Development of microwave-assisted thermal electrocyclic reaction of an 67π-azahexatriene system and the applied to synthesis of bioactivity natural products
| Project/Area Number |
15590033
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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 | Fukuyama University |
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Principal Investigator |
CHOSHI Tominari Fukuyama University, Faculty of Pharmacy & Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (10248297)
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| Co-Investigator(Kenkyū-buntansha) |
HIBINO Satoshi Fukuyama University, Faculty of Pharmacy & Pharmaceutical Sciences, Professor, 薬学部, 教授 (60112885)
NOBUHIRO Junko Fukuyama University, Faculty of Pharmacy & Pharmaceutical Sciences, Assistant, 薬学部, 助手 (70352002)
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| Project Period (FY) |
2003 – 2005
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| Project Status |
Completed (Fiscal Year 2005)
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| Budget Amount *help |
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 2005: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2004: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2003: ¥1,100,000 (Direct Cost: ¥1,100,000)
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| Keywords | microwave / electrocyclic reaction / 1-azahexatriene / isoquinoline / TMC-120A, B, and C / bicolorine / trospheridine / scorpinone / benzo[c]isoquinoline / azaanthraquinone / nitroisoquinoline / methoxyisoquinoline / TMC-120A, B, and C / furo[3,2-h]isoquinoline / interleukin-5 |
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| Research Abstract |
Features of the microwave-assisted organic reaction are that the reproducibility is high in order to uniformly heat in reaction system. In the pericyclic reaction, its application to Diels-Alder reaction and Claisen rearrangement reaction was examined. However, that application to the electrocyclic reaction was not yet reported.
We have examined the efficient synthesis of biological activity heterocyclic compounds through a construction of isoquinoline based on a microwave-assisted thermal electrocyclic reaction of an 6π-electrocn system.
(1)Effect of microwave to thermal electrocyclic reaction of azahexatriene system
(2)Synthesis of the new furo[3,2-h]isoquinoline alkaloid, TMC-120A, B, and C possessing inhibitory activity against the interleukin-5.
(3)Synthetic study of phenanthridine alkaloid, trispheridine
(4)Synthetic study of azaanthraquinone alkaloid, scorpinone
We established the new synthetic method of isoquinolines based on a microwave-assisted thermal electrocyclic reaction. This method was applied, and the total. synthesis of the furo[3,2-h]isoquinoline alkaloid, TMC-120A,B,C, phenanthridine alkaloid, trispheridine, and azaanthraquinone alkaloid, scorpinone were achieved.
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Report
(4 results)
Research Products
(9 results)
