Experimental and QSAR Studies on Antimicrobial Activity of Benzimidazole Derivatives

• Puratchikody Ayarivan

  Department of Pharmaceutical Engineering and Technology, Anna University

• Nagalakshmi Govindasamy

  Department of Pharmaceutical Chemistry, Erode College of Pharmacy

• Doble Mukesh

  Department of Biotechnology, Indian Institute of Technology Madras

抄録

Twenty eight analogues of benzimidazoles had been synthesized and tested for their antimicrobial activity against four bacteria (Staphylococcus auerus, Escherichia coli, Bacillus pumilus and Proteus vulgaris) and two fungi (Aspergillus flavus and Aspergilus niger). Compounds with R as C₆H₄NO₂ and R′ as SO₂C₆H₄–CH₃(p), with R as C₆H₄OCH₃ and R′ as SO₂C₆H₄–CH₃(p), and with R as CH₂C₆H₅ and R′ as CH₂(CH₂)₉Cl exhibited comparable or higher antibacterial activity than Ciprofloxacin against S. auerus and E. coli and, higher activity than Nystatin against A. flavus. Several other compounds showed better activity than the standard antibiotic for E. coli. Compounds with R as CCl₃ and R′ as SO₂C₆H₄–CH₃(p) or COC₆H₅ exhibited the lowest activity against all the organisms. Addition of methylene groups in the R′ position increased activity. Many of the compounds showed better activity than Ciprofloxacin for one or more organisms. Compound with R as CH₂OC₆H₅ and R′ as CH₂(CH₂)₉Cl exhibited higher activity against both the fungii than the control Nystatin. Quantitative structure activity relationships (QSARs) developed were good for all the organisms (R²=0.65 to 0.88; R_adj² = 0.63 to 0.86) and the predictive capability of the developed models was also reasonable (q²=0.52 to 0.83). The models had two to three independent variables. The data for the models which had three independent variables were divided into training and test/validation sets. The former set was used to develop the QSAR and these developed models were used to predict the activity of the test set data. In all the three cases the predictive capability of the models was good. The molecular descriptors identified were predominantly log P, electronic parameters, molecular size, shape and area. A positive correlation existed between the antibacterial activity and the first principal component.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 56 (3), 273-281, 2008

  公益社団法人 日本薬学会

キーワード

• benzimidazole
• quantitative structure activity relationship
• anti-infective activity
• electronic descriptor
• Log P
• Genetic function algorithm

詳細情報

• CRID: 1390282679145735680
• NII論文ID: 110006622628
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.56.273
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 9394390
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I9394390
• Web Site: https://www.jstage.jst.go.jp/article/cpb/56/3/56_3_273/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2008187936
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可