31145-02-5

Upstream product

• 14378-09-7 2-Cyano-3-<4-(N,N-dimethylamino)phenyl>propenoic acid 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 7605-28-9 2-(phenylsulfonyl)acetonitrile 
• 75-05-8 acetonitrile 
• 97221-11-9 (E)-4-(((4-methoxyphenyl)imino)methyl)-N,N-dimethylaniline 
• 372-09-8 cyanoacetic acid 
• 3252-43-5 dibromoacetonitrile 
• 41463-93-8 4-N,N-dimethylaminobenzaldehyde hydrazone 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 141692-09-3 (E)-3-(4-(dimethylamino)phenyl)-2(phenylsulfonyl)acrylonitrile 

Relevant academic research and scientific papers

Optimization of chemical functionalities of indole-2-carboxamides to improve allosteric parameters for the cannabinoid receptor 1 (CB1)

5-Chloro-3-ethyl-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide (1; ORG27569) is a prototypical allosteric modulator for the cannabinoid type 1 receptor (CB1). Here, we reveal key structural requirements of indole-2-carboxamides for allosteric modulation of CB1: a critical chain length at the C3-position, an electron withdrawing group at the C5-position, the length of the linker between the amide bond and the phenyl ring B, and the amino substituent on the phenyl ring B these significantly impact the binding affinity (KB) and the binding cooperativity (α). A potent CB1 allosteric modulator 5-chloro-N-(4-(dimethylamino)phenethyl)-3-propyl-1H-indole- 2-carboxamide (12d) was identified. It exhibited a KB of 259.3 nM with a strikingly high binding α of 24.5. We also identified 5-chloro-N-(4-(dimethylamino)phenethyl)-3-hexyl-1H-indole-2-carboxamide (12f) with a KB of 89.1 nM, which is among the lowest KB values obtained for any allosteric modulator of CB1 these positive allosteric modulators of orthosteric agonist binding nonetheless antagonized the agonist-induced G-protein coupling to the CB1 receptor, yet induced β-arrestin mediated ERK1/2 phosphorylation.

A new method for the synthesis of cinnamonitriles by catalytic olefination

Catalytic olefination of hydrazones of aromatic aldehydes with dibromoacetonitrile affords cinnamonitriles.

Pathways for the solvent-free condensation between schiff bases and methylenic compounds

Pathways for the solvent-free condensation between Schiff Bases and methylenic compounds are discussed taking into account the reported mechanistic purposes and new experimental data.

Synthetic studies related to diketopyrrolopyrrole (DPP) pigments. Part 1: The search for alkenyl-DPPs. Unsaturated nitriles in standard DPP syntheses: A novel cyclopenta[c]pyrrolone chromophore

Reactions of the anion of ethyl 4,5-dihydro-5-oxo-2-phenylpyrrole-3-carboxylate with the Diels-Alder adducts of acrylonitrile and various dienes rarely yield the expected DPP derivatives. The reaction with cyclohex-3-enecarbonitrile provides a noteworthy exception: thermolysis of the resulting cyclohexenyl-DPP gives butadiene and impure 3-ethenyl-6-phenyl-DPP, the latter being thermally unstable. Michael additions predominate when the above anion reacts with α,β-unsaturated nitriles: acrylonitrile and methacrylonitrile give 4,4-bis(cyanoethyl) and 4,4-bis(2-cyanopropyl) derivatives, and cinnamonitrile, substituted cinnamonitriles and 3-(2-thienyl)acrylonitrile give deep red 3-aryl-5-cyano-4-hydroxy-2H-cyclopenta[c]pyrrol-1-ones. These ambident nucleophiles may undergo N- and either O- or C-alkylation according to the alkylating agent used.

STEREOSELECTIVE SYNTHESIS OF (2Z)-α,β-UNSATURATED NITRILES VIA TANDEM CONDENSATION-DESULFONYLATION OF α-CYANOSULFONES WITH ALDEHYDES

In the presence of sodium telluride, α-cyanosulfones undergo tandem condensation-desulfonylation reaction with aromatic aldehydes to give (2Z)-α,β-unsaturated nitriles with good stereoselectivity.

Transmiision of substituent effects through extended systems II. Substituted cis and trans cinnamonitriles

Infrared data and 13C chemical shifts are reported for a series of p-substituted cis and m-substituted trans cinnamonitriles.The i.r. values include intensities for the benzene, ethylene and cyanide vibrations which allow an estimation of resonance effect