Synthesis and Inhibitory Activity towards Monoamine Oxidase A and B of 8‐Functionalized 3‐Fluoro‐2‐methyl‐benzo[4,5]thiazolo[3,2‐ a ]pyrimidin‐4‐ones

Behzad Jafari, Saquib Jalil, Sumera Zaib, Sayfidin Shahobidinovich Safarov, Muattar Khalikova, Meirambek Ospanov, Nazym S. Yelibayeva, Zharylkasyn A. Abilov, Mirgul Zh. Turmukhanova, Sergey Kalugin

3 more authors

Peter Ehlers, Jamshed Iqbal, Peter Langer

2019

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DOI 10.1002/slct.201900916
Data confidence 70 medium
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Abstract

Abstract 8 ‐ Chloro ‐ 3 ‐ fluoro ‐ 2 ‐ methyl‐benzo[4,5]thiazolo[3,2‐ a ]pyrimidin ‐ 4 ‐ one was synthesized and employed in various palladium catalysed cross‐coupling‐reactions, including Suzuki ‐ Miyaura, Sonogashira and Buchwald ‐ Hartwig reactions, delivering 8 ‐ aryl‐, 8‐alkynyl‐ and 8‐amino ‐ 3 ‐ fluoro ‐ 2 ‐ methyl ‐ benzo[4,5]thiazolo[3,2‐ a ]pyrimidin ‐ 4 ‐ ones in good to excellent yields. The synthesized derivatives were analysed for their monoamine oxidase (MAO−A and MAO−B) inhibitory potential. Most of the compounds exhibited moderate to good inhibitory activity towards MAO−A and/or MAO−B. Docking analysis was performed to verify the experimental results. Hence, 8 ‐ substituted ‐ 3 ‐ fluoro ‐ 2 ‐ methyl ‐ benzo[4,5]thiazolo[3,2‐ a ]pyrimidin ‐ 4 ‐ ones might be potential lead compounds towards novel monoamine oxidase inhibitors.