Synthesis of bridged analogues of the antidepressant drug tianeptine. Representatives of a new ring system

被引：2

作者：

Berecz, Gabor ^{[1
]}

Dancso, Andras ^{[1
]}

Lauritz, Maria Tothne ^{[1
]}

Simig, Gyula ^{[1
]}

Volk, Balazs ^{[1
]}

机构：

[1] Egis Pharmaceuticals Plc, Directorate Drug Subst Dev, POB 100, H-1475 Budapest, Hungary

来源：

TETRAHEDRON | 2023年 / 134卷

关键词：

Sulfonamides; N-alkylation; Friedel-Crafts cyclization; IntramolecularN-alkylation; New ring system; Single-crystal X-ray diffraction; Halogen exchange reaction;

D O I：

10.1016/j.tet.2023.133300

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In continuation of our efforts to synthesize new analogues of antidepressant drug tianeptine, we have incorporated a two-carbon bridge between the two nitrogen atoms of the 11-amino-dibenzo[c,f][1,2] thiazepine core structure of the tricyclic parent compound, resulting in a new tetracyclic ring system closely related to tianeptine. The synthetic route leading to the tetracyclic ring system is suitable for the introduction of various substituents to the amine-type nitrogen. The pharmacophore moiety charac-teristic of tianeptine has been introduced into the new tetracyclic molecule with two different methods. Altogether 32 new compounds are described in the present manuscript, 3 of them are also characterized by single-crystal X-ray diffraction.(c) 2023 Elsevier Ltd. All rights reserved.

引用

页数：8

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