Synthesis of 1,3-thiazoline derivatives from ?-dicarbonyl compounds and phenacyl thiocyanate

Abstract In living systems, nucleophilic amino acid residues are prone to non-enzymatic post-translational modification by electrophiles. α-Dicarbonyl compounds are a special type of electrophiles that can react irreversibly with lysine, arginine, and cysteine residues via complex mechanisms to form post-translational modifications known as advanced glycation end-products (AGEs). Glyoxal, methylglyoxal, and 3-deoxyglucosone are the major endogenous dicarbonyls, with methylglyoxal being the most well-studied. There are several routes that lead to the formation of dicarbonyl compounds, most originating from glucose and glucose metabolism, such as the non-enzymatic decomposition of glycolytic intermediates and fructosyl amines. Although dicarbonyls are removed continuously mainly via the glyoxalase system, several conditions lead to an increase in dicarbonyl concentration and thereby AGE formation. AGEs have been implicated in diabetes and aging-related diseases, and for this reason the elucidation of their structure as well as protein targets is of great interest. Though the dicarbonyls and reactive protein side chains are of relatively simple nature, the structures of the adducts as well as their mechanism of formation are not that trivial. Furthermore, detection of sites of modification can be demanding and current best practices rely on either direct mass spectrometry or various methods of enrichment based on antibodies or click chemistry followed by mass spectrometry. Future research into the structure of these adducts and protein targets of dicarbonyl compounds may improve the understanding of how the mechanisms of diabetes and aging-related physiological damage occur.

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Analysis of Bioactive Chemical Compounds of Trogoderma granarium (Insecta: Coleoptera: Dermestidae) Using Gas Chromatography – Mass Spectrometry

INTERNATIONAL JOURNAL OF TOXICOLOGICAL AND PHARMACOLOGICAL RESEARCH ◽

10.25258/ijtpr.v9i03.9071 ◽

2017 ◽

Vol 9 (03) ◽

Author(s):

Jenan Mohammed Ubaid ◽

Abeer Fauzi Al-Rubaye ◽

Imad Hadi Hameed

Keyword(s):

Acetic Acid ◽

Benzoyl Chloride ◽

Methanolic Extract ◽

Biological Activities ◽

Chemical Compounds ◽

Gas Chromatography Mass Spectrometry ◽

Pentanoic Acid ◽

Trogoderma Granarium ◽

Trans Methyl ◽

Phenacyl Thiocyanate

Methanolic extract of bioactive compounds of Trogoderma granarium was assayed. GC-MS analysis of Trogoderma granarium revealed the existence of the Pentanoic acid , 1,1-dimethylpropyl ester , (1H)-Pyrimidinone , 5-chloro-4,6- diphenyl, Cyclobutanemethanol , α-methyl- , Nitro-2-methyl-1,3-propanediol , Hydroxylamine ,O-(2-methylpropyl)- , Uridine , 2',3'-O-(phenylmethylene)- ,Acetic acid ,2-benzoylthio-,2-oxo-2-phenylethyl ester , methylpropyl)- , Uridine , 2',3'-O-(phenylmethylene)- , 5'-(4-methylbenzenesulfo , Indolinol , 1-benzoyl-, Benzeneethanol , β-methyl-,(s)- , Acetic acid ,2-benzoylthio-,2-oxo-2-phenylethyl ester , Phenacyl thiocyanate , Deoxy-L-ribose-2,5-dibenzoate , Methenamine , Alanine , N-methyl-n-propargyloxycarbonyl-, decyl ester , Benzoyl chloride , Thiophene-2-ol , benzoate , Ethanone , -(5- nitrotetrazol-2-yl)-1-phenyl- , 2,5-Dimethylhexane-2,5-dihydroperoxide , Benzamide , N-(3-benzylthio-1,2,4-thiadiazol- 5-yl)- , Methyl p-(2-phenyl-1-benzimidazolyl)benzoate , Methyl-2-phenoxyethylamine , Pentaborane(11) , cis-Methoxy- 5-trans-methyl-1R-cyclohexanol , Nitro-1-phenyl-3-(tetrahydropyran-2-yloxy)propan-1-one , cis-Methoxy-5-transmethyl-1R-cyclohexanol. Trogoderma granarium produce many important secondary metabolites with high biological activities.

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Pentafluorophenylammonium Triflate (PFPAT): An Efficient, Practical, and Cost-Effective Catalyst for One-Pot Condensation of β-Naphthol, Aldehydes and Cyclic 1,3-Dicarbonyl Compounds

Combinatorial Chemistry & High Throughput Screening ◽

10.2174/138620712803901153 ◽

2012 ◽

Vol 15 (10) ◽

pp. 845-848 ◽

Cited By ~ 1

Author(s):

Samad Khaksar ◽

Nosratollah Behzadi

Keyword(s):

Cost Effective ◽

One Pot ◽

Dicarbonyl Compounds ◽

Effective Catalyst ◽

One Pot Condensation

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ChemInform Abstract: CONDENSATION OF O-AMINOPHENOL AND α-DICARBONYL COMPOUNDS. PART 1. BENZOXAZINES

Chemischer Informationsdienst ◽

10.1002/chin.197818254 ◽

1978 ◽

Vol 9 (18) ◽

Author(s):

E. BELGODERE ◽

R. BOSSIO ◽

V. PARRINI ◽

R. PEPINO

Keyword(s):

Dicarbonyl Compounds

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Stereoselective Tandem Iridium-Catalyzed Alkene Isomerization-Cope Rearrangement of ω-diene Epoxides: Efficient Access to Acyclic 1,6-Dicarbonyl Compounds

Chemical Science ◽

10.1039/d1sc02575a ◽

2021 ◽

Author(s):

Rahul Suresh ◽

Itai Massad ◽

Ilan Marek

Keyword(s):

Bond Cleavage ◽

Cope Rearrangement ◽

Dicarbonyl Compounds ◽

Alkene Isomerization ◽

Efficient Access

The Cope rearrangement of 2,3-divinyloxiranes, a rare example of epoxide C-C bond cleavage, results in 4,5-dihydrooxepines which are amenable to hydrolysis, furnishing 1,6-dicarbonyl compounds containing two contiguous stereocenters at the 3- and 4- positions. We employ...

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