123808-74-2

Upstream product

• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 95437-43-7 (S)-2-(N,N-dibenzylamino)-3-phenylpropanoic acid 
• 100-39-0 benzyl bromide 
• 63-91-2 L-phenylalanine 
• 121-44-8 triethylamine 
• 111060-52-7 (S)-2-(dibenzylamino)-3-phenylpropan-1-ol 
• 191228-86-1 2S-[bis(phenylmethyl)amino]-1-hydroxy-3-phenylpropylsulfonic acid, sodium salt 
• 79-37-8 oxalyl dichloride 
• 3182-95-4 L-Phenylalaninol 
• 111138-83-1 N,N-dibenzyl-L-phenylalanine benzyl ester 
• 180684-58-6 N,N-Dibenzylphenylalanine benzyl ester 
• 150-30-1 Phenylalanine 
• 190076-24-5 (RS)-2-(N,N-dibenzylamino)-3-phenylpropan-1-ol 

Downstream Products

• 145127-98-6 (1S^*,2S^*,3S^*)-3-(Dibenzylamino)-1,4-diphenyl-1-(phenylthio)-2-butanol 
• 145127-98-6 (1R^*,2S^*,3S^*)-3-(Dibenzylamino)-1,4-diphenyl-1-(phenylthio)-2-butanol 
• 145128-05-8 3-(Dibenzylamino)-1-(dimethylamino)-1,4-diphenyl-2-butanol 
• 132576-44-4 (2RS,3RS,4SR)-2-(N,N-dibenzylamino)-1-phenyl-4-phenylseleno-3-octanol 
• 132576-44-4 (2RS,3RS,4RS)-2-(N,N-dibenzylamino)-1-phenyl-4-phenylseleno-3-octanol 
• 145127-96-4 cis-N,N-Dibenzyl-1,4-diphenyl-3-buten-2-amine 
• 145127-97-5 trans-N,N-Dibenzyl-1,4-diphenyl-3-buten-2-amine 
• 132620-10-1 (2S,3S,4S)-2-(N,N-dibenzylamino)-1-phenyl-4-(phenylseleno)-3-octanol 
• 132576-44-4 (2S,3S,4R)-2-(N,N-dibenzylamino)-1-phenyl-4-(phenylseleno)-3-octanol 

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.

Regioselective Fluorination of α-Hydroxy-β-aminophosphonates by Using PyFluor

We report a simple protocol for the synthesis of α-fluoro-β-aminophosphonates by the regioselective fluorination of α-hydroxy-β-aminophosphonates under mild conditions. The fluorination reactions were mediated by the PyFluor reagent and occurred with the retention of configuration. The main products of this reaction were a series of α-fluoro-β-aminophosphonates, which can be used as precursors in the preparation of medicinally important compounds (e.g., dipeptide analogues).

Synthesis of Optically Active α-Trifluoromethylamines by Rearrangement of β-Amino-α-trifluoromethyl Alcohols

The synthesis of various optically active α-trifluoromethylamines has been realized from β-amino-α-trifluoromethyl alcohols via an aziridinium ion intermediate under kinetic conditions.

A - And B -fluorinated aminophosphonates-Synthesis and properties

Interest in synthesis of fluorinated aminophosphonates has grown significantly in recent years due to their promising applications in medicinal and bioorganic chemistry. We report herein efficient and general methods for the synthesis of α- and β-monofluo

An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: Generality, applications and mechanistic investigations

The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.

Synthesis and identification of unprecedented selective inhibitors of CK1ε

A small and structure-biased library of enantiopure anti-β-amino alcohols was prepared in a straightforward manner by a simplified version of the Reetz protocol. Antiproliferative activity testing against a panel of five human solid tumor cell lines gave GI50 values in the range 1-20 μM. The reverse screening by computational methods against 58 proteins involved in cancer pointed to kinases as possible therapeutic target candidates. The experimental determination of the interaction with 456 kinases indicated that the compounds behave as selective CK1ε inhibitors. Our results demonstrate that the lead compound represents the first selective CK1ε inhibitor with proven antiproliferative activity in cancer cell lines.

Direct stereoselective synthesis of enantiomerically pure anti -β-amino alcohols

Enantiomerically pure anti-β-amino alcohols were synthesized from optically pure α-(N,N-dibenzylamino)benzyl esters, derived from α-amino acids, by the sequential reduction to aldehyde with DIBAL-H at -78 °C and subsequent in situ addition of Grignard reagents. Besides anti-β-amino alcohols, anti-2-amino-1,3-diols and anti-3-amino-1,4-diols were obtained in good yields (60-95%) and excellent stereoselectivity (de > 95%). Our technique is compatible with free hydroxyl groups present in the substrate. To demonstrate the versatility of the method, spisulosine and sphinganine were synthesized in two steps from the appropriate N,N-dibenzyl-l-aminobenzyl ester in 42% and 45% yield, respectively.

Organocatalytic asymmetric biomimetic transamination of α-keto acetals to chiral α-amino acetals

This paper describes a chiral base-catalyzed asymmetric biomimetic transamination of α-keto acetals. A wide variety of α-amino acetals containing various functional groups can be synthesized in 50-85% yield and 82-86% ee.

A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-Γ-aminated nitroalkenes derived from L-α-amino acids

New chiral (S,E)-γ-N,N-dibenzylated nitroalkenes 2a-c were synthesized from natural L-(α)-amino acids in five steps with overall yields of 68-88%. The conjugate addition of hydride, methoxide, nitronate and azide nucleophiles to 2a-c led to the corresponding chiral 1,3-nitroamines in 74-90% yield. The conjugate addition of cyanide anion to 2a,b was followed by HNO2 elimination affording chiral aminated acrylonitriles (73-98%). On the other hand, the azide anion reacted with 2a, in acetonitrile, via a [3 + 2]-cycloaddition in which HNO2 was lost, providing the corresponding 1,2,3-triazole derivative. Direct reduction of 1,3- nitroamine derivatives 9a,b produced the corresponding 1,3-diamines in good yields.

An Efficient Synthesis of a Hydroxyethylamine (HEA) Isostere and Its α-Aminophosphonate and Phosphoramidate Derivatives as Potential Anti-HIV Agents

HIV protease is a promising drug target for AIDS therapy, and several potent HIV-1 protease inhibitors have been reported to date. Although existing inhibitors exhibit high selectivity, they have also been associated with severe side effects and the possi