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

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

National University of Ireland

Research output: Contribution to journal › Article › peer-review

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
DOIs	https://doi.org/10.1039/C003511D
Publication status	Published - 10 May 2010
Externally published	Yes

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

day = "10",

doi = "10.1039/C003511D",

language = "English",

volume = "8",

pages = "3149--3156",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

}

One-pot double intramolecular homolytic aromatic substitution routes to dialicyclic ring fused imidazobenzimidazolequinones and preliminary analysis of anti-cancer activity. / Fagan, Vincent; Bonham, Sarah; Carty, Michael P. et al.
In: Organic and Biomolecular Chemistry, Vol. 8, 10.05.2010, p. 3149-3156.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

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

AU - Fagan, Vincent

AU - Bonham, Sarah

AU - Carty, Michael P.

AU - Aldabbagh, Fawaz

PY - 2010/5/10

Y1 - 2010/5/10

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).

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

ER -

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

Abstract

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