35824-98-7

Usage

Uses

Used in Carbohydrate Chemistry:
1,3-DIMETHYL-5-[(DIMETHYLAMINO)METHYLENE]2,4,6-(1H,3H,5H)-TRIOXOPRYIMIDINE is used as a non-acidic reagent for the protection of base-sensitive primary amines in carbohydrate chemistry. Its application is valuable due to its ability to protect these amines without causing unwanted side reactions or degradation, thus maintaining the integrity of the carbohydrate structure during chemical modifications.

InChI:InChI=1/C9H13N3O3/c1-10(2)5-6-7(13)11(3)9(15)12(4)8(6)14/h5H,1-4H3

Upstream product

• 769-42-6 1,3-dimethylbarbituric acid 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1345974-23-3 1,3-dimethyl-5-[(4-pyridylamino)methylene]barbituric acid 
• 324545-66-6 5-(((2-chlorophenyl)amino)methylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione 
• 1578264-37-5 C₁₉H₁₈N₄O₄ 
• 282526-31-2 2-[(1,3-dimethyl-2,4,6(1H,3H,5H)-trioxopyrimidin-5-ylidene)methylamino]-ethyl 2-[(1,3-dimethyl-2,4,6(1H,3H,5H)-trioxopyrimidin-5-ylidene)methylamino]-4-O-benzyl-6-O-(4-chlorobenzyl)-2-deoxy-3-O-pentamethylbenzyl-α,β-D-glucopyranoside 
• 350239-10-0 5-[((2S,4aR,6S,7R,8R,8aR)-8-Hydroxy-6-methylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ylamino)-methylene]-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 223921-80-0 5-(4-methoxyanilinomethylene)-1,3-dimethylbarbituric acid 
• 602-04-0 tris(2-methyl-1H-indol-3-yl)methane 
• 198220-35-8 1,3-dimethyl-5-[(1H-indol-3-yl)methylidene]-2,4,6(1H,3H,5H)-pyrimidinetrione 

Relevant academic research and scientific papers

DMF in acetic anhydride: A useful reagent for multiple-component syntheses of merocyanine dyes

A simple and highly efficient method for the preparation of merocyanine dyes is reported from mixtures of CH-acidic heterocycles and electron-rich dialkylaminothiazoles or methylene bases and various formylating reagents without isolation of the formylated intermediates. With the particularly useful formylation-condensation system of DMF in acetic anhydride and highly acidic 1,2,5,6-tetrahydro-2,6-dioxo-3-pyridinecarbonitriles 8, the transformations could be carried out as multicomponent reactions to give pure dyes 3-6 in 50-90% yield directly from the reaction mixtures.

Synthesis and characterisation of thiobarbituric acid enamine derivatives, and evaluation of their α-glucosidase inhibitory and anti-glycation activity

A new series of thiobarbituric (thiopyrimidine trione) enamine derivatives and its analogues barbituric acid derivatives was synthesised, characterised, and screen for in vitro evaluation of α-glucosidase enzyme inhibition and anti-glycation activity. This series of compounds were found to inhibit α-glucosidase activity in a reversible mixed-type manner with IC50 between 264.07 ± 1.87 and 448.63 ± 2.46 μM. Molecular docking studies indicated that compounds of 3g, 3i, 3j, and 5 are located close to the active site of α-glucosidase, which may cover the active pocket, thereby inhibiting the binding of the substrate to the enzyme. Thiopyrimidine trione derivatives also inhibited the generation of advanced glycation end-products (AGEs), which cause long-term complications in diabetes. While, compounds 3a–k, 5, and 6 showed significant to moderate anti-glycation activity (IC50 = 31.5 ± 0.81 to 554.76 ± 9.1 μM).

SPHINGOSINE/SPHINGOID BASE PRODUCTION

The present invention relates to sphingolipids, and more particularly to a method for the production of sphingoid bases, especially sphingosine, and novel derivatives thereof. The sphingoid bases are herein produced by making use of a vinylogous amide-type protecting group. The resulting vinylogous amide compounds enable an easy and effective production of sphingoid bases, especially sphingosine.

1-(2-hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile derivatives as potent and tissue selective androgen receptor modulators

We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.

AGENT EXHIBITING THE PROPERTIES OF A COGNITIVE FUNCTION PROMOTER (EMBODIMENTS)

The present invention relates to the field of chemical-pharmaceutical industry and medicine. An agent, exhibiting the properties of a cognitive function promoter, was selected from 1,3-dimethyl-5-[(4-pyridylamino)methylene]barbituric acid and 4-amino-1-(3-nitro-2-oxo-1-pheny-1,2-dihydro-1,6-naphthyridin-5-yl)pyridinium chloride. The compounds, that are proposed as agents, exhibit potent biological activity.

Orthogonally protected monosaccharide building blocks for solid phase production of diversity oriented libraries

The large scale synthesis of three orthogonally protected monosaccharide scaffolds suitable for use in the solid phase preparation of large diversity libraries is presented. Scaffolds based on 2-amino-2-deoxy-d-glucopyranose, 2-amino-2-deoxy-d-allopyranos

Protecting groups for carbohydrate synthesis

The invention provides collections of orthogonally-protected monosaccharides as universal building blocks for the synthesis of glycoconjugates of non-carbohydrate molecules, neo-glycoconjugates and oligosaccharides. This orthogonal protection strategy all

Rapid microwave-assisted solution phase synthesis of substituted 2-pyridone libraries

2-Pyridone and 2-quinolone analogues are well-known biologically active heterocyclic scaffolds. Libraries of 3,5,6-substituted 2-pyridone derivatives are generated by rapid microwave assisted solution phase methods using a one-pot, two-step protocol. The three-component condensation of CH-acidic carbonyl compounds, N,N-dimethylformamide dimethylacetal and methylene active nitriles, leads to 2-pyridones and fused analogues in moderate to good overall yields and high purities. The proposed mechanism of this novel multi-component reaction, structure elucidation of products and intermediates are discussed.

Dimethylamine substitution in N,N-dimethyl enamines. Synthesis of aplysinopsin analogues and 3-aminotetrahydrocoumarin derivatives

Some new six-membered aplysinopsin analogues were prepared from 5-dimethylaminomethylidene-2,4,6(1H,3H,5H)-pyrimidinetriones and indole derivatives. Also 2-[[(2,4,6-trioxohexahydropyrimidin-5-ylidene)methyl]amino]-3- dimethylaminopropenoates were synthesized and employed in the synthesis of fused 2H-pyran-2-ones.

A novel amino protecting group: DTPM

A novel hydrazine and primary amine labile (1,3-dimethyl-2,4,6 (1H,3H,5H)-trioxopyrimidine-5-ylidene)methyl (DTPM) vinylogous amide type protecting group was developed to protect aminosugars and other primary amines in a facile and cost effective manner.