Synthesis of dimethyl substituted benzimidazoles containing cyclopropane fused onto five to eight membered [1,2-a]alicyclic rings and influence of methyl group substituents on cytotoxicity of benzimidazolequinones

Sarah Hehir; Liz O'Donovan; Michael P. Carty; Fawaz Aldabbagh

doi:10.1016/j.tet.2008.02.093

Synthesis of dimethyl substituted benzimidazoles containing cyclopropane fused onto five to eight membered [1,2-a]alicyclic rings and influence of methyl group substituents on cytotoxicity of benzimidazolequinones

Sarah Hehir
, Liz O'Donovan
, Michael P. Carty
, Fawaz Aldabbagh

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

Abstract

Upon thermolysis 5,6-dimethyl-N-[(allyl, but-3-enyl, pent-4-enyl and hex-5-enyl-benzimidazol-2-yl)methylene]-(trans)-2,3-diphenylaziridin-1-amines (Eschenmoser hydrazones) form cyclopropane fused onto pyrrolo-, pyrido-, azepino- and azocino[1,2-a]benzimidazoles in 70, 50, 77 and 11% yield, respectively. The latter reaction also gave carbene insertion products. Dimethyl group substituents were found to significantly reduce the cytotoxicity of benzimidazolequinone towards human skin fibroblast cells.

Original language	English
Pages (from-to)	4196-4203
Number of pages	8
Journal	Tetrahedron
Volume	64
Issue number	19
Early online date	4 Mar 2008
DOIs	https://doi.org/10.1016/j.tet.2008.02.093
Publication status	Published - 5 May 2008
Externally published	Yes

Keywords

Antitumor agents
Aziridinylimines
Cycloaddition
Heterocycles

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@article{c77d1c8f3abd4e59bee8982ee710a20d,

title = "Synthesis of dimethyl substituted benzimidazoles containing cyclopropane fused onto five to eight membered [1,2-a]alicyclic rings and influence of methyl group substituents on cytotoxicity of benzimidazolequinones",

abstract = "Upon thermolysis 5,6-dimethyl-N-[(allyl, but-3-enyl, pent-4-enyl and hex-5-enyl-benzimidazol-2-yl)methylene]-(trans)-2,3-diphenylaziridin-1-amines (Eschenmoser hydrazones) form cyclopropane fused onto pyrrolo-, pyrido-, azepino- and azocino[1,2-a]benzimidazoles in 70, 50, 77 and 11\% yield, respectively. The latter reaction also gave carbene insertion products. Dimethyl group substituents were found to significantly reduce the cytotoxicity of benzimidazolequinone towards human skin fibroblast cells.",

keywords = "Antitumor agents, Aziridinylimines, Cycloaddition, Heterocycles",

author = "Sarah Hehir and Liz O'Donovan and Carty, \{Michael P.\} and Fawaz Aldabbagh",

year = "2008",

month = may,

day = "5",

doi = "10.1016/j.tet.2008.02.093",

language = "English",

volume = "64",

pages = "4196--4203",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "19",

}

Synthesis of dimethyl substituted benzimidazoles containing cyclopropane fused onto five to eight membered [1,2-a]alicyclic rings and influence of methyl group substituents on cytotoxicity of benzimidazolequinones. / Hehir, Sarah; O'Donovan, Liz; Carty, Michael P. et al.
In: Tetrahedron, Vol. 64, No. 19, 05.05.2008, p. 4196-4203.

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

TY - JOUR

T1 - Synthesis of dimethyl substituted benzimidazoles containing cyclopropane fused onto five to eight membered [1,2-a]alicyclic rings and influence of methyl group substituents on cytotoxicity of benzimidazolequinones

AU - Hehir, Sarah

AU - O'Donovan, Liz

AU - Carty, Michael P.

AU - Aldabbagh, Fawaz

PY - 2008/5/5

Y1 - 2008/5/5

N2 - Upon thermolysis 5,6-dimethyl-N-[(allyl, but-3-enyl, pent-4-enyl and hex-5-enyl-benzimidazol-2-yl)methylene]-(trans)-2,3-diphenylaziridin-1-amines (Eschenmoser hydrazones) form cyclopropane fused onto pyrrolo-, pyrido-, azepino- and azocino[1,2-a]benzimidazoles in 70, 50, 77 and 11% yield, respectively. The latter reaction also gave carbene insertion products. Dimethyl group substituents were found to significantly reduce the cytotoxicity of benzimidazolequinone towards human skin fibroblast cells.

AB - Upon thermolysis 5,6-dimethyl-N-[(allyl, but-3-enyl, pent-4-enyl and hex-5-enyl-benzimidazol-2-yl)methylene]-(trans)-2,3-diphenylaziridin-1-amines (Eschenmoser hydrazones) form cyclopropane fused onto pyrrolo-, pyrido-, azepino- and azocino[1,2-a]benzimidazoles in 70, 50, 77 and 11% yield, respectively. The latter reaction also gave carbene insertion products. Dimethyl group substituents were found to significantly reduce the cytotoxicity of benzimidazolequinone towards human skin fibroblast cells.

KW - Antitumor agents

KW - Aziridinylimines

KW - Cycloaddition

KW - Heterocycles

U2 - 10.1016/j.tet.2008.02.093

DO - 10.1016/j.tet.2008.02.093

M3 - Article

AN - SCOPUS:41549123952

SN - 0040-4020

VL - 64

SP - 4196

EP - 4203

JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -