Synthesis, antitumour activity and structure–activity relationships of 5H-benzo[b]carbazoles

Asche, Christian; Frank, Walter; Albert, A.; Kucklaender, U.

doi:10.1016/j.bmc.2004.10.038

Cited by 65 publications

(22 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All the synthesized compounds 4a-o were evaluated for their anticancer activity against the human breast cancer cell line MCF7 by the SRB assay The in vitro anticancer study was realised at the Tata Memorial Centre, Advanced Centre for Treatment Research and Education in Cancer (ACTREC), Navi Mumbai, India. 1 In the present study, it was established that presence of an electronegative atom on the benzene ring makes MCF7 cell lines Синтетисана је серија нових деривата 5-[(9H-карбазол-9-ил)метил]-N-[(супституисани фенил)(пиперазин-1-ил)метил]-1,3,4-оксадиазол-2-амина (4a-o), полазећи од карбазола. It was found that for a large variety of polycyclic compounds, basic moieties attached to the ring system not only improve the solubility under physiological conditions, but also lead to an increase in anticancer activity.…”

Section: Pharmacological Screeningmentioning

confidence: 81%

Synthesis, characterization and biological evaluation of some newer carbazole derivatives

2014

View full text Add to dashboard Cite

A series of novel 5-[(9H-carbazol-9-yl)methyl]-N-[(substituted phenyl)(piperazin-1-yl)methyl]-1,3,4-oxadiazol-2-amines (4a-o) derivatives was synthesized by starting with carbazole, which on reaction with ethyl chloroacetate yielded ethyl 2-(9H-carbazole-9-yl)acetate (1). Compound 1 on reaction with semicarbazide followed by cyclisation with sulphuric acid gave 5-((9H-carbazole-9-yl)-1,3,4-oxadiazol-2-amine (3), which through Mannich reaction with piperazine and a variety of aromatic aldehydes in the presence of acetic acid yielded the titled compounds (4a-o). The structures of compounds were characterized by UV, FT-IR, 1 H-NMR and MS spectral studies, and by elemental analysis. All the derivatives were evaluated for their antibacterial, antifungal and anticancer activities. Among the tested compounds, 4a, 4d, 4e and 4n exhibited significant antibacterial and antifungal activity, while the compounds 4a, 4d, 4k and 4n were found to be active on the human breast cancer cell line MCF7.

show abstract

Section: Pharmacological Screeningmentioning

confidence: 81%

Synthesis, characterization and biological evaluation of some newer carbazole derivatives

2014

View full text Add to dashboard Cite

show abstract

“…They were reported to possess many biological activities, such as antitumor activity [21], HIV integrase inhibition [22], prolonged analgesic activity [23], heat shock protein 90 (Hsp90) inhibition [24], mitogen-activated protein kinaseactivated protein kinase-2 (MAPKAP-k2) inhibition [25], antibacterial and antifungal activities [26]. Moreover, they had been increasingly important intermediates in the syntheses of various biological active heterocyclic compounds because of their unique structure, such as indolo [2,3-a]carbazoles [22], furo [2,3-a]carbazoles [27], pyrimidino [4,5-a]carbazoles [28], pyrazolino[3,2,1-j,k]carbazoles [29], thieno [2,3-a]carbazoles [30], and so on.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and In‐Vitro Antitumor Activities of Some Mannich Bases of 9‐Alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones

Chen

Lou

Liu

et al. 2009

Archiv der Pharmazie

View full text Add to dashboard Cite

A novel series of 2-substituted aminomethyl-9-alkyl-1,2,3,4-tetrahydrocarbazole-1-ones 5a-q was synthesized via aminomethylation of 9-alkyl-1,2,3,4-tetrahydrocarbazole-1-ones 4a-e with hydrochlorides of the respective amines 6a-m. The structures of these newly synthesized compounds were characterized by (1)H-NMR, MS, and elemental analysis. All the compounds were tested for their cytotoxic activity in vitro against four human tumor cell lines including human non-small lung cancer cells (A549), human gastric adenocarcinoma (SGC), human colon cancer cell (HCT116), human myeoloid leukemia cells (K562), and one multi-drug resistant subline (KB-VCR). Most compounds showed moderate to potent cytotoxic activity against the tested cell lines. Preliminary mechanism research indicated that the most promising compound, 2-diethylaminomethyl-9-methyl-1,2,3,4-tetrahydrocarbazole-1-one 5c, exhibited a potential inhibitory effect against microtubule.

show abstract

“…Carbazole derivatives having nitrogen containing rigid aromatic heterocyclic moiety with desirable electronic charge transfer properties along with an extended π -conjugated system [8] exhibit diverse biological activities such as antibacterial [3, 9, 10], antifungal [11, 12], antiviral [13], anticancer [14], and various other activities. Besides the general antibacterial activity, carbazoles were shown to have a significant antituberculosis activity [15, 16].…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Activity of Murrayaquinone A and 6-Methoxy-3,7-dimethyl-2,3-dihydro-1H-carbazole-1,4(9H)-dione

Chakraborty

Saha

2014

International Journal of Microbiology

View full text Add to dashboard Cite

The antibacterial activity of Murrayaquinone A (10), a naturally occurring carbazoloquinone alkaloid, and 6-methoxy-3,7-dimethyl-2,3-dihydro-1H-carbazole-1,4(9H)-dione (11), a synthetic carbazoloquinone, both obtained during the development of the synthesis of Carbazomycin G, having unique quinone moiety, was studied against Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative (Escherichia coli and Pseudomonas sp.) bacteria. Compound 10 showed antibacterial activities against both of Escherichia coli and Staphylococcus aureus whereas compound 11 indicated the activity against Staphylococcus aureus only. Both compounds 10 and 11 exhibited minimum inhibitory concentration (MIC) of 50 μg mL−1 against Staphylococcus aureus.

show abstract

Synthesis, antitumour activity and structure–activity relationships of 5H-benzo[b]carbazoles

Cited by 65 publications

References 20 publications

Synthesis, characterization and biological evaluation of some newer carbazole derivatives

Synthesis, characterization and biological evaluation of some newer carbazole derivatives

Synthesis and In‐Vitro Antitumor Activities of Some Mannich Bases of 9‐Alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones

Antibacterial Activity of Murrayaquinone A and 6-Methoxy-3,7-dimethyl-2,3-dihydro-1H-carbazole-1,4(9H)-dione

Contact Info

Product

Resources

About