Potential antidepressants. Synthesis of 6,11-dihydrodibenzo[b,e]thiepin-11-yl 4-(dimethylamino-methyl)phenyl ketone and of some related compounds
Karel Šindelář
1
,
Jiří Holubek
1
,
Emil Svátek
1
,
Oluše Matoušová
1
,
Jiřina Metyšová
1
,
Miroslav Protiva
1
1
Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3, Czechoslovakia
|
|
Publication type: Journal Article
Publication date: 1989-09-01
scimago Q3
wos Q2
SJR: 0.362
CiteScore: 4.7
Impact factor: 2.4
ISSN: 0022152X, 19435193
Organic Chemistry
Abstract
Reactions of dibenzo[b,e]thiepin-11(6H)-one (4) with 2-, 3- and 4-(dimethylaminomethyl)phenylmagnesium bromide afforded the tertiary alcohols 5a,b,c. The aldehydes 7 and 8 gave similarly the secondary alcohols 9a,b,c and 10c. Numerous attempts to prepare the corresponding ketones, especially by oxidation of 9a,b,c and 10c were unsuccessful. Only the oxidation of 9c with tetrabutylammonium chromate in chloroform afforded the desired ketone 16. Its formation was accompanied by an important side reaction consisting in a cleavage of the “retro-ene-reaction” type leading to compound 11 and the aldehyde 13c which reacted with the chloroform present to give the alcohol 17. Compounds 5a,b,c, 9a,b,c and 16 were tested as potential antidepressants but with the exception of some effects in the test of potentiation of yohimbine toxicity in mice, they proved inactive in this line.
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Šindelář K. et al. Potential antidepressants. Synthesis of 6,11-dihydrodibenzo[b,e]thiepin-11-yl 4-(dimethylamino-methyl)phenyl ketone and of some related compounds // Journal of Heterocyclic Chemistry. 1989. Vol. 26. No. 5. pp. 1325-1330.
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Šindelář K., Holubek J., Svátek E., Matoušová O., Metyšová J., Protiva M. Potential antidepressants. Synthesis of 6,11-dihydrodibenzo[b,e]thiepin-11-yl 4-(dimethylamino-methyl)phenyl ketone and of some related compounds // Journal of Heterocyclic Chemistry. 1989. Vol. 26. No. 5. pp. 1325-1330.
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TY - JOUR
DO - 10.1002/jhet.5570260519
UR - https://doi.org/10.1002/jhet.5570260519
TI - Potential antidepressants. Synthesis of 6,11-dihydrodibenzo[b,e]thiepin-11-yl 4-(dimethylamino-methyl)phenyl ketone and of some related compounds
T2 - Journal of Heterocyclic Chemistry
AU - Šindelář, Karel
AU - Holubek, Jiří
AU - Svátek, Emil
AU - Matoušová, Oluše
AU - Metyšová, Jiřina
AU - Protiva, Miroslav
PY - 1989
DA - 1989/09/01
PB - Wiley
SP - 1325-1330
IS - 5
VL - 26
SN - 0022-152X
SN - 1943-5193
ER -
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BibTex (up to 50 authors)
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@article{1989_Šindelář,
author = {Karel Šindelář and Jiří Holubek and Emil Svátek and Oluše Matoušová and Jiřina Metyšová and Miroslav Protiva},
title = {Potential antidepressants. Synthesis of 6,11-dihydrodibenzo[b,e]thiepin-11-yl 4-(dimethylamino-methyl)phenyl ketone and of some related compounds},
journal = {Journal of Heterocyclic Chemistry},
year = {1989},
volume = {26},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002/jhet.5570260519},
number = {5},
pages = {1325--1330},
doi = {10.1002/jhet.5570260519}
}
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MLA
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Šindelář, Karel, et al. “Potential antidepressants. Synthesis of 6,11-dihydrodibenzo[b,e]thiepin-11-yl 4-(dimethylamino-methyl)phenyl ketone and of some related compounds.” Journal of Heterocyclic Chemistry, vol. 26, no. 5, Sep. 1989, pp. 1325-1330. https://doi.org/10.1002/jhet.5570260519.