Abstract
Both tetrahydroisoquinolines (THIQs) and oxindoles (OXs) display a broad range of biological activities including anti-cancer activity, and are therefore recognized as two privileged scaffolds in drug discovery. In the present study, 24 3′,4′-dihydro-2′H-spiro[indoline-3,1′-isoquinolin]-2-ones, designed as molecular hybrids of THIQ and OX, were synthesized and screened in vitro against 59 cell lines in the NCI-60 screen. Twenty compounds displayed weak to moderate inhibition of cell proliferation; among them, three compounds displayed at least 50% inhibition of cell proliferation. The compounds appeared to target primarily renal cell cancer lines; however, leukaemia, melanoma, non-small cell lung cancer, prostate, ovarian and even breast cancer cell lines were also affected. Therefore, this class of spirooxindoles may provide useful leads in the search for new anti-cancer agents.
Highlights
The term cancer refers to a group of more than 100 diseases characterized by a common feature of rapid and uncontrolled cell proliferation, invasiveness and metastasis, leading to death
In view of the antiproliferative activity of both THIQs and OXs, we proposed that this particular class of spirofused molecular hybrids of THIQ and OX would display anti-proliferative activity
The target compounds were synthesized by the Pictet–Spengler reaction of a substituted phenethylamine with isatin or a substituted isatin
Summary
The term cancer refers to a group of more than 100 diseases characterized by a common feature of rapid and uncontrolled cell proliferation, invasiveness and metastasis, leading to death. Spirooxindoles, 30,40-dihydro-20H-spiro[indoline-3,10-isoquinoline]-2-ones, that are obtained from the Pictet–Spengler type reaction between phenethylamines, another class of naturally occurring compounds, with isatin have received scant attention. The present study focuses on the synthesis of 30,40-dihydro-20H-spiro[indoline-3,10-isoquinolin]-2ones as molecular hybrids of THIQ and OX, and the evaluation of their anti-proliferative activity (figure 2).
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