402848-98-0

Usage

Type of compound

Chemical compound, derivative of thymine

Usage

Protective group for the nucleobase thymine in organic chemistry

Function

Temporary protection for the thymine nucleobase, allowing manipulation of other parts of a molecule without affecting the thymine moiety

Applications

Synthesis of nucleosides, nucleotides, and other biological compounds; development of pharmaceuticals and materials science

Role

Valuable tool for the modification and manipulation of thymine-containing molecules in chemical synthesis

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 65-71-4 thymin 

Downstream Products

• 917081-56-2 3-(4-(tert-butyl)benzyl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 4160-72-9 1-methylthymine 
• 21473-22-3 3-benzyl-5-methyl-2,4(1H)-pyrimidinedione 
• 114884-15-0 1-((1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 119451-90-0 3-((benzyloxy)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 883556-25-0 1-((1R,3S,4R)-3-Benzyloxy-4-benzyloxymethyl-cyclopentyl)-3-benzyloxymethyl-5-methyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Customizable and Regioselective One-Pot N?H Functionalization of DNA Nucleobases to Create a Library of Nucleobase Derivatives for Biomedical Applications

DNA is one of the most exciting biomolecules in nature for developing supramolecular biofunctional nanoarchitectures owing to the highly specific and selective interactions between complementary Watson-Crick base pairing. Herein, simple and one-pot synthetic procedures have been implemented for producing a library of DNA nucleobase derivatives endowed with reactive functional groups for bioconjugation and cross-linking strategies with other (bio)molecules. Purine and pyrimidine molecules have been regioselectively N?H functionalized either via N-alkylation, N-allylation, N-propargylation or Michael-type reactions and structurally characterized. The influence of the reaction conditions was assessed and discussed. The in vitro biocompatibility of the native and nucleobase derivatives was evaluated by culturing them with human fibroblasts, revealing their cytocompatibility. The library of nucleobase derivatives holds great promise for being coupled to different biomolecules, including biopolymeric materials, lipids, and peptides, thus potentially leading to modular supramolecular nanobiomaterials for biomedicine.

A diversity of alkylation/acylation products of uracil and its derivatives: Synthesis and a structural study

tert-Butyl dicarbonate (Boc2O) and ethyl iodide (EtI) reactions with uracil (U), thymine (T) and 6-methyluracil (6-MU) were performed following routine procedures in pyridine/DMF solvents and with DMAP as the catalyst. Among 20 synthesized compounds, a derivative of 6-methyluracil substituted by the Boc-pyridine moiety at the C5 position appeared unexpectedly. The NMR spectra confirmed the molecular structure of all uracil derivatives. Parallel quantum mechanical DFT calculations supported the experimental findings.

New Dimamine compd.

PROBLEM TO BE SOLVED: To provide a novel diamine compound having a photoreactive group useful for production of polyamic acid, polyamic acid ester and/or polyimide contained in liquid crystal aligning agent with photo-aligning properties.SOLUTION: This in

Studies on molecular properties prediction and histamine H3 receptor affinities of novel ligands with uracil-based motifs

The histamine H3 receptor (H3R) plays a role in cognitive and memory processes and is involved in different neurological disorders, including Alzheimer's disease, schizophrenia, and narcolepsy. Therefore, several hH3R antagonists/inverse agonists entered clinical phases for a broad spectrum of mainly centrally occurring diseases. However, many other promising candidates failed due to their pharmacokinetic profile, mostly because of their strong lipophilicity accompanied with low solubility. Analysis of previous potential H3R selective antagonists/inverse agonists, e.g. pitolisant, revealed promising results concerning physicochemical properties and drug-likeness. Herein, a series of new hH3R ligands 8-20 consisting of piperidin-1-yl or piperidin-1-yl-propoxyphenyl coupled to different uracil, thymine, and 5,6-dimethyluracil related moieties, were synthesized, evaluated on their binding properties at the hH3R and the estimation of different physicochemical and drug-likeness properties. Due to the coupling to various positions at pyrimidine-2,4-(1H,3H)-dione, affinity at hH3Rs and drug-likeness parameters have been improved. For instance, compound 9 showed in addition to high affinity at the hH3R (pKi (hH3R) Combining double low line 8.14) clog S, clog P, LE, LipE, and drug-likeness score values of -'4.36, 3.47, 0.34, 4.63, and 1.54, respectively. Also, the methyl substituted analog 17 (pKi (hH3R) Combining double low line 8.15) revealed LE, LipE and drug-likeness score values of -'3.29, 2.47, 0.49, 5.52, and 1.76, respectively.

Synthesis of (Carbo)nucleoside analogues by [3+2] annulation of aminocyclopropanes

(Carbo)nucleoside derivatives constitute an important class of pharmaceuticals, yet there are only few convergent methods to access new analogues. Here, we report the first synthesis of thymine-, uracil-, and 5-fluorouracil-substituted diester donor-acceptor cyclopropanes and their use in the indium- and tin-catalyzed [3+2] annulations with aldehydes, ketones, and enol ethers. The obtained diester products could be easily decarboxylated and reduced to the corresponding alcohols. The method gives access to a broad range of new (carbo)nucleoside analogues in only four or five steps and will be highly useful for the synthesis of libraries of bioactive compounds.

Influence of the N3-protection group on N1- vs. O2-alkylation in the Mitsunobu reaction

The influence of the N3-protection group of thymine on the regioselectivity of the N1- vs. O2-alkylation under Mitsunobu conditions is described. A series of N3-protected thymine derivatives 8a-f was prepared and coupled to cyclopentanol as mod

Efficient N-arylation and N-alkenylation of the five DNA/RNA nucleobases

(Chemical Equation Presented) A general approach to N-arylation and N-alkenylation of all five DNA/RNA nucleobases at the nitrogen atom normally attached to the sugar moiety in DNA or RNA has been developed. Various protected or masked nucleobases engaged

Synthesis, pharmacology and pharmacokinetics of 3-(4-Arylpiperazin-1-ylalkyl)-uracils as uroselective α1A-antagonists

Predominance in the urethra and prostate of the α1A-adrenoceptor subtype, which is believed to be the receptor mediating noradrenaline induced smooth muscle contraction in these tissues, led to the preparation of α1A-selective antagonists to be tested as uroselective compounds for the treatment of benign prostatic hyperplasia. Thus, a number of selective α1A-adrenoceptor antagonists were synthesized and assayed in vitro for potency and selectivity. Dog pharmacokinetic parameters of 12 (RO700004) and its metabolite 40 (RO1104253) were established. The relative selectivity of intravenously administered 12, 40 and standard prazosin to inhibit hypogastric nerve stimulation-induced increases in intraurethral prostatic pressure versus phenylephrine-induced increases in diastolic blood pressure in anesthetized dogs was 76, 71 and 0.6, respectively.

N-3-alkylation of uracil and derivatives via N-1-BOC protection

An easy and efficient synthesis of 3-alkyluracils is described. Thus, BOC-protection at N-1 of uracil permits selective alkylation at N-3. This protecting group can be removed under very mild conditions.