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Papers by John Brinkman
Organic Letters, 2000
General Experimental Conditions. Proton magnetic resonance (1 H NMR) spectra were recorded on Bru... more General Experimental Conditions. Proton magnetic resonance (1 H NMR) spectra were recorded on Bruker ARX300 and Bruker DPX300 spectrometers using tetramethylsilane (TMS) as internal reference. Chemical shifts are reported on the δ scale in parts per million (ppm) downfield from TMS; peak multiplicities are indicated as s (singlet), d (doublet), t (triplet), q (quartet), dd (doublet of doublet), m (multiplet), and br (broad); coupling constants (J) are reported in Hertz. Carbon magnetic resonance (13 C NMR) spectra were recorded on Bruker ARX 300 and Bruker DPX 300 spectrometers using the carbon signal of the deuterated solvent as the internal reference. Infrared spectra (IR) were recorded on a Midac FTIR spectrometer. Peaks are reported in cm-1. Elemental analysis were performed by Robertson Microlit Laboratories, Inc., Madison, NJ. Analytical thin layer chromatography (TLC) was performed on Macherey-Nagel Polygram® Sil G/UV 254 silica gel plates with 0.2 mm thick, 254-F indicator; visualization was accomplished by UV (254 nm) illumination and by staining with potassium permanganate (KMnO 4) in an aqueous solution of potassium carbonate. Flash chromatography was performed according to Still i with use of silica gel (0.040-0.063 mm, E. Merck). High pressure liquid chromatography (HPLC) was performed with a Waters Nova-Pak C-18 column (Waters Instrument Co., 3.9 x 150 mm) on a Waters liquid chromatogram with a UV detector.
Bioorganic & Medicinal Chemistry Letters, 2010
Acetamide-4-methoxy-2-aminobenzothiazole 4-fluorobenzamide (compound 1) was chosen as a drug-like... more Acetamide-4-methoxy-2-aminobenzothiazole 4-fluorobenzamide (compound 1) was chosen as a drug-like and non-xanthine based starting point for the discovery of A 2B receptor antagonists because of its slight selectivity against A 1 and A 2A receptors and modest A 2B potency. SAR exploration of compound 1 described herein included modifications to the 7-N-acetamide group, substitution of the 4-methoxy group by halogens as well as replacement of the p-flouro-benzamide side chain. This work culminated in the identification of compound 37 with excellent A 2B potency, modest selectivity versus A 2A and A 1 receptors, and good rodent PK properties.
Bioorganic & Medicinal Chemistry Letters, 2011
Organic Letters, 2000
General Experimental Conditions. Proton magnetic resonance (1 H NMR) spectra were recorded on Bru... more General Experimental Conditions. Proton magnetic resonance (1 H NMR) spectra were recorded on Bruker ARX300 and Bruker DPX300 spectrometers using tetramethylsilane (TMS) as internal reference. Chemical shifts are reported on the δ scale in parts per million (ppm) downfield from TMS; peak multiplicities are indicated as s (singlet), d (doublet), t (triplet), q (quartet), dd (doublet of doublet), m (multiplet), and br (broad); coupling constants (J) are reported in Hertz. Carbon magnetic resonance (13 C NMR) spectra were recorded on Bruker ARX 300 and Bruker DPX 300 spectrometers using the carbon signal of the deuterated solvent as the internal reference. Infrared spectra (IR) were recorded on a Midac FTIR spectrometer. Peaks are reported in cm-1. Elemental analysis were performed by Robertson Microlit Laboratories, Inc., Madison, NJ. Analytical thin layer chromatography (TLC) was performed on Macherey-Nagel Polygram® Sil G/UV 254 silica gel plates with 0.2 mm thick, 254-F indicator; visualization was accomplished by UV (254 nm) illumination and by staining with potassium permanganate (KMnO 4) in an aqueous solution of potassium carbonate. Flash chromatography was performed according to Still i with use of silica gel (0.040-0.063 mm, E. Merck). High pressure liquid chromatography (HPLC) was performed with a Waters Nova-Pak C-18 column (Waters Instrument Co., 3.9 x 150 mm) on a Waters liquid chromatogram with a UV detector.
Bioorganic & Medicinal Chemistry Letters, 2010
Acetamide-4-methoxy-2-aminobenzothiazole 4-fluorobenzamide (compound 1) was chosen as a drug-like... more Acetamide-4-methoxy-2-aminobenzothiazole 4-fluorobenzamide (compound 1) was chosen as a drug-like and non-xanthine based starting point for the discovery of A 2B receptor antagonists because of its slight selectivity against A 1 and A 2A receptors and modest A 2B potency. SAR exploration of compound 1 described herein included modifications to the 7-N-acetamide group, substitution of the 4-methoxy group by halogens as well as replacement of the p-flouro-benzamide side chain. This work culminated in the identification of compound 37 with excellent A 2B potency, modest selectivity versus A 2A and A 1 receptors, and good rodent PK properties.
Bioorganic & Medicinal Chemistry Letters, 2011