One-pot double intramolecular homolytic aromatic substitution routes to dialicyclic ring fused imidazobenzimidazolequinones and preliminary analysis of anticancer activity

Vincent Fagan; Sarah Bonham; Michael P. Carty; Fawaz Aldabbagh

doi:10.1039/c003511d

One-pot double intramolecular homolytic aromatic substitution routes to dialicyclic ring fused imidazobenzimidazolequinones and preliminary analysis of anticancer activity

Vincent Fagan
, Sarah Bonham
, Michael P. Carty
, Fawaz Aldabbagh

Molecular Biosciences

University of Galway

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

26 Citations (Scopus)

Abstract

Bu₃SnH/1,1′-azobis(cyclohexanecarbonitrile) (ACN)-mediated five, six, and seven-membered double alkyl radical cyclizations onto imidazo[5,4-f]benzimidazole and imidazo[4,5-f]benzimidazole are described. The quinone derivatives evaluated show selective toxicity towards human cervical (HeLa) and prostate (DU145) cancer cell lines (with negligible toxicity towards a normal human cell line, GM00637). Only the Fremy oxidation of the 6-aminoimidazo[5,4-f]benzimidazole gave iminoquinone, which showed high specificity towards the prostate cancer cell line (DU145).

Original language	English
Pages (from-to)	3149-3156
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	8
Issue number	14
DOIs	https://doi.org/10.1039/c003511d
Publication status	Published - 21 Jul 2010

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Authors (Note for portal: view the doc link for the full list of authors)

Authors
Fagan, V,Bonham, S,Carty, MP,Aldabbagh, F

Access to Document

10.1039/c003511d

Cite this

@article{8e5dfc4a8bfd43139bf6f52842b23bf7,

title = "One-pot double intramolecular homolytic aromatic substitution routes to dialicyclic ring fused imidazobenzimidazolequinones and preliminary analysis of anticancer activity",

abstract = "Bu3SnH/1,1′-azobis(cyclohexanecarbonitrile) (ACN)-mediated five, six, and seven-membered double alkyl radical cyclizations onto imidazo[5,4-f]benzimidazole and imidazo[4,5-f]benzimidazole are described. The quinone derivatives evaluated show selective toxicity towards human cervical (HeLa) and prostate (DU145) cancer cell lines (with negligible toxicity towards a normal human cell line, GM00637). Only the Fremy oxidation of the 6-aminoimidazo[5,4-f]benzimidazole gave iminoquinone, which showed high specificity towards the prostate cancer cell line (DU145).",

author = "Vincent Fagan and Sarah Bonham and Carty, \{Michael P.\} and Fawaz Aldabbagh",

year = "2010",

month = jul,

day = "21",

doi = "10.1039/c003511d",

language = "English",

volume = "8",

pages = "3149--3156",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "14",

}

One-pot double intramolecular homolytic aromatic substitution routes to dialicyclic ring fused imidazobenzimidazolequinones and preliminary analysis of anticancer activity. / Fagan, Vincent; Bonham, Sarah; Carty, Michael P. et al.
In: Organic and Biomolecular Chemistry, Vol. 8, No. 14, 21.07.2010, p. 3149-3156.

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

TY - JOUR

T1 - One-pot double intramolecular homolytic aromatic substitution routes to dialicyclic ring fused imidazobenzimidazolequinones and preliminary analysis of anticancer activity

AU - Fagan, Vincent

AU - Bonham, Sarah

AU - Carty, Michael P.

AU - Aldabbagh, Fawaz

PY - 2010/7/21

Y1 - 2010/7/21

N2 - Bu3SnH/1,1′-azobis(cyclohexanecarbonitrile) (ACN)-mediated five, six, and seven-membered double alkyl radical cyclizations onto imidazo[5,4-f]benzimidazole and imidazo[4,5-f]benzimidazole are described. The quinone derivatives evaluated show selective toxicity towards human cervical (HeLa) and prostate (DU145) cancer cell lines (with negligible toxicity towards a normal human cell line, GM00637). Only the Fremy oxidation of the 6-aminoimidazo[5,4-f]benzimidazole gave iminoquinone, which showed high specificity towards the prostate cancer cell line (DU145).

AB - Bu3SnH/1,1′-azobis(cyclohexanecarbonitrile) (ACN)-mediated five, six, and seven-membered double alkyl radical cyclizations onto imidazo[5,4-f]benzimidazole and imidazo[4,5-f]benzimidazole are described. The quinone derivatives evaluated show selective toxicity towards human cervical (HeLa) and prostate (DU145) cancer cell lines (with negligible toxicity towards a normal human cell line, GM00637). Only the Fremy oxidation of the 6-aminoimidazo[5,4-f]benzimidazole gave iminoquinone, which showed high specificity towards the prostate cancer cell line (DU145).

UR - https://www.scopus.com/pages/publications/77954606737

U2 - 10.1039/c003511d

DO - 10.1039/c003511d

M3 - Article

SN - 1477-0520

VL - 8

SP - 3149

EP - 3156

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 14

ER -

One-pot double intramolecular homolytic aromatic substitution routes to dialicyclic ring fused imidazobenzimidazolequinones and preliminary analysis of anticancer activity

Abstract

UN SDGs

Authors (Note for portal: view the doc link for the full list of authors)

Access to Document

Other files and links

Fingerprint

Cite this