14003-46-4

Usage

Uses

Used in Pharmaceutical Industry:
2-(quinolin-4-yl)acetonitrile is used as a synthetic reagent for the development of potential bone morphogenetic protein (BMP) signaling inhibitors. These inhibitors play a crucial role in regulating the BMP signaling pathway, which is involved in various cellular processes, including cell proliferation, differentiation, and apoptosis. By targeting this pathway, these inhibitors can potentially be used in the treatment of diseases characterized by abnormal cell growth or tissue repair, such as cancer and osteoporosis.
Additionally, 2-(quinolin-4-yl)acetonitrile can be utilized in the synthesis of other bioactive compounds with potential applications in the pharmaceutical industry. Its unique structure allows for the development of novel drugs with improved efficacy and selectivity, contributing to the advancement of therapeutic options for various medical conditions.

InChI:InChI=1/C11H8N2/c12-7-5-9-6-8-13-11-4-2-1-3-10(9)11/h1-4,6,8H,5H2

Upstream product

• 91973-99-8 3-[4]quinolyl-2-hydroxyimino-propionic acid 
• 4363-93-3 quinoline-4-carboxaldehyde 
• 2942-58-7 diethyl cyanophosphonate 
• 6281-32-9 4-quinolylmethanol 
• 5632-17-7 4-(chloromethyl)quinoline 
• 13119-77-2 2-oxo-3-quinolin-4-yl-propionic acid ethyl ester 
• 611-35-8 4-chloroquinoline 
• 18852-51-2 sodium cyanoacetic acid ethyl ester 
• 109558-06-7 benzoyloxy-[4]quinolyl-acetonitrile 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 18773-77-8 methyl(phenyl)cyanamide 

Downstream Products

• 24675-10-3 2-[4]quinolyl-3c-(4-dimethylamino-phenyl)-acrylonitrile 
• 109553-90-4 [4]quinolyl-(4-dimethylamino-phenylimino)-acetonitrile 
• 4789-81-5 ethyl 4-quinolineacetate 
• 1062368-21-1 4-quinolin-4-yl-2H-pyrazol-3-ylamine 
• 1062368-22-2 C₂₁H₁₃BrN₄ 
• 1062368-24-4 LDN-193189 
• 1062368-23-3 C₃₃H₂₈N₆O₂ 
• 1187313-01-4 C₂₆H₂₃N₅ 
• 1187313-00-3 C₂₇H₂₅N₅O 
• 1187313-20-7 C₃₁H₃₁N₅O₂ 
• 1187313-18-3 C₃₁H₂₉N₅O₂ 
• 1187313-23-0 C₃₁H₃₁N₅O₃ 
• 1187313-12-7 C₃₂H₃₃N₅O₃ 

Relevant academic research and scientific papers

INHIBITORS OF THE BMP SIGNALING PATHWAY

The present invention provides small molecule inhibitors of BMP signaling. These compounds may be used to modulate cell growth, differentiation, proliferation, and apoptosis, and thus may be useful for treating diseases or conditions associated with BMP signaling, including inflammation, cardiovascular disease, hematological disease, cancer, and bone disorders, as well as for modulating cellular differentiation and/or proliferation.

Structure-activity relationship study of bone morphogenetic protein (BMP) signaling inhibitors

A structure-activity relationship study of dorsomorphin, a previously identified inhibitor of SMAD 1/5/8 phosphorylation by bone morphogenetic protein (BMP) type 1 receptors ALK2, 3, and 6, revealed that increased inhibitory activity could be accomplished by replacing the pendent 4-pyridine ring with 4-quinoline. The activity contributions of various nitrogen atoms in the core pyrazolo[1,5-a]pyrimidine ring were also examined by preparing and evaluating pyrrolo[1,2-a]pyrimidine and pyrazolo[1,5-a]pyridine derivatives. In addition, increased mouse liver microsome stability was achieved by replacing the ether substituent on the pendent phenyl ring with piperazine. Finally, an optimized compound 13 (LDN-193189 or DM-3189) demonstrated moderate pharmacokinetic characteristics (e.g., plasma t1/2 = 1.6 h) following intraperitoneal administration in mice. These studies provide useful molecular probes for examining the in vivo pharmacology of BMP signaling inhibition.

An improved method for direct conversion of heteroaryl-aldehydes to heteroaryl-acetonitriles

Treatment of heteroaryl-aldehydes with diethyl cyanophosphonate in the presence of a catalytic amount of LiCN affords phosphorylated cyanohydrins which are reduced in situ with SmI2 to give heteroaryl-acetonitriles in generally good overall yields (50-100%). The generality of the process is demonstrated.

Chemistry of Thienopyridines. XXXV. Synthesis, Tautomerism, and Reactions of Quinoline and Thienopyridine Systems Which Bear a 1-Carboethoxy-1-cyanomethyl Substituent in the Pyridine Ring, Part 2

A comparison is made amongst the isosteric systems quinoline, thienopyridine, and thieno-pyridine which bear the 1-carboethoxy-1-cyanomethyl substituent (R) alpha or gamma to the heterocyclic nitrogen atom.Treatment of thienopyridine 4-oxide with ethyl cyanoacetate and acetic anhydride at room temperature (Hamana reaction) gives the alpha R-derivative 6 (27percent), formulated as an intramolecular H-bonded structure.Neither 6 nor its quinoline alpha analog reacts with refluxing acetic anhydride, while the quinoline gamma isomer 8, existing as NH and CH tautomers, yields an N-acetyl derivative 10 (70percent) under similar conditions.For each of 6 and 8 one can isolate two crystalline forms which differ considerably in color.Compound 10 and its gamma analog in the thienopyridine series (previously obtained directly from a Hamana reaction) serve as acetylating agents for aniline, 1-aminobutane, morpholine, and cholesterol.Correlations and contrasts in the three systems are presented.