61679-83-2

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 3-(carbamoylamino)-2-cyanoprop-2-enoate is utilized as an intermediate in the manufacturing of various pharmaceutical drugs. Its unique chemical structure allows it to be a key component in the synthesis of new and existing medications, contributing to the development of novel therapeutic agents.
Used in Organic Synthesis:
In the realm of organic synthesis, ethyl 3-(carbamoylamino)-2-cyanoprop-2-enoate serves as a versatile reagent. It is employed in a range of chemical reactions to form diverse organic compounds, facilitating the creation of complex molecules and contributing to advancements in chemical research and development.
Used in Research and Development:
Ethyl 3-(carbamoylamino)-2-cyanoprop-2-enoate is also used as a research tool in pharmaceutical and chemical laboratories. Its properties and reactivity are studied to understand its potential applications and to develop new methods for synthesizing other compounds, thereby expanding the scope of chemical knowledge and innovation.

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 105-56-6 ethyl 2-cyanoacetate 
• 57-13-6 urea 
• 420-04-2 CYANAMID 
• 94-05-3 ethyl (ethoxymethylene)cyanoacetate 
• 16849-87-9 2-(4b-dimethylaminomethylene)-2-cyano ethyl acetate 

Downstream Products

• 1123-95-1 5-hydroxymethylcytosine 
• 4425-56-3 5-cyano-2,4-dihydroxy pyrimidine 

Relevant academic research and scientific papers

5-Methylcytosine is Oxidized to the Natural Metabolites of TET Enzymes by a Biomimetic Iron(IV)-Oxo Complex

Ten-eleven-translocation (TET) methyl cytosine dioxygenases play a key role in epigenetics by oxidizing the epigenetic marker 5-methyl cytosine (5mC) to 5-hydroxymethyl cytosine (5hmC), 5-formyl cytosine (5fC), and 5-carboxy cytosine (5cC). Although much of the metabolism of 5mC has been studied closely, certain aspects—such as discrepancies among the observed catalytic activity of TET enzymes and calculated bond dissociation energies of the different cytosine substrates—remain elusive. Here, it is reported that the DNA base 5mC is oxidized to 5hmC, 5fC, and 5cC by a biomimetic iron(IV)-oxo complex, reminiscent of the activity of TET enzymes. Studies show that 5hmC is preferentially turned over compared with 5mC and 5fC and that this is in line with the calculated bond dissociation energies. The optimized syntheses of d3-5mC and d2-5hmC are also reported and in the reaction with the biomimetic iron(IV)-oxo complex these deuterated substrates showed large kinetic isotope effects, confirming the hydrogen abstraction as the rate-limiting step. Taken together, these results shed light on the intrinsic reactivity of the C?H bonds of epigenetic markers and the contribution of the second coordination sphere in TET enzymes.

A method for synthesis of cytosine

The invention discloses a synthesis method of cytosine. According to the method, ethyl cyanoacetate, urea and triethyl orthoformate are utilized as raw materials, ethyl 3-cyano-2-ureido-acrylate, 5-ethoxycarbonyl cytosine, and 5-carboxyl cytosine are sequentially synthesized, decarboxylation is performed to synthesize cytosine and refining, correction, perfection and other various process steps are sequentially performed. Therefore, the yield of the synthesis method is high, the highest total yield can achieve 75.14%, the comprehensive benefits are finally improved and the method has the advantages of simplicity in operation, small difficulty in actual production and convenience in large-scale application.

Syntheses with Nitriles, XCV: Deamination of Cytosine Derivatives

Treatment of 2-formyl-3-dimethylamino-propenenitrile (1a) and 2-ethoxycarbonyl-3-dimethylamino-propenenitrile (1b), resp., with substituted ureas led to the 2-cyano-3-ureidoacrylates 2, which can be cyclized under alkaline conditions to give 5-formyl-5-cy