Synthesis, anticancer evaluation and molecular docking studies of 2,5-bis(indolyl)-1,3,4-oxadiazoles, Nortopsentin analogues

Sreenivasulu, Reddymasu; Tej, Mandava Bhuvan; Jadav, Surender Singh; Sujitha, Pombala; Kumar, C. Ganesh; Raju, Rudraraju Ramesh

doi:10.1016/j.molstruc.2020.127875

Cited by 41 publications

(15 citation statements)

References 38 publications

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“…Because of their unique properties, metal complexes, especially those containing transition metals have gained tremendous attention as anticancer agents . Most recently, the metal complexes derived from pyrrole moieties have shown good antiproliferative activity against lymphocytic, cervical, and breast cancer cells. − A series of pyrrole-based ferrocene complexes were also reported to be cytotoxic against breast cancer (MCF-7), colon cancer (HT-29) cell lines, and noncancerous breast cells (MCF-10A) . Equally, the known cancer drug to date, cisplatin has undergone various derivatization.…”

Section: Introductionmentioning

confidence: 99%

New Palladium(II) and Platinum(II) Complexes Based on Pyrrole Schiff Bases: Synthesis, Characterization, X-ray Structure, and Anticancer Activity

et al. 2020

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New palladium (Pd)II and platinum (Pt)II complexes (C1–C5) from the Schiff base ligands, R-(phenyl)methanamine (L1), R-(pyridin-2-yl)methanamine (L2), and R-(furan-2-yl)methanamine (L3) (R-(E)-N-((1H-pyrrol-2-yl) methylene)) are herein reported. The complexes (C1–C5) were characterized by FTIR, 1H and 13C NMR, UV–vis, and microanalyses. Single-crystal X-ray crystallographic analysis was performed for the two ligands (L1–L2) and a Pt complex. Both L1 and L2 belong to P21/n monoclinic and P-1 triclinic space systems, respectively. The complex C5 belongs to the P21/c monoclinic space group. The investigated molar conductivity of the complexes in DMSO gave the range 4.0–8.8 μS/cm, suggesting neutrality, with log P values ≥ 1.2692 ± 0.004, suggesting lipophilicity. The anticancer activity and mechanism of the complexes were investigated against various human cancerous (Caco-2, HeLa, HepG2, MCF-7, and PC-3) and noncancerous (MCF-12A) cell lines using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and Apopercentage assays, respectively. C5 demonstrated strong DNA-binding affinity for calf thymus DNA (CT-DNA) with a binding constant of 8.049 × 104 M–1. C3 reduced cell viability of all the six cell lines, which included five cancerous cell lines, by more than 80%. The C5 complex also demonstrated remarkably high selectivity with no cytotoxic activity toward the noncancerous breast cell line but reduced the viability of the five cancerous cell lines, which included one breast cancer cell line, by more than 60%. Further studies are required to evaluate the selective toxicity of these two complexes and to fully understand their mechanism of action.

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Section: Introductionmentioning

confidence: 99%

New Palladium(II) and Platinum(II) Complexes Based on Pyrrole Schiff Bases: Synthesis, Characterization, X-ray Structure, and Anticancer Activity

et al. 2020

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“…This compound act on the colchicine binding site of the tubulin polymer and blocks its polymerization. [38] The effects of substitution on potency and selectivity of the compounds were thus assessed by synthesizing and evaluating novel bis indolyl hydroxy maleimides functionalized at the…”

Section: Bis Indole Derivativesmentioning

confidence: 99%

Indole Derived Anticancer Agents

et al. 2022

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Indole moiety is a magnificent nucleus in the development of anticancer drugs. The pharmacological profile of indole is excellent in targeting a wide range of proteins, enzymes. An indole has a nitrogen atom that is capable of forming hydrogen bonds with the targets emphasizing its potential. Many studies have demonstrated the effectiveness of indole in the treatment of cancer by working through various pathways. Indole-based drugs got market approval to be used as chemotherapeutics, such as vincristine and vinblastine which encourage researchers to work on indole derivatives for cancer treatment with a better pharmacokinetic profile. This prompted us to review on indole derivatives as anticancer agents to bring out their potential derivatives under study. This study encompasses literature published between 2014 and 2021 on indole scaffold that exhibits in vitro and in vivo potential against cancer by searching PubMed, Google Scholar, and Science Direct databases. The search terms were "anticancer", "indole", "cell lines", "structure-activity relationship" and "cytotoxic activity."[a] A.

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“…Interestingly, none of the compounds was cytotoxic to normal human embryonic kidney cells HEK-293. It was worth noting that compound 37a is a promising lead drug 44 .…”

Section: Oxadiazolementioning

confidence: 99%

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Wang

Sun

Jia

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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Oxadiazole is a five-membered heterocyclic compound containing two nitrogen atoms and one oxygen atom. The 1,3,4-oxadiazole and 1,2,4-oxadiazole have favourable physical, chemical, and pharmacokinetic properties, which significantly increase their pharmacological activity via hydrogen bond interactions with biomacromolecules. In recent years, oxadiazole has been demonstrated to be the biologically active unit in a number of compounds. Oxadiazole derivatives exhibit antibacterial, anti-inflammatory, anti-tuberculous, anti-fungal, anti-diabetic and anticancer activities. In this paper, we report a series of compounds containing oxadiazole rings that have been published in the last three years only (2020–2022) as there was no report or their activities described in any article in 2019, which will be useful to scientists in research fields of organic synthesis, medicinal chemistry, and pharmacology.

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Synthesis, anticancer evaluation and molecular docking studies of 2,5-bis(indolyl)-1,3,4-oxadiazoles, Nortopsentin analogues

Cited by 41 publications

References 38 publications

New Palladium(II) and Platinum(II) Complexes Based on Pyrrole Schiff Bases: Synthesis, Characterization, X-ray Structure, and Anticancer Activity

New Palladium(II) and Platinum(II) Complexes Based on Pyrrole Schiff Bases: Synthesis, Characterization, X-ray Structure, and Anticancer Activity

Indole Derived Anticancer Agents

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

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