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Book: Lead generation

Holenz, Jörg

methods, strategies, and case studies

(Methods and principles in medicinal chemistry ; volume 68 a-b)

2016

Author's details	edited by Jörg Holenz
Series title	Methods and principles in medicinal chemistry ; volume 68 a-b
MeSH term(s)	Drug Discovery/methods ; Chemistry, Pharmaceutical/methods ; Technology, Pharmaceutical/trends ; Pharmaceutical Preparations/chemistry ; Structure-Activity Relationship
Language	English
Size	2 volumes (xxxii, 785 pages) :, illustrations.
Document type	Book
ISBN	9783527333295 ; 9783527677078 ; 9783527677061 ; 9783527677054 ; 978352767704 ; 3527333290 ; 3527677070 ; 3527677062 ; 3527677054 ; 9783527677047 ; 3527677046
Database	Catalogue of the US National Library of Medicine (NLM)

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Article ; Online: Advances in Lead Generation.

Holenz, Joerg / Stoy, Patrick

Bioorganic & medicinal chemistry letters

2018 Volume 29, Issue 4, Page(s) 517–524

Abstract: Lead Generation represents a critical drug discovery phase where chemical starting points and their respective mechanism of action, quality, and potential liabilities are largely predefined. Recent advances such as DNA-encoded libraries or fragment-, ... ...

Abstract	Lead Generation represents a critical drug discovery phase where chemical starting points and their respective mechanism of action, quality, and potential liabilities are largely predefined. Recent advances such as DNA-encoded libraries or fragment-, chemical biology-, and virtual screening-based approaches are today as common as traditional High Throughput Screening. Innovations in characterizing lead quality have allowed more informed decision-making by discovery teams. The key challenge today is to individually tailor the right mix of methods for each project to facilitate data integration with the purpose of creating multiple high-quality lead series, ultimately translating to reduced chemistry-related pipeline attrition.
MeSH term(s)	Cell Line ; Drug Discovery ; High-Throughput Screening Assays/methods ; Humans ; Small Molecule Libraries/chemistry
Chemical Substances	Small Molecule Libraries
Language	English
Publishing date	2018-12-03
Publishing country	England
Document type	Journal Article ; Review
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2018.12.001
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Book ; Thesis: Synthese und Optimierung von Naphthylisochinolin-Alkaloiden als neuen Leitstrukturen für Pharma und Pflanzenschutz und Isolierung von Sekundärmetaboliten ausgewählter tropischer Heilpflanzen

Holenz, Jörg

1997

Author's details	vorgelegt von Jörg Holenz
Language	German
Size	159 S., Ill., graph. Darst.
Document type	Book ; Thesis
Thesis / German Habilitation thesis	Univ., Diss.--Würzburg, 1997
Database	Former special subject collection: coastal and deep sea fishing

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Book ; Thesis: Synthese und Optimierung von Naphthylisochinolin-Alkaloiden als neuen Leitstrukturen für Pharma und Pflanzenschutz und Isolierung von Sekundärmetaboliten ausgewählter tropischer Heilpflanzen

Holenz, Jörg

1997

Author's details	vorgelegt von Jörg Holenz
Language	German
Size	159 S., Ill., graph. Darst.
Document type	Book ; Thesis
Thesis / German Habilitation thesis	Univ., Diss.--Würzburg, 1997
Database	Library catalogue of the German National Library of Science and Technology (TIB), Hannover

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Article ; Online: Thiophene bioisosteres of spirocyclic σ receptor ligands: relationships between substitution pattern and σ receptor affinity.

Oberdorf, Christoph / Schepmann, Dirk / Vela, Jose Miguel / Buschmann, Helmut / Holenz, Jörg / Wünsch, Bernhard

Journal of medicinal chemistry

2012 Volume 55, Issue 11, Page(s) 5350–5360

Abstract: On the basis of the 6',7'-dihydrospiro[piperidine-4,4'-thieno[3,2-c]pyran] framework, a series of more than 30 σ ligands with versatile substituents in 1-, 2'-, and 6'-position has been synthesized and pharmacologically evaluated in order to find novel ... ...

Abstract	On the basis of the 6',7'-dihydrospiro[piperidine-4,4'-thieno[3,2-c]pyran] framework, a series of more than 30 σ ligands with versatile substituents in 1-, 2'-, and 6'-position has been synthesized and pharmacologically evaluated in order to find novel structure-affinity relationships. It was found that a cyclohexylmethyl residue at the piperidine N-atom instead of a benzyl moiety led to increased σ(2) affinity and therefore to decreased σ(1)/σ(2) selectivity. Small substituents (e.g., OH, OCH(3), CN, CH(2)OH) in 6'-position adjacent to the O-atom were well tolerated by the σ(1) receptor. Removal of the substituent in 6'-position resulted in very potent but unselective σ ligands (13). A broad range of substituents with various lipophilic and H-bond forming properties was introduced in 2'-position adjacent to the S-atom without loss of σ(1) affinity. However, very polar and basic substituents in both 2'- and 6'-position decreased the σ(1) affinity considerably. It is postulated that the electron density of the thiophene moiety has a big impact on the σ(1) affinity.
MeSH term(s)	Animals ; Brain/metabolism ; Guinea Pigs ; Ligands ; Liver/metabolism ; Models, Molecular ; Piperidines/chemical synthesis ; Piperidines/chemistry ; Piperidines/pharmacology ; Pyrans/chemical synthesis ; Pyrans/chemistry ; Pyrans/pharmacology ; Radioligand Assay ; Rats ; Receptors, sigma/metabolism ; Spiro Compounds/chemical synthesis ; Spiro Compounds/chemistry ; Spiro Compounds/pharmacology ; Structure-Activity Relationship ; Thiophenes/chemical synthesis ; Thiophenes/chemistry ; Thiophenes/pharmacology
Chemical Substances	Ligands ; Piperidines ; Pyrans ; Receptors, sigma ; Spiro Compounds ; Thiophenes
Language	English
Publishing date	2012-06-14
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/jm300302p
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Article ; Online: Synthesis and pharmacological evaluation of a potent and selective σ1 receptor antagonist with high antiallodynic activity.

Utech, Tina / Köhler, Jens / Buschmann, Helmut / Holenz, Jörg / Vela, Jose Miguel / Wünsch, Bernhard

Archiv der Pharmazie

2011 Volume 344, Issue 7, Page(s) 415–421

Abstract: Based on the pharmacophore model of Glennon the conformationally restricted σ(1) receptor ligand 2 with a 1,3-dioxane moiety has been designed and synthesized. The three step synthesis (transacetalization with pentane-1,3,5-triol, tosylation, and ... ...

Abstract	Based on the pharmacophore model of Glennon the conformationally restricted σ(1) receptor ligand 2 with a 1,3-dioxane moiety has been designed and synthesized. The three step synthesis (transacetalization with pentane-1,3,5-triol, tosylation, and nucleophilic substitution with benzylamine) provided diastereoselectively the cis-configured 1,3-dioxane 2 in good yields. The 1,3-dioxane 2 represents a potent σ(1) receptor ligand (K(i) = 19 nM) with moderate selectivity over the σ(2) subtype (K(i) = 92 nM) and excellent selectivity against more than 60 other targets. Additionally the hERG K(+) channel is not affected by 2. In the capsaicin assay 2 showed extraordinarily high analgesic activity with more than 70% analgesia at the very low dose of 0.25 mg/kg body weight, which indicates σ(1) antagonistic activity. Since 2 does only interact with σ(1) receptors, the in-vivo antiallodynic activity of 2 must be attributed to the σ(1) antagonistic activity.
MeSH term(s)	Analgesics/chemical synthesis ; Analgesics/chemistry ; Analgesics/pharmacology ; Animals ; CHO Cells ; Capsaicin ; Cricetinae ; Cricetulus ; Dioxanes/chemical synthesis ; Dioxanes/chemistry ; Dioxanes/pharmacology ; Disease Models, Animal ; Ether-A-Go-Go Potassium Channels/drug effects ; Ether-A-Go-Go Potassium Channels/metabolism ; Guinea Pigs ; Humans ; Hyperalgesia/drug therapy ; Male ; Mice ; Rats ; Receptors, sigma/antagonists & inhibitors ; Sigma-1 Receptor
Chemical Substances	Analgesics ; Dioxanes ; Ether-A-Go-Go Potassium Channels ; Receptors, sigma ; Capsaicin (S07O44R1ZM)
Language	English
Publishing date	2011-05-20
Publishing country	Germany
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	6381-2
ISSN	1521-4184 ; 0365-6233 ; 1437-1014
ISSN (online)	1521-4184
ISSN	0365-6233 ; 1437-1014
DOI	10.1002/ardp.201000365
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Article ; Online: Toward β-Secretase-1 Inhibitors with Improved Isoform Selectivity.

Johansson, Patrik / Kaspersson, Karin / Gurrell, Ian K / Bäck, Elisabeth / Eketjäll, Susanna / Scott, Clay W / Cebers, Gvido / Thorne, Philip / McKenzie, Michael J / Beaton, Haydn / Davey, Paul / Kolmodin, Karin / Holenz, Jörg / Duggan, Mark E / Budd Haeberlein, Samantha / Bürli, Roland W

Journal of medicinal chemistry

2018 Volume 61, Issue 8, Page(s) 3491–3502

Abstract: BACE1 is responsible for the first step in APP proteolysis, leading to toxic Aβ production, and has been indicated to play a key role in the pathogenesis of Alzheimer's disease. The related isoform BACE2 is thought to be involved in processing of the ... ...

Abstract	BACE1 is responsible for the first step in APP proteolysis, leading to toxic Aβ production, and has been indicated to play a key role in the pathogenesis of Alzheimer's disease. The related isoform BACE2 is thought to be involved in processing of the pigment cell-specific melanocyte protein. To avoid potential effects on pigmentation, we investigated the feasibility for developing isoform-selective BACE1 inhibitors. Cocrystal structures of 47 compounds were analyzed and clustered according to their selectivity profiles. Selective BACE1 inhibitors were found to exhibit two distinct conformational features proximal to the flap and the S3 subpocket. Several new molecules were designed and tested to make use of this observation. The combination of a pyrimidinyl C-ring and a methylcyclohexyl element resulted in lead molecule 28, which exhibited ∼50-fold selectivity. Compared to a nonselective BACE1/2 inhibitor, 28 showed significantly less inhibition of PMEL processing in human melanocytes, indicating good functional selectivity of this inhibitor class.
MeSH term(s)	Amyloid Precursor Protein Secretases/antagonists & inhibitors ; Amyloid Precursor Protein Secretases/chemistry ; Amyloid beta-Peptides/metabolism ; Animals ; Aspartic Acid Endopeptidases/antagonists & inhibitors ; Aspartic Acid Endopeptidases/chemistry ; Brain/metabolism ; Catalytic Domain ; Dogs ; Female ; Humans ; Madin Darby Canine Kidney Cells ; Male ; Mice, Inbred C57BL ; Molecular Structure ; Oxazoles/chemical synthesis ; Oxazoles/chemistry ; Oxazoles/pharmacokinetics ; Oxazoles/pharmacology ; Peptide Fragments/metabolism ; Protease Inhibitors/chemical synthesis ; Protease Inhibitors/chemistry ; Protease Inhibitors/pharmacokinetics ; Protease Inhibitors/pharmacology ; Protein Isoforms/antagonists & inhibitors ; Protein Isoforms/chemistry ; Rats ; Spiro Compounds/chemical synthesis ; Spiro Compounds/chemistry ; Spiro Compounds/pharmacokinetics ; Spiro Compounds/pharmacology ; Structure-Activity Relationship ; gp100 Melanoma Antigen/metabolism
Chemical Substances	Amyloid beta-Peptides ; Oxazoles ; PMEL protein, human ; Peptide Fragments ; Protease Inhibitors ; Protein Isoforms ; Spiro Compounds ; amyloid beta-protein (1-42) ; gp100 Melanoma Antigen ; Amyloid Precursor Protein Secretases (EC 3.4.-) ; Aspartic Acid Endopeptidases (EC 3.4.23.-) ; BACE2 protein, human (EC 3.4.23.45) ; BACE1 protein, human (EC 3.4.23.46)
Language	English
Publishing date	2018-04-10
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/acs.jmedchem.7b01716
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Article ; Online: Biotransformation of two β-secretase inhibitors including ring opening and contraction of a pyrimidine ring.

Lindgren, Anders / Eklund, Göran / Turek, Dominika / Malmquist, Jonas / Swahn, Britt-Marie / Holenz, Jörg / von Berg, Stefan / Karlström, Sofia / Bueters, Tjerk

Drug metabolism and disposition: the biological fate of chemicals

2013 Volume 41, Issue 5, Page(s) 1134–1147

Abstract: Recently, the discovery of the aminoisoindoles as potent and selective inhibitors of β-secretase was reported, including the close structural analogs compound (S)-1-pyridin-4-yl-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine [(S)-25] and (S)-1- ...

Abstract	Recently, the discovery of the aminoisoindoles as potent and selective inhibitors of β-secretase was reported, including the close structural analogs compound (S)-1-pyridin-4-yl-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine [(S)-25] and (S)-1-(2-(difluoromethyl)pyridin-4-yl)-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine hemifumarate (AZD3839), the latter being recently progressed to the clinic. The biotransformation of (S)-25 was investigated in vitro and in vivo in rat, rabbit, and human and compared with AZD3839 to further understand the metabolic fate of these compounds. In vitro, CYP3A4 was the major responsible enzyme and metabolized both compounds to a large extent in the commonly shared pyridine and pyrimidine rings. The main proposed metabolic pathways in various in vitro systems were N-oxidation of the pyridine and/or pyrimidine ring and conversion to 4-pyrimidone and pyrimidine-2,4-dione. Both compounds were extensively metabolized, and more than 90% was excreted in feces after intravenous administration of radiolabeled compound to the rat. Here, the main pathways were N-oxidation of the pyridine and/or pyrimidine ring and a ring contraction of the pyrimidine ring into an imidazole ring. Ring-contracted metabolites accounted for 25% of the total metabolism in the rat for (S)-25, whereas the contribution was much smaller for AZD3839. This metabolic pathway was not foreseen on the basis of the obtained in vitro data. In conclusion, we discovered an unusual metabolic pathway of aryl-pyrimidine-containing compounds by a ring-opening reaction followed by elimination of a carbon atom and a ring closure to form an imidazole ring.
MeSH term(s)	Amyloid Precursor Protein Secretases/antagonists & inhibitors ; Animals ; Biotransformation ; Chromatography, Liquid ; Cyclization ; Enzyme Inhibitors/chemistry ; Enzyme Inhibitors/pharmacology ; Humans ; Indoles/pharmacokinetics ; Male ; Mass Spectrometry ; Pyrimidines/chemistry ; Pyrimidines/pharmacokinetics ; Rabbits ; Rats ; Rats, Sprague-Dawley
Chemical Substances	AZD3839 ; Enzyme Inhibitors ; Indoles ; Pyrimidines ; Amyloid Precursor Protein Secretases (EC 3.4.-) ; pyrimidine (K8CXK5Q32L)
Language	English
Publishing date	2013-05
Publishing country	United States
Document type	Journal Article
ZDB-ID	186795-7
ISSN	1521-009X ; 0090-9556
ISSN (online)	1521-009X
ISSN	0090-9556
DOI	10.1124/dmd.112.050351
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Article ; Online: Microwave assisted synthesis of spirocyclic pyrrolidines -σ1 receptor ligands with modified benzene-N-distance.

Jasper, Annemarie / Schepmann, Dirk / Lehmkuhl, Kirstin / Vela, Jose Miguel / Buschmann, Helmut / Holenz, Jörg / Wünsch, Bernhard

European journal of medicinal chemistry

2012 Volume 53, Page(s) 327–336

Abstract: Two series of σ(1) ligands with a spiro[[2]benzopyran-1,3'-pyrrolidine] (3) and a spiro[[2]benzofuran-1,3'-pyrrolidine] (4) framework were synthesized and pharmacologically evaluated. Several reaction steps were considerably improved by microwave ... ...

Abstract	Two series of σ(1) ligands with a spiro[[2]benzopyran-1,3'-pyrrolidine] (3) and a spiro[[2]benzofuran-1,3'-pyrrolidine] (4) framework were synthesized and pharmacologically evaluated. Several reaction steps were considerably improved by microwave irradiation. The σ(1) affinity of the spirocyclic ligands correlates nicely with the benzene-N-distance, i.e. 2 < 3 < 4 < 1. The σ(1) affinity of both compound classes could be increased with large N-substituents (e.g. 2-phenylethyl, octyl). Nevertheless the benzyl derivative 4a represents the most promising σ(1) ligand (K(i) = 25 nM) due to its high selectivity against the σ(2) subtype (>40-fold), the NMDA receptor and 5-HT(6) and 5-HT(7) receptors. Moreover, 4a did not inhibit the hERG channel in the heart.
MeSH term(s)	Animals ; Benzene/chemistry ; Chemistry Techniques, Synthetic ; Ether-A-Go-Go Potassium Channels/antagonists & inhibitors ; Guinea Pigs ; Humans ; Ligands ; Microwaves ; Nitrogen/chemistry ; Pyrrolidines/chemical synthesis ; Pyrrolidines/chemistry ; Pyrrolidines/metabolism ; Pyrrolidines/pharmacology ; Receptors, sigma/metabolism ; Spiro Compounds/chemistry ; Substrate Specificity
Chemical Substances	Ether-A-Go-Go Potassium Channels ; Ligands ; Pyrrolidines ; Receptors, sigma ; Spiro Compounds ; Benzene (J64922108F) ; Nitrogen (N762921K75)
Language	English
Publishing date	2012-07
Publishing country	France
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	188597-2
ISSN	1768-3254 ; 0009-4374 ; 0223-5234
ISSN (online)	1768-3254
ISSN	0009-4374 ; 0223-5234
DOI	10.1016/j.ejmech.2012.04.018
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Article ; Online: Thiophene bioisosteres of spirocyclic sigma receptor ligands. 1. N-substituted spiro[piperidine-4,4'-thieno[3,2-c]pyrans].

Oberdorf, Christoph / Schepmann, Dirk / Vela, Jose Miguel / Diaz, Jose Luis / Holenz, Jörg / Wünsch, Bernhard

Journal of medicinal chemistry

2008 Volume 51, Issue 20, Page(s) 6531–6537

Abstract: Herein, the synthesis and pharmacological evaluation of thiophene bioisosteres of the highly potent spirocyclic benzopyran 1 are detailed. The synthesis of 1-benzyl-6'-methoxy-6',7'-dihydrospiro[piperidine-4,4'-thieno[3.2- c]pyran] (2a) was performed ... ...

Abstract	Herein, the synthesis and pharmacological evaluation of thiophene bioisosteres of the highly potent spirocyclic benzopyran 1 are detailed. The synthesis of 1-benzyl-6'-methoxy-6',7'-dihydrospiro[piperidine-4,4'-thieno[3.2- c]pyran] (2a) was performed starting with 3-bromothiophene (3). After introduction of the acetaldehyde substructure (7), halogen metal exchange, addition of 1-benzylpiperidin-4-one, and cyclization led to the spirocyclic thienopyran 2a. The removal of the benzyl group afforded the secondary amine 2f, which was substituted with various residues. With respect to sigma 1 affinity the N-benzyl derivative 2a, the N-cyclohexylmethyl derivative 2d, and the N-p-fluorobenzyl derivative 2i represent the most potent compounds of this series binding with K i values of 0.32, 0.29, and 0.62 nM, respectively. Electronic properties of the substituents have only little impact on sigma 1 affinity. The most potent sigma 1 ligands display high selectivity against sigma 2, 5-HT 1A, 5-HT 6, 5-HT 7, alpha 1A, alpha 2, and NMDA receptors. The activity of 2a in the mouse capsaicin assay seems to indicate sigma 1 antagonistic activity.
MeSH term(s)	Alkylation ; Animals ; Cyclization ; Ligands ; Mice ; Models, Molecular ; Molecular Structure ; Oxidation-Reduction ; Pain/drug therapy ; Pain/metabolism ; Piperidines/chemistry ; Protein Binding ; Pyrans/chemistry ; Pyrans/therapeutic use ; Rats ; Receptors, sigma/antagonists & inhibitors ; Receptors, sigma/chemistry ; Receptors, sigma/metabolism ; Spiro Compounds/chemistry ; Spiro Compounds/therapeutic use ; Structure-Activity Relationship ; Thiophenes/chemistry
Chemical Substances	Ligands ; Piperidines ; Pyrans ; Receptors, sigma ; Spiro Compounds ; Thiophenes ; piperidine (67I85E138Y)
Language	English
Publishing date	2008-10-23
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/jm8007739
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