Isotetronic acids from an oxidative cyclization

Zhou, Zhe; Walleser, Patrick M.; Tius, Marcus A.

doi:10.1039/c5cc04051e

Cited by 9 publications

(7 citation statements)

References 30 publications

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“…Selenium dioxide (SeO 2 ) is often used as oxidizing agent or catalyst in organic chemistry, [94–97] but very seldom used for the synthesis of organoselenium compounds [98,99] . Few reported works using SeO 2 are, synthesis of diarylselenides from arylboronic acids, [100] biphenols from phenols, [101] α‐selenoamidation of aryl methyl ketones [102] .…”

Section: Overview On Selenium‐catalyzed/selenium Incorporating Transfmentioning

confidence: 99%

“…The practicality of the reaction was also extended towards bioactive scaffolds like indole and 2-amino naphthaquinone to provide selenylated products 36a and 36b in 92% and 95% yields, respectively. Selenium dioxide (SeO 2 ) is often used as oxidizing agent or catalyst in organic chemistry, [94][95][96][97] but very seldom used for the synthesis of organoselenium compounds. [98,99] Few reported works using SeO 2 are, synthesis of diarylselenides from arylboronic acids, [100] biphenols from phenols, [101] α-selenoamidation of aryl methyl ketones.…”

Section: Selenofunctionalization Of Carbocyclic Heterocyclic and Unsmentioning

confidence: 99%

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Insights into the Recent Synthetic Advances of Organoselenium Compounds

2021

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The ever-growing interest for organoselenium compounds amongst the chemists has made commendable impact in the field of medicinal chemistry, material chemistry, chemical biology and biochemistry. Researchers have progressively contributed in the development of organoselenium compounds over the years which has been periodically reviewed. On the similar note, this review attempts at providing an overview of the recent advances made in organoselenium chemistry while covering their catalytic indulgence in different transformational approaches, their role in asymmetric synthesis, and synthetic approaches steering their synthesis. These approaches encompass selenofunctionalization and/or cyclization, electrochemical selenylation, bromolactonization, [2,3]-or [1,2]-sigmatropic rearrangement reactions among others. Herein, we have focused on the synthetic approaches developed for the past three years that have not been covered in previously reviewed scientific material. With the knowledge of the recent progress covered, this review could contribute towards future development of organoselenium compounds along with the improvement of the current status.

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Section: Overview On Selenium‐catalyzed/selenium Incorporating Transfmentioning

confidence: 99%

Section: Selenofunctionalization Of Carbocyclic Heterocyclic and Unsmentioning

confidence: 99%

Insights into the Recent Synthetic Advances of Organoselenium Compounds

2021

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“…Pyruvic acid as an important synthon is well-exploited in the chemical synthesis of many derivatives of isotetrone, with substitutions at C-3 to C-5 carbons. [38][39][40] Enantioselective synthesis led to a paradigm shift and syntheses of stereochemically pure butyrolactones are also achieved. [41][42][43][44][45][46][47][48][49] Recognizing the importance of deamination of amino acids to the corresponding substituted pyruvic acids, we undertook to synthesize isotetrones that possess variations of the substituent at C-4 carbon of the furanone scaffold.…”

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C-4-Modified Isotetrones Prevent Biofilm Growth and Persister Cell Resuscitation inMycobacterium smegmatis

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Pal

Basu

et al. 2022

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Hyperphosphorylated guanosine nucleotide (p)ppGpp, synthesized by Rel proteins, regulates the stringent response pathway responsible for biofilm growth and persister cell formation in the stationary phase of mycobacteria. The discovery of vitamin C as a potent inhibitor of Rel protein activities raises the prospect of such a tetrone lactone to prevent biofilm growth and persister cell formation. The closely related isotetrone lactone derivatives are identified in the present study as potent inhibitors of the above processes in a mycobacterium. Isotetrone lactone derivatives are synthesized from appropriate α-ketocarboxylic acids, derived from the a-amino acids. Aldol condensation with formaldehyde, followed by the lactone formation, completes synthesis of isotetrone derivatives, possessing varied substituents atC-4 carbon, in good yields. A series of biochemical evaluations of biofilm growth and persister cell formation inM. smegmatisis conducted. Among the derivatives, isotetrone possessing phenyl substituent atC-4 carbon completely inhibit the biofilm formation at 400 μg mL-1concentration, 84 h of post-exposure, followed by a moderate inhibition by the isotetrone possessingp-hydroxyphenyl substituent. Whereas, the latter isotetrone inhibits the growth of cells at 400 μg mL-1f.c. when monitored for 2 weeks, under PBS starvation condition. Isotetrones also potentiate the inhibition of antibiotic tolerant regrowth of cells by ciprofloxacin antibiotic (0.75 μg mL-1) and thus act as bio-enhancers. The combination is shown to significantly arrest the emergence of ciprofloxacin-resistant genetic mutants. The observations suggest that isotetrones in combination with ciprofloxacin are therapeutically superior when administered together. Systematic molecular dynamics studies show that isotetrone derivative binds to Rel protein more efficiently than vitamin C and the binding is aided by hydrogen bonding, van der Waals and electrostatic interactions at a binding site possessing serine, threonine, lysine and arginine residues. The present study establishes that the identified isotetrone derivatives (i) act as inhibitors ofM. smegmatisbiofilm growth and (ii) arrest the re-emergence of recalcitrant persister cells when administered together with ciprofloxacin antibiotic. Results of this study establish that isotetrones as new chemical entities that interfere with stringent response pathways in a mycobacterium under stress and permit overcoming the multidrug-resistant persister cell emergence in the bacterium.

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“…4 Therefore, the development of simple and efficient methods for the preparation of functionalized 3hydroxyfuran-2(5H)-ones is essential for organic chemistry. Several modern methods for the preparation of compounds containing the 3-hydroxyfuran-2(5H)-one core have been described: (a) condensation of pyruvic acid derivatives with carbonyl compounds; 5 (b) cyclization of silyl enol ethers with oxalyl chloride; 6 (c) oxidative cyclization of ,-unsaturated methyl ketones, 7 and others 8 (Scheme 1).…”

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confidence: 99%

“…trichloroacetyl)furan-2,3-dione (2a) Compound 2a was synthesized from 1a.Yield: 0.22 g (68%); yellow crystals; mp 122-123 °C (decomp). IR (Nujol): 1832 (C 2 =O), 1736 (COCCl 3 ), 1711 (C 3 =O) cm -1 .1 H NMR (400 MHz, CDCl 3 ):  = 7.62 (m, J = 8 Hz, 2 H, C 6 H 5 ),7.80 (m, J = 8 Hz, 1 H, C 6 H 5 ), 7.89-7.91 (d, J = 8 Hz, 2 H, C 6 H 5 ) 13. C NMR (100 MHz, CDCl 3 ):  = 94.3, 111.6, 125.0, 129.0, 129.2, 136.0, 151.2, 172.3 (C=O), 178.4 (C=O), 179.0 (C=O).…”

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confidence: 99%