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Discovery of a Potent Anti-tumor Agent through Regioselective Mono-N-acylation of 7H-Pyrrolo[3,2-f]quinazoline-1,3-diamine.

ABSTRACT: 7H-Pyrrolo[3,2-f]quinazoline-1,3-diamine (1) is a privileged chemical scaffold with significant biological activities. However, the currently accessible chemical space derived from 1 is rather limited. Here we expanded the chemical space related to 1 by developing efficient methods for regioselective monoacylation at N1 , N3 and N7 , respectively. With this novel methodology, a focused library of mono-N-acylated pyrroloquinazoline-1,3-diamines were prepared and screened for anti-breast cancer activity. The structure-activity relationship (SAR) results showed that N3 -acylated compounds were in general more potent than N1 -acylated compounds while N7 -acylation significantly reduced their solubility. Among the compounds evaluated, 7f possessed 8-fold more potent activity than 1 in MDA-MB-468 cells. More importantly, 7f was not toxic to normal human cells. These results suggest that 7f is a novel compound as a potential anti-breast cancer agent without harming normal cells.

SUBMITTER: Chen J 

PROVIDER: S-EPMC3806641 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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Discovery of a Potent Anti-tumor Agent through Regioselective Mono-<i>N</i>-acylation of 7<i>H</i>-Pyrrolo[3,2-<i>f</i>]quinazoline-1,3-diamine.

Chen Jingjin J   Kassenbrock Alina A   Li Bingbing X BX   Xiao Xiangshu X  

MedChemComm 20130901 9

7<i>H</i>-Pyrrolo[3,2-<i>f</i>]quinazoline-1,3-diamine (<b>1</b>) is a privileged chemical scaffold with significant biological activities. However, the currently accessible chemical space derived from <b>1</b> is rather limited. Here we expanded the chemical space related to <b>1</b> by developing efficient methods for regioselective monoacylation at <i>N<sup>1</sup></i> , <i>N<sup>3</sup></i> and <i>N<sup>7</sup></i> , respectively. With this novel methodology, a focused library of mono-<i>N</  ...[more]

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