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KMID : 0370220080520010020
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Yakhak Hoeji
2008 Volume.52 No. 1 p.20 ~ p.26
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Synthesis of 6-amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan
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Kim Min-Kyeom
Ma Eun-Sook
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Abstract
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2-Aminothiazole ring as a bioisoster of catechol in dopamine has provided with good oral availability and lipophilic property. Selenium was reported to have an improved antioxidant ability and to reduce the loss of dopamine. 2-Aminoindan, is a rigid form of dopamine, was evaluated as a dopamine agonist with low neurotoxocity. In order to develop a novel dopamine agonist, we tried to synthesize the selenazoloaminoindan derivative that is a hybrid structure of aminoindan and aminoselenazole instead of aminothiazole. 2-Indanone-2-oxime was reduced with TiCl₄and NaBH₄to form 2-aminoindan, which was reacted with propionyl chloride to give 2-N-n-propionylaminoindan (2). Compound 2 was reduced with TiCl₄and NaBH₄ to afford 2-N-n-propylaminoindan (3) and it was nitrated and reduced to form 5-amino-2-N-n-propylaminoindan (5), which was reacted with KSeCN, Br₂, and glacial acetic acid to give 4,6-dibromo-5- amino-2-N-n-propylaminoindan (7) instead of selenazole ring formation. Otherwise, compound 2 was nitrated and hydrogenated to form 5-amino-2-N-n-propionylaminoindan (9), which was treated with KSeCN, , and glacial acetic acid to give 4,6-dibromo-5-amino-2-N-n-propionylaminoindan (10). Compound 9 was cyc1ized with KSeCN and glacial acetic acid in the absence of Br₂to give 6-amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan (11).
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KEYWORD
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Parkinson’s disease, Selenazoloaminoindan, Dopamine D, Agonist
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