Lack of NQO1 induction in human tumor cells is not due to changes in the promoter region of the gene

Begleiter, Asher; Lange, L

doi:10.3892/ijo.20.4.835

Cited by 5 publications

(4 citation statements)

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“…Some important ring transformations of 1,2-dithiole-3H-thiones include the 1,3-dipolar cycloaddition to alkynes, isonitriles and nitrilimines, and recyclization to other heterocyles, which resulted in a series of heterocyclic systems, namely, 1,3-dithioles, spiro-1,3-dithiolothiopyrans, 1,3-dithiethanes, 1,3,4-thiadiazolines, and pyrrolo [1,2-a]pyrazines. In recent years, a number of new transformations of 1,2-dithiole-3H-thiones have been discovered, including the replacement of one or two endocyclic sulfur atoms with carbon-or carbon-nitrogen containing moieties to give important sulfur-containing heterocyclic systems, such as pyrazino[2,1-b] [1,3]thiazines, thienothiopyranethions, tritiapentalenes, 1,3-dithiine-4-thiones, and many others. I hope that this review will give strong impetus to the development of this scientifically interesting and practically important field of heterocyclic chemistry.…”

Section: Discussionmentioning

confidence: 99%

“…1,2-Dithioles have been an important class of sulfur heterocycles since 1884, when the first representative of this class, 4,5-dimethyl-1,2-dithiole-3-thione (1) was synthesized [1]. 1,2-Dithiole derivatives show many types of significant pharmacological activity, including antitumor, antioxidant, chemotherapeutic, antithrombotic and radioprotective properties [2][3][4][5][6][7][8][9]. In addition to the above applications, 1,2-dithioles show anti-HIV activity [10,11].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Reactivity of 3H-1,2-dithiole-3-thiones

Ракитин

2021

Molecules

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3H-1,2-Dithiole-3-thiones are among the best studied classes of polysulfur-containing heterocycles due to the almost explosive recent interest in these compounds as sources of hydrogen sulfide as an endogenously produced gaseous signaling molecule. This review covers the recent developments in the synthesis of these heterocycles, including both well-known procedures and important novel transformations for building the 1,2-dithiole-3-thione ring. Diverse ring transformations of 3H-1,2-dithiole-3-thiones into various heterocyclic systems through 1,3-dipolar cycloaddition, replacement of one or two sulfur atoms to form carbon- and carbon-nitrogen containing moieties, and other unexpected reactions are considered.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Reactivity of 3H-1,2-dithiole-3-thiones

Ракитин

2021

Molecules

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“…Furthermore, 3 H -1,2-dithiole-3-thione derivatives have diverse biological activities such as chemotherapeutic, antioxidant, and radio protective properties ( Smith et al, 2001 ; Begleiter and Lange, 2002 ), besides being treated as chemo preventive, and sialagogue agents in various biomodels ( Munday et al, 2006 ). In addition, the 1,2-dithiole-3-thione derivatives were found to possess anti-HIV activities ( Munday et al, 2010 ) and cytoprotective effects ( Zhu et al, 2009 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking Analysis and in Vitro Biological Evaluation of Some New Heterocyclic Scaffolds-Based Indole Moiety as Possible Antimicrobial Agents

Hassan

Shehadi

El‐Maghraby

et al. 2022

Front. Mol. Biosci.

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In the present study, a general approach for the synthesis of 1-(1H-indol-3-yl)-3,3-dimercaptoprop-2-en-1-one (1) and 5-(1H-indol-3-yl)-3H-1,2-dithiole-3-thione (2) was performed. They are currently used as efficient precursors for the synthesis of some new compounds bearing five- and/or six-membered heterocyclic moieties, e.g., chromenol (3, 4), 3,4-dihydroquinoline (7, 8) and thiopyran (10, 12)-based indole core. In addition, molecular docking studies were achieved, which showed that all the newly synthesized compounds are interacting with the active site region of the target enzymes, the targets UDP-N-acetylmuramatel-alanine ligase (MurC), and human lanosterol14α-demethylase, through hydrogen bonds and pi-stacked interactions. Among these docked ligand molecules, the compound (9) was found to have the minimum binding energy (−11.5 and −8.5 Kcal/mol) as compared to the standard drug ampicillin (−8.0 and −8.1 Kcal/mol) against the target enzymes UDP-N-acetylmuramatel-alanine ligase (MurC), and Human lanosterol14α-demethylase, respectively. Subsequently, all new synthesized analogues were screened for their antibacterial activities against Gram-positive (Bacillus subtilis), and Gram-negative bacteria (Escherichia coli), as well as for antifungal activities against Candida albicans and Aspergillus flavus. The obtained data suggest that the compounds exhibited good to excellent activity against bacterial and fungi strains. The compound (E)-2-(6-(1H-indole-3-carbonyl)-5-thioxotetrahydrothieno [3,2-b]furan-2(3H)-ylidene)-3-(1H-indol-3-yl)-3-oxopropanedithioic acid (9) showed a high binding affinity as well as an excellent biological activity. Therefore, it could serve as the lead for further optimization and to arrive at potential antimicrobial agent.

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“…1,2-Dithiole derivatives show many significant pharmacological activities . Compounds having 3 H -1,2-dithiole-3-thione as a core nucleus exhibit chemotherapeutic, antioxidant, and radioprotective properties . Further, dithiolethiones are used as chemopreventive, choleretic, and sialagogue agents in various biomodels .…”

Section: Introductionmentioning

confidence: 99%

Switching Selectivity of α-Enolic Dithioesters: One Pot Access to Functionalized 1,2- and 1,3-Dithioles

et al. 2016

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An operationally simple cascade protocol has been developed for the construction of 1,2- and 1,3-dithiole derivatives from α-enolic dithioesters. 1,2-Dithioles are achieved by the reaction of dithioesters with elemental sulfur in the presence of InCl under solvent-free conditions. 1,3-Dithioles have been constructed via DABCO mediated self-coupling of dithioesters in open air enabling the formation of two new C-S bonds and one ring in a single operation in contiguous fashion. The reactions proceeded smoothly affording the desired sulfur-rich heterocycles in good to excellent yields, exhibiting gram-scale ability and broad functional group tolerance utilizing easy to handle cheap and easily available reagents. The probable mechanisms for the formation of 1,2- and 1,3-dithioles from α-enolic dithioesters have been suggested.

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Lack of NQO1 induction in human tumor cells is not due to changes in the promoter region of the gene

Cited by 5 publications

References 0 publications

Synthesis and Reactivity of 3H-1,2-dithiole-3-thiones

Synthesis and Reactivity of 3H-1,2-dithiole-3-thiones

Synthesis, Molecular Docking Analysis and in Vitro Biological Evaluation of Some New Heterocyclic Scaffolds-Based Indole Moiety as Possible Antimicrobial Agents

Switching Selectivity of α-Enolic Dithioesters: One Pot Access to Functionalized 1,2- and 1,3-Dithioles

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