950192-21-9

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 84890-94-8 (S)-2-Isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 95-53-4 o-toluidine 

Downstream Products

• 950192-22-0 C₁₇H₂₄N₂O₂S 
• 1004960-66-0 C₃₃H₄₀N₄O₃ 
• 245058-20-2 (S)-N-(o-tolyl)pyrrolidine-2-carboxamide 

Relevant academic research and scientific papers

A New Class of Amide Ligands Enable Cu-Catalyzed Coupling of Sodium Methanesulfinate with (Hetero)aryl Chlorides

((2S,4R)-4-Hydroxy-N-(2-methylnaphthalen-1-yl)pyrrolidine-2-carboxamide (HMNPC), an amide derived from 4-hydroxy-L-proline and 2-methyl naphthalen-1-amine, is a powerful ligand for Cu-catalyzed coupling of (hetero)aryl halides with sulfinic acid salts, allowing for first time the metal-catalyzed coupling of (hetero)aryl chlorides and NaSO2Me. A considerable number of (hetero)aryl chlorides worked well, providing the pharmaceutically important (hetero)aryl methylsulfones in good to excellent yields.

Synthesis of Analogues of BCTC Incorporating a Pyrrolidinyl Linker and Biological Evaluation as Transient Receptor Potential Vanilloid 1 Antagonists

A series of novel pyrrolidinyl linker TRPV1 antagonists were prepared in an effort to lower the hyperthermic side-effects of first-generation antagonist BCTC. These compounds were investigated for antagonism of hTRPV1 activation by capsaicin and acid in vitro. Preliminary results suggested the compounds 10a, 10b, 10c and 10j had favorable TRPV1 antagonism activity. In further studies in vivo, 10b, comparable to BCTC, showed potent analgesic activity in capsaicin-induced and heat-induced pain models. In addition, 10b indicated a reduced risk of body temperature elevation. All of these demonstrated that 10b can be considered as a safe candidate for the further development of analgesic drugs. A series of novel pyrrolidinyl linker TRPV1 antagonists were prepared in an effort to lower the hyperthermic side-effects of first-generation antagonist BCTC. These compounds were investigated for antagonism of hTRPV1 activation by capsaicin and acid in vitro. Preliminary results suggested the compounds 10a, 10b, 10c and 10j had favorable TRPV1 antagonism activity. In further studies in vivo, 10b, comparable to BCTC, showed potent analgesic activity in capsaicin-induced and heat-induced pain models. In addition, 10b indicated a reduced risk of body temperature elevation. All of these demonstrated that 10b can be considered as a safe candidate for the further development of analgesic drugs.

Screening method for the evaluation of asymmetric catalysts for the reduction of aliphatic ketones

ATH reductions of aliphatic ketones in water catalyzed by ruthenium coordinated by prolinamide ligands produce alcohols with moderate enantiomeric excesses in most cases. A set of seven aliphatic ketones is proposed for a rapid evaluation of the enantioselectivity of catalysts by one-pot multi-substrates reduction. The screening of a library of prolinamides shows that according to the structure of the ketones different ligands give the best asymmetric inductions.

Antagonists of inhibitor of apoptosis proteins based on thiazole amide isosteres

A series of IAP antagonists based on thiazole or benzothiazole amide isosteres was designed and synthesized. These compounds were tested for binding to the XIAP-BIR3 and ML-IAP BIR using a fluorescence polarization assay. The most potent of these compound

Design of chiral hydroxyalkyl- and hydroxyarylazolinium salts as new chelating diaminocarbene ligand precursors devoted to asymmetric copper-catalyzed conjugate addition

The design and the synthesis of a set of new chiral hy- droxyalkyl- and hydroxyaryl-chelating diaminocarbene ligands is reported. Comparative catalytic studies show the importance of the scaffold design around the NHC unit to obtain a high enantiocontrol in Cu-catalyzed asymmetric conjugate addition (ACA). Whereas low selectivities are observed when the stereogenic centre is placed within the N-heterocyclic ring, an interesting match effect can be observed when central chirality is located within both of the two side chains, which enables up to 92 % ee in the catalysis reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.

INHIBITORS OF IAP

The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds having the general formula U1 - M - U2 wherein M is a linking group covalently joining R2, R3, R4 or R5 of U1 to an R2, R3, R4 or R5 group of U2; U1 and U2 have the general formula (I) and G, X1, X2, R2, R3, R3', R4, R4' and R5, are as described herein.

INHIBITORS OF IAP

The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds have the general formula (I): wherein Q, X1, X2, Y, Z1, Z2, Z3, Z4, R1, R2, R3, R3', R4, R4', R5, R6, R6' and n are as described herein.

Catalytic asymmetric cyano-ethoxycarbonylation reaction of aldehydes using a novel C2-symmetric chiral N,N′-dioxide titanium complex

The asymmetric addition of ethyl cyanoformate to a range of aldehydes was efficiently catalyzed by a easily prepared C2-symmetric chiral N,N′-dioxide-Ti(IV) complex in high yields with up to 90% ee under mild conditions. A linear effect between

Diastereoselective hydrogenation of (S)-proline-2-methylanilide

The diastereoselective hydrogenation of o-toluidine covalently linked to the chiral auxiliary (S)-proline has been studied. The hydrogenation of (S)-proline-2-methylanilide on supported noble metal catalysts yielded both the cis and the trans isomers of (