Electrophilic Substitution of Dimethyl 1-Methylcarbazole-2,3-dicarboxylate: Synthesis of New<i>b</i>-Fused Carbazoles as Potential Antitumor Agents

Haider, N.; Marian, Brigitte; Nagel, Thomas; Tarnai, Markus; Tropper, Katharina

doi:10.5935/0103-5053.20140178

Cited by 2 publications

(4 citation statements)

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“…Tricyclic carbazole nucleus is an integral part of naturally occurring alkaloids and synthetic derivatives, possessing various biological activities such as antiviral [1] antibacterial [2] antimicrobial [3] anti-inflammatory [4] antifungal, antiprotozoological [5] antioxidant [6] antidiarrhoeal [7] anticancer [8] etc. The derivatization of carbazole derivatives, especially with fused heterocyclic compounds has attained a significant attention in search of newer antimicrobial molecules and anticancer with an enhanced pharmacological activity using bio-isosteric replacements [9,10]. The development of newer compounds with enhanced activity of carbazole nucleus is constantly under investigation due to their high affinity towards DNA.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Pharmacological Evaluation of Tricyclic Carbazole Annulated with Substituted Benzothiazole-2-Amine Under Microwave Irradiation

Sharma¹

2018

BJSTR

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Tricyclic carbazole nucleus is an integral part of naturally occurring alkaloids and synthetic derivatives, possessing various potential biological activities such as anticancer, antimicrobial and antiviral. Binding mechanism of carbazole with target receptor as molecule or fused molecule exhibit potential lethal effect. In the present work, development of microwave assisted organic synthesis (MAOS) methods for synthesis of a novel series of N-Mannich bases of carbazole annulled with substituted benzothiazole-2-amine with carbazole (secondary aromatic amine) and aldehyde derivatives has been presented. All the synthesized compounds were characterized by physicochemical and spectral methods viz. ultra-violet, FT-IR, 1H-NMR, Mass and elemental analysis. The newly developed MAOS method evident the improvement in percentage yield (% yield) and reaction time compared to conventional method. The synthesized compounds were screened for antibacterial (B. subtilis, S. aureus, E. coli and P. aeruginosa) and antifungal activities (A. niger and C. albicans) using impregnated paper-disc diffusion method. Compounds posses electronegative functional group at C5 and C6 position showed significant potential for antibacterial (compd. 2c and 3c) and antifungal (compd. 1b, 2b and 7b). Furthermore, in silico (PASS prediction) analysis predicts the possible mechanism of synthesized compounds could be a glycosylphosphatidylinositol phospholipase D inhibitor (antifungal action) and potassium channel blocker (antibacterial action).

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Section: Introductionmentioning

confidence: 99%

Synthesis and Pharmacological Evaluation of Tricyclic Carbazole Annulated with Substituted Benzothiazole-2-Amine Under Microwave Irradiation

Sharma¹

2018

BJSTR

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“…To a solution of dimethyl 1-methyl-6-nitro-9H-carbazole-2,3-dicarboxylate [11] (1) (171 mg, 0.5 mmol) and 98% hydrazine monohydrate (510 mg, 10 mmol) in MeOH (30 mL) was added 10% Pd/C (20 mg), and the mixture was refluxed for 30 min. The catalyst was removed by filtration and rinsed carefully with MeOH.…”

Section: Dimethyl 6-amino-1-methyl-9h-carbazole-23-dicarboxylate (2)mentioning

confidence: 99%

“…methyl-9H-carbazole-2,3-dicarboxylate (2) from the corresponding 6-nitro compound (1) [11] by a catalytic transfer hydrogenation protocol.…”

Section: M849 (Page 2)mentioning

confidence: 99%

“…As a key intermediate for the synthesis of these tetracycles, 1-methylcarbazole-2,3-dicarboxylic esters have been used and the latter were found to provide a convenient access also to some cytotoxic 4-methylpyrrolo [3,4-b]carbazole-1,3(2H,5H)-diones [10], which again feature the 1-methylcarbazole motif. In the course of extensive structural variation of the A-ring substitution pattern of such b-fused 1-methylcarbazoles, we recently reported the synthesis and cyclisation reactions of some halo-and nitro-substituted 1-methylcarbazole-2,3-dicarboxylic acid dimethyl esters [11]. As a further extension of our building-block library, we here describe the convenient preparation of dimethyl 6-amino-1-OPEN ACCESS…”

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Dimethyl 6-Amino-1-methyl-9H-carbazole-2,3-dicarboxylate

Haider

Tropper

2015

Molbank

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Abstract:The title compound (2) was prepared in high yield by catalytic transfer hydrogenation of the 6-nitro precursor (1), using hydrazine hydrate as the hydrogen source. Under the conditions employed, the ester groups remain unaffected. The new compound was fully characterised by elemental analysis, . Such compounds are known to act as topoisomerase II poisons and as another common structural feature they possess a heteroaromatic ring fused to the carbazole 2,3-bond. Typically, this is a pyridine unit (like in olivacine and its isomer, ellipticine [3]), but there are also examples for various diazine-fused 1-methyl-and 1,4-dimethylcarbazoles, exhibiting antitumor activity [4]. Among them, pyridazino [4,5-b]carbazoles (representing a 3-aza-olivacine scaffold) have been reported by us [5][6][7][8] and others [9]. As a key intermediate for the synthesis of these tetracycles, 1-methylcarbazole-2,3-dicarboxylic esters have been used and the latter were found to provide a convenient access also to some cytotoxic 4-methylpyrrolo [3,4-b]carbazole-1,3(2H,5H)-diones [10], which again feature the 1-methylcarbazole motif. In the course of extensive structural variation of the A-ring substitution pattern of such b-fused 1-methylcarbazoles, we recently reported the synthesis and cyclisation reactions of some halo-and nitro-substituted 1-methylcarbazole-2,3-dicarboxylic acid dimethyl esters [11]. As a further extension of our building-block library, we here describe the convenient preparation of dimethyl 6-amino-1-OPEN ACCESS

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Electrophilic Substitution of Dimethyl 1-Methylcarbazole-2,3-dicarboxylate: Synthesis of Newb-Fused Carbazoles as Potential Antitumor Agents

Cited by 2 publications

References 1 publication

Synthesis and Pharmacological Evaluation of Tricyclic Carbazole Annulated with Substituted Benzothiazole-2-Amine Under Microwave Irradiation

Synthesis and Pharmacological Evaluation of Tricyclic Carbazole Annulated with Substituted Benzothiazole-2-Amine Under Microwave Irradiation

Dimethyl 6-Amino-1-methyl-9H-carbazole-2,3-dicarboxylate

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