87281-16-1

Upstream product

• 2491-20-5 L-alanine methyl ester hydrochloride 
• 100-39-0 benzyl bromide 
• 10065-72-2 L-Alanine methyl ester 
• 17392-83-5 (R)-Methyl lactate 
• 103-49-1 dibenzylamine 
• 584-08-7 potassium carbonate 
• 75-05-8 acetonitrile 

Downstream Products

• 1258239-48-3 2-dibenzylamino-3-(2-fluoro-phenyl)-propionic acid methyl ester 
• 123725-86-0 ethyl (4S,2E)-4-(N,N-dibenzylamino)pent-2-enoate 
• 136964-88-0 (S,E)-methyl 4-(dibenzylamino)pent-2-enoate 
• 111060-70-9 (2S,3R)-2-(dibenzylamino)pentan-3-ol 
• 1539314-81-2 (S)-3-(dibenzylamino)-2-methylbutan-2-ol 
• 174198-34-6 N-benzyl-N-((1S)-1-methoxycarbonyl)ethyl-3-aminopyrazine-2-carboxamide 
• 111060-69-6 (2S,3S)-2-(dibenzylamino)pentan-3-ol 

Relevant academic research and scientific papers

Design, synthesis and evaluation of the antibacterial activity of new Linezolid dipeptide-type analogues

Worldwide studies towards development of new drugs with a lower rate in emergence of bacterial resistance have been conducted. The molecular docking analysis gives a possibility to predict the activity of new compounds before to perform their synthesis. In this work, the molecular docking analysis of 64 Linezolid dipeptide-type analogues was performed to predict their activity. The most negative scores correspond to six Fmoc-protected analogues (9as, 9bs, 9bu, 10as, 10ax and 10ay) where Fmoc group interacts in PTC for Linezolid. Twenty-six different Fmoc-protected Linezolid dipeptide-type analogues 9(as-bz) and 10(as-bz) were synthesized and tested in antimicrobial experiments. Compounds 9as, 9ay, 9ax, 10as, 10ay and 9bu show significant activity against group A Streptococcus clinical isolated. Analogue 10ay also display high activity against ATCC 25923 Staphylococcus aureus strain and MRSA-3, MRSA-4 and MRSA-5 clinical isolates, with MIC values lower than Linezolid. The highest activity against multidrug-resistant clinical isolates of Mycobacterium tuberculosis was exhibited by 9bu. Finally, a cytotoxicity assay with ARPE-19 human cells revealed a non-cytotoxic effect of 9bu and 10ay at 50 and 25 μM, respectively.

INDOLECARBONITRILES AS SELECTIVE ANDROGEN RECEPTOR MODULATORS

This invention relates to non-steroidal compounds that are modulators of androgen receptor, and also to the methods for the making and use of such compounds.

Synthesis of enantiomerically enriched indolines and tetrahydroisoquinolines from (S)-amino acid-derived chiral carbocations: An easy access to (3S,4R)-demethoxy-3-isopropyl diclofensine

Enantiomerically enriched indolines and tetrahydroisoquinolines were synthesized within 5 min to 2 h in high yields from easily accessible (S)-amino acid derived chiral carbocations. The diastereoselective Friedel-Crafts reaction is promoted by a Lewis acid (AlCl3) offering trans-diastereoselectivity. The rate of the reaction and diastereoselectivity of the product are significantly influenced by steric hindrance of the amino acids substituents and aryl groups. The methodology can be applied for the synthesis of the enantiomerically enriched bioactive scaffold (3S,4R)-demethoxy-3-isopropyl diclofensine. This journal is

Palladium-catalyzed β arylation of carboxylic esters

Alter ego: In the presence of an appropriate palladium(0) catalyst, carboxylic esters underwent β arylation instead of the more common α-arylation reaction with aryl halides containing an ortho electronegative substituent (see scheme; Cy = cyclohexyl). An asymmetric version of the reaction gave the product with an enantiomeric ratio of up to 77:23.

The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity

The importance of visual imagery and relational thinking manifests itself in a heuristic approach to the design and synthesis of potential morphinomimetics as agonists of the human-receptor. The well-known class of alkaloids represented by the isopavine n

Stereoselective cyanosilylation of α-sulfinylketimines or its covalently stabilized enamine tautomers. Synthesis of enantiomerically pure α-sulfinylmethyl-α-amino nitriles

α-Sulfinylketimines and β-sulfinylenamines undergo reaction with delivery cyanide reagents such as TMSCN or TBDMSCN in the presence of either stoichiometric excesses of ZnCl2 or ZnBr2, or catalytic amount of Yb(TfO)3. The use of ZnCl2 in alcohol solvents provides the best diastereoselectivity. It is mediated by a chelated transition state, the p-tolyl group driving the anti attack of the reagent. By using Yb(TfO)3 poor diastereoselectivities but good yields are obtained. It seems that an iminium derivative originated by metal coordination with either the nitrogen or oxygen atom in the substrate is responsible for the observed results. Interestingly, β-sulfinylenamines provide analogous α-amino nitriles in the same reaction conditions. It allowed the cyanosilylation of the covalently stabilized enamines arising from unstable β-sulfinyl aldehydes.

Boron-mediated aldol reactions of ethyl α-(N,N)-dibenzylamino ketones: Control of enolisation geometry and aldehyde π-facial selectivity

The boron-mediated aldol reactions of a range of chiral α-(N,N)-dibenzylamino ketones with aldehydes can be controlled to provide stereodefined adducts. Complementary induction can be achieved with cHex2BCl/Me2NEt leading to preferential formation of the 1,2-anti-2,4-syn adducts, while Bu2BOTfiPr2NEt provides 1,2-syn-2,4-anti adducts.

Spisulosine compounds

The present invention is directed to the isolation and bioactive characterization of compounds isolated from the clam Spisula polynyma. These compounds include three sphingoid-type bases, spisulosines 285, 299 and 313 (1-3), each of which shows unique cytotoxicity against L1210 murine lymphocytic leukemia cells. In addition, sphingosine (also referred to as 4-sphingenine or octadeca-4-shpingenine, 4) and two related compounds, nonadeca-4-sphingenine (a one carbon longer homolog, 5) and sphinga-4,10-diene (a dehydrosphingosine deravitive, 6) were also obtained, These compounds also contribute to the cytotoxicity of the Spisula polynyma extracts, but did not cause the morphology changes observed with compounds 1-3.

Condensation of Dimethyl-3-methylglutaconate with Aminoaldehydes : A Diastereoselective Synthesis of 5,6-Dihydro-(2H)-pyran-2-ones

Dimethyl-3-methylglutaconate reacts with chiral α-aminoaldehydes under basic conditions to afford substituted 5,6-dihydro(2H)-pyran-2-ones. The anti derivatives were obtained in a diastereoselective manner.

Synthesis of enantiopure syn-β-amino alcohols. A simple case of chelation-controlled additions of diethylzinc to α-(dibenzylamino) aldehydes

Enantiomerically pure syn-2-amino alcohols 6 are prepared by addition of diethylzinc to chiral α-(dibenzylamino) aldehydes 4. The addition is highly stereoselective, leading to syn-2-(dibenzylamino) alcohols 5 with excellent diastereomeric excesses (76-98%). Debenzylation of 5 by hydrogenolysis on Pearlman's catalyst yields quantitatively the amino alcohols 6.