504-07-4Relevant academic research and scientific papers
Photoinduced reduction of thymine and uracil derivatives by hypophosphite: Unusual high quantum yield of chromophore loss
Wang, Kongjiang,Chai, Zhifang
, p. 1543 - 1544 (1998)
The quantum yield of chromophore loss of thymine, uracil and their corresponding nucleosides and nucleoside-5′-monophosphates undergoing irradiation with 254 nm UV light was found to be sharply enhanced by hypophosphite; thymine and uracil were reduced by hypophosphite to give 5,6-dihydrothymine and 5,6-dihydrouracil respectively.
Reactivity of damaged pyrimidines: Formation of a schiff base intermediate at the glycosidic bond of saturated dihydrouridine
Jian, Yajun,Lin, Gengjie,Chomicz, Lidia,Li, Lei
, p. 3318 - 3329 (2015)
DNA glycosylases catalyze the first step of the base excision repair (BER) pathway. The chemistry used by these enzymes for deglycosylation has been largely considered as the chemistry of the oxocarbenium ion, e.g., direct rupture of the C1-N1 bond resulting in an oxocarbenium ion intermediate. Here we present mechanistic studies revealing the 2-deoxyribose isomerization and subsequent deglycosylation processes in two pyrimidine lesions: 5,6-dihydro-2-deoxyuridine (dHdU) and 5,6-dihydrothymidine (dHT), formed via ionizing radiation damage to 2-deoxycytidine and thymidine, respectively, under anoxic conditions. Acid or heat treatment of these two lesions leads to the production of two pairs of C1 epimers containing a pyranose and a furanose, respectively, indicating that both lesions favor the rupture of the C1-O4 bond, resulting in a Schiff base intermediate at the N-glycosidic bond. Such a Schiff base intermediate was trapped and characterized by either Pd-catalyzed hydrogenation or thiol-mediated addition reaction. In contrast, in undamaged 2-deoxyuridine and thymidine, reactions at elevated temperatures lead to the release of nucleobases most likely via the traditional oxocarbenium ion pathway. DFT calculations further support the experimental findings, suggesting that the oxocarbenium ion intermediate is responsible for the deglycosylation process if the integrity of the pyrimidine ring is maintained, while the Schiff base intermediate is preferred if the C5=C6 bond is saturated. Currently, the oxocarbenium ion pathway is indicated to be solely responsible for the deglycosylation in BER enzymes, however our results suggest an alternative Schiff base mechanism which may be responsible for the repair of saturated pyrimidine damages.
4,5-Dihydroxyimidazolidin-2-ones in the α-ureidoalkylation reaction of N-(carboxyalkyl)-, N-(hydroxyalkyl)-, and N-(aminoalkyl)ureas 1. α-Ureidoalkylation of N-(carboxyalkyl)ureas
Kravchenko,Lyssenko,Chikunov,Belyakov,Il'In,Baranov,Nelyubina,Davankov,Pivina,Makhova,Antipin
, p. 395 - 405 (2009)
The α-ureidoalkylation of N-(carboxyalkyl)ureas (ureido acids) with 1,3-H2 s-, 1,3-Me 2 s-, and 1,3-Et2 s-4,5-dihydroxyimidazolidin-2-ones was systematically studied. The yields of glycolur
BIFUNCTIONAL DEGRADERS AND THEIR METHODS OF USE
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Page/Page column 315, (2021/04/01)
Described herein are bifunctional degrader compounds, their various targets, their preparation, pharmaceutical compositions comprising them, and their use in the treatment of conditions, diseases, and disorders mediated by various target proteins.
A uracil green production process
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Paragraph 0035-0048, (2018/07/30)
The present invention provides a uracil green production process, comprising the following steps: 1) to thio uracil as raw materials, adding water, also adding halide or sulfonic acid compound, heating overnight, cooling, filtering and drying, to obtain high-purity uracil; 2) step 1) filtering the resulting stock solution continue adding thio uracil, heating, circulating the above-mentioned operation. The invention has the following advantages: the reaction mother liquor and material can be applied mechanically, and yield and purity is not affected, is a environmental friendly technology. High purity can be obtained uracil, namely detection HPLC purity of 95% or more, or even 98% or more of the uracil.
Transfer hydrogenation as a redox process in nucleotides
Achrainer, Florian,Emel'yanenko, Vladimir N.,Tantawy, Waled,Verevkin, Sergey P.,Zipse, Hendrik
, p. 10426 - 10429 (2015/04/14)
Using a combined theoretical and experimental strategy, the heats of hydrogenation of the nucleotide bases uracil, thymine, cytosine, adenine, and guanine have been determined. The most easily hydrogenated base is uracil, followed by thymine and cytosine. Comparison of these hydrogenation enthalpies with those of ketones and aldehydes derived from sugar models indicates the possibility of near-thermoneutral hydrogen transfer between uracil and the sugar phosphate backbone in oligonucleotides. (Figure Presented)
Mechanochemical preparation of hydantoins from amino esters: Application to the synthesis of the antiepileptic drug phenytoin
Konnert, Laure,Reneaud, Benjamin,De Figueiredo, Renata Marcia,Campagne, Jean-Marc,Lamaty, Frdric,Martinez, Jean,Colacino, Evelina
, p. 10132 - 10142 (2015/02/19)
The eco-friendly preparation of 5- and 5,5-disubstituted hydantoins from various amino ester hydrochlorides and potassium cyanate in a planetary ball-mill is described. The one-pot/two-step protocol consisted in the formation of ureido ester intermediates, followed by a base-catalyzed cyclization to hydantoins. This easy-handling mechanochemical methodology was applied to a large variety of α- and β-amino esters, in smooth conditions, leading to hydantoins in good yields and with no need of purification steps. As an example, the methodology was applied to the "green" synthesis of the antiepileptic drug Phenytoin, with no use of any harmful organic solvent.
Regioselective reactions of N-(carboxyalkyl)- and N-(aminoethyl)ureas with glyoxal and 1,2-dioxo-1,2-diphenylethane
Kravchenko,Baranov,Gazieva,Chikunov,Nelyubina
, p. 416 - 421 (2015/02/02)
Regioselective reactions of N-(carboxyalkyl)ureas (ureido acids) and N-(aminoethyl)ureas with 1,2-dioxo-1,2-diphenylethane (benzyl) and glyoxal are studied in detail. The structure of the reactants affects the reaction regioselectivity. Acid-catalyzed rea
Meteorites as catalysts for prebiotic chemistry
Saladino, Raffaele,Botta, Giorgia,Delfino, Michela,Di Mauro, Ernesto
, p. 16916 - 16922 (2014/01/06)
From outer space: Twelve meteorite specimens, representative of their major classes, catalyse the synthesis of nucleobases, carboxylic acids, aminoacids and low-molecular-weight compounds from formamide (see figure). Different chemical pathways are identified, the yields are high for a prebiotic process and the products come in rich and composite panels.
Dibutylphosphate (DBP) mediated synthesis of cyclic N,N′- disubstituted urea derivatives from amino esters: A comparative study
Agrawal, Sumit K.,Sathe, Manisha,Kaushik, M. P.,Halve, A. K.
supporting information, p. 5996 - 5999,4 (2020/08/20)
The N,N′-disubstituted urea derivatives such as amino acid hydantoins and dihydrouracil derivatives were prepared starting from natural and unnatural amino acid esters using dibutylphosphate (DBP). During the attempted synthesis of N-heterocycles with larger than six-membered rings containing the N,N′-disubstituted urea functionalities, three unexpected products namely squamolone, N-methyl pyrrolidine-2-one, and diketopiperazine were isolated.
