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MOLECULAR BUILDING USING N-METHYLBENZANILIDES AS A MOLECULAR SPRINT

Research Project

Project/Area Number 08672409
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionCHIBA UNIVERSITY

Principal Investigator

YAMAGUCHI Kentaro  CHEMICAL ANALYSIS CENTER,CHIBA UNIVERSITY,ASSOCIATE PROFESSOR, 分析センター, 助教授 (50159208)

Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1997: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1996: ¥1,200,000 (Direct Cost: ¥1,200,000)
KeywordsN-methylbenzanilide / X-ray crystallography / molecular building / molecular sprint / N-メチルベンズアミド / Nメチルベンズアミド / ベンツアニリド / ウレア / 分子副木 / 結晶構造
Research Abstract

The amide moiety has conformational and electronic characteristics which often determine the physicochemical or biological properties of a molecule, and it plays role in a variety of molecular recognition events. Most compounds having a secondary amide bond, which has a proton on the nitrogen atom, exist trans (Z) form. We found in the course of investigations on various biologically active substances that N-methylation of aromatic secondary amides or ureas causes a dramatic loss of the biological activity due to conformational change of the amide or urea structre. The importance of trans/cis stereochemistry is clear, for example in the biochemistry of immunosuppressants.
Conformation of benzanilide, N-methylbenzanilide and those with a methyl group (s) ortho to the amide bond in solution and in the crystal have been studied. N-Methylbenzanilide exists in cis-amide (E) form in the crystal. In CDCl_3 solution, cis-amide form is also predominant (99%), whele benzanilide exists in trans-am … More ide (Z) form in the crystal and in solution. In the crystal, all the methyl-substituted benzanilides exists in trans-amide conformation and the introduction of an ortho-methyl group (s) makes the interplanar angle of the aromatic rings and the amide group (Ar-amide) larger. N-Methylbenzanilides exist in cis form in the crystal except the compound (26) which has four methyl groups ortho to the amide bond. For the N-methylbenzanilides, the effects of introduction of one or two ortho-methyl group on the dihedral angles of Ar-amide are smaller than that of the secondary benzanilides. In solution, benzanilides exist exclusively in trans conformation except for the compound (12) which has a minor cis conformer (3%) in CDDl_3, whereas N-methylbenzanilides exist in equilibrium between the major cis-form and the minortrans-from. The tetramethyl derivative exists in trans conformation in solution as observed in the crystal. For, N-metylbenzanilides, an introduction of a methyl group (s) ortho to the amide bond seems to destabilize the cis-amide conformation in solution, resulting in an increased ratio of the trans-amide conformation. Less

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (15 results)

All Other

All Publications (15 results)

  • [Publications] K.Yamaguchi: "Disodium Fluoresein Octahydral" Acta Crystallogr. C53. 284-285 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.Yamaguchi: "Molecular Structure of the Zwitterionic Form of Phenolsulfonphthalein" Analytical Science. 13. 521-522 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] T.Ohwada: "On the Planarity of Amides Nitrogen.Pyramidal Nitrogen Atoms of Amides and Intrinsin to 7-Azabicyclo[2,2,1]heptanes" Tetrahedron Lett.39. 865-868 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] A.Tanatani: "Hellical Arowatic Vrea and Guanidine" Tetrahedron Lett.4425-4428 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] T.Ohwada, T.Achiwa, I.Okamoto, K.Shudo, K.Yamaguchi: "On the Planarity of Amides Nitrogne. Pyramidal Nitrogen Atoms of Amide and Intrinsic to 7-Azabicyclo-[2.2.1] heptanes." Tetrahedron Lett.39. 865-868 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.Yamaguchi, Z.Tamura, M.Maeda: "Disodium Fluoresein Octahedral" Acta Crystallogr.C53. 284-285 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.Yamaguchi, Z.Tamura, M.Maeda: "Molecular Structure of the Zwitterionic Form of Phenolsulfonphthalein" Analytical Science. 13. 521-522 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] A.Tanatani, H.Kagechika, I.Azumaya, R.Fukutomi K.Yamaguchi.K.Shudo: "Helical Aromatic Urea and Guanidine" Tetrahedron Lett.38. 4425-4428 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.Yamayuchi: "Disodium Fluoresein Octahydral." Acta Crystallogr.C53. 284-285 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] K.Yamaguchi: "Molecular Sturucture of the Zwitterionic Form of Pherolsulforphthalein" Analytical Science. 13. 521-522 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] T.Ohwada: "On the Planarity of Amides Nitrogen.Pyramidal Nitrogen Atoms of Amides and Intrinsic to 7-Azabicyclo[2.2.1]heptanes" Tetrahedron Lett. 39. 865-868 (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] A.Tanatari: "Helical Aromatic Urea and Guuhidine" Tetrahedron Lett. 4425-4428 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] K.Yamaguchi 他: "Facile Formation of Aromatic Cyclic-Methylamides Based on cis Conformation Preference." Tetrahedron Letters. 37. 5003-5006 (1976)

    • Related Report
      1996 Annual Research Report
  • [Publications] K.Yamaguchi 他: "Sterical Properties of N,N'-Dimethylurea Moiety Enhance Formation of Triple Hydrogen-Bond Complex." Chem.Pharm.Bull.44. 460-462 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] K.Yamaguchi 他: "Helical Aromatic Urea and Guanidine." 発表予定.

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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