Synthesis of 2H-1,3-benzoxazin-4(3H)-one derivatives containing indole moiety: Their in vitro evaluation against PDE4B

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• 作者：Raja Mohan Rao ; Bethala Jawahar Luther ; Chekuri Sharmila Rani ; Namburi Suresh ; Ravikumar Kapavarapu ; Kishore V.L. Parsa ; M ; ava V. Basaveswara Rao ; Manojit Pal
• 关键词：2H-1 ; 3-Benzoxazin-4(3H)-one ; Indole ; Benzofuran ; Pd/C ; PDE4
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：15 February, 2014
• 年：2014
• 卷：24
• 期：4
• 页码：1166-1171
• 全文大小：2189 K

文摘

A number of 2H-1,3-benzoxazin-4(3H)-one derivatives containing indole or benzofuran moieties were synthesized by using Pd/C-Cu mediated coupling-cyclization strategy as a key step. The o-iodoanilides or o-iodophenol were coupled with 3-{2-(prop-2-ynyloxy)ethyl}-2H-benzo[e][1,3]oxazin-4(3H)-one using 10%Pd/C-CuI-PPh₃ as a catalyst system and Et₃N as a base to give the target compounds. All the synthesized compounds were tested for their PDE4B inhibitory potential in vitro using a cell based cAMP reporter assay. Some of them showed fold increase of the cAMP level when tested at 30 渭M. A representative compound showed encouraging PDE4B inhibitory properties that were supported by its docking results.