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Organic chemistry in drug discovery

Maccoss, Malcolm ; Baillie, Thomas A

Science (New York, N.Y.), 19 March 2004, Vol.303(5665), pp.1810-3 [Peer Reviewed Journal]

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A notable conversion of a thiolacetate to its corresponding sulfonyl chloride

Huang, Yuhua ; Bennett, Frank ; Verma, Vishal ; George Njoroge, F ; Maccoss, Malcolm

Tetrahedron Letters, 27 June 2012, Vol.53(26), pp.3203-3205 [Peer Reviewed Journal]

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Importance of Rigidity in Designing Small Molecule Drugs To Tackle Protein-Protein Interactions (PPIs) through Stabilization of Desired Conformers

Lawson, Alastair D G ; Maccoss, Malcolm ; Heer, Jag P

Journal of medicinal chemistry, 24 May 2018, Vol.61(10), pp.4283-4289 [Peer Reviewed Journal]

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Rings in drugs

Taylor, Richard D ; Maccoss, Malcolm ; Lawson, Alastair D G

Journal of medicinal chemistry, 24 July 2014, Vol.57(14), pp.5845-59 [Peer Reviewed Journal]

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Combining Molecular Scaffolds from FDA Approved Drugs: Application to Drug Discovery

Taylor, Richard D ; Maccoss, Malcolm ; Lawson, Alastair D G

Journal of medicinal chemistry, 09 March 2017, Vol.60(5), pp.1638-1647 [Peer Reviewed Journal]

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Novel methods to functionalize thiazolo[4,5- c]pyridines

Girijavallabhan, Vinay ; Arasappan, Ashok ; Bennett, Frank ; Huang, Yuhua ; George Njoroge, F ; Maccoss, Malcolm

Tetrahedron Letters, 2010, Vol.51(21), pp.2797-2799 [Peer Reviewed Journal]

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Syntheses of 4- and 6-substituted thiazolo[4,5- c]pyridines

Huang, Yuhua ; Bennett, Frank ; Girijavallabhan, Vinay ; Alvarez, Carmen ; Chan, Tze-Ming ; Osterman, Rebecca ; Senior, Mary ; Kwong, Cecil ; Bansal, Namita ; George Njoroge, F ; Maccoss, Malcolm

Tetrahedron Letters, 2010, Vol.51(21), pp.2800-2802 [Peer Reviewed Journal]

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C−H Cyanation of 6‐Ring N‐Containing Heteroaromatics

Elbert, Bryony L. ; Farley, Alistair J. M. ; Gorman, Timothy W. ; Johnson, Tarn C. ; Genicot, Christophe ; Lallemand, Bénédicte ; Pasau, Patrick ; Flasz, Jakub ; Castro, José L. ; Maccoss, Malcolm ; Paton, Robert S. ; Schofield, Christopher J. ; Smith, Martin D. ; Willis, Michael C. ; Dixon, Darren J.

Chemistry – A European Journal, 20 October 2017, Vol.23(59), pp.14733-14737 [Peer Reviewed Journal]

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Sustained viral response in a hepatitis C virus-infected chimpanzee via a combination of direct-acting antiviral agents

Olsen, David B ; Davies, Mary-Ellen ; Handt, Larry ; Koeplinger, Kenneth ; Zhang, Nanyan Rena ; Ludmerer, Steven W ; Graham, Donald ; Liverton, Nigel ; Maccoss, Malcolm ; Hazuda, Daria ; Carroll, Steven S

Antimicrobial agents and chemotherapy, February 2011, Vol.55(2), pp.937-9 [Peer Reviewed Journal]

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10
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An expeditious synthesis of 3-(difluoromethoxy)- and 3-(trifluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridines

Guiadeen, Deodialsingh ; Kothandaraman, Shankaran ; Yang, Lihu ; Mills, Sander G ; Maccoss, Malcolm

Tetrahedron Letters, 2008, Vol.49(44), pp.6368-6370 [Peer Reviewed Journal]

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Concise preparation of 8-trifluoromethyltetrahydro-6 H-pyrido [1,2- a] pyrazine-6-one

Kothandaraman, Shankaran ; Guiadeen, Deodialsingh ; Butora, Gabor ; Doss, George ; Mills, Sander G ; Maccoss, Malcolm ; Yang, Lihu

Tetrahedron Letters, 2009, Vol.50(28), pp.4050-4053 [Peer Reviewed Journal]

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Cyclic hydroxyamidines as amide isosteres: discovery of oxadiazolines and oxadiazines as potent and highly efficacious γ-secretase modulators in vivo

Sun, Zhong-Yue ; Asberom, Theodros ; Bara, Thomas ; Bennett, Chad ; Burnett, Duane ; Chu, Inhou ; Clader, John ; Cohen-Williams, Mary ; Cole, David ; Czarniecki, Michael ; Durkin, James ; Gallo, Gioconda ; Greenlee, William ; Josien, Hubert ; Huang, Xianhai ; Hyde, Lynn ; Jones, Nicholas ; Kazakevich, Irina ; Li, Hongmei ; Liu, Xiaoxiang ; Lee, Julie ; Maccoss, Malcolm ; Mandal, Mihir B ; Mccracken, Troy ; Nomeir, Amin ; Mazzola, Robert ; Palani, Anandan ; Parker, Eric M ; Pissarnitski, Dmitri A ; Qin, Jun ; Song, Lixin ; Terracina, Giuseppe ; Vicarel, Monica ; Voigt, Johannes ; Xu, Ruo ; Zhang, Lili ; Zhang, Qi ; Zhao, Zhiqiang ; Zhu, Xiaohong ; Zhu, Zhaoning

Journal of medicinal chemistry, 12 January 2012, Vol.55(1), pp.489-502 [Peer Reviewed Journal]

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Syntheses of all four possible diastereomers of the acyclonucleoside 9-(1,3,4-trihydroxy-2-butoxymethyl)guanine from carbohydrate precursors

Maccoss, Malcolm ; Chen, Anna ; Tolman, Richard L

Tetrahedron Letters, 1985, Vol.26(36), pp.4287-4290 [Peer Reviewed Journal]

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Synthesis of the chiral acyclonucleoside antiherpetic agent (S)-9-(2,3-dihydroxy-1-propoxymethyl)guanine

Maccoss, Malcolm ; Chen, Anna ; Tolman, Richard L

Tetrahedron Letters, 1985, Vol.26(15), pp.1815-1818 [Peer Reviewed Journal]

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The elusive 8-fluoroadenosine: a simple non-enzymatic synthesis and characterization

Butora, Gabor ; Schmitt, Christoph ; Levorse, Dorothy A ; Streckfuss, Eric ; Doss, George A ; Maccoss, Malcolm

Tetrahedron, 2007, Vol.63(18), pp.3782-3789 [Peer Reviewed Journal]

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16
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Synthesis of 2′-β- C-methyl-neplanocin derivatives as anti-HCV agents

Liao, Xibin ; Butora, Gabor ; Olsen, David B ; Carroll, Steven S ; Mcmasters, Daniel R ; Leone, Joseph F ; Stahlhut, Mark ; Doss, George A ; Yang, Lihu ; Maccoss, Malcolm

Tetrahedron Letters, 2008, Vol.49(26), pp.4149-4152 [Peer Reviewed Journal]

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17
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Synthesis and structure determination of [8- 13C]guanosine 5′-diphosphate

Poe, Martin ; Germershausen, John I ; Maccoss, Malcolm

Analytical Biochemistry, 1987, Vol.164(2), pp.450-456 [Peer Reviewed Journal]

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18
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17O NMR spectroscopy of nucleoside derivatives; bonding characteristics of pyrimidine carbonyls

Schwartz, Herbert M ; Maccoss, Malcolm ; Danyluk, Steven S

Tetrahedron Letters, 1980, Vol.21(40), pp.3837-3840 [Peer Reviewed Journal]

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19
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Novel, orally bioavailable gamma-aminoamide CC chemokine receptor 2 (CCR2) antagonists

Pasternak, Alexander ; Marino, Dominick ; Vicario, Pasquale P ; Ayala, Julia Marie ; Cascierri, Margaret A ; Parsons, William ; Mills, Sander G ; Maccoss, Malcolm ; Yang, Lihu

Journal of medicinal chemistry, 10 August 2006, Vol.49(16), pp.4801-4 [Peer Reviewed Journal]

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20
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Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2′- C-methyladenosine

Butora, Gabor ; Olsen, David B ; Carroll, Steven S ; Mcmasters, Daniel R ; Schmitt, Christoph ; Leone, Joseph F ; Stahlhut, Mark ; Burlein, Christine ; Maccoss, Malcolm

Bioorganic & Medicinal Chemistry, 2007, Vol.15(15), pp.5219-5229 [Peer Reviewed Journal]

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21
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Antiviral efficacy upon administration of a HepDirect prodrug of 2'-C-methylcytidine to hepatitis C virus-infected chimpanzees

Carroll, Steven S ; Koeplinger, Kenneth ; Vavrek, Marissa ; Zhang, Nanyan Rena ; Handt, Laurence ; Maccoss, Malcolm ; Olsen, David B ; Reddy, K Raja ; Sun, Zhili ; Van Poelje, Paul D ; Fujitaki, James M ; Boyer, Serge H ; Linemeyer, David L ; Hecker, Scott J ; Erion, Mark D

Antimicrobial agents and chemotherapy, August 2011, Vol.55(8), pp.3854-60 [Peer Reviewed Journal]

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22
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Direct sulfonylation of anilines mediated by visible light

Johnson, Tarn C ; Elbert, Bryony L ; Farley, Alistair J M ; Gorman, Timothy W ; Genicot, Christophe ; Lallemand, Bénédicte ; Pasau, Patrick ; Flasz, Jakub ; Castro, José L ; Maccoss, Malcolm ; Dixon, Darren J ; Paton, Robert S ; Schofield, Christopher J ; Smith, Martin D ; Willis, Michael C

Chemical science, 21 January 2018, Vol.9(3), pp.629-633 [Peer Reviewed Journal]

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23
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Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection

Gardelli, Cristina ; Attenni, Barbara ; Donghi, Monica ; Meppen, Malte ; Pacini, Barbara ; Harper, Steven ; Di Marco, Annalise ; Fiore, Fabrizio ; Giuliano, Claudio ; Pucci, Vincenzo ; Laufer, Ralph ; Gennari, Nadia ; Marcucci, Isabella ; Leone, Joseph F ; Olsen, David B ; Maccoss, Malcolm ; Rowley, Michael ; Narjes, Frank

Journal of medicinal chemistry, 10 September 2009, Vol.52(17), pp.5394-407 [Peer Reviewed Journal]

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24
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Discovery of 3-piperidinyl-1-cyclopentanecarboxamide as a novel scaffold for highly potent CC chemokine receptor 2 antagonists

Yang, Lihu ; Butora, Gabor ; Jiao, Richard X ; Pasternak, Alex ; Zhou, Changyou ; Parsons, William H ; Mills, Sander G ; Vicario, Pasquale P ; Ayala, Julia M ; Cascieri, Margaret A ; Maccoss, Malcolm

Journal of medicinal chemistry, 31 May 2007, Vol.50(11), pp.2609-11 [Peer Reviewed Journal]

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25
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Synthesis and study of alendronate derivatives as potential prodrugs of alendronate sodium for the treatment of low bone density and osteoporosis

Vachal, Petr ; Hale, Jeffrey J ; Lu, Zhe ; Streckfuss, Eric C ; Mills, Sander G ; Maccoss, Malcolm ; Yin, Daniel H ; Algayer, Kimberly ; Manser, Kimberly ; Kesisoglou, Filippos ; Ghosh, Soumojeet ; Alani, Laman L

Journal of medicinal chemistry, 01 June 2006, Vol.49(11), pp.3060-3 [Peer Reviewed Journal]

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26
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Synthesis and evaluation of S-acyl-2-thioethyl esters of modified nucleoside 5'-monophosphates as inhibitors of hepatitis C virus RNA replication

Prakash, Thazha P ; Prhavc, Marija ; Eldrup, Anne B ; Cook, P Dan ; Carroll, Steven S ; Olsen, David B ; Stahlhut, Mark W ; Tomassini, Joanne E ; Maccoss, Malcolm ; Galloway, Sheila M ; Hilliard, Catherine ; Bhat, Balkrishen

Journal of medicinal chemistry, 24 February 2005, Vol.48(4), pp.1199-210 [Peer Reviewed Journal]

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27
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Synthesis and SAR of geminal substitutions at the C5′ carbosugar position of pyrimidine-derived HCV inhibitors

Verma, Vishal A ; Rossman, Randall ; Bennett, Frank ; Chen, Lei ; Gavalas, Stephen ; Girijavallabhan, Vinay ; Huang, Yuhua ; Kim, Seong-Heon ; Kosinski, Aneta ; Pinto, Patrick ; Rizvi, Razia ; Shankar, Bandarpalle ; Tong, Ling ; Velazquez, Francisco ; Venkatraman, Srikanth ; Kozlowski, Joseph ; Maccoss, Malcolm ; Kwong, Cecil D ; Bansal, Namita ; Kezar, Hollis S ; Reynolds, Robert C ; Maddry, Joseph A ; Ananthan, Subramaniam ; Secrist, John A ; Li, Cheng ; Chase, Robert ; Curry, Stephanie ; Huang, Hsueh-Cheng ; Tong, Xiao ; Njoroge, F. George ; Arasappan, Ashok

Bioorganic & Medicinal Chemistry Letters, 15 November 2012, Vol.22(22), pp.6967-6973 [Peer Reviewed Journal]

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28
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Pyridofuran substituted pyrimidine derivatives as HCV replication (replicase) inhibitors

Bennett, Frank ; Kezar, Hollis S ; Girijavallabhan, Vinay ; Huang, Yuhua ; Huelgas, Regina ; Rossman, Randall ; Shih, Neng-Yang ; Piwinski, John J ; Maccoss, Malcolm ; Kwong, Cecil D ; Clark, Jeremy L ; Fowler, Anita T ; Geng, Feng ; Roychowdhury, Abhijit ; Reynolds, Robert C ; Maddry, Joseph A ; Ananthan, Subramaniam ; Secrist, John A ; Li, Cheng ; Chase, Robert ; Curry, Stephanie ; Huang, Hsueh-Cheng ; Tong, Xiao ; George Njoroge, F ; Arasappan, Ashok

Bioorganic & Medicinal Chemistry Letters, 01 August 2012, Vol.22(15), pp.5144-5149 [Peer Reviewed Journal]

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Discovery of N-{N-(3-cyanophenyl)sulfonyl-4(R)-cyclobutylamino-(L)-prolyl}-4-(3',5'-dichloroisonicotinoyl) amino-(L)-phenylalanine (MK-0668), an extremely potent and orally active antagonist of very late antigen-4

Lin, Linus S ; Lanza, Thomas ; Jewell, James P ; Liu, Ping ; Jones, Carrie ; Kieczykowski, Gerard R ; Treonze, Kelly ; Si, Qian ; Manior, Salony ; Koo, Gloria ; Tong, Xinchun ; Wang, Junying ; Schuelke, Anne ; Pivnichny, James ; Wang, Regina ; Raab, Conrad ; Vincent, Stella ; Davies, Philip ; Maccoss, Malcolm ; Mumford, Richard A ; Hagmann, William K

Journal of medicinal chemistry, 11 June 2009, Vol.52(11), pp.3449-52 [Peer Reviewed Journal]

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30
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Inhibition of hepatitis C virus RNA replication by 2'-modified nucleoside analogs

Carroll, Steven S ; Tomassini, Joanne E ; Bosserman, Michele ; Getty, Krista ; Stahlhut, Mark W ; Eldrup, Anne B ; Bhat, Balkrishen ; Hall, Dawn ; Simcoe, Amy L ; Lafemina, Robert ; Rutkowski, Carrie A ; Wolanski, Bohdan ; Yang, Zhucheng ; Migliaccio, Giovanni ; De Francesco, Raffaele ; Kuo, Lawrence C ; Maccoss, Malcolm ; Olsen, David B

The Journal of biological chemistry, 04 April 2003, Vol.278(14), pp.11979-84 [Peer Reviewed Journal]

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31
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Binding of 2-aryl-4-(piperidin-1-yl)butanamines and 1,3,4-trisubstituted pyrrolidines to human CCR5: a molecular modeling-guided mutagenesis study of the binding pocket

Castonguay, Laurie A ; Weng, Youmin ; Adolfsen, William ; Di Salvo, Jerry ; Kilburn, Ruth ; Caldwell, Charles G ; Daugherty, Bruce L ; Finke, Paul E ; Hale, Jeffrey J ; Lynch, Christopher L ; Mills, Sander G ; Maccoss, Malcolm ; Springer, Martin S ; Demartino, Julie A

Biochemistry, 18 February 2003, Vol.42(6), pp.1544-50 [Peer Reviewed Journal]

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32
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Liver-targeted prodrugs of 2'-C-methyladenosine for therapy of hepatitis C virus infection

Hecker, Scott J ; Reddy, K Raja ; Van Poelje, Paul D ; Sun, Zhili ; Huang, Wenjian ; Varkhedkar, Vaibhav ; Reddy, M Venkat ; Fujitaki, James M ; Olsen, David B ; Koeplinger, Kenneth A ; Boyer, Serge H ; Linemeyer, David L ; Maccoss, Malcolm ; Erion, Mark D

Journal of medicinal chemistry, 09 August 2007, Vol.50(16), pp.3891-6 [Peer Reviewed Journal]

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33
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5-Benzothiazole substituted pyrimidine derivatives as HCV replication (replicase) inhibitors

Arasappan, Ashok ; Bennett, Frank ; Girijavallabhan, Vinay ; Huang, Yuhua ; Huelgas, Regina ; Alvarez, Carmen ; Chen, Lei ; Gavalas, Stephen ; Kim, Seong-Heon ; Kosinski, Aneta ; Pinto, Patrick ; Rizvi, Razia ; Rossman, Randall ; Shankar, Bandarpalle ; Tong, Ling ; Velazquez, Francisco ; Venkatraman, Srikanth ; Verma, Vishal A ; Kozlowski, Joseph ; Shih, Neng-Yang ; Piwinski, John J ; Maccoss, Malcolm ; Kwong, Cecil D ; Clark, Jeremy L ; Fowler, Anita T ; Geng, Feng ; Kezar, Hollis S ; Roychowdhury, Abhijit ; Reynolds, Robert C ; Maddry, Joseph A ; Ananthan, Subramaniam ; Secrist, John A ; Li, Cheng ; Chase, Robert ; Curry, Stephanie ; Huang, Hsueh-Cheng ; Tong, Xiao ; Njoroge, F. George

Bioorganic & Medicinal Chemistry Letters, 01 May 2012, Vol.22(9), pp.3229-3234 [Peer Reviewed Journal]

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34
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Synthesis and SAR of pyridothiazole substituted pyrimidine derived HCV replication inhibitors

Girijavallabhan, Vinay M ; Alvarez, Carmen ; Bennett, Frank ; Chen, Lei ; Gavalas, Stephen ; Huang, Yuhua ; Kim, Seong-Heon ; Kosinski, Aneta ; Pinto, Patrick ; Rizvi, Razia ; Rossman, Randall ; Shankar, Bandarpalle ; Tong, Ling ; Velazquez, Francisco ; Venkatraman, Srikanth ; Verma, Vishal A ; Kozlowski, Joseph ; Shih, Neng-Yang ; Piwinski, John J ; Maccoss, Malcolm ; Kwong, Cecil D ; Bansal, Namita ; Clark, Jeremy L ; Fowler, Anita T ; Kezar, Hollis S ; Valiyaveettil, Jacob ; Reynolds, Robert C ; Maddry, Joseph A ; Ananthan, Subramaniam ; Secrist, John A ; Li, Cheng ; Chase, Robert ; Curry, Stephanie ; Huang, Hsueh-Cheng ; Tong, Xiao ; Njoroge, F. George ; Arasappan, Ashok

Bioorganic & Medicinal Chemistry Letters, 01 September 2012, Vol.22(17), pp.5652-5657 [Peer Reviewed Journal]

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Synthesis and biological evaluation of 5R- and 5S-methyl substituted d- and l-configuration 1,3-dioxolane nucleoside analogs

Bera, Sanjib ; Malik, Leila ; Bhat, Balkrishen ; Carroll, Steven S ; Hrin, Renee ; Maccoss, Malcolm ; Mcmasters, Daniel R ; Miller, Michael D ; Moyer, Greg ; Olsen, David B ; Schleif, William A ; Tomassini, Joanne E ; Eldrup, Anne B

Bioorganic & Medicinal Chemistry, 01 December 2004, Vol.12(23), pp.6237-6247 [Peer Reviewed Journal]

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36