芳香族N-メチルアミドのcis型優先性の発見およびその分子構築への応用

• 東屋 功

  北里大学薬学部

書誌事項

タイトル別名

• Discovery of cis-Preference of Aromatic N-Methylamides and Its Application to Molecular Constructions
• ホウコウゾク N メチルアミド ノ cisガタ ユウセンセイ ノ ハッケン オヨビ ソノ ブンシ コウチク エ ノ オウヨウ

抄録

Aromatic secondary amides such as benzanilide (1) exist in a trans-amide form both in the crystal and in the solution, whereas N-methylbenzanilide (2) exists in cis form in the crystal, and predominantly in a cis form in the solution. Similar cis conformational preferences were observed in aromatic N,N'-dimethylated ureas and guanidines, in which two aromatic rings are located face to face. The cis preferences of N-methylated amides, ureas and guanidines could be utilized to construct interesting aromatic architecture. N,N',N''-Trimethyl-N,N',N''-triphenyl-1,3,5-benzenetricarboxamide (20) and a cyclic triamide (24) have crystal structures in which three N-phenyl groups direct to the same orientation (syn conformation). 1,2-Bis(N-benzoyl-N-methylamino)benzene (22), which have no fixed asymmetric center, afforded chiral crystals by simple recrystallization. Furthermore, aromatic multi-layered structures could be built and applied to obtain aromatic molecules which have potent DNA-binding ability.

収録刊行物

• 薬学雑誌

  薬学雑誌 121 (2), 117-129, 2001-02-01

  公益社団法人 日本薬学会

キーワード

• amide
• urea
• guanidine
• cis conformation
• syn conformation
• aromatic architecture

詳細情報

• CRID: 1390001206128746368
• NII論文ID: 110003661147
• NII書誌ID: AN00284903
• DOI: 10.1248/yakushi.121.117
• COI: 1:CAS:528:DC%2BD3MXnsFeruw%3D%3D
• ISSN: 13475231
• ISSN: 00316903
• NDL書誌ID: 5650724
• PubMed: 11218725
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I5650724
• Web Site: https://www.jstage.jst.go.jp/article/yakushi/121/2/121_2_117/_pdf
• 本文言語コード: ja
• 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