Synthesis, antimicrobial activity and cytotoxicity of some new carbazole derivatives

Kaplancıklı, Zafer Asım; Yurttaş, Leyla; Turan-Zitouni, Gülhan; Özdemir, Ahmet; Ozic, Rasime; Ulusoylar-Yildirim, Şafak

doi:10.3109/14756366.2011.622273

Cited by 21 publications

(17 citation statements)

References 30 publications

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“…An extensive number of carbazoles with a very diverse set of substitutions were previously reported to exhibit large variations in their biological activities. 25 , 26 , 27 , 28 , 29 Of particular interest is that certain carbazoles, displaying a similar scaffold substitution to those reported in this article, have previously been reported as antifungal agents, but with no report on the antifungal mode of action. 25 The halogenated carbazole wiskostatin was identified as an antifungal compound, 25 but is also known to be a potent inhibitor of actin polymerization through inhibition of neural Wiskott-Aldrich syndrome protein (N-WASP) by interaction in a cleft in the regulatory GTPase-binding protein.…”

Section: Introductionmentioning

confidence: 64%

Elucidation of antimicrobial activity and mechanism of action by N-substituted carbazole derivatives

Clausen¹,

Kjellerup

Cohrt³

et al. 2017

Bioorganic & Medicinal Chemistry Letters

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Section: Introductionmentioning

confidence: 64%

Elucidation of antimicrobial activity and mechanism of action by N-substituted carbazole derivatives

Clausen¹,

Kjellerup

Cohrt³

et al. 2017

Bioorganic & Medicinal Chemistry Letters

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“…These compounds showed notable antimicrobial activity against the tested organisms. The compounds were also studied for their cytotoxic effects using MTT assay, where quinoline bearing derivative had the poor cytotoxic activity against NIH 3T3 (the murine fibroblast) cells [19].…”

Section: Antibacterial and Antifungal Activitymentioning

confidence: 99%

Mini Review on Therapeutic Profile of Phenoxy Acids and Thier Derivatives

Begum

Bharathi

S.r.g

2016

Int J Pharm Pharm Sci

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“…For example, 9-(9-ethyl-9H-carbazol-3-yl)-2-(phenoxy)acetamide derivatives, obtained by reacting 2-chloro-N-(9-ethyl-9H-carbazol-3-yl)acetamide with substituted phenols have shown antimicrobial activity [10].…”

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, antimicrobial activity and cytotoxicity of some new carbazole derivatives

Cited by 21 publications

References 30 publications

Elucidation of antimicrobial activity and mechanism of action by N-substituted carbazole derivatives

Elucidation of antimicrobial activity and mechanism of action by N-substituted carbazole derivatives

Mini Review on Therapeutic Profile of Phenoxy Acids and Thier Derivatives

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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