Synthesis of 2-Aryl-3,4-dihydroisoquinolin-2-ium Bromides and Their in Vitro Acaricidal Activity against Psoroptes cuniculi

• Ma Yan-Ni

  College of Science, Northwest A&F University

• Yang Xin-Juan

  College of Life Science, Northwest A&F University College of Science, Northwest A&F University

• Pan Le

  College of Life Science, Northwest A&F University

• Hou Zhe

  College of Science, Northwest A&F University

• Geng Hui-Ling

  College of Science, Northwest A&F University

• Song Xiao-Ping

  Department of Veterinary Medicine, Northwest A&F University

• Zhou Le

  College of Science, Northwest A&F University

• Miao Fang

  College of Life Science, Northwest A&F University

書誌事項

タイトル別名

• Synthesis of 2-Aryl-3,4-dihydroisoquinolin-2-ium Bromides and Their <i>in Vitro</i> Acaricidal Activity against <i>Psoroptes cuniculi</i>

抄録

By employing sanguinarine, a natural active quaternary isoquinoline alkaloid, as a model molecule, a series of structurally simple quaternary 2-aryl-3,4-dihydroisoquinolin-2-ium compounds were designed and synthesized and evaluated for in vitro acaricidal activity against P. cuniculi. A new approach towards the title compounds was developed with isochroman as starting material. The results showed that 22 of 24 tested compounds displayed the activity in varying degrees at 0.4 mg/mL. Fourteen compounds were significantly more effective than ivermectin, a standard acaricide, and 6-methoxy dihydrosanguinarine, a derivative of sanguinarine (p<0.05). And their comprehensive relative activity was 1.4 to 16.5 times than that of ivermectin and 1.5 to 18.8 times than that of 6-methoxy dihydrosanguinarine. The structure–activity relationship indicated that the introduction of a substituent to N-benzene ring, especially halogen atom and trifluoromethyl group, led to great improvement of the activity. The position of fluorine atom, methyl group and hydroxyl group made very significant effects on the activity. It was concluded that 2-aryl-3,4-dihydroisoquinolin-2-iums are very promising candidates for the development of new isoquinoline acaricidal agents.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 61 (2), 204-211, 2013

  公益社団法人 日本薬学会

キーワード

• acaricidal activity
• <i>Psoroptes cuniculi</i>
• 2-aryl-3,4-dihydroisoquinolin-2-ium
• 6-methoxy dihydrosanguinarine
• sanguinarine
• structure–activity relationship

詳細情報

• CRID: 1390001204176994304
• NII論文ID: 130002460112
• NII論文ID: 40019558674
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.c12-00876
• COI: 1:STN:280:DC%2BC3s7pvVSitA%3D%3D
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 024220376
• PubMed: 23221611
• Web Site: http://id.ndl.go.jp/bib/024220376
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I024220376
• Web Site: https://www.jstage.jst.go.jp/article/cpb/61/2/61_c12-00876/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2013228922
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可