed furan and thiophene‐based cycloheterophane amides

“…As seen in these examples, there are lots of macrocyclic compounds derived from natural products that then are used as commercial drugs, and as a result, the interest of exploring these types of macrocyclic compounds is increasing day by day . In medicinal chemistry, we encounter the biomimetic synthesis of cyclic peptide analogues and marvelous new macrocyclic derivatives that are selective antimicrobials, new therapeutic, and more resistant agents to proteolytic degradation and fluorescent . Another important aspect of these macrocyclic compounds is that these compounds are carrier for biologically important ions, neutral molecules, or catalysts …”

“…encounter the biomimetic synthesis of cyclic peptide analogues [27] and marvelous new macrocyclic derivatives that are selective antimicrobials, [28][29][30][31] new therapeutic, [25] and more resistant agents to proteolytic degradation [32,33] and fluorescent. [34] Another important aspect of these macrocyclic compounds is that these compounds are carrier for biologically important ions, neutral molecules, or catalysts.…”