A structure–activity relationship study of compounds with antihistamine activity

Abstract

A structure-activity relationship (SAR) analysis of H(1)-, H(2)- and H(3)-antihistamine activity was carried out and chromatographic data of 2-[2-(phenylamino)thiazol-4-yl]ethanamine, 2-(2-benzyl-4-thiazolyl)ethanamine, 2-(2-benzhydrylthiazol4-yl)ethanamine, 2-(1-piperazinyl- and 2-(hexahydro-1H-1,4-diazepin-1-yl)benzothiazole, 2-(1-piperazinyl)benzothiazole, 2-[4-(1-alkyl)piperidinyl]benzothiazole, 2-(N,N',N'-dimethylalkyl-1,2-ethanediamino)benzothiazole, 2[1-(4-aminopiperidinyl)]benzothiazole, 2-[2-phenyl-4-thiazolyl]ethanamine derivatives and selected H(1)- and H(2)-antihistamine drugs were obtained. NP TLC and RP2 TLC plates (silica gel NP 60F(254) and silica gel RP2 60F(254) silanized precoated), impregnated with a solution of aspartic acid (L-Asp) and a solution of an analogue of aspartic acid (propionic acid), were used in two developing solvents as H(1)-, H(2)- and H(3)-antihistaminic interaction models. The lipophilicity data of the examined compounds were obtained and used in the SAR assay. Biochromatographic tests using TLC plates impregnated with solutions of asparic acid or propionic acid were found to be a source of useful data for the qualitative analysis of compounds with different structures, demonstrating activity to histamine H(1)-, H(2)- and H(3)-receptors. The four presented discriminant models based on biochromatographic studies are an efficient tool in the SAR analysis for initial prediction of compound activity direction within histamine receptors.

Comparative (Q)SAR analysis of benzodiazepine derivatives with different biological activity

“…SAR modeling has been applied to a multitude of biological systems and has aided in the development of new drugs. DFA is a technique used to determine which variables discriminate between two or more naturally occurring groups [47,50].…”

One-Pot Chemoenzymatic Multicomponent Synthesis of Thiazole Derivatives

“…The model reaction and yields are shown in Scheme 1 and Table 1. Eight candidates such as trypsin from porcine pancreas (PPT), α-amylase from hog pancreas, diastase from Aspergillus oryzae, α-amylase from Aspergillus oryzae, lipase AT30, Amano lipase M from Mucor javanicus, and bovine serum albumin (BSA) were screened ( Table 1, entries [1][2][3][4][5][6][7][8]. The yield of product was the monitored parameter to evaluate the catalytic activity of enzymes.…”

“…Thiazoles and their derivatives are an important class of heterocyclic compounds which possess broad biological activities, such as antimicrobial [1], antipyretic [2], antiparasitic [3], antihistaminic [4], and antiviral properties [5]. Aryl-substituted thiazoles are also important functional materials in applications such as fluorescent dyes and liquid crystals [6].…”

Relationships between structure, retention and biological activity of some Schiff base ligands and their complexes

“…activity of the compounds investigated is also related to the molecular structure, and these correlations are known as the quantitative structure-activity relationship (QSAR) (Brzezinska and Koska, 2006;Lazewska et al, 2007). Statistical methods are frequently used for the elucidation of these relationships.…”