24115-37-5

Upstream product

• 106-47-8 4-chloro-aniline 
• 122-51-0 orthoformic acid triethyl ester 
• 109-77-3 malononitrile 
• 123-06-8 Ethoxymethylenemalononitrile 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 1220748-69-5 3-amino-1-(4-chlorophenyl)-1H-pyrrole-2,4-dicarbonitrile 
• 889997-48-2 5-acetyl-4-amino-1-(4-chlorophenyl)-1H-pyrrole-3-carbonitrile 
• 145162-33-0 ethyl 3-amino-1-(4-chlorophenyl)-4-cyano-1H-pyrrole-2-carboxylat 

Relevant academic research and scientific papers

Synthesis, three-dimensional structure, conformation and correct chemical shift assignment determination of pharmaceutical molecules by NMR and molecular modeling

This work includes the synthesis of phenanthrenequinone guanylhydrazone and phenanthro[9,10-e][1,2,4]triazin-3-amine to be tested as intercalate with DNA for treatment of cancer. The other synthesized product, 2-[(4-chlorophenylamino)methylene]malononitrile, was designed for future determination of its activity against leishmaniasis. A common problem about some articles on the literature is that some previously published compounds display error of their molecular structures. In this article it is shown the application of several procedures of nuclear magnetic resonance (NMR) to determine the complete molecular structure and the non questionable chemical shift assignment of the synthesized compounds, and also their analysis by molecular modeling to confirm the NMR results. To determine the capacity of pharmacological compounds to interact with biological targets is determined by docking. This work is to motivate the application of NMR and molecular modeling on organic synthesis, being a process that is very important for the study of the prepared compounds as interactions with biological targets by NMR.

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 and biological evaluation of new tacrine analogues under microwave irradiation

Efficient routes to various kinds of heterocycles incorporating the p-halophenyl moiety have been synthesized. Different pyrrole derivatives have been synthesized, as well, by Thorpe–Ziegler cyclization. Therefore, we synthesized different analogues of tacrine by Friedl?nder reaction of o-amino nitriles (pyrazolo, furano and pyrrolo) with different cycloalkanones. The use of microwave irradiation leads to shorter production times and high product conversion. These synthesized compounds were biologically evaluated by Ellman’s test on acetylcholinesterase inhibition.

Synthesis of new tacrine analogues from 4-amino-1H-pyrrole-3-carbonitrile

An easy preparation of 4-amino-1H-pyrrole-3-carbonitrile derivatives and their transformation into new substituted pyrrolo[3,2-b]pyridines is described. The one-step transformation was carried out via Friedlaender reaction under microwave irradiation and

PYRROLOPYRIMIDINE DERIVATIVES

The invention provides pyrrolo[3,2-d]pyrimidine derivatives represented by formula (I), and their medically acceptable salts. The compounds of the invention exhibit GSK-3 inhibiting activity and are therefore expected to be useful as therapeutic or prophylactic agents for conditions in which GSK-3 is implicated, such as diabetes, diabetes complications, Alzheimer's disease, neurodegenerative diseases, manic depression, traumatic encephalopathy, alopecia, inflammatory diseases, cancer and immune deficiency.

One Pot Synthesis of 3-Amino-1H-pyrazole-4-carbonitrile

Condensation of malodinitrile with trimethoxymethan and aniline affords 3-anilino-2-cyanoacrylonitrile, which on treatment with hydrazine gives the title compound.Aniline can be recovered almost quantitatively. Keywords: Enaminonitrile; Amine exchange; Cyclisation