Synthesis and antifungal activity of 2/3-arylthio- and 2,3-bis(arylthio)-5-hydroxy-/5-methoxy-1,4-naphthoquinones

Ryu, Chong Kul; Shim, Ju-Yeon; Chae, M. J.; Choi, Ik Hwa; Han, Ju; Jung, Ok-Jai; Lee, Jung Yoon; Jeong, Seong Hee

doi:10.1016/j.ejmech.2004.12.004

Cited by 41 publications

(9 citation statements)

References 13 publications

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“…Quinazolinedione 7 and naphthoquinone 8 depicted in Figure are among a series of quinone derivatives that have been reported in the recent literature to deliver antifungal activity against diverse Candida and Aspergillus species. , Generation of hydrogen peroxide via redox cycling of quinone has been described in the literature . Recently, quinazolinediones have been specifically reported to act as redox modulators .…”

Section: Discussionmentioning

confidence: 99%

Pan Assay Interference Compounds (PAINS) and Other Promiscuous Compounds in Antifungal Research

2015

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Every week, articles disclosing new antifungal leads reported as promising starting points for optimization projects are published. In many cases, the mechanism that accounts for their antifungal activity has not been fully elucidated. More significantly, the detrimental impact that could result from certain embedded chemical features has been underestimated or even overlooked. In the course of our research in the agrochemical area, we have concluded that in many cases such leads are actually nonoptimizable because they either contain what are now recognized as pan assay interference compounds (PAINS) or other promiscuous groups. This article is aimed at highlighting the pitfalls we have encountered and hopefully to steer other research groups away from them.

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Section: Discussionmentioning

confidence: 99%

Pan Assay Interference Compounds (PAINS) and Other Promiscuous Compounds in Antifungal Research

2015

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“…[17][18][19][20][21][22][23] There have also been reports on naphthoquinone sulfides demonstrating anticancer and antifungal activities. [24][25][26][27][28][29][30] The goal of our research was to use biocatalysis to access novel compounds that can have potential pharmaceutical value in addition to developing green methods of synthesis. Laccases catalyze CÀN [31a,b] or C=N [32] bond formation in their reactions with amines as well as CÀC, [33] CÀO, [34] and C=C [35] bond formation in their reactions with phenolic substrates.…”

Section: Introductionmentioning

confidence: 99%

Laccase‐Catalyzed CS and CC Coupling for a One‐Pot Synthesis of 1,4‐Naphthoquinone Sulfides and 1,4‐Naphthoquinone Sulfide Dimers

et al. 2013

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Oxidative CS and CC bond formation with aryl and alkyl thiols was catalyzed under mild conditions in a reaction vessel open to air at pH 4.5 in the presence of a commercial laccase (Novozym 51003 or Suberase) and a cosolvent (DMF) to afford 1,4‐naphthoquinone sulfides. Although both monothiolation and dithiolation of the 1,4‐naphthohydroquinone were accomplished, the latter was favored. In addition, unprecedented dimerization of monothiolated intermediates occurred through CC coupling. These commercial laccases provide a facile and a more environmentally friendly synthetic approach to both 1,4‐naphthoquinone sulfides and 1,4‐naphthoquinone sulfide dimers.

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“…On the other hand, the compound 2-methoxy-1,4-naphtoquininone obtained from Impatiens balsamina presents antifungal activity against four strains of Candida albicans and Aspergillus niger . The incorporation of an arylamino, arylthiol group, or halogen atoms in the 1,4-naphthoquinone structures increased the effectiveness of the biological activity [22].…”

Section: Resultsmentioning

confidence: 99%

Detoxification Mechanism of 8,8-Dimethyl-3-[(R-phenyl)amino]-1,4,5(8H)-naphthalentrione Derivatives by Botrytis cinerea

et al. 2019

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The effect of 8,8-dimethyl-3-[(R-phenyl)amino]-1,4,5(8H)-naphthalentrione derivatives (compounds 1–13) on the mycelial growth of Botrytis cinerea was evaluated. The fungitoxic effect depended on the substituent and its position in the aromatic ring. Compounds substituted with halogens in meta and/or para positions (compounds 3, 4, 5 and 7), methyl (compounds 8 and 9), methoxyl (compounds 10 and 11), or ethoxy-carbonyl groups (compound 12) presented higher antifungal activity than compound 1, which had an unsubstituted aromatic ring. In addition, compounds with halogens in the ortho position, such as compounds 2 and 6, and a substitution with an acetyl group in the para position (compound 13) were less active. The role of the ABC efflux pump Bctr B-type as a defense mechanism of B. cinerea against these naphthalentrione derivatives was analyzed. This pump could be involved in the detoxification of compounds 2, 6, and 13. On the contrary, this mechanism would not participate in the detoxification of compounds 1, 7, 9 and 12. Finally, the biotransformation of compound 7 by B. cinerea was studied. A mixture of two biotransformed products was obtained. One of them was compound 7A, which is reduced at C1 and C4, compared to compound 7. The other product of biotransformation, 7B, is oxidized at C7.

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Synthesis and antifungal activity of 2/3-arylthio- and 2,3-bis(arylthio)-5-hydroxy-/5-methoxy-1,4-naphthoquinones

Cited by 41 publications

References 13 publications

Pan Assay Interference Compounds (PAINS) and Other Promiscuous Compounds in Antifungal Research

Pan Assay Interference Compounds (PAINS) and Other Promiscuous Compounds in Antifungal Research

Laccase‐Catalyzed CS and CC Coupling for a One‐Pot Synthesis of 1,4‐Naphthoquinone Sulfides and 1,4‐Naphthoquinone Sulfide Dimers

Detoxification Mechanism of 8,8-Dimethyl-3-[(R-phenyl)amino]-1,4,5(8H)-naphthalentrione Derivatives by Botrytis cinerea

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