Some new 1-nitro acridine derivatives as antimicrobial agents

Ngadi, Léon; Galy, Anne-Marie; Galy, Jean‐Pierre; Barbe, Jacques; Crémieux, A; Chevalier, Jacqueline; Sharples, Derek

doi:10.1016/0223-5234(90)90166-z

Cited by 54 publications

(19 citation statements)

References 17 publications

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“…The intermediary 6-nitro-4H-benzo [1,4]-oxazin-3-one, which were not isolated, were obtained as a result of the Knoevenagel condensation of activated 4-alkyl-6-nitro-4H-benzo [1,4]thiazin-3-one 2-3 with 4-methoxy or 4-bromobenzaldehydes in the presence of sodium methoxide in DMF. 9 The (2Z)-2-(4-methoxybenzylidene)-4-methyl-6-nitro-4H-benzo [1,4]thiazin-3-one 8 was first condensed in position 2; subsequently, alkylation was carried out at position 4.…”

Section: Resultsmentioning

confidence: 99%

Efficient synthesis of benzothiazine and acrylamide compounds

Souza¹,

Walfrido²,

Leite³

et al. 2010

Quím. Nova

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This article describes the synthesis of the new (2Z)-2-(4-methoxybenzylidene)-6-nitro-4H -benzo[1,4]thiazin-3-one, (2Z)-2-(4-methoxybenzylidene)-4-methyl-6-nitro-4H-benzo[1,4]thiazin-3-one, (2Z)-6-amino-2-(4-methoxybenzylidene)-4H -benzo[1,4]thiazin-3-one, (2Z)-6-butylamino-2-(4-methoxybenzylidene)-4-methyl-4H-benzo[1,4]-thiazin-3-one and (2E)-N-alkyl-N-(2-hydroxy-5-nitrophenyl)-3-phenylacrylamides and the spectroscopic data. The arylidenebenzothiazine compounds were prepared using the Knoevenagel condensation with substituted benzaldehydes in the presence of sodium methoxide in DMF. The presence of a nitro substituent in the 4-position, water and a slightly acid reaction medium in this condensation caused the rupture of the benzothiazine ring and subsequent formation of the phenylacrylamide compounds. A crystallographic data was presented for (2E)-3-(4-bromophenyl)-N-dodecyl-N -(2-hydroxy-5-nitrophenyl) acrylamide

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Section: Resultsmentioning

confidence: 99%

Efficient synthesis of benzothiazine and acrylamide compounds

Souza¹,

Walfrido²,

Leite³

et al. 2010

Quím. Nova

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“…Acridines are known to be biologically versatile compounds possessing several pharmacological activities, including antimicrobial (Wainwright, 2001;Ngadi et al,1990). Some researchers reported that all of the synthesized acridine derivatives exhibited moderate antibacterial and antifungal activity (Patel et al 2006).…”

Section: Antimicrobial Activitymentioning

confidence: 99%

“…Acridine and acridine-1,8-dione derivatives are important compounds because these compounds have pharmaceutical properties such as antitumor (Mikata et al, 1998), cytotoxic (Antonini et al, 1999), anticancer (Gamega et al, 1999), antimicrobial (Ngadi et al, 1990;Wainwright, 2001), fungicidal (Wainwright, 2001;Srivastava and Nizamuddin, 2004), anti-multidrug-resistant (Gallo et al, 2003), and widely prescribed as calcium b-blockers Vater, 1971, 1989;Berkan et al, 2002). They have similarities in structure to the biologically important compounds NADH and NADPH (Singh et al, 1982;Odabasoglu et al, 2007;Srividya et al, 1996).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial activities of novel bisacridine-1,8-dione derivatives

2010

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A series of bisacridine-1,8-dione derivatives were synthesized by one-pot reaction of aromatic dialdehydes, dimedone or cyclohexane-1,3-dione and primer aromatic amines in acetonitrile to utilizing Amberlyst-15 as a heterogeneous catalyst. The structures of compounds were characterized by FT-IR, NMR, and elemental analysis. Antimicrobial activities of these compounds were determined by using the disc diffusion method against to these gram-positive and gram-negative bacteria and yeast. The results were compared with reference discs.

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“…The 1,8‐dioxodecahydroacridine derivatives are important nitrogen containing heterocyclic compounds with applications in medicinal chemistries such as anti‐malarial, antimicrobial, antifungal, anti‐cancer and anti‐tumor agents, calcium β‐blockers, and in the production of laser colors ,. Furthermore, due to the intercalation versatility of some natural and synthesized acridine derivatives, they also function as DNA‐ and RNA‐binding structural motifs .…”

Section: Introductionmentioning

confidence: 99%

β‐Cyclodextrin Monosulphonic Acid Promoted Multicomponent Synthesis of 1,8‐Dioxodecahydroacridines in Water

Madankumar

Pitchumani

2018

ChemistrySelect

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A simple and efficient route for the synthesis of 1,8‐dioxodecahydroacridine derivatives in water is described using β‐cyclodextrin monosulphonic acid (prepared readily from β‐cyclodextrin obtained by enzymatic degradation of starch and chlorosulphonic acid), as an environmentally friendly acid catalyst. In this one‐pot method, 1,8‐dioxodecahydroacridine derivatives (19 compounds) are synthesized from dimedone, ammonium chloride and aromatic aldehydes in high yields (upto 94 %). All the synthesized compounds are extensively characterized by 1H and 13C‐NMR, ESI‐MS and also by their melting points. A plausible mechanism involving a multifunctional role for β‐cyclodextrin monosulphonic acid is proposed. The other key benefits and green credentials of this protocol are nitrogen assimilation (formation of organic nitrogen compounds from ammonium chloride in laboratory), use of water which is an environmentally benign solvent, solid acid catalyst, easy workup, reusability upto five times, milder reaction conditions and broad substrate scope.

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Some new 1-nitro acridine derivatives as antimicrobial agents

Cited by 54 publications

References 17 publications

Efficient synthesis of benzothiazine and acrylamide compounds

Efficient synthesis of benzothiazine and acrylamide compounds

Synthesis and antimicrobial activities of novel bisacridine-1,8-dione derivatives

β‐Cyclodextrin Monosulphonic Acid Promoted Multicomponent Synthesis of 1,8‐Dioxodecahydroacridines in Water

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