18456-68-3

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 100-13-0 4-nitrostyrene 
• 186581-53-3 diazomethane 
• 555-16-8 4-nitrobenzaldehdye 
• 946-39-4 ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate 
• 946-38-3 cis-1-ethoxycarbonyl-2-phenylcyclopropane 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 16633-46-8 trans-2-(p-Nitrophenyl-)cyclopropanecarboxylic acid 
• 1206479-02-8 ethyl 5-(4-nitrophenyl)-4,5-dihydroisoxazole-3-carboxylate 
• 159670-70-9 ethyl 5-(4-nitrophenyl)isoxazole-3-carboxylate 
• 141794-89-0 ethyl cis-2-(p-aminophenyl)-1-cyclopropanecarboxylate 
• 141794-89-0 (1R*,2R*)-ethyl 2-(4-aminophenyl)cyclopropanecarboxylate 

Relevant academic research and scientific papers

Multigram Synthesis and C?C/C?N Couplings of Functionalized 1,2-Disubstituted Cyclopropyltrifluoroborates

A convenient approach to the multigram synthesis of functionalized 1,2-disubstituted cyclopropyltrifluoroborates was developed, based on Pd(II)- or Cu(I)-catalyzed reaction of vinyltrifluoroborate and diazo compounds. Optimized protocols allowed for the preparation of the target products as pure diastereomers on multigram scale. It was shown that the title compounds were good coupling partners for the Suzuki-Miyaura and Chan-Lam reactions, which provide medicinally relevant (het)arylcyclopropanes with high diastereoselectivity. (Figure presented.).

Synthesis of Photosensitive Cyclopropane-Containing Polymers

New cyclopropyl methacrylate monomers were prepared, their radical polymerization was performed, and the composition and structure of the polymers obtained, containing reactive UV-sensitive fragments, were determined. Experiments on photochemical cross-li

Pure enantiomers of benzoylamino-tranylcypromine: LSD1 inhibition, gene modulation in human leukemia cells and effects on clonogenic potential of murine promyelocytic blasts

The pure enantiomers of the N-(2-, 3-, and 4-(2-aminocyclopropyl)phenyl)benzamides hydrochlorides 11a-j were prepared and tested against LSD1 and MAO enzymes. The evaluation of the regioisomers 11a-j highlighted a net increase of the anti-LSD1 potency by

Biochemical, structural, and biological evaluation of tranylcypromine derivatives as inhibitors of histone demethylases LSD1 and LSD2

LSD1 and LSD2 histone demethylases are implicated in a number of physiological and pathological processes, ranging from tumorigenesis to herpes virus infection. A comprehensive structural, biochemical, and cellular study is presented here to probe the potential of these enzymes for epigenetic therapies. This approach employs tranylcypromine as a chemical scaffold for the design of novel demethylase inhibitors. This drug is a clinically validated antidepressant known to target monoamine oxidases A and B. These two flavoenzymes are structurally related to LSD1 and LSD2. Mechanistic and crystallographic studies of tranylcypromine inhibition reveal a lack of selectivity and differing covalent modifications of the FAD cofactor depending on the enantiomeric form. These findings are pharmacologically relevant, since tranylcypromine is currently administered as a racemic mixture. A large set of tranylcypromine analogues were synthesized and screened for inhibitory activities. We found that the common evolutionary origin of LSD and MAO enzymes, despite their unrelated functions and substrate specificities, is reflected in related ligand-binding properties. A few compounds with partial enzyme selectivity were identified. The biological activity of one of these new inhibitors was evaluated with a cellular model of acute promyelocytic leukemia chosen since its pathogenesis includes aberrant activities of several chromatin modifiers. Marked effects on cell differentiation and an unprecedented synergistic activity with antileukemia drugs were observed. These data demonstrate that these LSD1/2 inhibitors are of potential relevance for the treatment of promyelocytic leukemia and, more generally, as tools to alter chromatin state with promise of a block of tumor progression.

Cyclopropanation of olefins with diazo compounds catalyzed by a dicopper-substituted silicotungstate [γ-H2SiW 10O36Cu2(μ-1,1-N3) 2]4-

The dicopper-substituted γ-Keggin silicotungstate (TBA) 4[γ-H2SiW10O36Cu 2II(μ-1,1-N3)2] (I, TBA = tetra-n-butylammonium) could act as an efficient precatalyst for the chemoselective cylopropanation of olefins with diazo compounds. Various kinds of olefins were efficiently converted to the corresponding cyclopropane derivatives in good yields.

Reaction of esters of 2-arylcyclo-propanecarboxylic acids with nitrous acid. Synthesis of aryl-substituted 3-ethoxycarbonyl-4,5-dihydroisoxazoles and 3-ethoxycarbonylisoxazoles

Esters of 2-arylcyclopropanecarboxylic acids react with nitrous acid generated in situ with regioselective insertion of the nitrosyl cation into the cyclopropane ring. Depending on the substrate/nitrosylating agent ratio, the reaction proceeds with the formation of either aryl-substituted 3-ethoxycarbonyl-4,5-dihydroisoxazoles or the corresponding isoxazoles. The nature and position of the substituents in the aromatic ring of the starting 2-arylcyclopropanecarboxylic acid esters affect the reaction rate but have no effect on the regioselectivity of the attack by the nitrosyl cation on the three-membered ring. A dependence of the reactivity of isomeric substrates on their stereochemistry and position of the nitro group in the aromatic ring is noted for 2- and 4-nitrophenyl derivatives of esters of cis- and trans-2-arylcyclopropanecarboxylic acids.

One-pot approach for the synthesis of trans-cyclopropyl compounds from aldehydes. Application to the synthesis of GPR40 receptor agonists

A novel multicatalytic one-pot process providing trans-cyclopropyl compounds from corresponding aldehydes has been developed and applied to the synthesis of GPR40 small molecule agonists. The Royal Society of Chemistry.

Synthesis and activity of small molecule GPR40 agonists

The first report on the identification and structure-activity relationships of a novel series of GPR40 agonists based on a 3-(4-{[N-alkyl]amino}phenyl) propanoic acid template is described. Structural modifications to the original screening hit yielded co

On the mechanism of the copper-catalyzed cyclopropanation reaction

The selectivity-determining step in enantioselective copper-catalyzed cyclopropanation with diazo compounds has been studied by experimental and computational methods. The addition of the very reactive metallacarbene intermediate in an early transition st

Substituent Effects on the 13C NMR Spectra of Ethyl cis- and trans-2-(p-substituted-phenyl)-1-cyclopropanecarboxylates

13C NMR spectra were measured for a series of ethyl cis- and trans-2-(p-substituted-phenyl)-1-cyclopropanecarboxylates.The effects of the para substituents and the geometry on the chemical shifts are discussed.KEY WORDS 13C NMR Substituted cyclopropanes