Synthesis of eudistomin D analogues and its effects on adenosine receptors.

Ishiyama H; Ohshita K; Abe TNakata HKobayashi J

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Synthesis of eudistomin D analogues and its effects on adenosine receptors.

机译：Synthesis of eudistomin D analogues and its effects on adenosine receptors.

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摘要

Six analogues (1-6) of eudistomin D, a beta-carboline alkaloid from a marine tunicate Eudistoma olivaceum, were synthesized, and their affinity and selectivity for adenosine receptors A(1), A(2A), and A(3) were examined. All the synthetic compounds 1-6 did not show affinity to the adenosine A(1) receptor. Delta-carboline 3 exhibited the most potent affinity to the adenosine receptor A(3) among compounds 1-6. Delta-carbolines 3 and 4 showed better affinity than the corresponding beta-carbolines 1 and 2, respectively, while N-methylation (2, 4, and 6, respectively) of the pyrrole ring in 1, 3, and 5 resulted in the reduced affinity to the adenosine A(3) receptor. On the other hand, an eudistomin D derivative, BED, exhibited modest affinity to all the receptors A(1), A(2A), and A(3) but no selectivity.

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来源
《Bioorganic and medicinal chemistry》 |2008年第7期|3825-3830|共6页
作者
Ishiyama H; Ohshita K; Abe TNakata HKobayashi J;
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作者单位

Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.;

ost.saga-med.ac.jp;

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正文语种英语
中图分类药学;生物化学;
关键词
Carbolines; Cell Line; Humans; Molecular Structure; Receptors; Purinergic P1; 咔啉类; 细胞系; 分子结构; 受体; 嘌呤能P1; 构效关系;

Synthesis of eudistomin D analogues and its effects on adenosine receptors.

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