Synthesis and antimicrobial and antioxidant activities of simple saccharin derivatives with N-basic side chains

Abstract

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.

Synthesis and antioxidant evaluation of some new sulphadimidine incorporating thiophene moiety

“…Considering the facts that nearly all of the classes of heterocyclic compounds are biologically active and as a part of our continuous efforts towards the development of more potent antioxidant agents [16][17][18][19][20]. It was thought of interest to combine the above mentioned boilable rings together in a molecular framework to investigate the additive effect of these rings towards antioxidant activity.…”

Synthesis and Antioxidant Activity of Novel Series of Naphthoquinone Derivatives Attached to Benzothiophene Moiety

“…214°C. IR(KBr): ν/cm -1 = 3434(br,OH), 2933(C-H aliphatic), 1673 (br., 3CO), 1498 (N=N); 1 H-NMR (200 MHz, CDCl 3 ) δ (ppm): 1.45 (t, 3H, CH 3 , J = 6.9 Hz), 1.78-1.82 (m, 4H, C 5 -2H, C 6 -2H), 2.73-2.85 (m, 4H, C 4 -2H, C 7 -2H), 4.52 (q, 2H, CH 2 , J = 6.9 Hz), 7.79-8.40 (m, 4H, Ar-H), 13.52 (br, 1H, OH); 13 2-((3,4-dioxo-3,4-dihydronaphthalen-1-yl…”

“…Moreover many biological properties for 2-aminothiophene derivatives have been reported, such as A1 adenosine receptor allosteric enhancers [6,7], antifungal [8], antibacterial [9], antiproliferative [8], anti-inflammatory [10], antitumor and anti-HIV activities [7]. In view of the above mention and as a part of our continuous efforts towards the development of more potent antioxidant agents [11][12][13][14][15], it was thought of interest to combine the above mentioned boilable rings together in a molecular framework to investigate the additive effect of these rings towards antioxidant activities.…”

Synthesis and investigations of antimicrobial, antioxidant activities of novel di-[2-(3-alkyl/ aryl-4,5-dihydro-1h-1,2,4-triazol-5-one-4-yl)- azomethinephenyl] isophtalates and mannich base derivatives

“…Mannich bases have applications the field medicinal chemistry, the product synthetic polymers, the petroleum industry, as products used in water treatment, cosmetics, the dyes industry, etc 1 . In addition, Mannich bases have biological activity such as anticancer 2,3 , antibacterial [4][5][6] , antimycobacterial [7][8][9] , anti inflammatory [10][11][12] , analgesic 13,14 , antifungal 15,16 , antitumor 17,18 namely the 1-aryl-2-dimethylaminomethyl-2-propen-1-one hydrochlorides 1a-e and 1-aryl-3-dimethylamino-2-hydroxymethyl-1-propanone hydrochlorides 2a-e. A number of these compounds possess marked cytotoxic potencies (IC(50, antiviral [19][20][21] , antidepressant 22,23 , antiulcer 24 , anticonvulsant 25 , antimalarial 26,27 and antioxidant activities 28 .…”