FACILE SODIUM METABISULFITE MEDIATED SYNTHESIS OF 1,2-DISUBSTITUTED BENZIMIDAZOLES AND CYTOTOXICITY EVALUATION

A library of twenty-four, structurally diverse, 2-substituted and 1,2-disubstituted benzimidazole derivatives (4a-x) was designed and synthesized. The benzimidazole derivatives were constructed by a one-pot condensation reaction between 1,2-phenylenediamines and aromatic aldehydes under mild oxidati...

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Published inHeterocycles Vol. 98; no. 5; pp. 650 - 665
Main Authors Bui Thi Buu Hue, Hien Minh Nguyen, Mai Van Hieu, Danh La Duc Thanh, Nguyen Hoang Son, Tran Quang De, Morita, Hiroyuki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.05.2019
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Abstract A library of twenty-four, structurally diverse, 2-substituted and 1,2-disubstituted benzimidazole derivatives (4a-x) was designed and synthesized. The benzimidazole derivatives were constructed by a one-pot condensation reaction between 1,2-phenylenediamines and aromatic aldehydes under mild oxidation conditions utilizing inexpensive and non-toxic inorganic salt sodium metabisulfite. These compounds were assayed for cytotoxicities against five cancer cell lines; cervical (HeLa), breast cancer (MCF7), lung cancer (A549), stomach cancer (GSU) and Kato III cell lines in vitro. Most of the compounds had slightly inhibitory effects against all or limited tested cell lines. Among them, compound 4q showed moderate cytotoxicity against HeLa, MCF-7, A549, and Kato III cell lines with IC50 values of 28.4 mu M, 28.3 mu M, 30.7 mu M, and 28.5 mu M, respectively. The structure-activity relationship analysis suggested that the substructure combination of benzimidazole and naphthalene bearing the free hydroxy group at C-1 and the three methoxy groups at the C-6, C-7, and C-8 of the naphthalene ring may exhibit a synergistic effect and an improved anticancer activity.
AbstractList A library of twenty-four, structurally diverse, 2-substituted and 1,2-disubstituted benzimidazole derivatives (4a-x) was designed and synthesized. The benzimidazole derivatives were constructed by a one-pot condensation reaction between 1,2-phenylenediamines and aromatic aldehydes under mild oxidation conditions utilizing inexpensive and non-toxic inorganic salt sodium metabisulfite. These compounds were assayed for cytotoxicities against five cancer cell lines; cervical (HeLa), breast cancer (MCF7), lung cancer (A549), stomach cancer (GSU) and Kato III cell lines in vitro. Most of the compounds had slightly inhibitory effects against all or limited tested cell lines. Among them, compound 4q showed moderate cytotoxicity against HeLa, MCF-7, A549, and Kato III cell lines with IC50 values of 28.4 mu M, 28.3 mu M, 30.7 mu M, and 28.5 mu M, respectively. The structure-activity relationship analysis suggested that the substructure combination of benzimidazole and naphthalene bearing the free hydroxy group at C-1 and the three methoxy groups at the C-6, C-7, and C-8 of the naphthalene ring may exhibit a synergistic effect and an improved anticancer activity.
Author Danh La Duc Thanh
Mai Van Hieu
Nguyen Hoang Son
Tran Quang De
Morita, Hiroyuki
Bui Thi Buu Hue
Hien Minh Nguyen
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  surname: Hien Minh Nguyen
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  organization: Univ Toyama, Inst Nat Med, Sugitani, Toyama 9300194, Japan
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Keywords IN-VITRO
SIRTUIN INHIBITORS
MICROWAVE-ASSISTED SYNTHESIS
MOLECULAR DOCKING
DERIVATIVES
ELECTROLUMINESCENCE
HYBRIDS
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  doi: 10.1016/j.jscs.2016.08.001
  contributor:
    fullname: Alaqeel, SI
– volume: 9
  start-page: 308
  year: 2017
  ident: 000482504500003.3
  article-title: Synthesis and antioxidant activity of 2-substituted-5-nitrobenzimidazole derivatives
  publication-title: Int J Pharm Pharm Sci.
  contributor:
    fullname: Archie, SR
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Snippet A library of twenty-four, structurally diverse, 2-substituted and 1,2-disubstituted benzimidazole derivatives (4a-x) was designed and synthesized. The...
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SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title FACILE SODIUM METABISULFITE MEDIATED SYNTHESIS OF 1,2-DISUBSTITUTED BENZIMIDAZOLES AND CYTOTOXICITY EVALUATION
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