129213-83-8

Upstream product

• 59410-82-1 (S)-α-phenylglycine ethyl ester hydrochloride 
• 124-40-3 dimethyl amine 
• 15962-49-9 (S)-phenylglycine ethyl ester 
• 74-89-5 methylamine 
• 875-74-1 (R)-phenylglycine 
• 108-86-1 bromobenzene 
• 6591-61-3 (S)-Phenylglycine methyl ester 
• 5491-18-9 (S)-N-(benzyloxycarbonyl)phenylglycine 
• 146118-22-1 Z-PhGly-OSu 
• 2935-35-5 (S)-2-phenylglycine 
• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 
• 1033883-20-3 (S)-tert-butyl 2-(methylamino)-2-oxo-1-phenylethylcarbamate 
• 15028-39-4 L-2-phenylglycine methyl ester hydrochloride 
• 744949-71-1 D-(-)-α-phenylglycylchloride 

Downstream Products

• 209161-43-3 (S)-2,2,3-trimethyl-5-phenylimidazolidin-4-one 
• 345579-89-7 (R)-2-tert-butyl-3-methyl-(S)-5-phenylimidazolidin-4-one 
• 871917-48-5 L-isoleucyl-L-phenylglycine methyl amide 
• 97443-96-4 (2S,5R)-2-(tert-Butyl)-3-methyl-5-phenylimidazoldin-4-on 
• 79513-96-5 (S)-N¹-methyl-2-phenylethane-1,2-diamine 
• 188728-68-9 L-cyclohexylglycine-N-methylamide 
• 188729-03-5 (R)-3-[((S)-Methylcarbamoyl-phenyl-methyl)-carbamoyl]-5-phenyl-pentanoic acid tert-butyl ester 
• 188729-09-1 (R)-3-[((S)-Methylcarbamoyl-phenyl-methyl)-carbamoyl]-6-phenyl-hexanoic acid tert-butyl ester 
• 334756-91-1 (R)-3-[((S)-Methylcarbamoyl-phenyl-methyl)-carbamoyl]-dodecanoic acid tert-butyl ester 
• 168158-25-6 2-{(R)-3-Methyl-1-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-butyl}-malonic acid dibenzyl ester 
• 168158-21-2 (R)-N⁴-Benzyloxy-2-isobutyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-succinamide 
• 188728-99-6 (2S,3R)-2,5-Dimethyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-hexanoic acid tert-butyl ester 
• 129155-75-5 (S)-2-(4-Methoxy-phenyl)-3-methyl-5-phenyl-imidazolidin-4-one 

Relevant academic research and scientific papers

A Concise Enantiodivergent Synthesis of Equol

Equol, a nonsteroidal estrogen produced from the metabolism of the isoflavonoid phytoestrogen daidzein, has been synthesized as both enantioenriched forms based on MacMillan's α-Arylation of carbonyl compound mediated by amino acid derived indazolidinones and copper precatalysts. The natural form of (S)-equol and its enantiomer (R)-equol have been synthesized in 8 steps from 2,4-dimethoxybenzaldehyde with good enantiomeric purity (90% ee and 90% ee, respectively).

Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids

Imidazolidinone derivatives of a range of aromatic α-amino acids, on treatment with phosgene and potassium iodide, undergo a mild Bischler-Napieralski-style cyclocarbonylation reaction that generates a tricyclic lactam by insertion of a C=O group between amino acid nitrogen and the ortho position of the aryl substituent. Regio- and diastereoselective functionalization of the lactam generates a library of substituted dihydroisoquinolinones and their congeners in enantioenriched form.

The asymmetric reduction of imidazolinones with trichlorosilane

It is shown how imidazolinones are reduced by trichlorosilane in a highly enantioselective fashion when treated with a novel Lewis base organocatalyst that is based on a 2,2′-bispyrrolidine core. Under mild reaction conditions and with low catalyst loading the hydrosilylation reaction provides a broad range of chiral imidazolidinones with various structural motifs including sterically demanding substituents, alkyls and aryls.

Asymmetric synthesis of 4-aryl-1,2,5-thiadiazolidin-3-one 1,1-dioxides via Pd-catalyzed hydrogenation of cyclic ketimines

An efficient access to optically active sulfahydantoins, 4-aryl-1,2,5-thiadiazolidin-3-one 1,1-dioxides, was developed through palladium-catalyzed asymmetric hydrogenation of the corresponding cyclic N-sulfonylketimines with up to 98% ee.

ERK INHIBITORS

The present invention provides a compound of Formula (I) or the pharmaceutically acceptable salts, esters, and prodrugs thereof, which are ERK2 inhibitors. The invention also provides a pharmaceutical composition comprising an effective amount of at least one compound of Formula (I) and a pharmaceutically acceptable carrier. The invention also provides a pharmaceutical composition comprising an effective amount of at least one compound of Formula (I) and an effective amount of at least one other pharmaceutically active ingredient (such as, for example, a chemotherapeutic agent), and a pharmaceutically acceptable carrier.

Squaric acid-based peptidic inhibitors of matrix metalloprotease-1

A series of squaric acid-peptide conjugates were synthesized and evaluated as inhibitors of MMP-1. The cyclobut-3-enedione core was substituted at the 3-position with several functional groups, such as -N(alkyl)OH, -NHOH, and -OH, that are designed to bind to the zinc atom in the active site of the metalloprotease. The 4-position of the cyclobut-3-enedione was derivatized with mono- or dipeptides that are designed to bind in the S1′ and S2′ subsites of the enzyme, and position the metal chelating group appropriately in the active site for binding to zinc. Positional scanning revealed that -N(Me)OH provided the highest level of inhibition among the chelating groups that were tested, and Leu-Tle-NHMe was the preferred amino acid sequence. A combination of these groups yielded an inhibitor with an IC50 value of 95 μM. For one inhibitor, conversion of one of the carbonyl groups on the cyclobut-3-enedione core to a thiocarbonyl group resulted in a 18-fold increase in potency, and yielded a compound with an IC50 value of 15 μM.

Asymmetric Synthesis of 4,4-Disubstituted-2-Imidazoli-dinones: Potent NK1 Antagonists

(Equation presented) A highly efficient and practical synthesis of 4,4-Disubstituted-2-Imidazolidinones utilizing a "self-reproduction of the center of chirality" strategy is described.

Organocatalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated enones using novel imidazoline catalysts

A new catalytic enantioselective conjugate addition of nitroalkanes to acyclic α,β-unsaturated enones catalyzed by novel organic catalysts has been developed. A series of chiral amines has been tested as catalysts for the addition of 2-nitropropane to benzylideneacetone, and it is found that a novel imidazoline catalyst, prepared from phenylalanine, can catalyze a highly enantioselective 1,4addition reaction. The reaction of various acyclic and cyclic nitroalkanes was found to proceed well with enantioselectivities up to 86% ee, and enantiopure products can be obtained by recrystallization. The potential of the reaction is documented by the reaction of a series of substituted α,β-unsaturated enones with different nitroalkanes. Furthermore, the synthetic applicability of the reaction is demonstrated by the formation of optically active functionalized pyrrolines and pyrrolidines by reductive amination of the products. On the basis of the absolute configuration of the conjugate addition products, the mechanism for the reaction is discussed and a transition state proposed.

Design and synthesis of new potent C2-symmetric HIV-1 protease inhibitors. Use of L-mannaric acid as a peptidomimetic scaffold

A study on the use of derivatized carbohydrates as C2-symmetric HIV-1 protease inhibitors has been undertaken. L-Mannaric acid (6) was bis-O- benzylated at C-2 and C-5 and subsequently coupled with amino acids and amines to give C2-s

Synthesis and biological evaluation of orally active matrix metaloproteinase inhibitors

The synthesis and biological evaluation of orally active inhibitors of matrix metalloproteinase are reported. Modifications of the P2' position and the α-substituent of hydroxamic acid derivatives were carried out, and revealed that the P2' substituent influenced the MMP inhibitory activities in vitro and in plasma after oral administration. The hydroxamates with phenylglycine at the P2' position were absorbed well orally. Compound 15e, which exhibited the longest duration of inhibitory activity in plasma after oral administration among the phenylglycine derivatives (5a-5d, 15a, 15c, 15e), was evaluated in a rat adjuvant arthritis model. A reduction in hind foot pad swelling and improvements of some inflammatory parameters were demonstrated when the compound was administered orally. These results indicate the potential of MMP inhibitors for rheumatoid arthritis.