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Synthesis of 5 H ‐indeno[1,2‐ b ]pyridine derivatives: Antiproliferative and antimetastatic activities against two human prostate cancer cell lines
Author(s) -
Charris Katiuska E.,
Rodrigues Juan R.,
Ramírez Hegira,
FernandezMoreira Esteban,
Ángel Jorge E.,
Charris Jaime E.
Publication year - 2021
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.202100092
Subject(s) - chemistry , lncap , pyridine , malononitrile , stereochemistry , ammonium acetate , cell growth , cell culture , acetic acid , cancer cell , medicinal chemistry , cancer , catalysis , biochemistry , organic chemistry , biology , genetics , high performance liquid chromatography
This study describes the direct synthesis of 2‐amino‐4‐(phenylsubstituted)‐5 H ‐indeno[1,2‐ b ]pyridine‐3‐carbonitrile derivatives 5 – 21 , through sequential multicomponent reaction of aromatic aldehydes, malononitrile, and 1‐indanone in the presence of ammonium acetate and acetic acid (catalytic). The biological study showed that compound 10 significantly impeded proliferation of the cell lines PC‐3, LNCaP, and MatLyLu. The antimetastatic effects of compound 10 could be related with inhibition of MMP9 in the PC‐3 and LNCaP human cell lines. On the basis of a study of the structure–activity relationship of these compounds, we propose that the presence of two methoxy groups at positions 6 and 7 of the indeno nucleus and a 4‐hydroxy‐3‐methoxy phenyl substitution pattern at position 4 of the pyridine ring is decisive for these types of molecules to exert very good antiproliferative and antimetastatic activities.