Pharmazeutische Chemie

Publications

 

2018

A Diverse and Versatile Regiospecific Synthesis of Tetrasubstituted Alkylsulfanylimidazoles p38α Mitogen-Activated Protein Kinase Inhibitors.
Ansideri, F., Andreev, S., Kuhn, A., Albrecht, W., Laufer, S. A., Koch, P.
Molecules 2018, 23, 221.

Targeting the Protein Kinases Cysteinome.
Chaikuad, A., Koch, P., Laufer, S. A., Knapp, S.
Angew. Chem. Int. Ed. 2018, 57, 4372-4385.

Das Cysteinom der Proteinkinasen als Zielstruktur in der Arzneistoffentwicklung
Chaikuad, A., Koch, P., Laufer, S. A., Knapp, S.
Angew. Chem. 2018, 130, 4456-4470.

Probing substituents in the 1- and 3-position: Tetrahydropyrazino-annelated water soluble xanthine derivatives as multi-target drugs with potent adenosine receptor antagonistic activity
Koch, P., Brunschweiger, A., Namasivayam, V., Ullrich, S., Maruca, A., Lazzaretto, B., Küppers, P., Hinz, S., Hockemeyer, J., Wiese, M., Alcaro, S., Kiec-Kononowiz, K., Müller, C. E.
Front. Chem. 2018, 6, 206.

Structural Optimization of a Pyridinylimidazole Scaffold: Shifting the Selectivity from p38α Mitogen-Activated Protein Kinase to c-Jun N-terminal Kinase 3.
Ansideri, F., Macedo, J. T., Eitel, M., El-Gokha, A., Zinad, D. S., Scarpellini, C., Kudolo, M., Schollmeyer, D., Boeckler, F. M., Blaum, B. S., Laufer, S. A., Koch, P.
ACS Omega 2018, 3, 7809-7831.

Special Issue: Kinase inhibitors.
Koch, P., Laufer, S. A.
Molecules 2018, 23, 1818.

The Symmetric Tetravalent Sulfhydryl-Specific Linker NATBA Facilitates a Combinatorial "Tool Kit" Strategy for Phage Display-Based Selection of Functional Bicyclic Peptides.
Ernst, C., Sindlinger, J., Schwarzer, D., Koch, P., Boeckler, F. M.
ACS Omega 2018, 3, 13261-13268.

Switching Between Biciclic and Linear Linker Peptides - The Sulfhydryl-Specific Linker TPSMB Enables Reversible Cyclization of Peptides.
Ernst, C., Heidrich, J., Sessler, C., Sindlinger, J., Schwarzer, D., Koch, P., Boeckler, F. M.
Frontiers Chem. 2018, 6, 484.

 

2017

Tri- and Tetra-substituted Pyridinylimidazoles as Covalent Inhbitors of c-Jun N-Terminal Kinase 3.
Muth, F., El-Gokha, A., Ansideri, F., Eitel, M., Döring, E., Sievers-Engler, A., Lange, A., Boeckler, F. M., Lämmerhofer, M., Koch, P., Laufer, S. A.
J. Med. Chem. 2017, 60, 594-607.

Fluorescence polarization-based competition binding assay for c-Jun N-terminal kinases 1 and 2.
Ansideri, F., Dammann, M., Boeckler, F. M., Koch, P.
Anal. Biochem. 2017, 532C, 26-28.

SK4 channels modulate Ca2+-signalling and cell cycle progression in murine breast cancer.
Steudel, F. A, Mohr, C. J., Steegen, B., Nguyen, H. Y., Barnert, A., Steinle, M., Berr-Hammer, S., Koch, P., Lo, W.-Y., Schroth, W., Hoppe, R., Brauch, H., Ruth, P., Huber, S. M., Lukowski, R.
Mol. Oncol. 2017, 11, 1172-1188.

From 2-Alkylsulfanylimidazoles to 2-Alkylimidazoles: An Approach towards Metabolically More Stable p38α MAP Kinase Inhibitors.
Heider F., Haun, U., Döring, E., Kudolo, M., Sessler, C., Albrecht, W., Laufer, S., Koch, P.
Molecules 2017, 22, 1729.

2-Alkylsulfanyl-4(5)-aryl-5(4)-heteroarylimidazoles: an Overview on Synthetic Strategies and Biological Activity.
Koch, P., Ansideri, F.
Arch. Pharm. 2017, 350, e1700258.

(E)-1-Pyridin-4-yl)-propran-1-one O-tosyl oxime.
Eitel, M., Schollmeyer, D., Koch, P.
IUCrData 2017, 2, x171602.

 

2016

Fluorescence polarization-based assay for detecting compounds binding to inactive JNK3 and p38α MAP Kinase.
Ansideri, F., Lange, A., El-Gokha, A., Boeckler, F. M., Koch, P.
Anal. Biochem. 2016, 503, 28-40.

(E)-1-Pyridin-4-yl)-propran-1-one oxime.
Eitel, M., Schollmeyer, D., Koch, P.
IUCrData 2016, 1, x160803.

4-Methyl-N-(4-methylpyridin-2-yl)-N-(3,4,5,6-tetrahydro-2H-pyran-4-yl)pyridin-2-amine.
El-Gokha A., Schollmeyer, D., Koch, P.
IUCrData 2016, 1, x160804.

1-(3',6'-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-5-yl)-3-[4-({4-[1-(4-fluorophenyl)-1H-imidazol-5-yl]pyridin-2-yl}amino)phenyl]thiourea methanol monosolvate.
Ansideri, F., Schollmeyer, D., Koch, P.
IUCrData 2016, 1, x160840.

8-Substituted 1,3-dimethyltetrahydropyrazino[2,1-f]purinediones: water-soluble adenosine receptor anagonists and monoamine oxidase B inhibitors.
Brunschweiger, A., Koch, P., Schlenk, M., Rafehi, M., Radjainia, H., Küppers, P., Hinu, S., Pineda, F., Wiese, M., Hockemeyer, J., Heer, J, Denonne, F., Müller, C. E.
Bioorg. Med. Chem. 2016, 24, 5462-5480.

High-quality draft genome sequence of the actinobacterium Nocardia terpenica IFM 0406, producer of the immunosuppressant brasilicardins, using Illumina and PacBio technologies.
Buchmann, A., Eitel, M., Koch, P., Schwarz, P. N., Stegmann, E., Wohlleben, W., Wolański, M., Krawiec, M., Zakrzewska-Czerwińska, J., Méndez, C., Botas, A., Núñez, L. E., Morís, F., Cortés, J., Gross H.
Genome Announc. 2016, 4, e01391-16.

 

2015

Inhibitors of c-Jun N-terminal kinase (an update).
Koch, P., Gehringer, M., Laufer, S. A.
J. Med. Chem. 2015, 58, 72-95.

Tetra-Substituted Pyridinylimidazoles As Dual Inhibitors of p38α Mitogen-Activated Protein Kinase and c-Jun N-Terminal Kinase 3 for Potential Treatment of Neurodegenerative Diseases.
Muth, F., Günther, M., Bauer, S. M., Döring, E., Fischer, S., Maier, J., Drückes, P., Köppler, J., Rothbauer, U., Koch, P., Laufer, S. A.
J. Med. Chem. 2015, 58, 72-95.

c-Jun N-terminal kinase inhibitors: a patent review (2010 - 2014).
Gehringer, M., Muth, F., Koch, P., Laufer, S. A.
Expert Opin. Ther. Pat. 2015, 25, 849-872.

Synthesis and Biological Actvity of a Brasilicardin A Analogue Featuring a Simplified Core.
Jung, M. E., Chamberlain, B. T., Koch, P., Niazi, K. R.
Org. Lett. 2015, 17, 3608-3611.

An optimized and versatile synthesis to pyridinylimidazole-type p38α mitogen activated protein kinase inhibitors.
Elgokha, A., Laufer, S. A., Koch, P.
Organic & Biomolecular Chemistry 2015, 13, 10699-10704.

Targeting the Gatekeeper MET146 of c-Jun N-terminal kinase (JNK3) Induces a Bivalent Halogen / Chalcogen Bond.
Lange, A., Günther, M., Buettner, F. M., Zimmermann, M. O., Heidrich, J., Hennig, S., Zahn, S., Schall, C., Sievers-Engler, A., Ansideri, F., Koch, P., Laemmerhofer, M., Stehle, T., Laufer, S. A., Boeckler, F. M.
Journal of the American Chemical Society 2015, 137, 14640-14652.

 

2014

8-Benzyltetrahydropyrazino[2,1-f]purinediones: water-soluble tricyclic xanthine derivatives as multi-target drugs for neurodegenerative diseases.
Brunschweiger A., Koch, P., Schlenk, M., Pineda, P., Küppers, P., Hinz, S., Köse, M., Ullrich, S., Hockemeyer, J., Wiese, M., Heer, J., Müller C. E.
ChemMedChem 2014, 9, 1704-1721.

Halogen-enriched fragment libraries as chemical probes for harnessing halogen bonding in fragment-based lead discovery.
Zimmermann, M. O., Lange, A., Wicken, R., Cieslik, M. B., Exner, T. E., Joerger, J. C., Koch, P., Boeckler, F. M.
Future Med. Chem. 2014, 6, 617-639.

 

2013

1,3-Dialkyl-substituted tetrahydropyrimido[1,2-f]purine-2,4-diones as multiple target drugs for the potential treatment of neurodegenerative diseases.
Koch, P., Akkari, R., Brunschweiger A., Borrmann, T., Schlenk, M., Küppers, P., Köse, M., Radjainia, H., Hockemeyer, J., Drabczynska, A., Kiec-Kononowicz, K., Müller C. E.
Bioorg. Med. Chem. 2013, 21, 7435-7452.

 

2012

Tri- and Tetrasubstituted Pyrazole Derivates: Regioisomerism Switches Activity from p38MAP Kinase to Important Cancer Kinases.
Abu Thaher, B., Arnsmann, M., Totzke, F., Ehlert, J. E., Kubbutat, M. H. G., Schachtele, C., Zimmermann, M. O., Koch, P., Boeckler, F. M., Laufer, S.
J. Med. Chem. 2012, 55, 961-965.

4-(4-Fluorophenyl)-1-phenyl-3-(pyridin-4-yl)-1H-pyrazol-5-amine.
Abu Thaher, B., Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2012, E68, o365.

4-(4-Fluorophenyl)-1-(4-nitrophenyl)-3-(pyridin-4-yl)-1H-pyrazol-5-amine.
Abu Thaher, B., Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2012, E68, o366.

Ethyl 5-amino-3-(pyridin-4-yl)-1-(2,4,6-trichlorophenyl)-1H-pyrazole-4-carboxylate dimethyl sulfoxide hemisolvate.
Abu Thaher, B., Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2012, E68, o917-918.

4-[5-Amino-4-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrazol-1-yl]benzonitrile.
Abu Thaher, B., Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2012, E68, o935.

4-(4-Fluorophenyl)-3-(pyridin-4-yl)-1-(2,4,6-trichlorophenyl)-1H-pyrazol-5-amine
Abu Thaher, B., Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2012, E68, o2603.

 

2011

An Efficient Synthesis of the Protected Carbohydrate Moiety of Brasilicardin A.
Jung, M. E., Koch, P.
Org. Lett. 2011, 13, 3710-3713.

Mild, selective deprotection of PMB ethers with triflic acid/1,3-dimethoxybenzene.
Jung, M. E., Koch, P.
Tetrahedron Lett. 2011, 52, 6051-6054.

 

2010

Pyridinylquinoxalines and Pyridinylpyridopyrazines as Lead Compounds for Novel p38α Mitogen-Activated Protein Kinase Inhibitors.
Koch, P., Jahns, H., Schattel, V., Goettert, M. Laufer, S.
J. Med. Chem. 2010, 53, 1128-1137.

Unexpected Reaction of 2-Alkylsulfanylimidazoles to Imidazol-2-ones: Pyridinylimidazol-2-ones as Novel Potent p38α Mitogen-Activated Protein Kinase Inhibitors
Koch, P., Laufer, S.
J. Med. Chem. 2010, 53, 4798-4802.

Tri- and tetrasubstituted imidazoles as p38α mitogen-activated protein kinase inhibitors.
Laufer, S., Hauser, D., Stegmiller, T., Bracht, C., Ruff, K., Schattel, V., Albrecht, W., Koch, P.
Bioorg. Med. Chem. Lett. 2010, 20, 6671-6675.

Biological Evaluation and Structural Determinants of p38α Mitogen-Activated-Protein Kinase and c-Jun-N-terminal Kinase 3 Inhibition by Flavonoids.
Goettert, M., Schattel, V., Koch, P., Merfort, I., Laufer, S.
ChemBioChem. 2010, 11, 2579-2588.

5-(4-Fluorophenyl)-4-(4-pyridyl)oxazol-2-amine.
Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2010, E66, o917.

 

2009

Role of the hydrogen bonding heteroatom-Lys53 interaction between the p38α Mitogen-Activated Protein (MAP) kinase and pyridinyl-substituted 5-membered heterocyclic ring inhibitors
Abu Thaher, B., Koch, P., Schattel, V., Laufer, S.
J. Med. Chem. 2009, 52, 2613-2617.

4-[2-(4-Fluorophenyl)-1H-pyrrol-3-yl]pyridine.
Abu Thaher, B., Koch, P., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, E65, o457.

4-[2-(4-Fluorophenyl)furan-3-yl]pyridine.
Abu Thaher, B., Koch, P., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, E65, o458.

4-[5-(4-Fluorophenyl)-1H-imidazol-4-yl]pyridine.
Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, E65, o573.

4-[3-(4-Fluorophenyl)quinoxalin-2-yl]-N-isopropylpyridin-2-amine.>
Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, E65, o1344.

1-(2-(Benzylamino)pyridin-4-yl)-2-(4-fluorophenyl)ethane-1,2-dione.
Jahns, H., Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, E65, o1451.

3-(4-Fluorophenyl)-6-methoxy-2-(pyridin-4-yl)quinoxaline.
Jahns, H., Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, E65, o1626.

2-(4-Fluorophenyl)-3-(4-pyridyl)pyrido[2,3-b]pyrazine.
Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, E65, o2512.

3-(4-Fluorophenyl)-2-(4-pyridyl)pyrido[2,3-b]pyrazine.
Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, E65, o2546.

N-{4-[3-(4-Fluorophenyl)pyrido[2,3-b]pyrazin-2-yl]-2-pyridyl}isopropylamine.
Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, E65, o2557.

 

2008

Towards the improvement of the synthesis of novel 4(5)-aryl-5(4)-heteroaryl-2-thio-substituted imidazoles and their p38 MAP kinase inhibitory activity.
Laufer, S., Koch, P.
Organic & Biomolecular Chemistry, 2008, 6, 437-439.

A convenient synthesis of 1-(4-fluorophenyl)-2-(4-pyridyl)cyclopentene from cyclopentanone.
Abu Thaher, B., Koch, P., Del Amo, V., Knochel, P., Laufer, S.
Synthesis 2008, 225-228.

Targeting the Ribose and Phosphate Binding Site of p38 Mitogen-Activated Protein (MAP) Kinase: Synthesis and Biological Testing of 2-Alkylsulfanyl-, 4(5)-Aryl-, 5(4)-Heteroaryl-Substituted Imidazoles.
Koch, P., Bäuerlein, C., Jank, H., Laufer, S.
J. Med. Chem. 2008, 51, 5630-5640.

Methyl 4-[5-(4-fluorophenyl)-4-(pyridin-4-yl)-1H-imidazol-2-ylsulfanyl]butanoate.
Koch, P., Bäuerlein, C., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2008, E64, o1183-o1184.

tert-Butyl N-(4-methyl-2-pyridyl)carbamate.'
Koch, P.
, Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2008, E64, o2216.

tert-Butyl N-benzyl-N-[4-4-fluorobenzoylmethyl)-2-pyridyl]carbamate.
Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2008, E64, o2221.

tert-Butyl N-benzyl-N-(4-methyl-2-pyridyl)carbamate.
Koch, P., Schollmeyer, D., Laufer, S.
Acta Crystallogr., Sect. E: Struct. Rep. Online 2008, E64, o2222.

 

Patent

Burnet, M., Laufer, S., Koch, P. 2-SULFANYL-SUBSTITUTED IMIDAZOLE DERIVATIVES AND THEIR USE AS CYTOKINE INHIBITORS U. S. Pat. Appl. Publ. 2009, US 2009270462 A1.