56791-34-5

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 96-34-4 methyl chloroacetate 
• 67-56-1 methanol 
• 33984-97-3 2,3-epoxy-3-(4-chlorophenyl)propanenitrile 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 20754-21-6 methyl 3-(4-chlorophenyl)propenoate 

Downstream Products

• 139618-71-6 Methyl trans-3-(4-chlorophenyl)aziridine-2-carboxylate 
• 646532-22-1 {N'-(2-benzyloxycarbonylamino-3-methyl-butyryl)-N-[3-(4-chloro-phenyl)-oxiranecarbonyl]-hydrazino}-acetic acid tert-butyl ester 
• 50693-98-6 methyl 2-((2-nitrophenyl)thio)acetate 
• 104-88-1 4-chlorobenzaldehyde 
• 94098-25-6 (2R,3S)-3-(4-Chloro-phenyl)-2-hydroxy-3-(2-nitro-phenylsulfanyl)-propionic acid methyl ester 

Relevant academic research and scientific papers

Regioselective syntheses of 3-hydroxy-4-aryl-3,4,5-trihydro-2H-benzo[b][1,4]diazepin-2(1H)-ones and 3-benzylquinoxalin-2(1H)-ones from arylglycidates when exposed to 1,2-diaminobenzenes

Representatives of two pharmacologically significant classes of compounds – 3-hydroxy-4-aryl-3,4,5-trihydro-2H-benzo[b][1,4]diazepin-2(1H)-ones and 3-benzylquinoxalin-2(1H)-ones – obtained in reactions of 1,2-diaminobenzenes with methyl 3-arylglycidates in boiling acetic acid. Substituents in arylglycidates determine the direction of processes. Electron withdrawing substituents (NO2), halogen atoms (Cl, Br, F), as well as the absence of substituents, provide the formation of benzo[b][1,4]diazepin-2(1H)-one derivatives, and electron donating groups (OMe, Me) contribute to the formation of 3-benzylquinoxalin-2(1H)-ones. As a result, a new rare representatives of 3-hydroxy-4-aryl-3,4,5-trihydro-2H-benzo[b][1,4]diazepin-2(1H)-ones were obtained and a new method for producing 3-benzylquinoxalin-2(1H)-ones has been proposed.

Enantiopure trans -3-arylaziridine-2-carboxamides: Preparation by bacterial hydrolysis and ring-openings toward enantiopure, unnatural D -α-amino acids

Several racemic trans-3-arylaziridine-2-carboxamides were prepared and then resolved by Rhodococcus rhodochrous IFO 15564-catalyzed hydrolysis. The resulting enantiopure (2R,3S)-3-arylaziridine-2-carboxamides are adequate substrates to undergo fully stereoselective nucleophilic ring-openings at the C-3 ring position to finally yield enantiopure, unnatural d-α- aminocarboxylic acids. Experimental evidence is provided that suggests the fate of the (2S,3R)-3-arylaziridine-2-carboxylic acids concomitantly formed during the resolution processes. In this context, the similar bacterial resolution of racemic 1-arylaziridine-2-carboxamides and -carbonitriles, previously investigated by our research group, has been partially re-examined.

Design, Synthesis, and Evaluation of Aza-Peptide Epoxides as Selective and Potent Inhibitors of Caspases-1, -3, -6, and -8

Aza-peptide epoxides, a novel class of irreversible protease inhibitors, are specific for the clan CD cysteine proteases. Aza-peptide epoxides with an aza-Asp residue at P1 are excellent irreversible inhibitors of caspases-1, -3, -6, and -8 with second-order inhibition rates up to 1 910 000 M-1 s-1. In general, the order of reactivity of aza-peptide epoxides is S,S > R,R > trans > cis. Interestingly, some of the R,R epoxides while being less potent are actually more selective than the S,S epoxides. Our aza-peptide epoxides designed for caspases are stable, potent, and specific inhibitors, as they show little to no inhibition of other proteases such as the aspartyl proteases porcine pepsin, human cathepsin D, plasmepsin 2 from P. falciparum, HIV-1 protease, and the secreted aspartic proteinase 2 (SAP-2) from Candida albicans; the serine proteases granzyme B and α-chymotrypsin; and the cysteine proteases cathepsin B and papain (clan CA), and legumain (clan CD).

A convenient synthesis of aziridine-2-carboxylic esters

Optically active oxirane-2-carboxylic esters, prepared from allylic alcohols employing the Sharpless epoxidation, were treated with sodium azide.The azido alcohols obtained were subsequently converted into aziridine-2-carboxylic esters by reaction with triphenylphosphine, in good yields and with high optical purity.Various racemic oxirane-2-carboxylic esters were subjected to the same sequence of reactions.

REACTION OF 4-SUBSTITUTED BENZALDEHYDES AND ACETOPHENONES WITH CHLOROACETONITRILE

Under conditions of phase-transfer catalysis or in homogeneous solution of potassium tert-butoxide the title compounds give stereoisomeric mixtures of substituted 2,3-epoxy nitriles III and IV.Alkaline hydrolysis of epoxy nitriles IV afforded the corresponding 2-arylpropanals in low yields.On treatment with methanol and potassium carbonate, epoxy nitriles III and IV were converted into epoxy esters in good yields.