28456-54-4

Usage

Uses

Used in Pharmaceutical Industry:
5,6-Dimethyl-2-Thiouracil is used as a heterocyclic building block for the synthesis of anti-HIV-1 pyrimidinones. Its chemical structure allows it to be a valuable component in the development of new drugs to combat HIV-1.
Used in Analytical Chemistry:
5,6-Dimethyl-2-Thiouracil is used as an internal standard for the quantification of thyreostats, such as 2-thiouracil, in bovine plasma. Its stability and compatibility with various analytical techniques make it an ideal choice for ensuring accurate and reliable measurements in this context.

InChI:InChI=1/C6H8N2OS/c1-3-4(2)7-6(10)8-5(3)9/h1-2H3,(H2,7,8,9,10)

Upstream product

• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 17356-08-0 thiourea 
• 17094-21-2 2-methyl-acetoacetic acid methyl ester 

Downstream Products

• 54855-79-7 5,6-dimethyl-2-(methylsulfanyl)-3,4-dihydropyrimidin-4-one 
• 34916-78-4 5,6-dimethyl-3H-pyrimidin-4-one 
• 26305-13-5 5,6-dimethyluracil 
• 1342843-79-1 diethyl 2-(cyclohexylamino)-6,7-dimethyl-8-oxo-4,8-dihydropyrimido[2,1-b][1,3]thiazine-3,4-dicarboxylate 
• 677024-69-0 C₁₃H₁₃BrN₂OS 
• 1450809-14-9 2-chloro-N-(4,4-difluorocyclohexyl)-5,6-dimethylpyrimidin-4-amine 
• 1780-32-1 2,4-dichloro-5,6-dimethylpyrimidine 
• 1450809-22-9 N₄-(4,4-difluorocyclohexyl)-5,6-dimethyl-N₂-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine 
• 1450808-81-7 2-chloro-N-cyclohexyl-5,6-dimethylpyrimidin-4-amine 
• 922581-39-3 2-(4-fluoro-benzylsulfanyl)-5,6-dimethyl-1H-pyrimidin-4-one 
• 877798-45-3 2,3-dimethylpyrimido[1,2-a]benzimidazol-4(10H)-one 
• 31408-09-0 5,6-dimethyl-3-methyluracil 
• 67434-65-5 4-chloro-5,6-dimethylpyrimidine 

Relevant academic research and scientific papers

Synthesis and Functionalization of 5-Alkyl-6-methyl-2-thiouracils

Abstract: A number of 5-alkyl-6-methyl-2-thiouracils were obtained, the further introduction of which into the reaction with dialkyl chloroethynylphosphonates afforded a series of new dialkyl (6-alkyl-5-oxo-7-methyl-5H-thiazolo[3,2-a]pyrimidin- 3-yl)phosphonates.

BRD4-KINASE INHIBITORS AS CANCER THERAPEUTICS

Disclosed herein are compounds that are inhibitors of BDR4 and their use in the treatment of cancer. Methods of screening for selective inhibitors of BDR4 are also disclosed. In certain aspects, disclosed are compounds of Formula I through IV.

Laccase-catalyzed green synthesis and cytotoxic activity of novel pyrimidobenzothiazoles and catechol thioethers

The laccase-catalyzed reaction between unsubstituted catechol and 2-thioxopyrimidin-4(1H)-ones using aerial O2 as the oxidant delivers novel pyrimidobenzothiazoles with high yields in an aqueous solvent system under mild reaction conditions. With 4-substituted catechols, catechol thioethers are formed exclusively. The synthetic protocols developed provide a sustainable approach for these compound classes. In addition, the cytotoxicity of the products against HepG2 cell line is reported. Most compounds exhibit antiproliferative activities with IC50 values at the micromolar level. A structure-activity relationship study will facilitate the further development of these compounds as cytotoxic agents.

Synthesis and evaluation of 5,6-disubstituted thiopyrimidine aryl aminothiazoles as inhibitors of the calcium-activated chloride channel TMEM16A/Ano1

Transmembrane protein 16A (TMEM16A), also called Ano1, is a Ca2+ activated Cl? channel expressed widely in mammalian epithelia, as well as in vascular smooth muscle and some tumors and electrically excitable cells. TMEM16A inhibitors have potential utility for treatment of disorders of epithelial fluid and mucus secretion, hypertension, some cancers and other diseases. 4-Aryl-2-amino thiazole T16Ainh-01 was previously identified by high-throughput screening. Here, a library of 47 compounds were prepared that explored the 5,6-disubstituted pyrimidine scaffold found in T16Ainh-01. TMEM16A inhibition activity was measured using fluorescence plate reader and short-circuit current assays. We found that very little structural variation of T16Ainh-01 was tolerated, with most compounds showing no activity at 10 μM. The most potent compound in the series, 9bo, which substitutes 4-methoxyphenyl in T16Ainh-01 with 2-thiophene, had IC50 ～1 μM for inhibition of TMEM16A chloride conductance.

POTENT DUAL BRD4-KINASE INHIBITORS AS CANCER THERAPEUTICS

Disclosed herein are compounds that are inhibitors of BRD4 and their use in the treatment of cancer. Methods of screening for selective inhibitors of BRD4 are also disclosed. In certain aspects, disclosed are compounds of Formula I-IV.

DIAMINOPYRIMIDINES USEFUL AS INHIBITORS OF THE HUMAN RESPIRATORY SYNCYTIAL VIRUS (RSV)

This disclosure relates to: (a) compounds and salts thereof that, inter alia, inhibit RSV infection and/or replication; (b) intermediates useful for the preparation of such compounds and salts; (c) compositions comprising such compounds and salts; (d) methods for preparing such intermediates, compounds, salts, and compositions; (e) methods of use of such compounds, salts, and compositions; and (f) kits comprising such compounds, salts, and compositions.

Identification of novel, exosite-binding matrix metalloproteinase-13 inhibitor scaffolds

Matrix metalloproteinase-13 (MMP-13) has been implicated as the protease responsible for collagen degradation in cartilage during osteoarthritis (OA). Compounds that inhibit the metalloproteinase at the Zn binding site typically lack specificity among MMP family members. Analogs of the low-micromolar lead MMP-13 inhibitor 4, discovered through high-throughput screening, were synthesized to investigate structure-activity relationships in this inhibitor series. Systematic modifications of 4 led to the discovery of MMP-13 inhibitors 20 and 24 which are more selective than 4 against other MMPs. Compound 20 is also approximately fivefold more potent as an MMP-13 inhibitor than the original HTS-derived lead compound 4.

Microwave-assisted synthesis of substituted: 2-(benzylthio)imidazo[1,2a] pyrimidin-5-ones

A microwave-assisted solid-phase synthesis of 2-(benzylthio)imidazo[1,2a] pyrimidin-5-ones has been developed. Using microwave irradiation, the reaction time was significantly reduced from a few days to 80 min. A representative set of 10 2-(benzylthio)-6,7-substituted-imidazo[1,2a]pyrimidin-5-ones was prepared. These compounds were subsequently N-alkylated and formylated in good yields.

The identification of clinical candidate SB-480848: A potent inhibitor of lipoprotein-associated phospholipase A2

Modification of the pyrimidone 5-substituent in clinical candidate SB-435495 has given a series of inhibitors of recombinant lipoprotein-associated phospholipase A2 with sub-nanomolar potency. Cyclopentyl fused derivative 21, SB-480848, showed an enhanced in vitro and in vivo profile versus SB-435495 and has been selected for progression to man.