Synthesis of Oligobipyridine Strands Bearing Nucleoside and Amino Acid Side Chains

1996 ◽  
Vol 49 (10) ◽  
pp. 1023 ◽  
Author(s):  
MM Harding ◽  
JM Lehn
Keyword(s):  
Amino Acid ◽  
Nucleic Acids ◽  
Organic Solvents ◽  
Metal Ion ◽  
Metal Ion Complexation ◽  
Biological Targets ◽  
Complexation Studies ◽  
Amide Derivatives ◽  
Amino Acid Side Chains ◽  
Derivatives Of

The synthesis is reported of derivatives of 6,6'-dimethyl-2,2'-bipyridine in which adenosine, thymidine aid tryptophan substituents are introduced at the 4,4'-positions as amide derivatives. Artificial oligonucleoside strands derived from the corresponding trisbipyridyl ligand , in which three bipyridyl ligands are separated by methyleneoxy bridges, have been prepared. The solubility of the nucleoside-substituted ligands in organic solvents is poor, but acylation of the ribose or deoxyribose units present in the ligands provides a mechanism whereby organic solubility can be improved. These ligands may be used for the preparation of metallo-exoreceptors , with the potential for recognition of biological targets such as nucleic acids. Preliminary metal ion complexation studies have been carried out.

Bis-amino Acid Derivatives of 1,1′-Ferrocenedicarboxylic Acid: Structural, Electrochemical, and Metal Ion Binding Studies

2014 ◽  
Vol 33 (18) ◽  
pp. 4873-4887 ◽  
Author(s):  
Bimalendu Adhikari ◽  
Alan J. Lough ◽  
Bryan Barker ◽  
Afzal Shah ◽  
Cuili Xiang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Metal Ion ◽  
Amino Acid Derivatives ◽  
Ion Binding ◽  
Metal Ion Binding ◽  
Binding Studies ◽  
Derivatives Of

Azomacrocyclic Derivatives of Imidazole: Synthesis, Structure, and Metal Ion Complexation Properties.

ChemInform ◽  
2007 ◽  
Vol 38 (35) ◽  
Author(s):  
Ewa Wagner-Wysiecka ◽  
Marzena Jamrogiewicz ◽  
Marina S. Fonari ◽  
J. F. Biernat
Keyword(s):  
Metal Ion ◽  
Metal Ion Complexation ◽  
Ion Complexation ◽  
Derivatives Of

Amino acid amide derivatives of 2-[3-(aminomethyl)-4H-1,2,4-triazol-4-yl]benzophenones, a novel class of annulated peptidoaminobenzophenones

1982 ◽  
Vol 25 (12) ◽  
pp. 1466-1473 ◽  
Author(s):  
Kentaro Hirai ◽  
Toshio Fujishita ◽  
Teruyuki Ishiba ◽  
Hirohiko Sugimoto ◽  
Shigeru Matsutani ◽  
...  
Keyword(s):  
Amino Acid ◽  
Acid Amide ◽  
Amino Acid Amide ◽  
Amide Derivatives ◽  
Derivatives Of

scholarly journals Сationic carboxamide derivatives of tricyclic heteroaromatic compounds: synthesis and preliminary evaluation of antiproliferative activity

2020 ◽  
Vol 15 (1) ◽  
pp. 34-41
Author(s):  
Valentina Kostina ◽  
Inna Alexeeva ◽  
Nadia Lysenko ◽  
Valentina Negrutska ◽  
Igor Dubey
Keyword(s):  
Antiproliferative Activity ◽  
Antitumor Agents ◽  
Preliminary Evaluation ◽  
Heteroaromatic Compounds ◽  
Biological Targets ◽  
Amide Derivatives ◽  
Tumor Cell Culture ◽  
Intercalating Agents ◽  
Derivatives Of

This research was aimed at the synthesis and study of biological activity of the carboxamides of tricyclic heteroaromatic systems, acridone, phenazine and thioxanthone, containing the aliphatic and aromatic cationic substituents at amide fragment. These heterocyclic cores are DNA intercalating agents, whereas the introduction of cationic groups provides additional ionic interactions of the ligands with their biological targets, such as DNA and enzymatic complexes of the system of nucleic acids biosynthesis. A convenient way of the introduction of such groups is a modification of heterocyclic carboxamides. A small library of new cationic amide derivatives of acridone-4-, phenazine-1- and thioxanthone-4-carboxylic acids was obtained. They were synthesized in 37-81% yield by mild and selective quaternization of the nitrogen atoms at N,N-dimethylaminoalkyl (alkyl = ethyl, propyl) and pyridylmethyl fragments of the neutral N-functionalized carboxamides with methyl iodide. Tricyclic heteroaromatic cores were not affected. Convenient protocol for the synthesis of thioxanthone-4-carboxylic acid (TCA) based on the reaction of 2-mercaptobenzoic and 2-iodobenzoic acids followed by cyclization of the intermediate was developed (yield 79%). A series of new N-functionalized neutral amides of TCA, the precursors of corresponding cationic carboxamide, were also obtained via the reaction of acyl chloride with amines. Preliminary in vitro testing of four compounds as potential antitumor agents in U87MG tumor cell culture (human malignant glioma) demonstrated their significant antiproliferative activity at low micromolar concentrations, with growth inhibition values GI50 in the range 1.7-11 µM. These results suggest that cationic carboxamides of tricyclic heteroaromatic systems are promising scaffolds for the design of new antitumor drugs.

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