Synthesis of 2-amino-8-chloro-4-phenyl-5,11-dihydro-6H-pyrido[2,3-a]carbazole-3-carbonitrile: Structural and biological evaluation

Indumathi, T.; Fronczek, Frank R.; Prasad, K. J. Rajendra

doi:10.1016/j.molstruc.2012.01.032

Cited by 19 publications

(8 citation statements)

References 22 publications

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“…The carbazole skeleton is a key structural motif contained in a wide variety of synthetic and natural compounds with biological activities. 6,7 Carbazole derivatives have demonstrated diverse pharmacological activities including antioxidant, 7 anti-inflammatory, 8 antibacterial, 9 antitumor, 10-11 anticonvulsant, 12 antipsychotic, 13 antidiabetic, 14 and larvicidal 15 properties. The cytotoxic activity of carbazole alkaloids has been correlated to their polycyclic, planar aromatic structure.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and biological evaluation of new carbazole derivatives as anti-cancer and anti-migratory agents

Vlaar

Castillo‐Pichardo

Medina

et al. 2018

Bioorganic & Medicinal Chemistry

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Based on the efficacy of EHop-016 as an inhibitor of migration and Rac1 activation, a new series of carbazole derivatives has been synthesized. Cytotoxic and anti-migratory effects of these compounds were evaluated in MCF-7 and MDA-MB-231 breast cancer cell lines. Preliminary investigations of their anticancer activity demonstrated that several compounds have moderate antiproliferative effects on cancer cell lines with GI values in the range of 13-50 µM. Furthermore, compounds 3b and 11b inhibit migration activity of metastatic cell line MDA-MB-231 by 32% and 34%, respectively. Compound 11b was shown to inhibit activation of the Rho GTPase Rac1 by 55% at 250 nM in both MDA-MB-231 and MDA-MB-435 cell lines. Compared with the IC of Rac1 inhibition by lead compound EHop-016 of 1.1 µM, compound 11b demonstrates 4X improved in vitro efficacy.

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Section: Introductionmentioning

confidence: 99%

Design, synthesis and biological evaluation of new carbazole derivatives as anti-cancer and anti-migratory agents

Vlaar

Castillo‐Pichardo

Medina

et al. 2018

Bioorganic & Medicinal Chemistry

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“…The Carbazole ring is present in a variety of naturally occurring medicinally active substances [6] e.g., carbazomycins [7,8] and murrayafoline A [9]. Series of carbazole derivatives including oxazinocarbazoles, isoxazolocarbazolequinone, pyrido-carbazolequinone [10], tetrahydrocarbazoles [11], benzocarbazoles [12], furo-carbazoles [13], pyridocarbazoles [14], pyrrolo-carbazoles [15,16], indolocarbazoles [17], oxazolinyl carbazoles [18], thienocarbazoles [19], imidazocarbazoles [20], thiazolocarbazoles [21], benzopyrano-carbazoles [22], benzofurano-carbazoles [23] and N -substituted carbazoles have been synthesized and are well known for their pharmacological activities [24] such as antioxidant [25], anti-inflammatory [26], antibacterial [27], antitumor [28,29], anticonvulsant [30], antipsychotic [31], antidiabetic [32], larvicidal [33] properties, etc. Keeping in view the so vast therapeutical potential of carbazoles, this review will summarize the biological activities so far reported for the N -substituted carbazoles.…”

Section: Introductionmentioning

confidence: 99%

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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“…Carbazole's rigid structure and large π‐conjugated system provide extra properties as photochromic compounds, in medicinal chemistry having antitumor, antihistaminic, antidiabetic, neuroprotective activity, anti TB activity, antineoplastic activity and also used as a fluorescent material . Carbazomycin A and Carbazomycin B are useful antibacterial and antifungal agents .…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Novel Pyrano‐Pyrido‐Carbazole Scaffolds Using Magnetic Fe₃O₄ Nanoparticles as a Heterogeneous Green and Reusable Catalyst

et al. 2020

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We reported a novel series of pyrano-pyrido-carbazol derivatives (PPCDs) 6(a-o), synthesized via the reaction of 4-hydroxypyridocarbazolone (3), aryl/heteroaryl aldehyde (4), and malononitrile (5), in water using Fe 3 O 4 magnetite nanoparticles (Fe 3 O 4 MNPs) as a heterogeneous novel catalyst at room temperature just in 60 mins under ultrasound. For this propose, Fe 3 O 4 MNPs with particle size 23.4 � 0.9 nm was successfully synthesized via a one-step novel coprecipitation method in aqueous medium by the use of a new alkaline agent i. e. 2-(ethylamino) ethanol and systematically characterized using field emission scanning electron microscopy (FESEM), highresolution transmission electron microscopy (HRTEM), energy dispersive analysis of X-ray (EDAX), X-ray diffraction (XRD), x-ray photoelectron spectroscopy (XPS) and Fourier transformed infrared (FTIR). Fe 3 O 4 MNPs show remarkably dramatic dispersion stability as evident from zetapotential (ζ) value of À 38.9 mV and hydrodynamic diameter (HD) of 238 nm and excellent specific surface area of 185 m 2 /g. Additionally, Fe 3 O 4 MNPs was easily separated after completion of the reaction, from the reaction mixture using the external magnet, and can be reused seven times without any considerable loss of its activity. The use of ultrasound made homogeneous dispersion of MNPs in water which accelerated the rate of reaction for the synthesis of PPCDs. This protocol has notable advantages like the synthesis of novel PPCDs with high yield in short reaction time, inexpensive catalyst, eco-safe, and also favour green chemistry protocol.

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Synthesis of 2-amino-8-chloro-4-phenyl-5,11-dihydro-6H-pyrido[2,3-a]carbazole-3-carbonitrile: Structural and biological evaluation

Cited by 19 publications

References 22 publications

Design, synthesis and biological evaluation of new carbazole derivatives as anti-cancer and anti-migratory agents

Design, synthesis and biological evaluation of new carbazole derivatives as anti-cancer and anti-migratory agents

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

Facile Synthesis of Novel Pyrano‐Pyrido‐Carbazole Scaffolds Using Magnetic Fe₃O₄ Nanoparticles as a Heterogeneous Green and Reusable Catalyst

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Synthesis of 2-amino-8-chloro-4-phenyl-5,11-dihydro-6H-pyrido[2,3-a]carbazole-3-carbonitrile: Structural and biological evaluation

Cited by 19 publications

References 22 publications

Design, synthesis and biological evaluation of new carbazole derivatives as anti-cancer and anti-migratory agents

Design, synthesis and biological evaluation of new carbazole derivatives as anti-cancer and anti-migratory agents

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

Facile Synthesis of Novel Pyrano‐Pyrido‐Carbazole Scaffolds Using Magnetic Fe3O4 Nanoparticles as a Heterogeneous Green and Reusable Catalyst

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Facile Synthesis of Novel Pyrano‐Pyrido‐Carbazole Scaffolds Using Magnetic Fe₃O₄ Nanoparticles as a Heterogeneous Green and Reusable Catalyst