Design, Synthesis and Evaluation of 5‐Substituted Amino‐2,4‐diamino‐8‐chloropyrimido‐[4,5‐b]quinolines (IX) as Novel Antimalarials.

Abstract

Fused pyrimidine derivatives R 0515 Design, Synthesis and Evaluation of 5-Substituted Amino-2,4-diamino--8-chloropyrimido-[4,5-b]quinolines (IX) as Novel Antimalarials. -(JOSHI, A. A.; NARKHEDE, S. S.; VISWANATHAN*, C. L.; Bioorg. Med. Chem. Lett. 15 (2005) 1, 73-76; Dep. Pharm. Chem., Bombay Coll. Pharm., Bombay 400 098, India; Eng.) -R. Langenstrassen 15-145

Quinolines and structurally related heterocycles as antimalarials

“…The compounds were synthesized and evaluated by Rane's test for blood schizontocidal activity in mice infected by P. berghei [129]. The compounds with bulky substitution on 9-anilino ring (93), and trisubstituted 9-anilino ring [ Becker et al reported a series of potent inhibitors of P. falciparum thioredoxin reductase (PfTrxR), which reduces thioredoxin (Trx) via a CysXXXXCys pair, located penultimate to the C-terminus Gly [133].…”

One‐Pot Multicomponent Reaction: A Highly Versatile Strategy for the Construction of Valuable Nitrogen‐Containing Heterocycles

“…However, the nature and size of the substituents present at the 5-amino function in the pyrimidoquinoline nucleus significantly determine the antimalarial activity. [59] Apart from this, pyrimido-quinolines also exhibit other important biological properties like antimicrobial, [60] anticancer, [61] and anti-inflammatory activities. [62]…”

Na2CO3-Mediated [3+3] Annulation Reaction of Substituted Benzamidines with 2-Benzylidenemalononitriles: Access to Substituted Pyrimidine-4,6-diamines

“…16 For example, Viswanathan and co-workers reported a synthesis by sodium alkoxide promoted cyclization of guanidine nitrate with malononitrile in dry ethanol or methanol (Scheme 1). 7 Soon afterwards, Jarvo and co-workers described a methodology for the synthesis of 4,6-diaminopyrimidines via the same reaction from 2-substituted malononitriles using potassium tert-butoxide as base. 17 A similar synthetic strategy also was reported by the Kobarfard group via the reaction of thiourea and malononitrile in absolute ethanol as solvent.…”

“…Recently, various special substitution types and specific biological activities of pyrimidine derivatives were reported; among the family of pyrimidines, the 4,6-diaminopyrimidines have been found to show diverse biological activities, such as anti-dengue and anti-HCV, 2 antimicrobial, 3 antiplatelet aggregation, 4 antitumor, 5 antiviral, 6 antimalarial, 7 potent dual M3 antagonistic and PDE4 inhibitory, 8 troponin I-interacting kinase (TNNI3K) inhibitory, 9 and Janus kinase 3 inhibitory 10 activity.…”