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Article ; Online: Modular, automated synthesis of spirocyclic tetrahydronaphthyridines from primary alkylamines.

Cao, Qiao / Tibbetts, Joshua D / Wrigley, Gail L / Smalley, Adam P / Cresswell, Alexander J

2023 Volume 6, Issue 1, Page(s) 215

Abstract: Spirocyclic tetrahydronaphthyridines (THNs) are valuable scaffolds for drug discovery campaigns, but access to this 3D chemical space is hampered by a lack of modular and scalable synthetic methods. We hereby report an automated, continuous flow ... ...

Abstract	Spirocyclic tetrahydronaphthyridines (THNs) are valuable scaffolds for drug discovery campaigns, but access to this 3D chemical space is hampered by a lack of modular and scalable synthetic methods. We hereby report an automated, continuous flow synthesis of α-alkylated and spirocyclic 1,2,3,4-tetrahydro-1,8-naphthyridines ("1,8-THNs"), in addition to their regioisomeric 1,6-THN analogues, from abundant primary amine feedstocks. An annulative disconnection approach based on photoredox-catalysed hydroaminoalkylation (HAA) of halogenated vinylpyridines is sequenced in combination with intramolecular S
Language	English
Publishing date	2023-10-04
Publishing country	England
Document type	Journal Article
ZDB-ID	2929562-2
ISSN	2399-3669 ; 2399-3669
ISSN (online)	2399-3669
ISSN	2399-3669
DOI	10.1038/s42004-023-01012-2
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Article: Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines

Askey, Hannah E. / Grayson, James D. / Tibbetts, Joshua D. / Turner-Dore, Jacob C. / Holmes, Jake M. / Kociok-Kohn, Gabriele / Wrigley, Gail L. / Cresswell, Alexander J.

Journal of the American Chemical Society. 2021 Sept. 20, v. 143, no. 39

2021

Abstract: Catalytic, intermolecular hydroaminoalkylation (HAA) of styrenes provides a powerful disconnection for pharmacologically relevant γ-arylamines, but current methods cannot utilize unprotected primary alkylamines as feedstocks. Metal-catalyzed HAA ... ...

Abstract	Catalytic, intermolecular hydroaminoalkylation (HAA) of styrenes provides a powerful disconnection for pharmacologically relevant γ-arylamines, but current methods cannot utilize unprotected primary alkylamines as feedstocks. Metal-catalyzed HAA protocols are also highly sensitive to α-substitution on the amine partner, and no catalytic solutions exist for α-tertiary γ-arylamine synthesis via this approach. We report a solution to these problems using organophotoredox catalysis, enabling a direct, modular, and sustainable preparation of α-(di)substituted γ-arylamines, including challenging electron-neutral and moderately electron-rich aryl groups. A broad range of functionalities are tolerated, and the reactions can be run on multigram scale in continuous flow. The method is applied to a concise, protecting-group-free synthesis of the blockbuster drug Fingolimod, as well as a phosphonate mimic of its in vivo active form (by iterative α-C–H functionalization of ethanolamine). The reaction can also be sequenced with an intramolecular N-arylation to provide a general and modular access to valuable (spirocyclic) 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydronaphthyridines. Mechanistic and kinetic studies support an irreversible hydrogen atom transfer activation of the alkylamine by the azidyl radical and some contribution from a radical chain. The reaction is photon-limited and exhibits a zero-order dependence on amine, azide, and photocatalyst, with a first-order dependence on styrene.
Keywords	azides ; drugs ; ethanolamine ; feedstocks ; hydrogen ; phosphonates ; photocatalysis ; photocatalysts ; styrene
Language	English
Dates of publication	2021-0920
Size	p. 15936-15945.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021/jacs.1c07401
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Article ; Online: Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines.

Askey, Hannah E / Grayson, James D / Tibbetts, Joshua D / Turner-Dore, Jacob C / Holmes, Jake M / Kociok-Kohn, Gabriele / Wrigley, Gail L / Cresswell, Alexander J

Journal of the American Chemical Society

2021 Volume 143, Issue 39, Page(s) 15936–15945

Abstract	Catalytic, intermolecular hydroaminoalkylation (HAA) of styrenes provides a powerful disconnection for pharmacologically relevant γ-arylamines, but current methods cannot utilize unprotected primary alkylamines as feedstocks. Metal-catalyzed HAA protocols are also highly sensitive to α-substitution on the amine partner, and no catalytic solutions exist for α-tertiary γ-arylamine synthesis via this approach. We report a solution to these problems using organophotoredox catalysis, enabling a direct, modular, and sustainable preparation of α-(di)substituted γ-arylamines, including challenging electron-neutral and moderately electron-rich aryl groups. A broad range of functionalities are tolerated, and the reactions can be run on multigram scale in continuous flow. The method is applied to a concise, protecting-group-free synthesis of the blockbuster drug Fingolimod, as well as a phosphonate mimic of its
Language	English
Publishing date	2021-09-20
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021/jacs.1c07401
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Article: Discovery of a Novel Benzodiazepine Series of Cbl-b Inhibitors for the Enhancement of Antitumor Immunity.

Boerth, Jeffrey A / Chinn, Alex J / Schimpl, Marianne / Bommakanti, Gayathri / Chan, Christina / Code, Erin L / Giblin, Kathryn A / Gohlke, Andrea / Hansel, Catherine S / Jin, Meizhong / Kavanagh, Stefan L / Lamb, Michelle L / Lane, Jordan S / Larner, Carrie J B / Mfuh, Adelphe M / Moore, Rachel K / Puri, Taranee / Quinn, Taylor R / Ye, Minwei /

Robbins, Kevin J / Gancedo-Rodrigo, Miguel / Tang, Haoran / Walsh, Jarrod / Ware, Jamie / Wrigley, Gail L / Reddy, Iswarya Karapa / Zhang, Yun / Grimster, Neil P

ACS medicinal chemistry letters

2023 Volume 14, Issue 12, Page(s) 1848–1856

Abstract: Casitas B-lineage lymphoma proto-oncogene-b (Cbl-b) is a RING finger E3 ligase that is responsible for repressing T-cell, natural killer (NK) cell, and B-cell activation. The robust antitumor activity observed in Cbl-b deficient mice arising from ... ...

Abstract	Casitas B-lineage lymphoma proto-oncogene-b (Cbl-b) is a RING finger E3 ligase that is responsible for repressing T-cell, natural killer (NK) cell, and B-cell activation. The robust antitumor activity observed in Cbl-b deficient mice arising from elevated T-cell and NK-cell activity justified our discovery effort toward Cbl-b inhibitors that might show therapeutic promise in immuno-oncology, where activation of the immune system can drive the recognition and killing of cancer cells. We undertook a high-throughput screening campaign followed by structure-enabled optimization to develop a novel benzodiazepine series of potent Cbl-b inhibitors. This series displayed nanomolar levels of biochemical potency, as well as potent T-cell activation. The functional activity of this class of Cbl-b inhibitors was further corroborated with ubiquitin-based cellular assays.
Language	English
Publishing date	2023-11-17
Publishing country	United States
Document type	Journal Article
ISSN	1948-5875
ISSN	1948-5875
DOI	10.1021/acsmedchemlett.3c00439
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Article ; Online: Discovery, Optimization, and Biological Evaluation of Arylpyridones as Cbl-b Inhibitors.

Mfuh, Adelphe M / Boerth, Jeffrey A / Bommakanti, Gayathri / Chan, Christina / Chinn, Alex J / Code, Erin / Fricke, Patrick J / Giblin, Kathryn A / Gohlke, Andrea / Hansel, Catherine / Hariparsad, Niresh / Hughes, Samantha J / Jin, Meizhong / Kantae, Vasudev / Kavanagh, Stefan L / Lamb, Michelle L / Lane, Jordan / Moore, Rachel / Puri, Taranee /

Quinn, Taylor R / Reddy, Iswarya / Robb, Graeme R / Robbins, Kevin J / Gancedo Rodrigo, Miguel / Schimpl, Marianne / Singh, Baljinder / Singh, Meha / Tang, Haoran / Thomson, Clare / Walsh, Jarrod J / Ware, Jamie / Watson, Iain D G / Ye, Min-Wei / Wrigley, Gail L / Zhang, Andrew X / Zhang, Yun / Grimster, Neil P

Journal of medicinal chemistry

2024 Volume 67, Issue 2, Page(s) 1500–1512

Abstract: Casitas B-lymphoma proto-oncogene-b (Cbl-b), a member of the Cbl family of RING finger E3 ubiquitin ligases, has been demonstrated to play a central role in regulating effector T-cell function. Multiple studies using gene-targeting approaches have ... ...

Abstract	Casitas B-lymphoma proto-oncogene-b (Cbl-b), a member of the Cbl family of RING finger E3 ubiquitin ligases, has been demonstrated to play a central role in regulating effector T-cell function. Multiple studies using gene-targeting approaches have provided direct evidence that Cbl-b negatively regulates T, B, and NK cell activation via a ubiquitin-mediated protein modulation. Thus, inhibition of Cbl-b ligase activity can lead to immune activation and has therapeutic potential in immuno-oncology. Herein, we describe the discovery and optimization of an arylpyridone series as Cbl-b inhibitors by structure-based drug discovery to afford compound
MeSH term(s)	Proto-Oncogene Proteins c-cbl/metabolism ; Ubiquitin-Protein Ligases/metabolism ; T-Lymphocytes/metabolism ; Phosphorylation ; Ubiquitin/metabolism
Chemical Substances	Proto-Oncogene Proteins c-cbl (EC 2.3.2.27) ; Ubiquitin-Protein Ligases (EC 2.3.2.27) ; Ubiquitin
Language	English
Publishing date	2024-01-16
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/acs.jmedchem.3c02083
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Article ; Online: The Discovery of 7-Methyl-2-[(7-methyl[1,2,4]triazolo[1,5-

Goldberg, Frederick W / Finlay, M Raymond V / Ting, Attilla K T / Beattie, David / Lamont, Gillian M / Fallan, Charlene / Wrigley, Gail L / Schimpl, Marianne / Howard, Martin R / Williamson, Beth / Vazquez-Chantada, Mercedes / Barratt, Derek G / Davies, Barry R / Cadogan, Elaine B / Ramos-Montoya, Antonio / Dean, Emma

Journal of medicinal chemistry

2020 Volume 63, Issue 7, Page(s) 3461–3471

Abstract: DNA-PK is a key component within the DNA damage response, as it is responsible for recognizing and repairing double-strand DNA breaks (DSBs) via non-homologous end joining. Historically it has been challenging to identify inhibitors of the DNA-PK ... ...

Abstract	DNA-PK is a key component within the DNA damage response, as it is responsible for recognizing and repairing double-strand DNA breaks (DSBs) via non-homologous end joining. Historically it has been challenging to identify inhibitors of the DNA-PK catalytic subunit (DNA-PKcs) with good selectivity versus the structurally related PI3 (lipid) and PI3K-related protein kinases. We screened our corporate collection for DNA-PKcs inhibitors with good PI3 kinase selectivity, identifying compound
MeSH term(s)	Animals ; Antineoplastic Agents/chemical synthesis ; Antineoplastic Agents/pharmacokinetics ; Antineoplastic Agents/therapeutic use ; Cell Line, Tumor ; Class Ib Phosphatidylinositol 3-Kinase/metabolism ; DNA-Activated Protein Kinase/antagonists & inhibitors ; Dogs ; Drug Discovery ; Humans ; Mice ; Molecular Structure ; Neoplasms/drug therapy ; Protein Kinase Inhibitors/chemical synthesis ; Protein Kinase Inhibitors/pharmacokinetics ; Protein Kinase Inhibitors/therapeutic use ; Purines/chemical synthesis ; Purines/pharmacokinetics ; Purines/therapeutic use ; Pyrans/chemical synthesis ; Pyrans/pharmacokinetics ; Pyrans/therapeutic use ; Rats ; Receptors, Granulocyte-Macrophage Colony-Stimulating Factor/antagonists & inhibitors ; Structure-Activity Relationship ; Triazoles/chemical synthesis ; Triazoles/pharmacokinetics ; Triazoles/therapeutic use ; Xenograft Model Antitumor Assays
Chemical Substances	AZD7648 ; Antineoplastic Agents ; Protein Kinase Inhibitors ; Purines ; Pyrans ; Receptors, Granulocyte-Macrophage Colony-Stimulating Factor ; Triazoles ; Class Ib Phosphatidylinositol 3-Kinase (EC 2.7.1.137) ; DNA-Activated Protein Kinase (EC 2.7.11.1)
Language	English
Publishing date	2020-01-15
Publishing country	United States
Document type	News
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.9b01684
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Article ; Online: Design and Synthesis of 56 Shape-Diverse 3D Fragments.

Downes, Thomas D / Jones, S Paul / Klein, Hanna F / Wheldon, Mary C / Atobe, Masakazu / Bond, Paul S / Firth, James D / Chan, Ngai S / Waddelove, Laura / Hubbard, Roderick E / Blakemore, David C / De Fusco, Claudia / Roughley, Stephen D / Vidler, Lewis R / Whatton, Maria Ann / Woolford, Alison J-A / Wrigley, Gail L / O'Brien, Peter

Chemistry (Weinheim an der Bergstrasse, Germany)

2020 Volume 26, Issue 41, Page(s) 8969–8975

Abstract: Fragment-based drug discovery is now widely adopted for lead generation in the pharmaceutical industry. However, fragment screening collections are often predominantly populated with flat, 2D molecules. Herein, we describe a workflow for the design and ... ...

Abstract	Fragment-based drug discovery is now widely adopted for lead generation in the pharmaceutical industry. However, fragment screening collections are often predominantly populated with flat, 2D molecules. Herein, we describe a workflow for the design and synthesis of 56 3D disubstituted pyrrolidine and piperidine fragments that occupy under-represented areas of fragment space (as demonstrated by a principal moments of inertia (PMI) analysis). A key, and unique, underpinning design feature of this fragment collection is that assessment of fragment shape and conformational diversity (by considering conformations up to 1.5 kcal mol
Language	English
Publishing date	2020-07-08
Publishing country	Germany
Document type	Journal Article
ZDB-ID	1478547-X
ISSN	1521-3765 ; 0947-6539
ISSN (online)	1521-3765
ISSN	0947-6539
DOI	10.1002/chem.202001123
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Article ; Online: Improving metabolic stability and removing aldehyde oxidase liability in a 5-azaquinazoline series of IRAK4 inhibitors.

Bioorganic & medicinal chemistry

2020 Volume 28, Issue 23, Page(s) 115815

Abstract: In this article, we report our efforts towards improving in vitro human clearance in a series of 5-azaquinazolines through a series of C4 truncations and C2 expansions. Extensive DMPK studies enabled us to tackle high Aldehyde Oxidase (AO) metabolism and ...

Abstract	In this article, we report our efforts towards improving in vitro human clearance in a series of 5-azaquinazolines through a series of C4 truncations and C2 expansions. Extensive DMPK studies enabled us to tackle high Aldehyde Oxidase (AO) metabolism and unexpected discrepancies in human hepatocyte and liver microsomal intrinsic clearance. Our efforts culminated with the discovery of 5-azaquinazoline 35, which also displayed exquisite selectivity for IRAK4, and showed synergistic in vitro activity against MyD88/CD79 double mutant ABC-DLBCL in combination with the covalent BTK inhibitor acalabrutinib.
MeSH term(s)	Aldehyde Oxidase/metabolism ; Animals ; Binding Sites ; Cell Line, Tumor ; Cell Survival/drug effects ; Crystallography, X-Ray ; Dogs ; Drug Stability ; Half-Life ; Hepatocytes/metabolism ; Humans ; Interleukin-1 Receptor-Associated Kinases/antagonists & inhibitors ; Interleukin-1 Receptor-Associated Kinases/metabolism ; Mice ; Microsomes, Liver/metabolism ; Molecular Dynamics Simulation ; Protein Kinase Inhibitors/chemistry ; Protein Kinase Inhibitors/metabolism ; Protein Kinase Inhibitors/pharmacology ; Quinazolines/chemistry ; Quinazolines/metabolism ; Quinazolines/pharmacology ; Rats ; Structure-Activity Relationship
Chemical Substances	Protein Kinase Inhibitors ; Quinazolines ; Aldehyde Oxidase (EC 1.2.3.1) ; IRAK4 protein, human (EC 2.7.11.1) ; Interleukin-1 Receptor-Associated Kinases (EC 2.7.11.1)
Language	English
Publishing date	2020-10-15
Publishing country	England
Document type	Journal Article
ZDB-ID	1161284-8
ISSN	1464-3391 ; 0968-0896
ISSN (online)	1464-3391
ISSN	0968-0896
DOI	10.1016/j.bmc.2020.115815
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Article ; Online: Correction to "Discovery of a Thiadiazole-Pyridazine-Based Allosteric Glutaminase 1 Inhibitor Series That Demonstrates Oral Bioavailability and Activity in Tumor Xenograft Models".

Finlay, M Raymond V / Anderton, Mark / Bailey, Andrew / Boyd, Scott / Brookfield, Joanna / Cairnduff, Ceri / Charles, Mark / Cheasty, Anne / Critchlow, Susan E / Culshaw, Janet / Debreczeni, Judit / Ekwuru, Tennyson / Hollingsworth, Ian / Jones, Neil / Leroux, Fred / Littleson, Mairi / McCarron, Hollie / McKelvie, Jennifer / Mooney, Lorraine /

Nissink, J Willem M / Patel, Joe / Perkins, David / Powell, Steve / Quesada, Mar Jimenez / Raubo, Piotr / Sabin, Verity / Smith, James / Smith, Peter D / Stark, Andrew / Ting, Attilla / Wang, Peng / Wilson, Zena / Winter-Holt, Jon J / Wood, J Matthew / Wrigley, Gail L / Yu, Guoqing / Zhang, Peng

Journal of medicinal chemistry

2023 Volume 66, Issue 13, Page(s) 9223–9224

Language	English
Publishing date	2023-06-21
Publishing country	United States
Document type	Published Erratum
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.3c00198
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Article: A novel approach to functionalised 5,7,8,9-tetrahydropyrimido[4,5-b][1,4]diazepin-6-ones using intramolecular palladium-catalysed amidation

Carr, Gregory R / Feron, James L / Johnson, Paul D / Roberts, Craig A / Rudge, David A / Simpson, Iain / Wrigley, Gail L

Tetrahedron letters. 2012 Sept. 19, v. 53, no. 38

2012

Abstract: The development of a novel palladium-catalysed amidation approach towards 5,7,8,9-tetrahydropyrimido[4,5-b][1,4]diazepin-6-one templates is highlighted. The route proceeds through the reaction of an amino amide, generated by 1,4-addition of an amine to ... ...

Abstract	The development of a novel palladium-catalysed amidation approach towards 5,7,8,9-tetrahydropyrimido[4,5-b][1,4]diazepin-6-one templates is highlighted. The route proceeds through the reaction of an amino amide, generated by 1,4-addition of an amine to an acrylamide, with 5-bromo-2,4-dichloropyrimidine and final palladium-catalysed cyclisation to provide the functionalised scaffold in up to 60% isolated yield over three steps. The route offers efficiency advantages over the previously reported nitro-reduction cyclisation approach to these molecules. It also provides alternative means to introduce bulky alkyl substituents at the amide nitrogen. The application of this route in the synthesis of a variety of analogues is described.
Keywords	acrylamides ; chemical reactions ; chemical structure ; nitrogen
Language	English
Dates of publication	2012-0919
Size	p. 5049-5055.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	204287-3
ISSN	1873-3581 ; 0040-4039
ISSN (online)	1873-3581
ISSN	0040-4039
DOI	10.1016/j.tetlet.2012.03.125
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