A facile synthesis of 2-acyl and 2-alkylaminobenzimidazoles for 5-lipoxygenase inhibitors

An Ha Lee, Mi Hyun An, Eun Hyun Choi, Hea Young Park Choo, Gyoonhee Han

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

2-Acylaminobenzimidazoles (2a-r) have been synthesized from o-phenylenediamines (4) with benzoylcarbonimidodithioic acid dimethyl ester (5a) or isobutyrylcarbonimidodithioic acid dimethyl ester (5b) in good yield. 2-Alkylaminobenzimidazoles could be prepared by the reaction of o-Phenylenediamines (4a, b) with benzyl isothiocyanate in moderate yields 8a, b or the reaction of 2-chlorobenzimidazole (9) with benzylamines (10a, b) in moderate yield 11a, b. Finally, the carbamate derivative of 2-aminobenzimidazole (13) was prepared by the reaction with pseudourea (12) in low yield. Most of the prepared analogues were evaluated in leukotriene inhibition assay and it found that benzamide derivatives (2a-i) are quite active among others.

Original languageEnglish
Pages (from-to)571-580
Number of pages10
JournalHeterocycles
Volume70
Publication statusPublished - 2006 Dec 31

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Lipoxygenase Inhibitors
pseudourea
Benzylamines
Esters
Derivatives
Acids
Carbamates
Leukotrienes
Assays
1,2-diaminobenzene
benzyl isothiocyanate
benzamide
2-aminobenzimidazole

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Lee, A. H., An, M. H., Choi, E. H., Choo, H. Y. P., & Han, G. (2006). A facile synthesis of 2-acyl and 2-alkylaminobenzimidazoles for 5-lipoxygenase inhibitors. Heterocycles, 70, 571-580.
Lee, An Ha ; An, Mi Hyun ; Choi, Eun Hyun ; Choo, Hea Young Park ; Han, Gyoonhee. / A facile synthesis of 2-acyl and 2-alkylaminobenzimidazoles for 5-lipoxygenase inhibitors. In: Heterocycles. 2006 ; Vol. 70. pp. 571-580.
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A facile synthesis of 2-acyl and 2-alkylaminobenzimidazoles for 5-lipoxygenase inhibitors. / Lee, An Ha; An, Mi Hyun; Choi, Eun Hyun; Choo, Hea Young Park; Han, Gyoonhee.

In: Heterocycles, Vol. 70, 31.12.2006, p. 571-580.

Research output: Contribution to journalArticle

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T1 - A facile synthesis of 2-acyl and 2-alkylaminobenzimidazoles for 5-lipoxygenase inhibitors

AU - Lee, An Ha

AU - An, Mi Hyun

AU - Choi, Eun Hyun

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AU - Han, Gyoonhee

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N2 - 2-Acylaminobenzimidazoles (2a-r) have been synthesized from o-phenylenediamines (4) with benzoylcarbonimidodithioic acid dimethyl ester (5a) or isobutyrylcarbonimidodithioic acid dimethyl ester (5b) in good yield. 2-Alkylaminobenzimidazoles could be prepared by the reaction of o-Phenylenediamines (4a, b) with benzyl isothiocyanate in moderate yields 8a, b or the reaction of 2-chlorobenzimidazole (9) with benzylamines (10a, b) in moderate yield 11a, b. Finally, the carbamate derivative of 2-aminobenzimidazole (13) was prepared by the reaction with pseudourea (12) in low yield. Most of the prepared analogues were evaluated in leukotriene inhibition assay and it found that benzamide derivatives (2a-i) are quite active among others.

AB - 2-Acylaminobenzimidazoles (2a-r) have been synthesized from o-phenylenediamines (4) with benzoylcarbonimidodithioic acid dimethyl ester (5a) or isobutyrylcarbonimidodithioic acid dimethyl ester (5b) in good yield. 2-Alkylaminobenzimidazoles could be prepared by the reaction of o-Phenylenediamines (4a, b) with benzyl isothiocyanate in moderate yields 8a, b or the reaction of 2-chlorobenzimidazole (9) with benzylamines (10a, b) in moderate yield 11a, b. Finally, the carbamate derivative of 2-aminobenzimidazole (13) was prepared by the reaction with pseudourea (12) in low yield. Most of the prepared analogues were evaluated in leukotriene inhibition assay and it found that benzamide derivatives (2a-i) are quite active among others.

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