YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Synthesis of 6-amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan

6-Amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan의 합성

  • Kim, Min-Kyeom (College of Pharmacy, Catholic University of Daegu) ;
  • Ma, Eun-Sook (College of Pharmacy, Catholic University of Daegu)
  • 김민겸 (대구가톨릭대학교 약학대학) ;
  • 마은숙 (대구가톨릭대학교 약학대학)
  • Published : 2008.02.29
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Abstract

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 $TiCl_4$ and $NaBH_4$ to form 2-aminoindan, which was reacted with propionyl chloride to give 2-N-n-propionylaminoindan (2). Compound 2 was reduced with $TiCl_4$ and $NaBH_4$ 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, $Br_2$, 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, $Br_2$, 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 $Br_2$ to give 6-amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan (11).

Keywords

References

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