57508-48-2

Usage

Uses

It is used as a pharmaceutical intermediate.

InChI:InChI=1/C5H10N2O2/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3,(H3,6,7)/p+1

Upstream product

• 27317-59-5 Ethyl 3-ethoxy-3-iminopropionate 
• 67-56-1 methanol 
• 50551-10-5 ethyl amidinoacetate 
• 105-56-6 ethyl 2-cyanoacetate 
• 2318-25-4 ethyl 3-ethoxy-3-iminopropanoate hydrochloride 

Downstream Products

• 38370-06-8 4-amino-2-(2-hydroxyphenyl)<1>benzopyrano<4,3-d>pyrimidin-5-one 
• 111222-44-7 2-Amino-5-methyl-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester 
• 116796-69-1 ethyl 2-amino-6-methyl-4-(2-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylate 
• 116796-70-4 2-Amino-6-methyl-5-(2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester 
• 111222-43-6 2-Amino-3-ethoxycarbonyl-4-methyl-5-phenylpyrrole 
• 111222-42-5 2-Amino-4,5-diphenyl-1H-pyrrole-3-carboxylic acid ethyl ester 
• 851266-02-9 ethyl 3-amino-7-nitroisoquinoline-4-carboxylate 
• 173458-92-9 2-amino-3-carboxethyl-5-(4-methoxyphenyl)-pyrrole 
• 173458-96-3 2-amino-3-ethoxycarbonyl-5-(2-methoxy-phenyl)-1H-pyrrole 
• 173458-95-2 2-amino-3-ethoxycarbonyl-5-(3-methoxy-phenyl)-1H-pyrrole 
• 187724-91-0 ethyl 2-amino-5-(4-(ethoxycarbonyl)phenyl)-1H-pyrrole-3-carboxylate 
• 88284-41-7 5-Decyl 3-ethyl 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate 
• 497841-33-5 ethyl 2-amino-5-(4-cyanophenyl)-1H-pyrrole-3-carboxylate 
• 132260-01-6 ethyl 2-(5-phenylmethoxypyrimidin-2-yl)acetate 

Relevant academic research and scientific papers

Microwave-Assisted Bohlmann-Rahtz Synthesis of Highly Substituted 2-Aminonicotinates

Microwave irradiation of 2-carbethoxyacetamidine and an ethynyl ketone under acidic or basic conditions in ethanol at 150 °C for 1.5 hours facilitated Bohlmann-Rahtz pyridine synthesis to give highly substituted ethyl 2-aminonicotinates with total regiocontrol and in reasonable to excellent yield, following purification by immobilization upon an acidic resin.

Synthesis and cholinesterase inhibition activity of new pyrrolopyrimidine derivatives

Cholinesterase plays a vital role in the decline of cholinergic transmission and thus can contribute to the development of Alzheimer's disease (AD). Thus, compounds that can inhibit acetylcholinesterase (AChe) and butyrylcholinesterase (BuChe) are the potential drugs for the treatment of AD. A series of novel pyrrolopyrimidine derivatives was synthesized and evaluated for their inhibitory activity against cholinesterase by Ellman method. Among the ten newly synthesized compounds, 4-(4-((4-(difluoromethoxy)phenyl)amino)-7H-pyrrolo [2,3-d]pyrimidin-6-yl)benzoate was the most potent molecule identified with the IC50 values of 18 μM and 17 uM on AChe and BuChe respectively.

Synthesis and in vitro EGFR (ErbB1) tyrosine kinase inhibitory activity of 4-N-substituted 6-aryl-7H-pyrrolo[2,3-d]pyrimidine-4-amines

A series of 4-N-substituted 6-aryl-7H-pyrrolo[2,3-d]pyrimidine-4-amines have been synthesised, characterised and tested for their in vitro EGFR (ErbB1) tyrosine kinase inhibitory activity. The compounds were prepared from ethyl cyanoacetate and α-bromoacetophenones via the 2-amino-3-ethoxycarbonyl-5- aryl-pyrroles and 4-chloro-6-arylpyrrolopyrimidines. Aromatic substitution with benzylic amines was performed by conventional thermal substitution, and palladium catalysed coupling. The two methods resulted in similar yields, but the palladium coupling had the benefit of lower chemical consumption and reduced reaction times. Eight of the new compounds had IC50 values in the range of 2.8-9.0 nM. Four of these have a fluorine atom positioned at sites otherwise potentially susceptible to oxidative metabolism. Structural variation of the 6-aryl group indicated that the inhibitory action was only moderately sensitive to modifications in this fragment. However, the potency depended strongly on the structure of the aromatic part of the 4-amino group, and any aromatic substitution except fluorine reduced the in vitro activity. The cellular EGFR internalization response of selected compounds was evaluated using HeLa cells. Three fluorinated derivatives had a pronounced effect in inhibiting EGFR internalization.

An efficient large-scale synthesis of alkyl 5-hydroxy-pyridin- and pyrimidin-2-yl acetate

The synthesis of methyl 2-(5-hydroxy-3-methoxypyridin-2-yl)acetate and alkyl 2-(5-hydroxypyrimidin-2-yl)acetate is described. Methodology for an efficient access to 5-hydroxy-pyridin- and pyrimidin-2-yl acetate cores has been developed. Based on the difference in halogen reactivity, 5-bromo-2-chloropyridine and its pyrimidine analogue were functionalized judiciously by SNAr and palladium-catalyzed reactions. The outlined strategy provides a high-yielding route suitable for large-scale synthesis of these compounds as well as paves the way for a potential rapid access to other heterocyclic analogues.

FUSED BICYCLIC PYRIMIDINES AS PTK INHIBITORS CONTAINING A ZINC BINDING MOIETY

The present invention relates to fused bicyclic pyrimidine containing zinc- binding moiety based derivatives that have unique properties as protein tyrosine kinase (PTK) inhibitors and their use in the treatment of PTK related diseases and disorders such as cancer. The said derivatives may further act as HDAC inhibitors.

MULTI-FUNCTIONAL SMALL MOLECULES AS ANTI-PROLIFERATIVE AGENTS

The present invention relates to the compositions, methods, and applications of a novel approach to selective inhibition of several cellular or molecular targets with a single small molecule. More specifically, the present invention relates to multi-functional small molecules wherein one functionality is capable of inhibiting histone deacetylases (HDAC) and the other functionality is capable of inhibiting a different cellular or molecular pathway involved in aberrant cell proliferation, differentiation or survival.

Novel 2-amino-1,4-dihydropyridine calcium antagonists. I. Synthesis and antihypertensive effects of 2-amino-1,4-dihydropyridine derivatives having nitroxyalkoxycarbonyl groups at 3- and/or 5-position

Novel 2-amino-1,4-dihydropyridine derivatives, which contain nitroxy-alkoxycarbonyl groups at the 3- and/or 5-position, were synthesized and their pharmaceutical effect was evaluated in spontaneously hypertensive rats. The structure-activity relationships are discussed in terms of potency, onset-rapidity, and duration of antihypertensive activity. Remarkably prolonged duration of antihypertensive action was observed when a tertiary amino group was introduced on either side of an ester chain.