Synthesis, characterization and biological evaluation of some newer carbazole derivatives

Sharma, Divyanshu; Kumar, Nitin; Pathak, Devender

doi:10.2298/jsc130123069s

Cited by 14 publications

(11 citation statements)

References 9 publications

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“…A series of N -substituted-carbazoles, synthesized by Sharma et al [48], have been screened for their antimicrobial activities. The compounds 5-[(9 H -carbazol-9-yl)methyl]- N -[(substituted phenyl)(piperazin-1-yl)methyl]-1,3,4-oxadiazol-2-amines 26 , 27 and 28 have displayed antimicrobial activity against bacterial strains ( S. aureus , B. subtilis , E. coli , P. aeruginosa ) and fungal strains ( C. albicans and A. niger ) with zones of inhibition of 11.1–24.0 mm in diameter at a concentration of 50 µg/mL (Figure 9).…”

Section: Biological Activities Of N-substituted Carbazolesmentioning

confidence: 99%

“…N -substituted carbazoles, synthesized by Sharma et al [48], have been screened for their antitumor activity. The compounds 5-[(9 H -carbazol-9-yl)-methyl]- N -[(substituted phenyl)(piperazin-1-yl)methyl]-1,3,4-oxadiazol-2-amines 41 – 45 were found to be effective against human breast cancer cell lines (MCF-7).…”

Section: Biological Activities Of N-substituted Carbazolesmentioning

confidence: 99%

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Recent Developments and Biological Activities of N-Substituted Carbazole Derivatives: A Review

et al. 2015

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Abstract:Carbazoles represent an important class of heterocycles. These have been reported to exhibit diverse biological activities such as antimicrobial, antitumor, antiepileptic, antihistaminic, antioxidative, anti-inflammatory, antidiarrhoeal, analgesic, neuroprotective and pancreatic lipase inhibition properties. A series of carbazole derivatives such as N-substituted carbazoles, benzocarbazoles, furocarbazoles, pyrrolocarbazoles, indolocarbazoles, imidazocarbazoles, etc. have been synthesized. The N-substituted derivatives have gained the attention of researchers due to their therapeutic potential against neurological disorders and cell proliferation. Herein an attempt is made to review the medicinal importance of recently synthesized N-substituted carbazoles.

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Section: Biological Activities Of N-substituted Carbazolesmentioning

confidence: 99%

Section: Biological Activities Of N-substituted Carbazolesmentioning

confidence: 99%

Recent Developments and Biological Activities of N-Substituted Carbazole Derivatives: A Review

et al. 2015

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“…Hence, it is an appropriate and sensitive assay to measure percentage growth inhibition. Percentage control growth was measured at four different concentrations (10,20,40 and 80 μg/ml) and compared with the standard. GI 50 was calculated for each compound and compared with standard.…”

Section: Resultsmentioning

confidence: 99%

“…It has been noticed that introduction of additional heterocyclic rings to the carbazole core tends to exert profound influence in increasing the anticancer activity. We recently investigated and reported the discovery of various carbazole derivatives having potent anticancer properties [18][19][20] . With this in mind, we envisaged the design and synthesis of a combination of carbazole with heterocyclic moiety like piperazine and imidazole to obtain therapeutically active anticancer agents.…”

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confidence: 99%

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2016

IJPSR

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Numerous carbazole derivatives were designed by the Chemsketch software followed by 3D optimization. Docking studies were performed using AUTODOCK 4.2.6 software to check their binding interactions with eukaryotic topoisomerase-I, based on the crystal structure of Human Topoisomerse-I-DNA complex (PDB ID: 1A35). Results of docking studies of designed carbazole derivatives were compared on the basis of their minimum binding energy with a well known topoisomerase-I inhibitor i.e. Adriamycin,. Above results were used to find out active compounds and two series of such active compounds i.e. 2-[(4, 5-dihydro-2-substitutedphenyl)imidazol-1-ylamino]-1-(9H-carbazol-9-yl)ethanone (3a-3e) and 2-(9H-carbazol-9-yl)-N'-[{(4-substitutedphenyl)(piperazin-1-yl)} methyl] aceto hydrazide (6a-6e) were synthesized. All the synthesized compounds were characterized by IR, 1 H NMR, 13C NMR, MASS spectrometry and elemental analysis and also screened for their in vitro anticancer activity against human breast cancer cell line (MCF 7) by sulphorodamine B (SRB) assay method. GI 50 was measured by using 10, 20, 40 and 80 µg/ml concentrations of tested compounds along with the standard i.e. Adriamycin. Results revealed that the tested compounds 3a, 3d, 6c, 6d and 6e were comparable to Adriamycin having GI 50 <10µg/ml. Compound 3a and 6c were found to be most active among all the tested compounds.

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“…Novel 5-[(9H-carbazol-9-yl)methyl]-N-[(substituted phenyl)(piperazin-1-yl)methyl]-1,3,4-oxadiazol-2-amines derivatives proved an antimicrobial effect and anti-proliferative activity, against the breast cancer cell line MCF7 [11].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and In Vitro Characterization of Novel Antimicrobial Agents Based on 6-Chloro-9H-carbazol Derivatives and 1,3,4-Oxadiazole Scaffolds

et al. 2020

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In this paper, we aimed to exploit and combine in the same molecule the carbazole and the 1,3,4-oxadiazole pharmacophores, to obtain novel carprofen derivatives, by using two synthesis pathways. For the first route, the following steps have been followed: (i) (RS)-2-(6-chloro-9H-carbazol-2-yl)propanonic acid (carprofen) treatment with methanol, yielding methyl (RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate; (ii) the resulted methylic ester was converted to (RS)-2-(6-chloro-9H-carbazol-2-yl)propane hydrazide (carprofen hydrazide) by treatment with hydrazine hydrate; (iii) reaction of the hydrazide derivative with acyl chlorides led to N-[(2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoil]-N′-R-substituted-benzoylhydrazine formation, which; (iv) in reaction with phosphorus oxychloride gave the (RS)-1-(6-chloro-9H-carbazol-2-yl)-1-(1,3,4-oxadiazol-2-yl)ethane derivatives. In the second synthesis pathway, new 1,3,4-oxadiazole ring compounds were obtained starting from carprofen which was reacted with isoniazid, in the presence of phosphorus oxychloride to form (RS)-1-(6-chloro-9H-carbazol-2-yl)-1-[5-(4-pyridyl)-1,3,4-oxadiazol-2-yl]ethane. The synthesized compounds were characterized by IR, 1H-NMR and 13C-NMR, screened for their drug-like properties and evaluated for in vitro cytotoxicity and antimicrobial activity. The obtained compounds exhibited a good antimicrobial activity, some of the compounds being particularly active on E. coli, while others on C. albicans. The most significant result is represented by their exceptional anti-biofilm activity, particularly against the P. aeruginosa biofilm. The cytotoxicity assay revealed that at concentrations lower than 100 μg/mL, the tested compounds do not induce cytotoxicity and do not alter the mammalian cell cycle. The new synthesized compounds show good drug-like properties. The ADME-Tox profiles indicate a good oral absorption and average permeability through the blood brain barrier. However, further research is needed to reduce the predicted mutagenic potential and the hepatotoxicity.

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Synthesis, characterization and biological evaluation of some newer carbazole derivatives

Cited by 14 publications

References 9 publications

Recent Developments and Biological Activities of N-Substituted Carbazole Derivatives: A Review

Recent Developments and Biological Activities of N-Substituted Carbazole Derivatives: A Review

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Design, Synthesis and In Vitro Characterization of Novel Antimicrobial Agents Based on 6-Chloro-9H-carbazol Derivatives and 1,3,4-Oxadiazole Scaffolds

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