Nitriles used to be known as cyanides; the smallest organic nitrile is ethanenitrile, CH3CN, (old name: methyl cyanide or acetonitrile – and sometimes now called ethanonitrile). 105-34-0, formula is C4H5NO2, Name is Methyl 2-cyanoacetate. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Formula: C4H5NO2.
Ferlenghi, Francesca;Maccioni, Paola;Mugnaini, Claudia;Brizzi, Antonella;Fara, Federica;Mostallino, Rafaela;Paola, Castelli M.;Colombo, Giancarlo;Mor, Marco;Vacondio, Federica;Corelli, Federico research published 《 The GABAB receptor positive allosteric modulator COR659: In vitro metabolism, in vivo pharmacokinetics in rats, synthesis and pharmacological characterization of metabolically protected derivatives》, the research content is summarized as follows. We report an in vitro phase I metabolism study on COR659 (1), a 2-acylaminothiophene derivative able to suppress alc. and chocolate self-administration in rats, likely via pos. allosteric modulation of the GABAB receptor and antagonism/inverse agonism at the cannabinoid CB1 receptor. High performance liquid chromatog. coupled to tandem and high resolution mass spectrometry was employed for the characterization of in vitro metabolism and in vivo pharmacokinetics of COR659 in rats. In vitro [35S]GTPγS binding assays on stimulated GABAB and CB1 receptors, in combination with alc. and chocolate self-administration experiments in rats, were employed to assess the pharmacol. profile of this novel set of analogs, using COR659 as reference compound Eight metabolites of COR659 were discovered in liver microsomal incubates; two of them (M1, M2) were identified by comparison with synthetic reference standards In the novel set of COR659 analogs, those bearing branched alkyl substituents on the ester group, showed an improved in vitro metabolic stability (2-4), had an in vitro GABAB PAM (2-4) and/or CB1 partial agonist/antagonist profile (2-3) and maintained the ability to reduce alc. (2-4) and/or chocolate (4) self-administration in rats. Both PK and PD data ruled out any involvement of metabolite M1 in the in vivo potency of COR659 and 4. The present results, therefore, highlight the importance to design and synthesize novel compounds endowed with the dual activity profile and devoid of metabolic liabilities.
Formula: C4H5NO2, Methyl cyanoacetate is an alkyl cyanoacetate ester.
Methyl cyanoacetate is the intermediate product in pharmaceutical organic synthesis as well as in the synthesis of some biologically active compounds used in agriculture. It undergoes calcite or fluorite catalyzed Knövenagel condensation with aromatic aldehydes, giving the corresponding arylidenemalononitriles and (E)-α -cyanocinnamic esters.
Methyl Cyanoacetate is often used as a nucleophile in the electrochemical oxidation of catechols. Methyl Cyanoacetate is also a reagent in the synthesis of Methyl 2-Amino-4-trifluoromethylthiophene-3-carboxylate (M287290); a compound used in the synthesis of DPP-IV inhibitors for treating type 2 diabetes., 105-34-0.
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts