POTENT ANTICONFLICT ACTIVITY AND LESSENING OF MEMORY IMPAIRMENT WITH A SERIES OF NOVEL [1]BENZOTHIENO[2,3-C]PYRIDINES AND 1,2,3,4-TETRAHYDRO[1]BENZOTHIENO[2,3-C]PYRIDINES

被引：13

作者：

KAWAKUBO, H ^{[1
]}

OKAZAKI, K ^{[1
]}

NAGATANI, T ^{[1
]}

TAKAO, K ^{[1
]}

HASIMOTO, S ^{[1
]}

SUGIHARA, T ^{[1
]}

机构：

[1] ASAHI CHEM IND CO LTD, INST LIFE SCI,DEPT MED CHEM,BIOSCI LAB, PHARMACOL SECT, NOBEOKA, MIYAZAKI 882, JAPAN

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1990年 / 33卷 / 11期

关键词：

D O I：

10.1021/jm00173a031

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

[1]Benzothieno[2,3-c]pyridines (10a-c, 11,12a-t, and 13a,b) and l,2,3,4-tetrahydro[1]benzothieno[2,3-c]pyridines (3a-c, 7, 8a-c, and 9) were synthesized. The compounds are bioisosteres of β-carbolines and 1,2,3,4-tetrahydro-β-carbolines where the indole nitrogen is replaced by sulfur. Their pharmacological activity was evaluated in a water lick conflict test in rats and a passive avoidance test in mice. In the l,2,3,4-tetrahydro[l]benzothieno[2,3-c]pyridine series, the presence of ethyl ester (3b) or cyclohexyl carboxamide (7) groups at C-3 conferred good anticonflict activity and lessening of memory impairment, while N-acylation of 3b abolished activity. In the [1]benzothieno[2,3-c]pyridine series, the aminoethyl carboxamide (12a) group at C-3 also conferred activity, but other amides studied were not active. The most potent compounds (3b, 7, and 12a) were also administered orally and had potent anticonflict and antiscopolamine amnesia-reversal activity. These compounds did not bind to the BZP receptor in spite of having structures similar to those of β-carbolines. Compound 7 bound strongly to 5-HT1Areceptors and would be expected to be a novel anxiolytic. © 1990, American Chemical Society. All rights reserved.

引用

页码：3110 / 3116

页数：7

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