Mark A. Olsen

Villanova University

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Lee J. Silverberg

Federal Correctional Institution Schuylkill

Anthony F. Lagalante

Villanova University

Tapas K. Mal

Pennsylvania State University

Hemant P. Yennawar

Pennsylvania State University

Carlos Pacheco

Pennsylvania State University

Grace C. Muench

Federal Correctional Institution Schuylkill

Tracy L. Garcia

Federal Correctional Institution Schuylkill

Madeline F. Malfara

Villanova University

Megan L. Povelones

Villanova University

Michael Fleming

Federal Correctional Institution Schuylkill

Cooperative Institutions

Pennsylvania State University

Federal Correctional Institution Schuylkill

Teva Pharmaceuticals (United States)

GlaxoSmithKline (United States)

New Frontier

Brandywine Photonics (United States)

Villanova University

University of Turin

West Chester University

Merck & Co., Inc., Rahway, NJ, USA (United States)

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CCDC 2265734: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Lee J. Silverberg Tapas K. Mal Carlos Pacheco Hemant P. Yennawar Anthony F. Lagalante

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, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc2g1p6f

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Synthesis and crystal structures of two racemic 2-heteroaryl-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-ones

Acta Crystallographica Section E Crystallographic Communications (2024)

Hemant P. Yennawar Tapas K. Mal Mark A. Olsen Anthony F. Lagalante Evelyn M. Louca

3-Phenyl-2-(thio-phen-3-yl)-2,3-di-hydro-4

10.1107/s2056989024005103

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CCDC 1043213: Experimental Crystal Structure Determination

The Cambridge Structural Database (2015)

Eugen F. Mesaros Thelma S. Angeles Mark S. Albom Jason Wagner Lisa D. Aimone

Crystal (programming language)

10.5517/cc140k1r

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A Practical Synthesis of the PDE4 Inhibitor, SB-207499, from a Cyclohexanone Precursor

Organic Process Research & Development (2002)

Neil F. Badham Jian‐Hao Chen Paul Cummings Philip C. Dell’Orco Ann M. Diederich

The synthesis of SB-207499 is described. Investigation and development of new strategies for the homologation of ketone, 4-cyano-4-[3-(cyclopentyloxy)-4-(methoxyphenyl)]-cyclohexan-1-one 2 are described which produce SB-207499. Our ultimate route of synthesis to SB-207499 is robust and operationally simple and produces the final drug substance in good yield and purity.

10.1021/op025584z

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Citations (8)

Electrospray ionization of neutral metal dithiocarbamate complexes using in-source oxidation

Journal of Mass Spectrometry (1999)

Dale Schoener Mark A. Olsen Paul Cummings Cecilia Basic

An electrospray ionization (ESI) mass spectral characterization of eight substituted tris(dithiocarbamato)iron(III) complexes (Fe(III)(dtc)(3)) and of the diethyldithiocarbamate (et(2)dtc)(-), complexes of Mn(III), Cu(II), Ni(II), and Co(III) is presented. Use is made of the inherent electrochemical potential of the ESI source to oxidize the neutral metal complexes and in-source collision-induced dissociation (CID) to characterize the resulting ions. The mass spectra obtained at low source offset voltages all show molecular ions of the oxidized complexes, in addition to ions due to the loss of a dithiocarbamate, (dtc)(-), ligand. Three of the Fe(III)(dtc)(3) complexes also show ions due to fragmentation of the (dtc)(-) ligands. Ions corresponding to the thiuram disulfide formed following the oxidation of excess (dtc)(-) in solution are also seen. In-source CID studies of the Fe(III), Mn(III), Cu(II), Ni(II) and Co(III) (et(2)dtc)(-) complexes all show [M(I)(et(2)dtc) + H](+) ions attributed to proton transfer from a protonated solvent ion to a M(I)(et(2)dtc) neutral formed upon following CID in the high-pressure region of the ion source. The results of the present in-source oxidation studies are compared with those obtained in previous ESI studies in which external oxidizing agents were added to the metal complex solutions prior to analysis. Copyright 1999 John Wiley & Sons, Ltd.

Dithiocarbamate

Fragmentation

Oxidizing agent

10.1002/(sici)1096-9888(199910)34:10<1069::aid-jms868>3.0.co;2-q

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Citations (19)

A strategy for characterization of polyethylene glycol-derivatized proteins. A mass spectrometric analysis of the attachment sites in polyethylene glycol-derivatized superoxide dismutase.

Drug Metabolism and Disposition (1993)

Martha M. Vestling Christine Murphy Douglas A. Keller Catherine Fenselau J Dedinas

Base treatment of polyethylene glycol-derivatized superoxide dismutase in which the polyethylene glycol is linked to the protein via a succinyl bridge, removes the polyethylene glycol leaving a succinyl marker. Exhaustive succinylation with d4-succinic anhydride completes the derivatization in order to minimize fractionation in proteolysis, chromatography, and desorption in the mass spectrometer. Production of peptides from the derivatized protein for high resolution and high-resolution tandem MS allows identification of the site that had been derivatized by polyethylene glycol and the determination of the amount of polyethylene glycol originally at each site. The mass spectrometric strategy outlined herein can be applied to other proteins derivatized for therapeutic administration.

Succinylation

10.1016/s0090-9556(25)08181-4

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The First Asymmetric Pilot-Scale Synthesis of TV-45070

Organic Process Research & Development (2017)

Joseph A. Sclafani Jian Chen Daniel V. Levy Harlan F. Reese Mina Dimitri

TV-45070 is a small-molecule lactam containing a chiral spiro-ether that has been reported as a potential topical therapy for pain associated with the Nav1.7 sodium ion channel encoded by the gene SCN9A. A pilot-scale synthesis is presented that is highlighted by an asymmetric aldol coupling at ambient temperature, used to create a quaternary chiral center. Although only a moderate ee is obtained, the removal of the undesired isomer is achieved through preferential precipitation of a near racemic mixture from the reaction, leaving the enantiopure isomer in solution. Cyclization to form the final API uses an uncommon diphenylphosphine-based leaving group which proved successful on the neopentyl system when other traditional leaving groups failed.

Enantiopure drug

Diphenylphosphine

Aldol reaction

10.1021/acs.oprd.7b00237

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Citations (17)

CCDC 2299677: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Katherine L. Moffa Claire N. Teahan Charlotte L. Montgomery Samantha L. Shepherd John C. Dickenson

10.5517/ccdc.csd.cc2h604w

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CCDC 2108519: Experimental Crystal Structure Determination

The Cambridge Structural Database (2022)

Lee J. Silverberg Tapas K. Mal Carlos Pacheco Megan L. Povelones Anthony F. Lagalante

10.5517/ccdc.csd.cc28s2rx

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Novel conversion of 2,3-Diaryl-2,3-dihydro-1,3-thiaza-4-ones to dimeric ring-opened thioacetals

Results in Chemistry (2023)

Lee J. Silverberg Tapas K. Mal Carlos Pacheco Hemant P. Yennawar Anthony F. Lagalante

It has been found that some six- and seven-membered 2,3-diaryl-2,3-dihydro-1,3-thiaza-4-ones will undergo acid-catalyzed reaction with water when dissolved in chloroform to give dimeric ring-opened thioacetals. In this communication, initial exploration of this reaction is reported.

10.1016/j.rechem.2023.101062

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Citations (1)