The condensation of rhodanine and derivatives with pyridine and quinoline aldehydes

Abstract

The condensation products of rhodanine, 3-ethylrhodanine, 3-phenylrhodanine, 3-allylrhodanine and 3-carboxymethylrhodanine with various substituted and unsubstituted pyridine and quinoline aldehydes have been prepared for bacterial and fungicidal evaluation. An earlier series of unsubstituted pyridylmethylene-rhodanines has thus been extended to include products substituted in either or both of the heterocyclic rings. Such substitution may enhance the already known fungicidal character of such rhodanine-aldehyde condensation products. The products obtained by the condensation of the quinoline aldehydes may be considered as substituted in a similar manner as the less accessible dialkylpyridine products and it is possible that these two types of compounds will show a similarity in biological activity. Condensations between the rhodanines and the aldehydes were carried out in acid medium and crystalline coloured condensation products were obtained in good yield.

Rhodanineacetic Acid Derivatives as Potential Drugs: Preparation, Hydrophobic Properties and Antifungal Activity of (5-Arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic Acids

“…In 2006, the compound was prepared under microwave irradiation [ 47 ]. The condensation products of rhodanine-3-acetic acid with pyridinecarbaldehydes were prepared in 1961 as potential antibacterial and antifungal agents [ 8 ]. {(5 Z )-[4-oxo-5-(pyridin-2-ylmethylidene)-2-thioxo-1,3-thiazolidin-3-yl]}acetic acid ( 2 ) was patented as a potential drug for the treatment of metabolic bone diseases [ 22 , 23 ].…”

“…{(5Z)-[4-oxo-5-(pyridin-2-ylmethylidene)-2-thioxo-1,3-thiazolidin-3-yl]}acetic acid ( 2 ). Yellow crystalline compound; Yield 76%; Mp 260-261 °C (253-254 °C, acetic acid [ 8 ]); Anal. Calcd.…”

“…Rhodanine-3-acetic acid (RAA) was prepared by Körner [ 2 ] in 1908, and condensation products of the acid with various aldehydes were reported in the same year [ 3 ]. Since that time, many (5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)alkanoic acids have been prepared and studied as potential antimycobacterial [ 4 , 5 ], antifungal [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 ], pesticidal [ 16 , 17 , 18 ], antihypertensive [ 19 ], and antineoplastic [ 20 , 21 ] agents. Rhodanine carboxylic acid derivatives have also be patented for the treatment and prevention of metabolic bone disorders.…”

Recent Pharmacological Developments on Rhodanines and 2,4-Thiazolidinediones

“…In 2006, similar derivatives have been prepared under microwave irradiation [ 23 ]. Further, the Knoevenagel products of rhodanine-3-acetic acid with pyridinecarbaldehydes were prepared in 1961 and they possess potential antibacterial and antifungal activities [ 8 ]. {(5 Z )-[4-Oxo-5-(pyridin-2-ylmethylidene)-2-thioxo-1,3-thiazolidin-3-yl]}acetic acid 3 were patented as a potential drug for the treatment of metabolic bone diseases [ 24 , 25 ].…”

Rhodanineacetic Acid Derivatives as Potential Drugs: Preparation and Hydrophobic Properties of 5-Arylalkylidene-3-carboxymethylrhodanines

“…Rhodanine-3-acetic acid was prepared by Korner [2] in 1908, and condensation products of the acid with various aldehydes were reported in the same year [3]. Since that time, many 5-arylalkylidene-3-carboxymethylrhodanines have been prepared and studied as potential antimycobacterial [4,5], antifungal [6][7][8][9][10][11][12], pesticidal [13][14][15], antihypertensive [16], and antineoplastic [17,18] agents. Rhodanine carboxylic acid derivatives have also be patented for the treatment and prevention of metabolic bone disorders.…”