Synthesis of pharmacologically important naphthoquinones and anticancer activity of 2-benzyllawsone through DNA topoisomerase-II inhibition

Kumar, B. Sathish; Ravi, Kusumoori; Verma, Amit Kumar; Fatima, Kaneez; Hasanain, Mohammad; Singh, Arjun; Sarkar, Jayanta; Luqman, Suaib; Chanda, Debabrata; Negi, Arvind S.

doi:10.1016/j.bmc.2016.12.043

Cited by 72 publications

(15 citation statements)

References 56 publications

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“…First, menadione carboxy derivatives 20, 21 and 22 that can be further anchored on the diruthenium unit were synthesized. This type of modification was previously used to prepare carboxy analogues of lawsone (2-hydroxynaphthalene-1,4-dione) [87][88][89], menadione or plumbagin (5-hydroxy-2-methylnaphthalene-1,4-dione) [90][91][92][93]. Compounds 20, 21 and 22, bearing linkers of different lengths between the 1,4-naphtoquinone moiety and the carboxylic group, were obtained from menadione and succinic, suberic and adipic acid, respectively, in the presence of AgNO 3 and (NH 4 ) 2 S 2 O 3 following literature procedures [90], and were isolated in medium yields of 70, 61 and 52%, respectively (Scheme 6).…”

Section: Conjugates With Menadionementioning

confidence: 99%

Synthesis and Antiparasitic Activity of New Conjugates—Organic Drugs Tethered to Trithiolato-Bridged Dinuclear Ruthenium(II)–Arene Complexes

et al. 2021

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Tethering known drugs to a metalorganic moiety is an efficient approach for modulating the anticancer, antibacterial, and antiparasitic activity of organometallic complexes. This study focused on the synthesis and evaluation of new dinuclear ruthenium(II)–arene compounds linked to several antimicrobial compounds such as dapsone, sulfamethoxazole, sulfadiazine, sulfadoxine, triclosan, metronidazole, ciprofloxacin, as well as menadione (a 1,4-naphtoquinone derivative). In a primary screen, 30 compounds (17 hybrid molecules, diruthenium intermediates, and antimicrobials) were assessed for in vitro activity against transgenic T. gondii tachyzoites constitutively expressing β-galactosidase (T. gondii β-gal) at 0.1 and 1 µM. In parallel, the cytotoxicity in noninfected host cells (human foreskin fibroblasts, HFF) was determined by an alamarBlue assay. When assessed at 1 µM, five compounds strongly impaired parasite proliferation by >90%, and HFF viability was retained at 50% or more, and they were further subjected to T. gondii β-gal dose-response studies. Two compounds, notably 11 and 13, amide and ester conjugates with sulfadoxine and metronidazole, exhibited low IC50 (half-maximal inhibitory concentration) values 0.063 and 0.152 µM, and low or intermediate impairment of HFF viability at 2.5 µM (83 and 64%). The nature of the anchored drug as well as that of the linking unit impacted the biological activity.

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Section: Conjugates With Menadionementioning

confidence: 99%

Synthesis and Antiparasitic Activity of New Conjugates—Organic Drugs Tethered to Trithiolato-Bridged Dinuclear Ruthenium(II)–Arene Complexes

et al. 2021

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“…Furthermore, naphthoquinones and their derivatives are compounds with important pharmacological activities such as anticancer, antibacterial, antifungal, antiviral and anti-parasitic (e.g. antimalarial and antileishmania) [ 23 , 24 ]. Pharmacological activities showed by naphthoquinones and derivatives can be explicated through two mechanisms: (1) as pro-oxidants, reducing oxygen to reactive oxygen species (ROS); and (2) as electrophiles, forming covalent bonds with tissue nucleophiles [ 25 , 26 ].…”

Section: Discussionmentioning

confidence: 99%

Chemical composition, in vitro antitumor and pro-oxidant activities of Glandora rosmarinifolia (Boraginaceae) essential oil

et al. 2018

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The biological properties of essential oils have been demonstrated in the treatment of several diseases and to enhance the bioavailability of other drugs. In natural habitats the essential oils compounds may play important roles in the protection of the plants as antibacterials, antivirals, antifungals, insecticides and also against herbivores by reducing their appetite for such plants or by repelling undesirable others. We analyzed by gas-chromatography mass spectrometry the chemical composition of the essential oil of aerial parts of Glandora rosmarinifolia (Ten.) D.C. Thomas obtained by hydrodistillation and verified some biological activities on a panel of hepatocellular carcinoma cell lines (HA22T/VGH, HepG2, Hep3B) and triple negative breast cancer cell lines (SUM 149, MDA-MB-231). In the essential oil we detected 35 compounds. The results of the biological assays indicate that essential oil of G. rosmarinifolia induces cell growth inhibition at concentration-dependent way in all cell line models. This oil does not seem to possess antioxidant activity, while the cytotoxicity of G. rosmarinifolia essential oil appeared to involve, at least in part, a pro-oxidant mechanism. Our results show for the first time the antitumoral and pro-oxidant activities of G. rosmarinifolia essential oil and suggest that it may represent a resource of pharmacologically active compounds.

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“…As such, N ‐bromosuccinimide (NBS) represents a more user‐friendly oxidative, and non‐toxic reagent widely utilized in laboratories and industries . In general, NBS is used for bromination,– and oxidative dearomatization reactions,, not only because it is very cheap, but also because its side product can be easily removed. As outlined in the Scheme , we envisioned that this privileged structure could be accessed through sequential NBS‐mediated bromination followed by oxidation in the presence of piperidine as a base.…”

Section: Figurementioning

confidence: 99%

Rapid, Operationally Simple, and Metal‐free NBS Mediated One‐pot Synthesis of 1,2‐Naphthoquinone from 2‐Naphthol

Sim

Choi

et al. 2017

Adv Synth Catal

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A metal-free, one-pot synthesis of 1,2naphthoquinone was accomplished from 2-naphthol by utilizing economically cheap NBS under open air conditions. Initial formation of 1,1-dibromonaphthalen-2-one and subsequent transformation afforded the 1,2-naphthoquinone. This oxidation was completed within 30 min and had broad substrate scope. Moreover, this system tolerated heterocyclic systems and was also applicable to 1,3dicarbonyl systems. This practical approach with short reaction times, a simple workup, and insensitivity to moisture could override the usage of expensive and hazardous oxidizing and metal reagents.

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Synthesis of pharmacologically important naphthoquinones and anticancer activity of 2-benzyllawsone through DNA topoisomerase-II inhibition

Cited by 72 publications

References 56 publications

Synthesis and Antiparasitic Activity of New Conjugates—Organic Drugs Tethered to Trithiolato-Bridged Dinuclear Ruthenium(II)–Arene Complexes

Synthesis and Antiparasitic Activity of New Conjugates—Organic Drugs Tethered to Trithiolato-Bridged Dinuclear Ruthenium(II)–Arene Complexes

Chemical composition, in vitro antitumor and pro-oxidant activities of Glandora rosmarinifolia (Boraginaceae) essential oil

Rapid, Operationally Simple, and Metal‐free NBS Mediated One‐pot Synthesis of 1,2‐Naphthoquinone from 2‐Naphthol

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