The Condensation of Rhodanine and Derivatives With 4-Antipyrinaldehyde

Abstract

More than three-quarters of a century has elapsed since antipyrine (Ia) was introduced into medicine by Knorr as an antipyretic and analgesic (1). Altllough pyrazolone analgesics have now virtually vanished from the scene in North America and the Scandinavian countries (2), they are still widely used in other areas and considerable efforts have been expended to improve their pharmacological properties (3, 4). 111 recent years seine of this effort has been focused on 4-antipyrinaldehyle (Ib)%and its derivatives (5-14), principally in connection wit11 antineuralgic and febrifugal effects. While insecticidal pyrazolones have been described (15-17), other nonanalgesic applications of 4-antipyrinaldehyde or its derivatives have received little attention other than brief reports of tuberculostatic (18) and bacteriostatic activity (10).

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.…”

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.…”