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1 Supplementary Information Development of Novel Amide–Derivatized 2,4- Bispyridyl Thiophenes as Highly Potent and Selective Dyrk1A Inhibitors. Part II: Identification of the cyclopropylamide moiety as a key modification AUTHOR NAMES Sarah S. Darwish 1 , Mohammad Abdel-Halim 1 , Ahmed K. ElHady 1 , Mohamed Salah 2 , Ashraf H.Abadi 1 , Walter Becker 3 and Matthias Engel 2 AUTHOR ADDRESS 1 Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Biotechnology, German University in Cairo, Cairo 11835, Egypt 2 Pharmaceutical and Medicinal Chemistry, Saarland University, Campus C2.3, D-66123 Saarbrücken, Germany 3 Institute of Pharmacology and Toxicology, Medical Faculty of the RWTH Aachen University, Wendlingweg 2, 52074 Aachen, Germany

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Page 1: 1H-NMR (500 MHz, DMSO) and 13C-NMR (126 MHz, … · Web viewDevelopment of Novel Amide–Derivatized 2,4-Bispyridyl Thiophenes as Highly Potent and Selective Dyrk1A Inhibitors. Part

1

Supplementary Information

Development of Novel Amide–Derivatized 2,4-Bispyridyl Thiophenes

as Highly Potent and Selective Dyrk1A Inhibitors. Part II:

Identification of the cyclopropylamide moiety as a key

modification

AUTHOR NAMES

Sarah S. Darwish1, Mohammad Abdel-Halim1, Ahmed K. ElHady1, Mohamed Salah2, Ashraf

H.Abadi1, Walter Becker3 and Matthias Engel2

AUTHOR ADDRESS

1Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Biotechnology, German

University in Cairo, Cairo 11835, Egypt

2Pharmaceutical and Medicinal Chemistry, Saarland University, Campus C2.3, D-66123

Saarbrücken, Germany

3Institute of Pharmacology and Toxicology, Medical Faculty of the RWTH Aachen University,

Wendlingweg 2, 52074 Aachen, Germany

Contents1 1H-NMR (500 MHz, DMSO) and 13C-NMR (126 MHz, DMSO) spectra of selected compounds.......2

2 Figure S1.............................................................................................................................................8

Page 2: 1H-NMR (500 MHz, DMSO) and 13C-NMR (126 MHz, … · Web viewDevelopment of Novel Amide–Derivatized 2,4-Bispyridyl Thiophenes as Highly Potent and Selective Dyrk1A Inhibitors. Part

2

1 1H-NMR (500 MHz, DMSO) and 13C-NMR (126 MHz, DMSO) spectra of selected compounds

Page 3: 1H-NMR (500 MHz, DMSO) and 13C-NMR (126 MHz, … · Web viewDevelopment of Novel Amide–Derivatized 2,4-Bispyridyl Thiophenes as Highly Potent and Selective Dyrk1A Inhibitors. Part

3

Page 4: 1H-NMR (500 MHz, DMSO) and 13C-NMR (126 MHz, … · Web viewDevelopment of Novel Amide–Derivatized 2,4-Bispyridyl Thiophenes as Highly Potent and Selective Dyrk1A Inhibitors. Part

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Page 5: 1H-NMR (500 MHz, DMSO) and 13C-NMR (126 MHz, … · Web viewDevelopment of Novel Amide–Derivatized 2,4-Bispyridyl Thiophenes as Highly Potent and Selective Dyrk1A Inhibitors. Part

5

Page 6: 1H-NMR (500 MHz, DMSO) and 13C-NMR (126 MHz, … · Web viewDevelopment of Novel Amide–Derivatized 2,4-Bispyridyl Thiophenes as Highly Potent and Selective Dyrk1A Inhibitors. Part

6

Page 7: 1H-NMR (500 MHz, DMSO) and 13C-NMR (126 MHz, … · Web viewDevelopment of Novel Amide–Derivatized 2,4-Bispyridyl Thiophenes as Highly Potent and Selective Dyrk1A Inhibitors. Part

7

2 Figure S1

B

AIle165

Ile165

Fig. S1. Comparison between the hydrophobic surface contacts of the acetyl side chain in compound 1b (A) and the cyclopropyl in compound 4b (B) with Ile165 in Dyrk1A. Van der Waals interactions are predicted for 4b, whereas the van der Waals volume of the acetyl moiety in 1b is too small to contact Ile165. Shown are the Connolly surfaces with the following colour coding: green, hydrophobic; magenta, hydrophilic.


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