Facile Synthesis and Quantitative Structure–Activity Relationship Study of Antitumor Active 2-(4-Oxo-thiazolidin-2-ylidene)-3-oxo-propionitriles

• Hanna Mona Maurice

  Pharmaceutical Chemistry Department, Faculty of Pharmacy, Cairo University

• George Riham François

  Pharmaceutical Chemistry Department, Faculty of Pharmacy, Cairo University

抄録

2-(5-Arylidene-4-oxo-3-phenyl-thiazolidin-2-ylidene)-3-oxo-propionitriles 4a–j were prepared via condensation of aromatic aldehydes with 4-thiazolidinones 3a, b. The latter was obtained via electrophilic attack of phenylisothiocyanate on 3-oxo-propionitriles 1a, b followed by reaction with chloroacetyl chloride under basic condition. Additionally, 2-(5-heteroalicyclic methylene) analogues 5a–h were prepared via Mannich reaction of the appropriate secondary amines and formaldehyde with 4-thiazolidinones 3a, b. Many of the synthesized compounds exhibited promising antitumor properties against colon HCT116 and breast T47D cell lines. 3D-Pharmacophore modeling and quantitative structure–activity relationship (QSAR) analysis were combined to explain the observed antitumor properties.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 60 (9), 1195-1206, 2012

  公益社団法人 日本薬学会

キーワード

• thiazolidinone
• quantitative structure–activity relationship
• antitumor activity
• 3-oxo-propionitrile
• HCT116
• T47D

詳細情報

• CRID: 1390282679155820288
• NII論文ID: 130001852546
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.c12-00498
• COI: 1:STN:280:DC%2BC38bmvVSmtw%3D%3D
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 023900200
• PubMed: 22976330
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I023900200
• Web Site: https://www.jstage.jst.go.jp/article/cpb/60/9/60_c12-00498/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2013357245
• 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