A new class of N-basic side chains was obtained from 2,3-dihydro-2H-3-oxobenzo [d]isothiazole and aliphatic or aromatic aldehydes. Secondary amines (morpholine, N-methylpiperazine and ethyl isonipecotate) afforded tertiary N-basic side chains (4-6), while dibasic secondary amines (such as piperazine) gave bis-tertiary N-basic side chains (2). On the other hand, the use of mono-or dibasic primary amines namely; aniline, anisidine, phenyl hydrazine, o-hydroxy benzoic acid hydrazide, hydrazine hydrate, and ethylenediamine (instead of secondary amines) afforded secondary N-basic side chain as mono component or as bis component 7a-c, 9a-c, 11 and 12a-c. In addition, secondary Mannich base was synthesized via Michael addition to the corresponding aldimine. The new compounds were investigated for antioxidant and antimicrobial activities. Compounds 2, 7c and 12a exhibited significant antimicrobial activity, whereas compounds 7a, 7b, 9b, 9c and 11 exhibited high antioxidant activity as compared to ascorbic acid, These compounds showed the best protective effect against DNA damage induced by bleomycin.
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8-Hydroxyquinolium chloroacetate (L 1 ) was synthesized and characterized. The results suggest that L 1 loses ethyl chloroacetate ion on coordination at low pH (2-5) and consequently it behaves as 8-hydoxyquinoline (L 2 ). Cu 2+ , Co 2+ , Pt 4+ , Pd 2+ , Au 3+ , Ag + and Nd 3+ complexes derived from L 2 have been synthesized and characterized using spectral, magnetic and thermal measurements. L 2 acts as a neutral bidentate ligand in the case of Cu 2+ , Co 2+ , Pt 4+ , Pd 2+ and Nd 3+ complexes and as a mononegative bidentate ligand in the case of Au 3+ and Ag + complexes. Octahedral geometry is proposed for Cu 2+ , Co 2+ (grey) and Pt 4+ complexes and square-planar for Co 2+ (green), Pd 2+ and Au 3+ complexes. The bond lengths, bond angles, chemical reactivities, binding energies and dipole moments for all compounds were evaluated using density functional theory and molecular electrostatic potential for L 1 . Superoxide dismutase radical scavenger-like activity and cytotoxic activity of the complexes towards HepG2 liver cancer cells has been screened. Cytotoxicity measurements show that Ag + and Pd 2+ complexes have the highest cytotoxic activity while L 1 , Cu 2+ , Co 2+ (grey), Co 2+ (green), Pt 4+ and Nd 3+ complexes have no cytotoxic activity.
The reaction of isatin 1 with benzaldehyde and a sec‐amine or the appropriate aldimine afforded the N‐Mannich bases 2–3 and the bis‐base 4. Treatment of 1 with glutaric dialdehyde and morpholine gave the bis‐base 5. Mannich reaction of the Schiff bases 6a–f derived from 1, led to the new Mannich bases and bis‐bases 7–9. The use of N‐methyl‐D‐glucamine as the amine component in the Mannich reaction with 6b–f led to the polyhydroxy Mannich bases 11–13.
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