Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents

Malhotra, Rajesh; Rarhi, Chhanda; Diveshkumar, K. V.; Barik, Rajib; D’cunha, Ruhee; Dhar, Pranab; Kundu, Mrinalkanti; Chattopadhyay, Subrata; Roy, Shibendu Shekhar; Basu, Sourav; Pradeepkumar, P. I.; Hajra, Saumen

doi:10.1016/j.bmc.2016.04.059

Cited by 17 publications

(6 citation statements)

References 45 publications

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“…Having assessed the antimicrobial effects of the berberine variants, we then turned to the construction of chelerythrine vari-ants. Numerous methods of synthesizing chelerythrine and other benzophenanthridines have been reported, but unlike with the berberine variants none are as easily modulated to rapidly install substituent diversity [31,[43][44][45][46][47][48]. The method deemed most amenable to varying substituents involves substituted 2-bromo-1-aminonaphthalenes which are used in subsequent palladium cross-coupling reactions [45].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

Villegas,

Ball,

Shouse

et al. 2023

Beilstein J. Org. Chem.

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Due to the lack of new antimicrobial drug discovery in recent years and an ever-growing prevalence of multidrug-resistant “superbugs”, there is a pressing need to explore alternative ways to combat pathogenic bacterial and fungal infections. Building upon our previous work in the field of medicinal phytochemistry, the present study is focused on designing, synthesizing, and testing the altered bioactivity of new variants of two original bioactive molecules found in the Argemone mexicana plant. Herein, we report upon 14 variants of berberine and four variants of chelerythrine that have been screened against a pool of 12 microorganisms (five Gram-positive and four Gram-negative bacteria, and three fungi). Additionally, the crystal structures of two berberine variants are described. Several berberine variants show enhanced antibacterial activity compared to the unaltered plant-derived molecule. We also report promising preliminary tumor cytotoxicity effects for a number of the berberine derivatives.

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Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

Villegas,

Ball,

Shouse

et al. 2023

Beilstein J. Org. Chem.

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“…2,6,7‐Tribromonaphthalen‐1‐ol ( 5f ): Compound 5f was synthesized according to a previously reported method (120 mg, 32%). [ 75 ]…”

Section: Methodsmentioning

confidence: 99%

Synthesis and biological evaluation of some 1‐naphthol derivatives as antioxidants, acetylcholinesterase, and carbonic anhydrase inhibitors

Erdoğan

Köse

Eşsiz

et al. 2021

Archiv der Pharmazie

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A series of some naphthol derivatives 4a–f, 5a,f, 6a, and 7a,b (six novel ones: 4c,d, 5a, 6a, 7a,b) bearing F, Cl, Br, OMe, and dioxole substituents at different positions of the aromatic rings was designed, synthesized, and characterized. The naphthol derivatives were synthesized in three steps, namely the addition reaction of furan via Diels–Alder cycloaddition reaction, copper(II) trifluoromethanesulfonate (Cu(OTf)2)‐catalyzed aromatization reaction, and the bromination reaction, respectively. The structures of the newly obtained compounds (4c,d, 5a, 6a, 7a,b) were characterized by spectroscopic techniques. In addition, some biological activity studies were investigated under in vitro conditions. Inhibition studies of these compounds were performed on human carbonic anhydrase (hCA) I and II isoenzymes purified from human erythrocytes as a biological evaluation. Moreover, their potential antioxidant and antiradical activities were studied by analytical methods like ABTS•+ and DPPH• scavenging, and it was determined that some molecules showed good activity. Also, inhibition of acetylcholinesterase (AChE), which is a marker of many degenerative neurological diseases, was tested and the results were discussed. Excellent enzyme inhibition results were recorded for most of the molecules. These 1‐naphthol derivatives were found as effective inhibitors for hCA I, hCA II, and AChE with K i values ranging from 0.034 ± 0.54 to 0.724 ± 0.18 µM for hCA I, 0.172 ± 0.02 to 0.562 ± 0.21 µM for hCA II, and 0.096 ± 0.01 to 0.177 ± 0.02 µM for AChE.

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“…Generally, in the quaternary alkaloids (such as palmatine, berberine, chelerythrine, sanguinarine, etc. ), the carbon atom in the C‐ring adjacent to the quaternary nitrogen has high reactivity and electrophilic character, which reacts with nucleophiles in vivo and produces neutral alkanolamine/iminium forms (Malhotra et al, 2016; Yang et al, 2012). Accordingly, these cationic alkaloids are more toxic than neutral alkaloids and can cause more unwanted interactions in the body (Ulrichová et al, 2001).…”

Section: Isoquinoline Alkaloids With a High Potential To Inhibit Sars...mentioning

confidence: 99%

Dual action anti‐inflammatory/antiviral isoquinoline alkaloids as potent naturally occurring anti‐SARS‐CoV‐2 agents: A combined pharmacological and medicinal chemistry perspective

Valipour

Hosseini

Sotto

et al. 2023

Phytotherapy Research

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In the search for compounds that inhibit the SARS‐CoV‐2 after the onset of the COVID‐19 pandemic, isoquinoline‐containing alkaloids have been identified as compounds with high potential to fight the disease. In addition to having strong antiviral activities, most of these alkaloids have significant anti‐inflammatory effects which are often manifested through the inhibition of a promising host‐based anti‐COVID‐19 target, the p38 MAPK signaling pathway. In the present review, our pharmacological and medicinal chemistry evaluation resulted in highlighting the potential of anti‐SARS‐CoV‐2 isoquinoline‐based alkaloids for the treatment of COVID‐19 patients. Considering critical parameters of the antiviral and anti‐inflammatory activities, mechanism of action, as well as toxicity/safety profile, we introduce the alkaloids emetine, cephaeline, and papaverine as high‐potential therapeutic agents for use in the treatment of COVID‐19. Although preclinical studies confirm that some isoquinoline‐based alkaloids reviewed in this study have a high potential to inhibit the SARS‐CoV‐2, their entry into drug regimens of COVID‐19 patients requires further clinical trial studies and toxicity evaluation.

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Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents

Cited by 17 publications

References 45 publications

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

Synthesis and biological evaluation of some 1‐naphthol derivatives as antioxidants, acetylcholinesterase, and carbonic anhydrase inhibitors

Dual action anti‐inflammatory/antiviral isoquinoline alkaloids as potent naturally occurring anti‐SARS‐CoV‐2 agents: A combined pharmacological and medicinal chemistry perspective

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