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Article ; Online: Discovery of JNJ-1802, a First-in-Class Pan-Serotype Dengue Virus NS4B Inhibitor.

2024 Volume 67, Issue 5, Page(s) 4063–4082

Abstract: Dengue is a global public health threat, with about half of the world's population at risk of contracting this mosquito-borne viral disease. Climate change, urbanization, and global travel accelerate the spread of dengue virus (DENV) to new areas, ... ...

Abstract	Dengue is a global public health threat, with about half of the world's population at risk of contracting this mosquito-borne viral disease. Climate change, urbanization, and global travel accelerate the spread of dengue virus (DENV) to new areas, including southern parts of Europe and the US. Currently, no dengue-specific small-molecule antiviral for prophylaxis or treatment is available. Here, we report the discovery of
MeSH term(s)	Mice ; Humans ; Animals ; Dengue Virus ; Serogroup ; Dengue/drug therapy ; Hydrocarbons, Halogenated ; Indoles
Chemical Substances	JNJ-1802 ; Hydrocarbons, Halogenated ; Indoles
Language	English
Publishing date	2024-02-28
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.3c02336
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Article: From Oxetane to Thietane: Extending the Antiviral Spectrum of 2'-Spirocyclic Uridines by Substituting Oxygen with Sulfur.

Grosse, Sandrine / Tahri, Abdellah / Raboisson, Pierre / Houpis, Yannis / Stoops, Bart / Jacoby, Edgar / Neefs, Jean-Marc / Van Loock, Marnix / Goethals, Olivia / Geluykens, Peggy / Bonfanti, Jean-François / Jonckers, Tim H M

ACS medicinal chemistry letters

2022 Volume 13, Issue 12, Page(s) 1879–1884

Abstract: In continuation of our efforts of finding novel nucleoside inhibitors for the treatment of viral diseases, we initiated a discovery research program aimed at identifying novel nucleos(t)ide inhibitors for emerging diseases like Dengue and Chikungunya. ... ...

Abstract	In continuation of our efforts of finding novel nucleoside inhibitors for the treatment of viral diseases, we initiated a discovery research program aimed at identifying novel nucleos(t)ide inhibitors for emerging diseases like Dengue and Chikungunya. Based on the previously reported 2'-spiro-oxetane uridine derivatives active against Hepatitis C Virus (HCV), we envisaged its sulfur analogue as an interesting congener both from a synthetic as well as biological point of view. Surprisingly, we found the 2'-spirothietane uridine derivatives not only to be active against HCV and Dengue virus (DENV), viruses belonging to the flavivirus family, but also to demonstrate activity against alphaviruses like Chikungunya virus (CHIKV) and Sindbis virus (SINV).
Language	English
Publishing date	2022-11-28
Publishing country	United States
Document type	Journal Article
ISSN	1948-5875
ISSN	1948-5875
DOI	10.1021/acsmedchemlett.2c00372
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Article ; Online: Discovery of Acyl-Indole Derivatives as Pan-Serotype Dengue Virus NS4B Inhibitors.

Journal of medicinal chemistry

2023 Volume 66, Issue 13, Page(s) 8808–8821

Abstract: In the absence of any approved dengue-specific treatment, the discovery and development of a novel small-molecule antiviral for the prevention or treatment of dengue are critical. We previously reported the identification of a novel series of 3-acyl- ... ...

Abstract	In the absence of any approved dengue-specific treatment, the discovery and development of a novel small-molecule antiviral for the prevention or treatment of dengue are critical. We previously reported the identification of a novel series of 3-acyl-indole derivatives as potent and pan-serotype dengue virus inhibitors. We herein describe our optimization efforts toward preclinical candidates
MeSH term(s)	Mice ; Animals ; Dengue Virus ; Serogroup ; Antiviral Agents/pharmacology ; Antiviral Agents/therapeutic use ; Dengue/drug therapy ; Indoles/pharmacology ; Indoles/therapeutic use
Chemical Substances	Antiviral Agents ; Indoles
Language	English
Publishing date	2023-06-30
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.3c00403
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Article ; Online: Structural and mechanistic insights into the inhibition of respiratory syncytial virus polymerase by a non-nucleoside inhibitor.

Yu, Xiaodi / Abeywickrema, Pravien / Bonneux, Brecht / Behera, Ishani / Anson, Brandon / Jacoby, Edgar / Fung, Amy / Adhikary, Suraj / Bhaumik, Anusarka / Carbajo, Rodrigo J / De Bruyn, Suzanne / Miller, Robyn / Patrick, Aaron / Pham, Quyen / Piassek, Madison / Verheyen, Nick / Shareef, Afzaal / Sutto-Ortiz, Priscila / Ysebaert, Nina /

Van Vlijmen, Herman / Jonckers, Tim H M / Herschke, Florence / McLellan, Jason S / Decroly, Etienne / Fearns, Rachel / Grosse, Sandrine / Roymans, Dirk / Sharma, Sujata / Rigaux, Peter / Jin, Zhinan

Communications biology

2023 Volume 6, Issue 1, Page(s) 1074

Abstract: The respiratory syncytial virus polymerase complex, consisting of the polymerase (L) and phosphoprotein (P), catalyzes nucleotide polymerization, cap addition, and cap methylation via the RNA dependent RNA polymerase, capping, and Methyltransferase ... ...

Abstract	The respiratory syncytial virus polymerase complex, consisting of the polymerase (L) and phosphoprotein (P), catalyzes nucleotide polymerization, cap addition, and cap methylation via the RNA dependent RNA polymerase, capping, and Methyltransferase domains on L. Several nucleoside and non-nucleoside inhibitors have been reported to inhibit this polymerase complex, but the structural details of the exact inhibitor-polymerase interactions have been lacking. Here, we report a non-nucleoside inhibitor JNJ-8003 with sub-nanomolar inhibition potency in both antiviral and polymerase assays. Our 2.9 Å resolution cryo-EM structure revealed that JNJ-8003 binds to an induced-fit pocket on the capping domain, with multiple interactions consistent with its tight binding and resistance mutation profile. The minigenome and gel-based de novo RNA synthesis and primer extension assays demonstrated that JNJ-8003 inhibited nucleotide polymerization at the early stages of RNA transcription and replication. Our results support that JNJ-8003 binding modulates a functional interplay between the capping and RdRp domains, and this molecular insight could accelerate the design of broad-spectrum antiviral drugs.
MeSH term(s)	Respiratory Syncytial Virus, Human ; RNA-Dependent RNA Polymerase/chemistry ; Protein Binding ; RNA/metabolism ; Nucleotides/metabolism
Chemical Substances	RNA-Dependent RNA Polymerase (EC 2.7.7.48) ; RNA (63231-63-0) ; Nucleotides
Language	English
Publishing date	2023-10-21
Publishing country	England
Document type	Journal Article
ISSN	2399-3642
ISSN (online)	2399-3642
DOI	10.1038/s42003-023-05451-4
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Article ; Online: Discovery of 3-({5-Chloro-1-[3-(methylsulfonyl)propyl]-1

Vendeville, Sandrine / Tahri, Abdellah / Hu, Lili / Demin, Samuel / Cooymans, Ludwig / Vos, Ann / Kwanten, Leen / Van den Berg, Joke / Battles, Michael B / McLellan, Jason S / Koul, Anil / Raboisson, Pierre / Roymans, Dirk / Jonckers, Tim H M

Journal of medicinal chemistry

2020 Volume 63, Issue 15, Page(s) 8046–8058

Abstract: Respiratory syncytial virus (RSV) is a seasonal virus that infects the lungs and airways of 64 million children and adults every year. It is a major cause of acute lower respiratory tract infection and is associated with significant morbidity and ... ...

Abstract	Respiratory syncytial virus (RSV) is a seasonal virus that infects the lungs and airways of 64 million children and adults every year. It is a major cause of acute lower respiratory tract infection and is associated with significant morbidity and mortality. Despite the large medical and economic burden, treatment options for RSV-associated bronchiolitis and pneumonia are limited and mainly consist of supportive care. This publication covers the medicinal chemistry efforts resulting in the identification of JNJ-53718678, an orally bioavailable RSV inhibitor that was shown to be efficacious in a phase 2a challenge study in healthy adult subjects and that is currently being evaluated in hospitalized infants and adults. Cocrystal structures of several new derivatives helped in rationalizing some of the structure-activity relationship (SAR) trends observed.
MeSH term(s)	Administration, Oral ; Antiviral Agents/administration & dosage ; Antiviral Agents/chemistry ; Crystallography, X-Ray/methods ; Drug Discovery/methods ; HeLa Cells ; Humans ; Imidazolidines/administration & dosage ; Imidazolidines/chemistry ; Indoles/administration & dosage ; Indoles/chemistry ; Protein Structure, Secondary ; Respiratory Syncytial Virus, Human/drug effects ; Respiratory Syncytial Virus, Human/physiology ; Viral Fusion Protein Inhibitors/administration & dosage ; Viral Fusion Protein Inhibitors/chemistry
Chemical Substances	Antiviral Agents ; Imidazolidines ; Indoles ; JNJ-53718678 ; Viral Fusion Protein Inhibitors
Language	English
Publishing date	2020-06-15
Publishing country	United States
Document type	Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.0c00226
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Article ; Online: Publisher Correction: A pan-serotype dengue virus inhibitor targeting the NS3-NS4B interaction.

Kaptein, Suzanne J F / Goethals, Olivia / Kiemel, Dominik / Marchand, Arnaud / Kesteleyn, Bart / Bonfanti, Jean-François / Bardiot, Dorothée / Stoops, Bart / Jonckers, Tim H M / Dallmeier, Kai / Geluykens, Peggy / Thys, Kim / Crabbe, Marjolein / Chatel-Chaix, Laurent / Münster, Max / Querat, Gilles / Touret, Franck / de Lamballerie, Xavier / Raboisson, Pierre /

Simmen, Kenny / Chaltin, Patrick / Bartenschlager, Ralf / Van Loock, Marnix / Neyts, Johan

Nature

2021 Volume 599, Issue 7883, Page(s) E2

Language	English
Publishing date	2021-10-20
Publishing country	England
Document type	Published Erratum
ZDB-ID	120714-3
ISSN	1476-4687 ; 0028-0836
ISSN (online)	1476-4687
ISSN	0028-0836
DOI	10.1038/s41586-021-04123-9
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Article ; Online: A pan-serotype dengue virus inhibitor targeting the NS3-NS4B interaction.

Simmen, Kenny / Chaltin, Patrick / Bartenschlager, Ralf / Van Loock, Marnix / Neyts, Johan

Nature

2021 Volume 598, Issue 7881, Page(s) 504–509

Abstract: Dengue virus causes approximately 96 million symptomatic infections annually, manifesting as dengue fever or occasionally as severe ... ...

Abstract	Dengue virus causes approximately 96 million symptomatic infections annually, manifesting as dengue fever or occasionally as severe dengue
MeSH term(s)	Animals ; Antiviral Agents/pharmacokinetics ; Antiviral Agents/pharmacology ; Antiviral Agents/therapeutic use ; Dengue/drug therapy ; Dengue/virology ; Dengue Virus/classification ; Dengue Virus/drug effects ; Dengue Virus/genetics ; Dengue Virus/metabolism ; Disease Models, Animal ; Female ; Male ; Membrane Proteins/antagonists & inhibitors ; Membrane Proteins/metabolism ; Mice ; RNA Helicases/antagonists & inhibitors ; RNA Helicases/metabolism ; Serine Endopeptidases/metabolism ; Viral Load/drug effects ; Viral Nonstructural Proteins/antagonists & inhibitors ; Viral Nonstructural Proteins/metabolism ; Viremia/drug therapy ; Viremia/virology ; Virus Replication/drug effects
Chemical Substances	Antiviral Agents ; Membrane Proteins ; NS3 protein, flavivirus ; NS4B protein, Dengue virus ; Viral Nonstructural Proteins ; Serine Endopeptidases (EC 3.4.21.-) ; RNA Helicases (EC 3.6.4.13)
Language	English
Publishing date	2021-10-06
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	120714-3
ISSN	1476-4687 ; 0028-0836
ISSN (online)	1476-4687
ISSN	0028-0836
DOI	10.1038/s41586-021-03990-6
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Article: Benzoxazole and benzothiazole amides as novel pharmacokinetic enhancers of HIV protease inhibitors

Jonckers, Tim H.M / Rouan, Marie-Claude / Haché, Geerwin / Schepens, Wim / Hallenberger, Sabine / Baumeister, Judith / Sasaki, Jennifer C

Bioorganic & medicinal chemistry letters. 2012 Aug. 1, v. 22, no. 15

2012

Abstract: A new class of benzoxazole and benzothiazole amide derivatives exhibiting potent CYP3A4 inhibiting properties was identified. Extensive lead optimization was aimed at improving the CYP3A4 inhibitory properties as well as overall ADME profile of these ... ...

Abstract	A new class of benzoxazole and benzothiazole amide derivatives exhibiting potent CYP3A4 inhibiting properties was identified. Extensive lead optimization was aimed at improving the CYP3A4 inhibitory properties as well as overall ADME profile of these amide derivatives. This led to the identification of thiazol-5-ylmethyl (2S,3R)-4-(2-(ethyl(methyl)amino)-N-isobutylbenzo[d]oxazole-6-carboxamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate (C1) as a lead candidate for this class. This compound together with structurally similar analogues demonstrated excellent ‘boosting’ properties when tested in dogs. These findings warrant further evaluation of their properties in an effort to identify valuable alternatives to Ritonavir as pharmacokinetic enhancers.
Keywords	amides ; chemistry ; dogs ; pharmacokinetics ; proteinase inhibitors
Language	English
Dates of publication	2012-0801
Size	p. 4998-5002.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2012.06.022
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Blocking NS3-NS4B interaction inhibits dengue virus in non-human primates.

Goethals, Olivia / Kaptein, Suzanne J F / Kesteleyn, Bart / Bonfanti, Jean-François / Van Wesenbeeck, Liesbeth / Bardiot, Dorothée / Verschoor, Ernst J / Verstrepen, Babs E / Fagrouch, Zahra / Putnak, J Robert / Kiemel, Dominik / Ackaert, Oliver / Straetemans, Roel / Lachau-Durand, Sophie / Geluykens, Peggy / Crabbe, Marjolein / Thys, Kim / Stoops, Bart / Lenz, Oliver /

Tambuyzer, Lotke / De Meyer, Sandra / Dallmeier, Kai / McCracken, Michael K / Gromowski, Gregory D / Rutvisuttinunt, Wiriya / Jarman, Richard G / Karasavvas, Nicos / Touret, Franck / Querat, Gilles / de Lamballerie, Xavier / Chatel-Chaix, Laurent / Milligan, Gregg N / Beasley, David W C / Bourne, Nigel / Barrett, Alan D T / Marchand, Arnaud / Jonckers, Tim H M / Raboisson, Pierre / Simmen, Kenny / Chaltin, Patrick / Bartenschlager, Ralf / Bogers, Willy M / Neyts, Johan / Van Loock, Marnix

Nature

2023 Volume 615, Issue 7953, Page(s) 678–686

Abstract: Dengue is a major health threat and the number of symptomatic infections caused by the four dengue serotypes is estimated to be 96 ... ...

Abstract	Dengue is a major health threat and the number of symptomatic infections caused by the four dengue serotypes is estimated to be 96 million
MeSH term(s)	Animals ; Humans ; Mice ; Antiviral Agents/adverse effects ; Antiviral Agents/pharmacology ; Antiviral Agents/therapeutic use ; Clinical Trials, Phase I as Topic ; Dengue/drug therapy ; Dengue/prevention & control ; Dengue/virology ; Dengue Virus/classification ; Dengue Virus/drug effects ; Dose-Response Relationship, Drug ; Drug Resistance, Viral ; In Vitro Techniques ; Molecular Targeted Therapy ; Primates/virology ; Protein Binding/drug effects ; Viral Nonstructural Proteins/antagonists & inhibitors ; Viral Nonstructural Proteins/metabolism ; Virus Replication
Chemical Substances	Antiviral Agents ; NS3 protein, flavivirus ; NS4B protein, Dengue virus ; Viral Nonstructural Proteins ; JNJ-1802
Language	English
Publishing date	2023-03-15
Publishing country	England
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ZDB-ID	120714-3
ISSN	1476-4687 ; 0028-0836
ISSN (online)	1476-4687
ISSN	0028-0836
DOI	10.1038/s41586-023-05790-6
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Article ; Online: Design and synthesis of tetrahydropyridopyrimidine based Toll-Like Receptor (TLR) 7/8 dual agonists.

McGowan, David C / Herschke, Florence / Khamlichi, Mourad D / Rosauro, Mari Luz / Benedicto, Sara M Pérez / Pauwels, Frederik / Stoops, Bart / Pande, Vineet / Scholliers, Annick / Van Schoubroeck, Bertrand / Mostmans, Wendy / Van Dijck, Kris / Thoné, Tine / Horton, Helen / Fanning, Gregory / Jonckers, Tim H M / Raboisson, Pierre

Bioorganic & medicinal chemistry letters

2018 Volume 28, Issue 19, Page(s) 3216–3221

Abstract: In a continuing effort to discover novel TLR agonists, herein we report on the discovery and structure-activity relationship of novel tetrahydropyridopyrimidine TLR 7/8 agonists. Optimization of this series towards dual agonist activity and a high ... ...

Abstract	In a continuing effort to discover novel TLR agonists, herein we report on the discovery and structure-activity relationship of novel tetrahydropyridopyrimidine TLR 7/8 agonists. Optimization of this series towards dual agonist activity and a high clearance profile resulted in the identification of compound 52a1. Evaluation in vivo revealed an interferon stimulated response (ISG) in mice with limited systemic exposure and demonstrated the potential in antiviral treatment or as a vaccine adjuvant.
MeSH term(s)	Administration, Oral ; Animals ; Drug Design ; Mice ; Pyrimidines/pharmacology ; Structure-Activity Relationship ; Toll-Like Receptor 7/agonists ; Toll-Like Receptor 8/agonists
Chemical Substances	Pyrimidines ; TLR7 protein, human ; TLR8 protein, human ; Toll-Like Receptor 7 ; Toll-Like Receptor 8
Language	English
Publishing date	2018-08-16
Publishing country	England
Document type	Journal Article
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2018.08.015
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