Synthesis of hetero annulated isoxazolo-, pyrido- and pyrimido carbazoles: Screened for in vitro antitumor activity and structure activity relationships, a novel 2-amino-4-(3'-bromo-4'-methoxyphenyl)-8-chloro-11 H -pyrimido[4,5- a ]carbazole as an antitumor agent

Murali, Karunanidhi; Sparkes, Hazel A.; Prasad, K. J. Rajendra

doi:10.1016/j.ejmech.2017.02.009

Cited by 18 publications

(3 citation statements)

References 30 publications

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“…Among pyrimidocarbazole derivatives 36a–d (Figure 46), 2-amino-4-(3′-bromo-4′-methoxyphenyl)-8-chloro-11 H -pyrimido[4,5- a ]carbazole 36d showed the best cytotoxic efficacy against both MCF-7 and A-459 cancer cell lines (IC 50 value of 20 and 25 µM, respectively). Compounds 36a–c also exhibited stronger cytotoxic activity against MCF-7 cell lines 80 .…”

Section: Tetracyclic Fused Carbazolesmentioning

confidence: 97%

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

Issa

Prandina

Bedel

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

121

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For over half a century, the carbazole skeleton has been the key structural motif of many biologically active compounds including natural and synthetic products. Carbazoles have taken an important part in all the existing anti-cancer drugs because of their discovery from a large variety of organisms, including bacteria, fungi, plants, and animals. In this article, we specifically explored the literature from 2012 to 2018 on the anti-tumour activities reported to carbazole derivatives and we have critically collected the most significant data. The most described carbazole anti-tumour agents were classified according to their structure, starting from the tricyclic–carbazole motif to fused tetra-, penta-, hexa- and heptacyclic carbazoles. To date, three derivatives are available on the market and approved in cancer therapy.

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Section: Tetracyclic Fused Carbazolesmentioning

confidence: 97%

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

Issa

Prandina

Bedel

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

121

View full text Add to dashboard Cite

show abstract

“…Compound 22 demonstrated substantial activity against MCF-7 with the IC 50 value of 20 µM as compared to cisplatin IC 50 value of 18 µM. All other compounds showed moderate to powerful activity and consequent apoptotic cell death, which was demonstrated by AO/EB and DAPI of fluorescence microscopy analysis [ 138 ]. Wang et al (2011) designed and synthesized substituted 11H-benzo[a] carbazole-5-carboxamides as novel anticancer agents and tested them against human cancer A549 and HCT-116 cell lines.…”

Section: Current Advances In Nitrogen Containing Heterocycles As Anti...mentioning

confidence: 99%

Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective

et al. 2023

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Cancer is one of the major healthcare challenges across the globe. Several anticancer drugs are available on the market but they either lack specificity or have poor safety, severe side effects, and suffer from resistance. So, there is a dire need to develop safer and target-specific anticancer drugs. More than 85% of all physiologically active pharmaceuticals are heterocycles or contain at least one heteroatom. Nitrogen heterocycles constituting the most common heterocyclic framework. In this study, we have compiled the FDA approved heterocyclic drugs with nitrogen atoms and their pharmacological properties. Moreover, we have reported nitrogen containing heterocycles, including pyrimidine, quinolone, carbazole, pyridine, imidazole, benzimidazole, triazole, β-lactam, indole, pyrazole, quinazoline, quinoxaline, isatin, pyrrolo-benzodiazepines, and pyrido[2,3-d]pyrimidines, which are used in the treatment of different types of cancer, concurrently covering the biochemical mechanisms of action and cellular targets.

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“…Many natural products or their derivatives have been demonstrated to have extensive antitumor activities by inducing apoptosis ( Chen et al, 2015 ; Liu et al, 2015 ; Padmaja et al, 2015 ; Bailly, 2020 ; Greco et al, 2021 ) and inhibiting mitosis ( Thomas et al, 2016 ; Davison and Sperry, 2017 ; Yokoyama et al, 2019 ). As an important class of aromatic heterocyclic compounds, carbazole alkaloid derivatives have long been used in medicinal chemistry ( Murali et al, 2017 ; Sun et al, 2017 ; Zhou et al, 2018 ; Cao et al, 2019 ; Issa et al, 2019 ; Liu et al, 2019 ; Rassias et al, 2019 ; Liu et al, 2020 ; Liu et al, 2021 ; Wang et al, 2022 ), agrochemicals ( Kong et al, 2016 ; Wang et al, 2017 ; Dang et al, 2018 ; Sun et al, 2020 ; Xie et al, 2020 ) and other fields. So, how to realize the functional modification of carbazole ring to improve its activity is always an important research direction.…”

Section: Introductionmentioning

confidence: 99%

Structural diversity-guided optimization of carbazole derivatives as potential cytotoxic agents

et al. 2023

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Carbazole alkaloids, as an important class of natural products, have been widely reported to have extensive biological activities. Based on our previous three-component reaction to construct carbazole scaffolds, we introduced a methylene group to provide a rotatable bond, and designed series of carbazole derivatives with structural diversity including carbazole amide, carbazole hydrazide and carbazole hydrazone. All synthesized carbazole derivatives were evaluated for their in vitro cytotoxic activity against 7901 (gastric adenocarcinoma), A875 (human melanoma) and MARC145 (African green monkey kidney) cell lines. The preliminary results indicated that compound 14a exhibited high inhibitory activities on 7901 and A875 cancer cells with the lowest IC50 of 11.8 ± 1.26 and 9.77 ± 8.32 μM, respectively, which might be the new lead compound for discovery of novel carbazole-type anticancer agents.

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Synthesis of hetero annulated isoxazolo-, pyrido- and pyrimido carbazoles: Screened for in vitro antitumor activity and structure activity relationships, a novel 2-amino-4-(3'-bromo-4'-methoxyphenyl)-8-chloro-11 H -pyrimido[4,5- a ]carbazole as an antitumor agent

Cited by 18 publications

References 30 publications

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective

Structural diversity-guided optimization of carbazole derivatives as potential cytotoxic agents

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