Novel halogenated pyrido[2,3-<i>a</i>]carbazoles with enhanced aromaticity as potent anticancer and antioxidant agents: rational design and microwave assisted synthesis

Badavath, Vishnu Nayak; Maji, Siddhartha; Muhammad, Shabbir; Sekar, M.

doi:10.1039/c8nj06504g

Cited by 15 publications

(5 citation statements)

References 42 publications

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“…Other methods have been tried to determine the binding modes. Compared to some literature, the binding constant of compound 2 appears to have a remarkable result [22] …”

Section: Resultsmentioning

confidence: 75%

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Synthesis, DNA Binding Properties, Molecular Docking and ADME Studies of Schiff Base Compound Containing Pyridine‐Propargyl Group

Güngör

2023

Chemistry & Biodiversity

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The structure of the pyridine‐based Schiff base compound containing the propargyl group was characterized by NMR spectroscopy. Binding of compound 2 with double‐stranded fish sperm DNA (Fsds‐DNA) was investigated using viscosity measurement studies and UV‐Vis and fluorescence spectral techniques. Binding of compound 2 with Fsds‐DNA results in minor hypochromism with no change in absorption maxima and fluorescence quenching with almost no shift in emission maxima, which can be attributed to the groove‐binding mode of the interaction. The binding constant was found to be 4.7 x 104 M‐1. The Fsds‐DNA viscosity measurement, KI quenching and NaCl quenching studies and the competitive interaction between compound 2 and ethidium bromide with DNA confirm the proposed binding mode. In addition, interactions between compound 2 and the DNA double helix were analysed by molecular docking study in order to determine the binding mode and binding affinity. As a result of molecular docking, the binding affinity of the 2‐DNA complex, which has the most stable conformation ‐8.10 kcal/mol and it is located in its minor groove. In addition, molecular docking and ADME studies for compound 2 were also performed.

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“…Other methods have been tried to determine the binding modes. Compared to some literature, the binding constant of compound 2 appears to have a remarkable result [22] …”

Section: Resultsmentioning

confidence: 75%

“…Compared to some literature, the binding constant of compound 2 appears to have a remarkable result. [22] The binding constants (Kb) of compound 2 to the FSdsDNA are comparable to that of the binding constant of the ethidium bromide (an intercalating agent with K b = 1.23 � 0.07×10 5 M À 1 ). [23]…”

Section: Dna Binding Properties Of Compoundmentioning

confidence: 94%

Synthesis, DNA Binding Properties, Molecular Docking and ADME Studies of Schiff Base Compound Containing Pyridine‐Propargyl Group

Güngör

2023

Chemistry & Biodiversity

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“…The majority of cancer chemotherapeutic drugs, on the other hand, have a negative impact on most normal cells [51] . Therefore, it is critical to discover novel anticancer chemical substances that are less harmful to the host cell [52–56] . The usage of heterocyclic chemicals was crucial in the control and elimination of cancer.…”

Section: Resultsmentioning

confidence: 99%

“…[51] Therefore, it is critical to discover novel anticancer chemical substances that are less harmful to the host cell. [52][53][54][55][56] The usage of heterocyclic chemicals was crucial in the control and elimination of cancer. Heterocyclic compounds are frequently employed as scaffolding for the arrangement of pharmacophores to produce effective and discerning medications.…”

Section: Antitumor Evaluationmentioning

confidence: 99%

Synthesis of Pyrazole, Pyridine, and Pyrimidine Derivatives Incorporating Glucaminoid Moiety and Their Antioxidant, Antitumor Activities and Docking Study

et al. 2023

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The reaction of N‐(4‐(phenyldiazenyl) phenyl) carbonohydrazonoyl dicyanide (2) with N‐methyl glucamine afforded 3‐amino‐3‐(methyl (2,3,4,5,6‐pentahydroxyhexyl)amino)‐2‐((4‐(phenyldiazenyl)phenyl)diazenyl)acrylonitrile (3). Additionally, compound 2 produced the pyrazole derivatives 4 and 6, respectively, by reactions with hydrazine hydrate and malononitrile. Moreover, when enaminonitrile 3 was treated with malononitrile, N,N‐Dimethylformamide ‐ dimethyl acetal, and thiourea, it generated the glucaminoid derivatives 9, 10, and 13, respectively. In pyridine, compound 19 was obtained when enaminonitrile 3 interacted with the carbon disulfide. While in sodium hydroxide in N,N‐Dimethylformamide, instead of pyridine, it afforded the methyl carbamodithioate 23. Finally, pyrimidinethione derivative 26 was produced when the enaminonitrile 3 and phenyl isothiocyanate interacted. All new compounds were well established by both spectral and elemental analyses. The antitumor activities were evaluated by testing their impact on the viability of four different cell lines: HepG2 (human hepatocellular liver carcinoma), WI‐38 (human lung fibroblast), VERO (African green monkey kidney epithelial), and MCF‐7 (human breast adenocarcinoma). The antitumor study showed that compound 23 has very strong antitumor activity against the HEPG‐2 cell line. The synthesized compounds were analyzed by docking studies that showed good binding scores against the diverse amino acids of the selected proteins B‐Cell Leukemia/Lymphoma‐2 (Bcl‐2). The conducted docking studies were found to be consistent with cytotoxic results.

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“…41,42 Carbazole is a promising scaffold for the development of new drugs owing to its good drug-like properties and excellent pharmacological activities. 43,44 Recent studies have showed that carbazole derivatives possessed various biological activities, that is, antitumor, 45 antiviral, 46 antioxidant, 47 antibacterial, 48 anti-inflammatory, 49 antituberculosis, 50 and so on. Currently, several commercial drugs contain the carbazole scaffold, including antihypertensive drugs carvedilol 51 and carazolol, 52 as well as anticancer drugs ellipticine 53 and elliptinium acetate.…”

Section: ■ Introductionmentioning

confidence: 99%

Development of Highly Potent Carbazole Amphiphiles as Membrane-Targeting Antimicrobials for Treating Gram-Positive Bacterial Infections

Lin

Liu

et al. 2020

J. Med. Chem.

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The development of new antimicrobial agents capable of curing drug-resistant bacteria-induced infections is becoming a major challenge to the global healthcare system. To develop antimicrobials with new molecular entities, a series of novel carbazole-based compounds were designed and synthesized by biomimicking the structural properties and biological function of antimicrobial peptides. Compound 29 was selected as a lead compound from the structure−activity relationship analyses and biological activity evaluation. Compound 29 showed excellent antimicrobial activity against Gram-positive bacteria (MICs = 0.78−1.56 μg/mL), poor hemolytic activity (HC 50 > 200 μg/mL), and low cytotoxicity to mammalian cells. Compound 29 had fast bactericidal properties and effectively prevented bacterial resistance in laboratory simulations. Antibacterial mechanism studies revealed that compound 29 directly destroyed bacterial cell membranes, leading to bacterial deaths. Importantly, compound 29 displayed an excellent efficacy in a murine bacterial keratitis model caused by Staphylococcus aureus ATCC29213.

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Novel halogenated pyrido[2,3-a]carbazoles with enhanced aromaticity as potent anticancer and antioxidant agents: rational design and microwave assisted synthesis

Abstract: Design and synthesis a series of pyrido[2,3-a]carbazoles for their anticancer and antioxidant activity.

Cited by 15 publications

References 42 publications

Synthesis, DNA Binding Properties, Molecular Docking and ADME Studies of Schiff Base Compound Containing Pyridine‐Propargyl Group

Synthesis, DNA Binding Properties, Molecular Docking and ADME Studies of Schiff Base Compound Containing Pyridine‐Propargyl Group

Synthesis of Pyrazole, Pyridine, and Pyrimidine Derivatives Incorporating Glucaminoid Moiety and Their Antioxidant, Antitumor Activities and Docking Study

Development of Highly Potent Carbazole Amphiphiles as Membrane-Targeting Antimicrobials for Treating Gram-Positive Bacterial Infections

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