The condensation of rhodanine and derivatives with benzaldehyde sulphonic acids

Abstract

The condensation products of rhodanine and some of its derivatives with benzaldehyde sulphonic acids have been prepared with a view to obtaining compounds of increased fungicidal properties. The products differ from the majority of previously prepared rhodanine-aldehyde condensation products in that they are appreciably soluble in water. From a fungitoxicological standpoint this increased solubility may well increase the activity of such fungicides as their availability in aqueous media is greatly increased. The condensation products formed relatively insoluble and often crystalline salts with many metallic ions. The precipitation of these salts was briefly considered from the analytical point of view. The condensations between the rhodanines and the benzaldehyde sulphonic acids were carried out in acid media and crystalline coloured products were obtained in good yield.In a series of papers14 from this department the syntheses of a variety of compounds of potential fungitoxicological value have been reported. The class of compounds obtained by the condensation of rhodanine or a 3-substituted congener with carbonylic compounds has been particularly studied. Rhodanine has been condensed with ali-

Recent Pharmacological Developments on Rhodanines and 2,4-Thiazolidinediones

“…Rhodanine-3-acetic acid (RAA) 1 was prepared by Korner [ 2 ] in 1908, and Knoevenagel condensation products of the acid with various aldehydes, namely, [(5 Z )-(5-benzylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)]acetic acids 2 were reported in the same year [ 3 ]. From 1960 onwards, studies revealed that such type of molecule exhibit potential antimycobacterial [ 4 , 5 ], antifungal [ 6 – 15 ], pesticidal [ 16 – 18 ], antihypertensive [ 19 ], and antineoplastic [ 20 , 21 ] activities. Their NMR characterization performed in 1982 [ 22 ].…”

Recent Advances in the Biological Importance of Rhodanine Derivatives

“…Because the latter is conjugated to the carbonyl group at position 4 of the rhodanine ring, such compounds are electrophilic and potentially reactive due to possible Michael addition of the nucleophilic protein residues to the exocyclic double bond [3][4][5]. Rhodanine have been found to possess various biological activities, such as antidiabetic, antibacterial, antifungal, anti-infective, pesticidal, antimycobacterial, antineoplastic, and so on [6][7][8][9][10][11][12][13][14][15][16][17][18][19]. They also exhibit antitubercular, anti-human immunodeficiency virus (HIV), and antimalarial activities.…”

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

“…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.…”