Vasilios M. Marathias

Mycofactocin-associated mycobacterial dehydrogenases with non-exchangeable NAD cofactors

Daniel H. Haft, Phillip G. Pierce, Stephen J. Mayclin, Amy H. Sullivan et autres

During human infection, Mycobacterium tuberculosis (Mtb) survives the normally bacteriocidal phagosome of macrophages. Mtb and related species may be able to combat this harsh acidic environment which contains reactive oxygen species due to the mycobacterial genomes encoding a large number of dehydrogenases. …

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N-Arylation of a hindered indoline as a route to 2-(2-methyl-1-(4-oxo-3,4-dihydrophthalazin-1-yl)-1H-indol-3-yl)acetic acid derivatives

Nikolaos Papaioannou, Vasilios M. Marathias, Zhao‐Kui Wan, Neelu Kaila et autres

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ChemInform Abstract: Total Synthesis of Enantiopure Phalarine via a Stereospecific Pictet—Spengler Reaction: Traceless Transfer of Chirality from L‐Tryptophan.

John D. Trzupek, Dongjoo Lee, Brendan M. Crowley, Vasilios M. Marathias et autres

Abstract The total synthesis of (V) is achieved with the construction of the intermediate (IV) with complete diastereoselectivity as a key step.

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Synthesis of (-)-Phalarine

Samuel J. Danishefsky, John D. Trzupek, D. Lee, Brendan M. Crowley et autres

Significance Phalarine is an indole-related alkaloid with interesting propeller-like interlocking ring systems. Danishefsky and co-workers previously published the racemic synthesis ( Angew. Chem. Int. Ed. 2007 , 46 , 1448) and, through mechanistic studies, have now circumvented the retro-Mannich reaction that previously …

Total Synthesis of Enantiopure Phalarine via a Stereospecific Pictet−Spengler Reaction: Traceless Transfer of Chirality from l -Tryptophan

John D. Trzupek, Dongjoo Lee, Brendan M. Crowley, Vasilios M. Marathias et autres

An appropriately constructed 2-substituted derivative of l-tryptophan undergoes conversion to a prephalarine structure in a single step. The reaction occurs in a diastereoselective fashion, leading shortly thereafter to the naturally occurring version of the alkaloid phalarine.

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The Synthesis and Biological Evaluation of Quinolyl-piperazinyl Piperidines as Potent Serotonin 5-HT1AAntagonists

Wayne E. Childers, Lisa M. Havran, Magda Asselin, James Bicksler et autres

As part of an effort to identify 5-HT(1A) antagonists that did not possess typical arylalkylamine or keto/amido-alkyl aryl piperazine scaffolds, prototype compound 10a was identified from earlier work in a combined 5-HT(1A) antagonist/SSRI program. This quinolyl-piperazinyl piperidine analogue displayed potent, selective 5-HT(1A) …

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An improved method for determining enantiomeric excess by 13C‐NMR in chiral liquid crystal media

Vasilios M. Marathias, Peter A. Tate, Nikolaos Papaioannou, Walter W. Massefski

By using a combination of inverse gated (1)H decoupled (13)C-NMR experiments1 with short acquisition times and NMR Cryo-probe technology, the sample requirements and experimental times necessary to accurately measure enantiomeric excess of small chiral molecules has been reduced 16-fold. Quality (13)C-NMR spectra …

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CCDC 785597: Experimental Crystal Structure Determination

John D. Trzupek, Dongjoo Lee, Brendan M. Crowley, Vasilios M. Marathias et autres

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, …

3,4-Dihydropyrimido(1,2-a)indol-10(2H)-ones as potent non-peptidic inhibitors of caspase-3

Lisa M. Havran, Dan C. Chong, Wayne E. Childers, Paul J. Dollings et autres

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First Scale-Up Synthesis of WAY-262398, a Novel, Dual-Acting SSRI/5HT1a Antagonist

Antonia A. Nikitenko, Asaf Alimardanov, Jay Afragola, Jean Martin Schmid et autres

An alternative synthesis of WAY-262398, 1, a novel, dual-acting SSRI/5-HT 1A antagonist, has been developed. The target compound was initially synthesized as a part of diastereomeric mixture which was separated by chiral preparative HPLC. The new route was designed around intermediates suitable …

Enantiomeric separation and determination of absolute stereochemistry of asymmetric molecules in drug discovery—Building chiral technology toolboxes

Oliver J. McConnell, A. Bach, Carl J. Balibar, Neal Byrne et autres

The application of Chiral Technology, or the (extensive) use of techniques or tools for the determination of absolute stereochemistry and the enantiomeric or chiral separation of racemic small molecule potential lead compounds, has been critical to successfully discovering and developing chiral drugs …

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Stereochemical identification of (R)‐ and (S)‐ibuprofen using residual dipolar couplings, NMR, and modeling

Vasilios M. Marathias, Gregory J. Tawa, Igor Goljer, A. Bach

In this work, we describe an NMR-based method that utilizes an orientation media composed of the chiral polypeptide liquid crystal poly-gamma-benzyl-L-glutamate (PBLG) dissolved in CDCl(3), to measure the (1)H-(1)H, (1)H-(13)C and (13)C-(13)C residual dipolar couplings (RDCs) of (R) and (S)-ibuprofen. Calculated RDCs, …

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