| Project/Area Number |
16590011
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Tokushima Bunri University |
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Principal Investigator |
AZUMAYA Isao Tokushima Bunri University, Faculty of Pharmaceutical Sciences at Kagawa Campus, Professor, 香川薬学部, 教授 (50276755)
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| Project Period (FY) |
2004 – 2005
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| Project Status |
Completed (Fiscal Year 2005)
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| Budget Amount *help |
¥2,300,000 (Direct Cost: ¥2,300,000)
Fiscal Year 2005: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 2004: ¥1,100,000 (Direct Cost: ¥1,100,000)
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| Keywords | Chiral transformation / Sulfonamide / Spontaneous resolution / X-ray crystallographic analysis / Crystal structure / Stereochemistry |
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| Research Abstract |
1)A chiral crystal of benzenesulfonanilide was used as an asymmetric ligand in addition reaction of ethyl group to Chalcone under the condition of diethylzinc and copper triflate. Any enantio excess of products, however, was not observed.
2)Other sulfonamides which show spontaneous resolution were explored. Substituted benzenesulfonyl chloride and substituted aniline with ether group etc. at the o-position of the benzene ring for metal coordination or to be slower in racemization were synthesized. In the result, it was found that 5 of 40 sulfoanilides showed spontaneous resolution.
3)The protocol in which compounds that show spontaneous resolution are searched effectively in shorter time was modified in combination with parallel synthesis using polymer-supported base, evaporation of filtrate to dryness with stirring, and solid state CD spectrum measurement. According to the procedure, it was found that 4 sulfonamides out of 12 combinations of sulfonyl chlorides and anilines, judging by the Cotton effect.
4)Crystallization was carried out under an irradiation of circular polarized light, but chiral induction was not observed in an enantiomer ratio of the sulfonamides which showed spontaneous resolution.
5)On the course of the investigation into the spontaneous resolution of aromatic sulfonamides, all the aromatic sulfonamides were found to exist in synclinal form in the crystal, some of which formed in intermolecular double hydrogen bonds.
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