Synthesis, Antimicrobial Screening and In Silico Appraisal of Iminocarbazole Derivatives

Jejurkar, Valmik P.; Mali, Suraj N.; Kshatriya, Rajpratap; Chaudhari, Hemchandra K.; Saha, Satyajit

doi:10.1002/slct.201901890

Cited by 26 publications

(5 citation statements)

References 30 publications

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“…In brief, the Vilsmeyer Haack formylation of 4‐hydroxy carbazole 1 resulted in the formation of 3‐formyl‐4‐hydroxy carbazole 2 a along with its isomer 1‐formyl‐3‐hydroxy carbazole 2 b in the ratio of 75 : 25 . Chromatographic separation of the two isomers and the Boc protection of the 3‐formyl‐4‐hydroxy carbazole 2 a followed by base‐catalyzed substitution and concomitant cyclocondensation generated the furocarbazole 5 .…”

Section: Resultsmentioning

confidence: 99%

Rationally Designed Furocarbazoles as Multifunctional Aggregation Induced Emissive Luminogens for the Sensing of Trinitrophenol (TNP) and Cell Imaging

et al. 2020

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Two structurally unique aggregation induced emission (AIE)‐active luminogens have been designed and synthesized based on the furocarbazole skeleton. Such small molecule AIEgens were designed based on forbidden planarity and engineering a twist into the scaffold to realize induction of emission in the aggregated states. The structures were fully characterized and their thermal stabilities, electronic properties, photophysical and electrochemical properties were systematically investigated. The unique twist in the molecules as evident from their X‐ray crystal structure along with the short intermolecular interactions enhances the structural rigidification and restricts detrimental π–π stacking interactions, restricting the internal rotations (RIR) accompanied by a curb of the ICT process, resulting in enhanced emission in the aggregated state. This intriguing luminescent property enabled one of the luminogens to selectively detect trinitrophenol (TNP) over other nitroaromatics in both aqueous and organic media at nanomolar concentrations. Moreover, the good photostabilities and biocompatibilities empowered both luminogens to function as fluorescent bioprobes for cancer cell imaging.

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Section: Resultsmentioning

confidence: 99%

Rationally Designed Furocarbazoles as Multifunctional Aggregation Induced Emissive Luminogens for the Sensing of Trinitrophenol (TNP) and Cell Imaging

et al. 2020

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“…It is considered as potential building block for synthesis of bioactive compounds and prominent pharmacophore which mostly found as essential in many plants' origin compound like alkaloid. [1][2][3] Carbazole and its derivative have attributed promising biological activities such as anti-inflammatory, 4 antitumor, anti-diabetic, 5 anti-oxidant, 6 anti-tubercular, anti-bacterial, 7 anti-fungal, 8 and anti-histaminic activity. 9 According to Drissa new carbazole alkaloids named calothrixins from cell extracts of cyanobacterial Calothrix species.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Biological Screening of Novel Carbazole Tethered Oxyethylamino Derivatives as Antimicrobial Agent

Sabale,

Sayyad B,

2023

Ind. J. Pharm. Edu. Res

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Background: Carbazole is an important scaffold known to be associated with several biological activities including antimicrobial activities. Incorporation 4-oxothiazolidine moiety in carbazole moiety may lead to a new series of antimicrobials compounds. Aim: In this study, design and synthesis of novel carbazole tethered oxyethylamino was started with carbazole as basic pharmacophore and evaluated for antimicrobial activity. Materials and Methods: Molecular docking of carbazole derivatives was carried out by Schrödinger (Maestro 10.5v) active compound were Synthesized and screened for in vitro antimicrobial activity against Candida albicans and gram-positive and gram-negative bacterial strains such as Staphylococcus aureus, Bacillus subtilis, E. coli. MIC was calculated by standard agar tube dilution method. Results: All Compounds shown good antimicrobial activity at 25 (µg/ml) -510 (µg/ml). The molecular docking studies demonstrated ligand protein interaction. Conclusion: carbazole represent novel set of lead for the designing of novel antimicrobial agents.

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“…[38][39][40] Analysis and review of small molecules based on TRAM with potent anticancer activities has prompted us to design a pyrazolone ring containing triarylmethanes which aligns with our ongoing research project on designing and developing bioactive molecules as well as molecules for applications in biology. [41][42][43][44][45][46][47][48][49] It was interesting to note that several compounds are known in the literature, that possess a triphenylmethyl motif, appear to be potent anticancer agents. We, therefore, created a series of pyrazolone-appended hetero triarylmethane scaffolds.…”

Section: Introductionmentioning

confidence: 99%

“…Analysis and review of small molecules based on TRAM with potent anticancer activities has prompted us to design a pyrazolone ring containing triarylmethanes which aligns with our ongoing research project on designing and developing bioactive molecules as well as molecules for applications in biology [41–49] …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Anticancer Activity of Pyrazolone Appended Triarylmethanes (TRAMs)

et al. 2021

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The present work describes the design, synthesis, and evaluation of the anticancer properties of pyrazolone ring appended triarylmethanes by the condensation of diarylmethanols with pyrazolone in presence of a catalytic amount of p-TSA catalyst. The use of an inexpensive catalyst and accessing the desired product in good yields within a short span are the merits associated with this protocol. Furthermore, the in-silico, as well as in-vitro analysis and molecular docking of the designed molecules, were performed followed by their anticancer activity evaluation against cancer cell lines like MCF7, MDA-MB-231, HeLa, and DU-145. Few of the synthesized molecules demonstrated significant anticancer activity and could provide a new direction in the development of anti-cancer molecules.

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Synthesis, Antimicrobial Screening and In Silico Appraisal of Iminocarbazole Derivatives

Cited by 26 publications

References 30 publications

Rationally Designed Furocarbazoles as Multifunctional Aggregation Induced Emissive Luminogens for the Sensing of Trinitrophenol (TNP) and Cell Imaging

Rationally Designed Furocarbazoles as Multifunctional Aggregation Induced Emissive Luminogens for the Sensing of Trinitrophenol (TNP) and Cell Imaging

Design, Synthesis and Biological Screening of Novel Carbazole Tethered Oxyethylamino Derivatives as Antimicrobial Agent

Synthesis and Evaluation of Anticancer Activity of Pyrazolone Appended Triarylmethanes (TRAMs)

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