Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. 105-34-0, formula is C4H5NO2, Name is Methyl 2-cyanoacetate. Both routes are green in the sense that they do not generate stoichiometric amounts of salts. Formula: C4H5NO2.
Eliwa, Essam M.;Frese, Marcel;Halawa, Ahmed H.;Soltan, Maha M.;Ponomareva, Larissa V.;Thorson, Jon S.;Shaaban, Khaled A.;Shaaban, Mohamed;El-Agrody, Ahmed M.;Sewald, Norbert research published 《 Metal-free domino amination-Knoevenagel condensation approach to access new coumarins as potent nanomolar inhibitors of VEGFR-2 and EGFR》, the research content is summarized as follows. A metal-free, atom-economy and simple work-up domino amination-Knoevenagel condensation approach to construct new coumarin analogous I [R1 = pyrrolidin-1-yl, morpholino, (4-hydroxy-1-piperidyl), etc.; R2 = cyano, methoxycarbonyl, (1-amino-2,2-dicyano-vinyl)] were described. Further, new formyl and nitro coumarin derivatives II [R1 = methoxy, pyrrolidin-1-yl, morpholino, etc.; R3 = formyl, nitro] were synthesized via C-N coupling reaction of various cyclic secondary amines and 4-chloro-3-(formyl-/nitro)coumarins resp. The confirmed compounds were screened for their in vitro anti-proliferative activity against KB-3-1, A549 and PC3 human cancer cell lines using resazurin cellular-based assay. Among them, coumarin derivatives I [R1 = (4-piperidylmethylamino); R2 = cyano, methoxycarbonyl] displayed the best anti-cervical cancer potency (KB-3-1) with IC50 values of 15.5 ± 3.54 and 21 ± 4.24μM, resp. Also, I [R1 = (4-piperidylmethylamino); R2 = methoxycarbonyl] showed the most promising cytotoxicity toward A549 with IC50 value of 12.94 ± 1.51μM. As well, II [R1 = morpholino; R3 = nitro]presented a more significant impact of potency against PC3 with IC50 7.31 ± 0.48μM. Moreover, I [R1 = morpholino; R2 = cyano] manifested selectivity against PC3 (IC50 = 20.16 ± 0.07μM), while I [R1 = (4-piperidylmethylamino); R2 = cyano] was selective toward KB-3-1 cell line (IC50 = 21 ± 4.24μM). Matching with docking profile, the enzymic assay divulged that I [R1 = (4-piperidylmethylamino); R2 = cyano] was a dual potent single-digit nanomolar inhibitor of VEGFR-2 and EGFR with IC50 values of 24.67 nM and 31.6 nM that were almost equipotent to sorafenib (31.08 nM) and erlotinib (26.79 nM), resp.
105-34-0, 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., Formula: C4H5NO2
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts