5688-83-5

Upstream product

• 109-77-3 malononitrile 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 

Downstream Products

• 354554-34-0 6-amino-3-propyl-4-(2,3,4-trimethoxy-phenyl)-2,4-dihydro-pyrano[2,3-c]pyrazole-5-carbonitrile 
• 330857-83-5 6-amino-5-tosyl-4-(2,3,4-trimethoxyphenyl)nicotinonitrile 
• 1353554-22-9 2-amino-5-oxo-4-(2,3,4-trimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile 

Relevant academic research and scientific papers

Synthesis, in vitro and in silico screening of 2-amino-4-aryl-6-(phenylthio) pyridine-3,5-dicarbonitriles as novel α-glucosidase inhibitors

Inhibition of α-glucosidase enzyme is of prime importance for the treatment of diabetes mellitus (DM). Apart of many organic scaffolds, pyridine based compounds have previously been reported for wide range of bioactivities. The current study reports a series of pyridine based synthetic analogues for their α-glucosidase inhibitory potential assessed by in vitro, kinetics and in silico studies. For this purpose, 2-amino-4-aryl-6-(phenylthio)pyridine-3,5-dicarbonitriles 1–28 were synthesized and subjected to in vitro screening. Several analogs, including 1–3, 7, 9, 11–14, and 16 showed many folds increased inhibitory potential in comparison to the standard acarbose (IC50 = 750 ± 10 μM). Interestingly, compound 7 (IC50 = 55.6 ± 0.3 μM) exhibited thirteen-folds greater inhibition strength than the standard acarbose. Kinetic studies on most potent molecule 7 revealed a competitive type inhibitory mechanism. In silico studies have been performed to examine the binding mode of ligand (compound 7) with the active site residues of α-glucosidase enzyme.

Synthesis, biological evaluation, and molecular modeling of nitrile-containing compounds: Exploring multiple activities as anti-Alzheimer agents

Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti-aggregating properties. Eighty-three nitrile-containing compounds, 13 of which are new, were synthesized and evaluated. in vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34 μM), MAO B (0.26 μM), and AChE (52 μM), while 32 exhibited a lead for selective MAO A (0.12 μM) inhibition coupled to AChE (48 μM) inhibition. Computational analysis revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand molecule and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1–42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1–42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65 μM), making it a potential lead for Alzheimer's disease application.

Synthesis of substituted 6-amino-4-aryl-5-cyano-2h,4h-pyrano[2,3-c]pyrazoles. Crystal and molecular structure of 6-amino-5-cyano-3-methyl-4-(2′,4′,6′-triethylphenyl)-2h,4h -pyrano[2,3-c]pyrazole

Substituted 6-aminopyrano[2,3-c]pyazoles were synthesized by the two-component condensation of arylidenemalononitriles and substituted 5-pyazolones or three-component condensation of aromatic aldehydes, malononitrile, and substituted 5-pyazolones. It was