1,3,4-Oxadiazoles

Suwiński, J.; Szczepankiewicz, Wojciech

doi:10.1016/b978-008044992-0.00506-x

Cited by 14 publications

(7 citation statements)

References 384 publications

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“…It is known that 1,3,4-oxadiazoles [ 26 ], 1,3,4-thiadiazole [ 27 ] and 1,2,4-triazoles [ 28 – 30 ] can be obtained from diacylhydrazines. Thus, 11 and 12 were converted to 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazole ( 13 ) and 2,5-bis[4-(hexyloxy)-2,2'-bithiophen-5-yl]-1,3,4-oxadiazole ( 14 ) by the reaction with phosphorus oxychloride, in 78 and 83% yields, respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

Kostyuchenko¹,

Yurpalov²,

Kurowska³

et al. 2014

Beilstein J. Org. Chem.

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SummaryA new synthetic approach towards the preparation of functionalised, soluble, donor–acceptor (DA) alkylbithiophene derivatives of oxadiazole, thiadiazole and triazole is reported. Taking advantage of the Fiesselmann reaction, reactive bithiophene synthons having alkyl or alkoxy substituents at designated positions are prepared. Following a synthetic strategy, featuring the bottom-up approach, sequential structural elements are built, starting from a simple thiophene compound, until the target molecule is obtained, all in good yield. Supplementing the well established methods of oxadiazole and thiadiazole synthesis, efficient ring closure reaction affording a 4H-1,2,4-triazole unit is presented. All target ambipolar compounds display strong photoluminescence with measured quantum yields up to 0.59. Modification of the demonstrated synthetic routes may be exploited for the preparation of longer, specifically functionalised oligothiophenes, coupled to other heteroaromatic cores.

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Section: Resultsmentioning

confidence: 99%

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

Kostyuchenko¹,

Yurpalov²,

Kurowska³

et al. 2014

Beilstein J. Org. Chem.

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“…2,5-Diaryl 1,3,4-oxadiazoles are of great importance due to their wide applications in pharmaceutical chemistry and material science. They have shown a wide range of biological properties, including antimicrobial, anti-inflammatory, anticonvulsant, and antiviral properties . They are also useful surrogates of acids, esters, and carboxamides .…”

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confidence: 99%

One-Pot Synthesis of 2,5-Diaryl 1,3,4-Oxadiazoles via Di-tert-butyl Peroxide Promoted N-Acylation of Aryl Tetrazoles with Aldehydes

et al. 2015

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A metal- and base-free protocol for one-pot synthesis of 2,5-diaryl 1,3,4-oxadiazoles via a radical-promoted cross-dehydrogenative coupling strategy was developed. This reaction involved the N-acylation of aryl tetrazoles with aryl aldehydes, followed by thermal rearrangement. A wide range of aryl tetrazoles and aryl aldehydes survived the reaction conditions to deliver the corresponding products in moderate to good yields.

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“…Since the 1990s, optical brighteners (OBs), otherwise known as fluorescent whitening agents, have been incorporated into the commercial world and their uses are constantly increasing; from the textile, plastic, laundry detergent, and paper industries to personal care and cosmetic products. The OBs are hydrophilic, water‐soluble compounds mainly derived from coumarins, diphenyl pyrazoline, heterocyclic dicarboxylic acid, naphthalene dicarboxylic acid, and diaminostilbenedisulphonic acid, the latter being the most used . The characteristic that makes these compounds attractive is that they transform ultraviolet light waves to enhance blue light and minimize the amount of yellow light reflected to make objects appear whiter.…”

Section: Introductionmentioning

confidence: 99%

Proteasome‐associated cysteine deubiquitinases are molecular targets of environmental optical brightener compounds

Castro

Ekinci

Huang

et al. 2019

J of Cellular Biochemistry

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The levels of organic pollutants, such as optical brightener (OB) compounds, in the global environment have been increasing in recent years. The toxicological effects and signal transduction systems associated with OB toxicity have not been thoroughly studied. The ubiquitin-proteasome system (UPS) plays a crucial role in regulating multiple essential cellular processes, and proteasomeassociated cysteine deubiquitinases (DUBs), ubiquitin C-terminal hydrolase L5 (UCHL5) and USP14, are two major regulators for (de)ubiquitination and stability of many important target proteins. Therefore, potential inhibition of UCHL5 and USP14 activities by some environmental chemicals might cause in vivo toxicity. In the current study we hypothesize that electrophilic OB compounds, such as 4,4′-diamino-2,2′-stilbenedisulfonic acid (DAST), fluorescent brightener 28 (FB-28) and FB-71, can interact with the catalytic triads (CYS, HIS, and ASP) of UCHL5 and USP14 and inhibit their enzymatic activities, leading to cell growth suppression. This hypothesis is supported by our findings presented in this study. Results from in silico computational docking and ubiquitin vinyl sulfone assay confirmed the UCHL5/USP14inhibitory activities of these OB compounds that have potencies in an order of: FB-71 > FB-28 > DAST. Furthermore, inhibition of these two proteasomal DUBs by OBs resulted in cell growth inhibition and apoptosis induction in two human breast cancer cell models. In addition, we found that OB-mediated DUB inhibition triggers a feedback reaction in which expression of UCHL5 and USP14 proteins is increased to compromise the suppressed activities. Our study suggests that these commonly used OB compounds may target and inhibit proteasomal cysteine DUBs, which should contribute to their toxicological effects in vivo. K E Y W O R D S degradation, environmental pollutant, fluorescent brightening agent, molecular target, posttranslational modification

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1,3,4-Oxadiazoles

Cited by 14 publications

References 384 publications

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

One-Pot Synthesis of 2,5-Diaryl 1,3,4-Oxadiazoles via Di-tert-butyl Peroxide Promoted N-Acylation of Aryl Tetrazoles with Aldehydes

Proteasome‐associated cysteine deubiquitinases are molecular targets of environmental optical brightener compounds

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