Bivalent glycoconjugates based on 1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione (“bimane”) as a central scaffold

Szabó, Tamás; Bényei, Attila; Szilágyi, László

doi:10.1016/j.carres.2019.01.002

Cited by 5 publications

(4 citation statements)

References 54 publications

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“…The exact reason for this deformation of 3 is unclear, but it is a common characteristic of previously reported syn - and anti -dioxobimanes. Thus, out of the 12 syn - and 6 anti -dioxobimanes currently found in the CSD, which are simply bicyclic, half of the syn -bimanes and a third of the anti -bimanes are bent, whereas the rest are planar. ,,− The CSD contains 11 additional syn -dioxobimanes, but these exhibit a fused tricyclic framework, wherein the two pyrazolinone rings are mutually bridged through their β-olefinic positions by an aliphatic or heteroaliphatic chain. All of these tricyclic bimanes are bent about their N–N bonds, with most being strongly deformed.…”

Section: Resultsmentioning

confidence: 99%

Thioxobimanes

Das,

Roy,

Nandi

et al. 2023

J. Org. Chem.

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Dioxobimanes, colloquially known as bimanes, are a well-established family of N-heterobicyclic compounds that share a characteristic core structure, 1,5-diazabicyclo[3.3.0]octadienedione, bearing two endocyclic carbonyl groups. By sequentially thionating these carbonyls in the syn and anti isomers of the known (Me,Me)dioxobimane, we were able to synthesize a series of thioxobimanes, representing the first heavy-chalcogenide bimane variants. These new compounds were extensively characterized spectroscopically and crystallographically, and their aromaticity was probed computationally. Their potential role as ligands for transition metals was demonstrated by synthesizing a representative gold(I)−thioxobimane complex.

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Section: Resultsmentioning

confidence: 99%

Thioxobimanes

Das,

Roy,

Nandi

et al. 2023

J. Org. Chem.

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“…In particular, both monosaccharide and disaccharide residues were attached to both the syn-bimane and anti-bimane central cores via thio-, disulfido or seleno-glycosidic linkages, leading to the formation of novel glycoconjugates with a range of photophysical properties. 17 Subsequent Cu(I)catalyzed Huisgen cycloaddition of glycosyl azides to a bimane diethynyl derivative furnished further bivalent glycoconjugates, with sugar residues linked to the central bimane core via 1,2,3-triazole rings. 16 Moreover, Grynszpan and Levine et al recently reported that an inclusion complex of 15 and β-cyclodextrin can be used for the effective detection of iodine.…”

Section: Recent Applications Of Bimanesmentioning

confidence: 99%

“…Recently, several novel bimane derivatives have been synthesized and used as components of both metal-containing and metal-free supramolecular complexes, with applications of such bimane-containing complexes in chemical sensing also described. [14][15][16][17][18]…”

Section: Introductionmentioning

confidence: 99%

A Short Review on Recent Advances and Applications of Bimane Chemistry

Karmakar,

Pramanik

2022

Prayogik Rasayan

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1,5-diazabicyclo[3.3.0]octadienediones, also known as bimanes, are heterobicyclic compounds with generally high quantum yields, low toxicity, and low molecular weight. During the 1970s, the bimane fluorophore, which was synthesized from the reaction of a beta-keto ester and hydrazine, was first reported by Kosower and co-workers. Since that time, significant effort has been invested in the introduction of functional groups at the alpha-positions of syn-bimane, the bimane isomer in which both carbonyl groups are oriented in the same direction. In spite of these efforts, the successful attachment of high value functional groups at the alpha-positions of syn-bimane remain scarce. A recent report from Prof. Flavio Grynszpan's group using a solvent-free, environmentally friendly (i.e. "green") method allowed for a rapid, large-scale synthesis of bimane and the preparation and study of differently-substituted bimane derivatives. In this review, we describe the advantages of the current green synthesis of bimanes and the applications of the newly formed bimane derivatives as fluorescent and colorimetric sensors, with special attention paid to the relationship between the bimane structures, their photophysical characteristics, and their performance as chemical sensors.

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“…8 Recently, Szilágyi and co-workers successfully used bimanes as the central scaffold for bivalent glycoconjugates. 9 Chemical modifications to the bimane skeleton attaching substituents with conjugated double or triple bonds and aromatic rings may lead to interesting molecules with expanded -systems and red-shifted fluorescence emissions suitable for biological applications. A key synthetic intermediate in the preparation of these derivatives can be found in the form of syn-(R 2 ,I)B.…”

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confidence: 99%

Re-enter the syn-(Me,I)Bimane: A Gateway to Bimane Derivatives with Extended π-Systems

Szumski¹,

Karmakar²,

Grynszpan³

2021

Synlett

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syn-α-Diiodobimane (syn-(R2,I)B) is a key intermediate for the derivatization of the bimane core in the α-positions. Here we describe an expeditious method to prepare symmetric α-bimane derivatives, such as syn-(R2,I)B, as well as unsymmetric ones. Our strategy turns the synthesis of α derivatives with extended π-systems practical and affordable. We applied this approach to the synthesis of ethynylbenzaldehyde bearing bimanes as potential selective probes for aldolase class I enzymes.

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Bivalent glycoconjugates based on 1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione (“bimane”) as a central scaffold

Abstract: Bivalent glycoconjugates based on 1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione("bimane") as a central scaffold.

Cited by 5 publications

References 54 publications

Thioxobimanes

Thioxobimanes

A Short Review on Recent Advances and Applications of Bimane Chemistry

Re-enter the syn-(Me,I)Bimane: A Gateway to Bimane Derivatives with Extended π-Systems

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