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Article ; Online: Sulfone-Mediated S

Patel, Nitinchandra D / Wei, Xudong / Byrne, Denis / Narayanan, Bikshandarkoil A / Pennino, Scott / Sarvestani, Max / Saha, Anjan / Haddad, Nizar / Kapadia, Suresh / Lorenz, Jon C / DeCroos, Philomen / Ye, Andrew / Lee, Heewon / Grinberg, Nelu / Hossain, Azad / Busacca, Carl A / Yee, Nathan K / Senanayake, Chris H

The Journal of organic chemistry

2020 Volume 85, Issue 13, Page(s) 8339–8351

Abstract: An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive ... ...

Abstract	An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive S
MeSH term(s)	Antiviral Agents ; Ethers ; Hepacivirus ; Hepatitis C ; Humans ; Protease Inhibitors/pharmacology ; Sulfones ; Viral Nonstructural Proteins
Chemical Substances	Antiviral Agents ; Ethers ; Protease Inhibitors ; Sulfones ; Viral Nonstructural Proteins
Language	English
Publishing date	2020-06-19
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.0c00554
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Article: Sulfone-Mediated SNAr Reaction as a Powerful Tool for the Synthesis of 4-Quinolinyl Ethers and More—Application to the Synthesis of HCV NS3/4a Protease Inhibitor BI 201420

Patel, Nitinchandra D. / Wei, Xudong / Byrne, Denis / Narayanan, Bikshandarkoil A. / Pennino, Scott / Sarvestani, Max / Saha, Anjan / Haddad, Nizar / Kapadia, Suresh / Lorenz, Jon C. / DeCroos, Philomen / Ye, Andrew / Lee, Heewon / Grinberg, Nelu / Hossain, Azad / Busacca, Carl A. / Yee, Nathan K. / Senanayake, Chris H.

Journal of organic chemistry. 2020 May 28, v. 85, no. 13

2020

Abstract: An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive SNAr reaction of 4-quinolinyl sulfones with a range of structurally diversified 1°, 2°, and 3° alcohols with a wide substrate scope and high ... ...

Abstract	An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive SNAr reaction of 4-quinolinyl sulfones with a range of structurally diversified 1°, 2°, and 3° alcohols with a wide substrate scope and high yields. By adapting this methodology, a convergent synthesis of a complex target of HCV NS3/4a protease inhibitor BI 201420 was accomplished.
Keywords	alcohols ; ethers ; journals ; organic chemistry ; proteinase inhibitors
Language	English
Dates of publication	2020-0528
Size	p. 8339-8351.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.0c00554
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Article ; Online: Enantioselective Synthesis of alpha,alpha-Disubstituted Amino Acid Derivatives via Enzymatic Resolution: Preparation of a Thiazolyl-Substituted alpha-Methyl alpha-Benzyl Amine.

Spero, Denice M. / Kapadia, Suresh R.

The Journal of organic chemistry

1996 Volume 61, Issue 21, Page(s) 7398–7401

Abstract: A new and efficient enantioselective synthesis of the (S)-alpha,alpha-disubstituted phenethylamine 1 via Lipase resolution of the esters 3 and 4 is described. The effect of pH, enzyme load, and solubilizing additives has been studied and optimized. ... ...

Abstract	A new and efficient enantioselective synthesis of the (S)-alpha,alpha-disubstituted phenethylamine 1 via Lipase resolution of the esters 3 and 4 is described. The effect of pH, enzyme load, and solubilizing additives has been studied and optimized. Conversion of the carboxylic acid 10 to the desired thiazole 1 is accomplished in high overall yield via an intermediate oxazolinone 13. This facile process requires only a single chromatographic step, and multigram quantities of 1 have been prepared.
Language	English
Publishing date	1996-10-18
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/jo9610671
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Article: A practical and improved synthesis of (3S,5S)-3-[(tert-butyloxycarbonyl)methyl]- 5-[(methanesulfonyloxy)methyl]-2- pyrrolidinone.

Yee, Nathan K / Dong, Yong / Kapadia, Suresh R / Song, Jinhua J

The Journal of organic chemistry

2002 Volume 67, Issue 24, Page(s) 8688–8691

Abstract: A practical and improved synthesis of (3S,5S)-3-[(tert-butyloxycarbonyl)methyl]-5-[(methanesulfonyloxy)methyl]-2-pyrrolidinone (1) is described. The key transformations involve a highly efficient reaction sequence consisting of ethoxycarbonylation, ... ...

Abstract	A practical and improved synthesis of (3S,5S)-3-[(tert-butyloxycarbonyl)methyl]-5-[(methanesulfonyloxy)methyl]-2-pyrrolidinone (1) is described. The key transformations involve a highly efficient reaction sequence consisting of ethoxycarbonylation, alkylation, hydrolysis, and decarboxylation to produce compound 10. The process described herein is practical, robust, and cost-effective, and it has been successfully implemented in a pilot plant to produce a multikilogram quantity of mesylate 1.
Language	English
Publishing date	2002-10-03
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/jo020433f
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Article: Synthesis of 5-bromopyridyl-2-magnesium chloride and its application in the synthesis of functionalized pyridines.

Song, Jinhua J / Yee, Nathan K / Tan, Zhulin / Xu, Jinghua / Kapadia, Suresh R / Senanayake, Chris H

Organic letters

2004 Volume 6, Issue 26, Page(s) 4905–4907

Abstract: reaction: see text] The 5-bromopyridyl-2-magnesium chloride (2), which was not accessible previously, was efficiently synthesized for the first time via an iodo-magnesium exchange reaction with 5-bromo-2-iodopyridine (1). This reactive intermediate was ... ...

Abstract	[reaction: see text] The 5-bromopyridyl-2-magnesium chloride (2), which was not accessible previously, was efficiently synthesized for the first time via an iodo-magnesium exchange reaction with 5-bromo-2-iodopyridine (1). This reactive intermediate was allowed to react with a variety of electrophiles to afford a range of useful functionalized pyridine derivatives. Application of this methodology to 5-bromo-2-iodo-3-picoline provided a simple and economical synthesis of a key intermediate for the preparation of Lonafarnib, a potent anticancer agent.
MeSH term(s)	Magnesium Chloride/chemical synthesis ; Magnesium Chloride/chemistry ; Molecular Structure ; Organometallic Compounds/chemical synthesis ; Organometallic Compounds/chemistry ; Pyridines/chemical synthesis ; Pyridines/chemistry
Chemical Substances	5-bromopyridyl-2-magnesium chloride ; Organometallic Compounds ; Pyridines ; Magnesium Chloride (02F3473H9O)
Language	English
Publishing date	2004-12-23
Publishing country	United States
Document type	Journal Article
ISSN	1523-7060
ISSN	1523-7060
DOI	10.1021/ol0400589
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Article: Tandem Pd(II)-catalyzed vinyl ether exchange-Claisen rearrangement as a facile approach to gamma,delta-unsaturated aldehydes.

Wei, Xudong / Lorenz, Jon C / Kapadia, Suresh / Saha, Anjan / Haddad, Nizar / Busacca, Carl A / Senanayake, Chris H

The Journal of organic chemistry

2007 Volume 72, Issue 11, Page(s) 4250–4253

Abstract: A sequential allyl vinyl ether formation-Claisen rearrangement process catalyzed by a palladium(II)-phenanthroline complex is reported. The effects of allylic alcohol structure, type of vinylating agent, and palladium catalysts are discussed. This method ...

Abstract	A sequential allyl vinyl ether formation-Claisen rearrangement process catalyzed by a palladium(II)-phenanthroline complex is reported. The effects of allylic alcohol structure, type of vinylating agent, and palladium catalysts are discussed. This method provides a convenient approach to gamma,delta-unsaturated aldehydes under mild conditions that avoid the use of toxic Hg(II) catalysts. The new methodology has been successfully demonstrated on the kilogram scale.
MeSH term(s)	Aldehydes/chemical synthesis ; Aldehydes/chemistry ; Catalysis ; Palladium/chemistry ; Phenanthrolines/chemistry ; Propanols/chemistry ; Stereoisomerism ; Thermodynamics ; Vinyl Compounds/chemistry
Chemical Substances	Aldehydes ; Phenanthrolines ; Propanols ; Vinyl Compounds ; vinyl ether (2H2T044E11) ; allyl alcohol (3W678R12M0) ; Palladium (5TWQ1V240M)
Language	English
Publishing date	2007-05-25
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/jo062548f
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Article: [No title information]

Busacca, Carl A. / Bartholomeyzik, Teresa / Cheekoori, Sreedhar / Raju, Ravinder / Eriksson, Magnus / Kapadia, Suresh / Saha, Anjan / Zeng, Xingzhong / Senanayake, Chris H.

Synlett

2009 Volume 2009, Issue 02, Page(s) 287–291

Abstract: Diisobutylaluminium hydride has been found to be an excellent reducing agent for phosphinites, phosphinates, and chlorophosphines. By performing reductions in situ, direct synthesis of secondary phosphine boranes from Grignard reagents has been achieved ... ...

Abstract	Diisobutylaluminium hydride has been found to be an excellent reducing agent for phosphinites, phosphinates, and chlorophosphines. By performing reductions in situ, direct synthesis of secondary phosphine boranes from Grignard reagents has been achieved without isolation or purification of any intermediates.
Keywords	phosphorus ; phosphines ; phosphine boranes ; reductions
Language	English
Publishing date	2009-01-15
Publishing place	Stuttgart ; New York
Document type	Article
ZDB-ID	2042012-2
ISSN	1437-2096 ; 0936-5214
ISSN (online)	1437-2096
ISSN	0936-5214
DOI	10.1055/s-0028-1087671
Database	Thieme publisher's database

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Article ; Online: Large-scale asymmetric synthesis of a cathepsin S inhibitor.

Lorenz, Jon C / Busacca, Carl A / Feng, XuWu / Grinberg, Nelu / Haddad, Nizar / Johnson, Joe / Kapadia, Suresh / Lee, Heewon / Saha, Anjan / Sarvestani, Max / Spinelli, Earl M / Varsolona, Rich / Wei, Xudong / Zeng, Xingzhong / Senanayake, Chris H

The Journal of organic chemistry

2010 Volume 75, Issue 4, Page(s) 1155–1161

Abstract: A potent reversible inhibitor of the cysteine protease cathepsin-S was prepared on large scale using a convergent synthetic route, free of chromatography and cryogenics. Late-stage peptide coupling of a chiral urea acid fragment with a functionalized ... ...

Abstract	A potent reversible inhibitor of the cysteine protease cathepsin-S was prepared on large scale using a convergent synthetic route, free of chromatography and cryogenics. Late-stage peptide coupling of a chiral urea acid fragment with a functionalized aminonitrile was employed to prepare the target, using 2-hydroxypyridine as a robust, nonexplosive replacement for HOBT. The two key intermediates were prepared using a modified Strecker reaction for the aminonitrile and a phosphonation-olefination-rhodium-catalyzed asymmetric hydrogenation sequence for the urea. A palladium-catalyzed vinyl transfer coupled with a Claisen reaction was used to produce the aldehyde required for the side chain. Key scale up issues, safety calorimetry, and optimization of all steps for multikilogram production are discussed.
MeSH term(s)	Alkenes/chemical synthesis ; Alkenes/chemistry ; Calorimetry/methods ; Catalysis ; Cathepsins/antagonists & inhibitors ; Cathepsins/chemistry ; Cyclization ; Enzyme Inhibitors/chemical synthesis ; Enzyme Inhibitors/pharmacology ; Indicators and Reagents/chemistry ; Models, Molecular ; Molecular Structure ; Palladium/chemistry ; Rhodium/chemistry ; Stereoisomerism ; Urea/chemical synthesis ; Urea/chemistry ; Vinyl Compounds/chemical synthesis ; Vinyl Compounds/chemistry
Chemical Substances	Alkenes ; Enzyme Inhibitors ; Indicators and Reagents ; Vinyl Compounds ; Palladium (5TWQ1V240M) ; Urea (8W8T17847W) ; Rhodium (DMK383DSAC) ; Cathepsins (EC 3.4.-) ; cathepsin S (EC 3.4.22.27)
Language	English
Publishing date	2010-02-19
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/jo9022809
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Article: Discovery of 2-phenylamino-imidazo[4,5-h]isoquinolin-9-ones: a new class of inhibitors of lck kinase.

Snow, Roger J / Cardozo, Mario G / Morwick, Tina M / Busacca, Carl A / Dong, Yong / Eckner, Robert J / Jacober, Stephen / Jakes, Scott / Kapadia, Suresh / Lukas, Susan / Panzenbeck, Maret / Peet, Gregory W / Peterson, Jeffrey D / Prokopowicz, Anthony S / Sellati, Rosemarie / Tolbert, Robert M / Tschantz, Matt A / Moss, Neil

Journal of medicinal chemistry

2002 Volume 45, Issue 16, Page(s) 3394–3405

Abstract: An imidazo[4,5-h]isoquinolin-7,9-dione (1) was identified as an adenosine 5'-triphosphate competitive inhibitor of lck by high throughput screening. Initial structure-activity relationship studies identified the dichlorophenyl ring and the imide NH as ... ...

Abstract	An imidazo[4,5-h]isoquinolin-7,9-dione (1) was identified as an adenosine 5'-triphosphate competitive inhibitor of lck by high throughput screening. Initial structure-activity relationship studies identified the dichlorophenyl ring and the imide NH as important pharmacophores. A binding model was constructed to understand how 1 binds to a related kinase, hck. These results suggested that removing the gem-dimethyl group and flattening the ring would enhance activity. This was realized by converting 1 to the imidazo[4,5-h]isoquinolin-9-one (20), resulting in an 18-fold improvement in potency against lck and a 50-fold increase in potency in a cellular assay.
MeSH term(s)	Animals ; Antibodies/pharmacology ; Binding Sites ; CD3 Complex/immunology ; Crystallography, X-Ray ; Enzyme Inhibitors/chemical synthesis ; Enzyme Inhibitors/chemistry ; Enzyme Inhibitors/pharmacology ; Female ; Humans ; Imidazoles/chemical synthesis ; Imidazoles/chemistry ; Imidazoles/pharmacology ; Interleukin-2/biosynthesis ; Isoquinolines/chemical synthesis ; Isoquinolines/chemistry ; Isoquinolines/pharmacology ; Jurkat Cells ; Lymphocyte Specific Protein Tyrosine Kinase p56(lck)/antagonists & inhibitors ; Mice ; Mice, Inbred BALB C ; Models, Molecular ; Molecular Conformation ; Structure-Activity Relationship ; T-Lymphocytes/drug effects ; T-Lymphocytes/metabolism
Chemical Substances	2-(2,6-dichlorophenylamino)-6,7-dimethyl-1,8-dihydroimidazo(4,5-h)isoquinoline-9-one ; Antibodies ; CD3 Complex ; Enzyme Inhibitors ; Imidazoles ; Interleukin-2 ; Isoquinolines ; Lymphocyte Specific Protein Tyrosine Kinase p56(lck) (EC 2.7.10.2)
Language	English
Publishing date	2002-08-01
Publishing country	United States
Document type	Journal Article
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/jm020113o
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Article: Optimization of 2-phenylaminoimidazo[4,5-h]isoquinolin-9-ones: orally active inhibitors of lck kinase.

Goldberg, Daniel R / Butz, Tanja / Cardozo, Mario G / Eckner, Robert J / Hammach, Abdelhakim / Huang, Jessica / Jakes, Scott / Kapadia, Suresh / Kashem, Mohammed / Lukas, Susan / Morwick, Tina M / Panzenbeck, Maret / Patel, Usha / Pav, Susan / Peet, Gregory W / Peterson, Jeffrey D / Prokopowicz, Anthony S / Snow, Roger J / Sellati, Rosemarie /

Takahashi, Hidenori / Tan, Jonathan / Tschantz, Matt A / Wang, Xiao-Jun / Wang, Yong / Wolak, John / Xiong, Pla / Moss, Neil

Journal of medicinal chemistry

2003 Volume 46, Issue 8, Page(s) 1337–1349

Abstract: The tyrosine kinase p56lck (lck) is essential for T cell activation; thus, inhibitors of lck have potential utility as autoimmune agents. Our initial disclosure of a new class of lck inhibitors based on the phenylaminoimidazoisoquinolin-9-one showed ... ...

Abstract	The tyrosine kinase p56lck (lck) is essential for T cell activation; thus, inhibitors of lck have potential utility as autoimmune agents. Our initial disclosure of a new class of lck inhibitors based on the phenylaminoimidazoisoquinolin-9-one showed reasonable cellular activity but did not work in vivo upon oral administration. Our current work highlights the further use of rational drug design and molecular modeling to produce a series of lck inhibitors that demonstrate cellular activity below 100 nM and are as efficacious as cyclosporin A in an in vivo mouse model of anti-CD3-induced IL-2 production.
MeSH term(s)	Administration, Oral ; Animals ; Antibodies, Monoclonal/pharmacology ; Benzimidazoles/chemical synthesis ; Benzimidazoles/chemistry ; Benzimidazoles/pharmacology ; CD3 Complex/immunology ; Crystallography, X-Ray ; Enzyme Inhibitors/chemical synthesis ; Enzyme Inhibitors/chemistry ; Enzyme Inhibitors/pharmacology ; Female ; Humans ; Immunosuppressive Agents/chemical synthesis ; Immunosuppressive Agents/chemistry ; Immunosuppressive Agents/pharmacology ; Interleukin-2/antagonists & inhibitors ; Interleukin-2/biosynthesis ; Interleukin-2/blood ; Isoquinolines/chemical synthesis ; Isoquinolines/chemistry ; Isoquinolines/pharmacology ; Jurkat Cells ; Lymphocyte Specific Protein Tyrosine Kinase p56(lck)/antagonists & inhibitors ; Mice ; Mice, Inbred BALB C ; Models, Molecular ; Molecular Conformation ; Protein Binding ; Structure-Activity Relationship
Chemical Substances	Antibodies, Monoclonal ; Benzimidazoles ; CD3 Complex ; Enzyme Inhibitors ; Immunosuppressive Agents ; Interleukin-2 ; Isoquinolines ; Lymphocyte Specific Protein Tyrosine Kinase p56(lck) (EC 2.7.10.2)
Language	English
Publishing date	2003-04-10
Publishing country	United States
Document type	Journal Article
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/jm020446l
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