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Journal articles on the topic 'Thiepine'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Nishino, Keitaro, Masanobu Takagi, Teruhisa Kawata, Ichiro Murata, Junji Inanaga, and Kazuhiro Nakasuji. "Thiepine-iron tricarbonyl: stabilization of thermally labile parent thiepine by transition metal complexation." Journal of the American Chemical Society 113, no. 13 (June 1991): 5059–60. http://dx.doi.org/10.1021/ja00013a051.

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2

Yoshinari, Nobuto, and Takumi Konno. "5,7-Dihydrodibenzo[c,e]thiepine." Acta Crystallographica Section E Structure Reports Online 65, no. 4 (March 14, 2009): o774. http://dx.doi.org/10.1107/s1600536809008769.

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3

Murata, Ichiro. "Some New Aspects of Thiepine and Thiazepine Chemistry." Phosphorus, Sulfur, and Silicon and the Related Elements 43, no. 3-4 (June 1989): 243–59. http://dx.doi.org/10.1080/10426508908040289.

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4

Bozinovic, Nina, Irena Novakovic, Sladjana Kostic-Rajacic, Igor Opsenica, and Bogdan Solaja. "Synthesis and antimicrobial activity of azepine and thiepine derivatives." Journal of the Serbian Chemical Society 80, no. 7 (2015): 839–52. http://dx.doi.org/10.2298/jsc150116013b.

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A series of new 5H-pyridobenzazepine and pyridobenzothiepine derivatives was synthesized by Pd-catalyzed formation of C-N and C-S bonds. All synthesized compounds were tested for their in vitro antimicrobial activity. The 5H-pyridobenzazepine derivatives showed better antibacterial and antifungal activity than corresponding 5H-dipyridoazepine analogs. Among the synthesized azepines, derivative 8 displayed potent activity against tested bacteria (MIC = 39-78 ?g/mL), while azepine 12 showed promising antifungal activity (MIC = 156-313 ?g/mL). The synthesized thiepine derivatives exhibited weak antibacterial activity, but showed pronounced antifungal activity.

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5

Zhang, Hai-Quan, Bao-Li, Guang-Di Yang, and Yu-Guang Ma. "3,9-Dibromo-6,7-dihydro-5H-dibenzo[c,e]thiepine." Acta Crystallographica Section E Structure Reports Online 64, no. 6 (May 10, 2008): o1027. http://dx.doi.org/10.1107/s1600536808013226.

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6

Foubelo, Francisco, Benjamín Moreno, Tatiana Soler, and Miguel Yus. "Reductive ring opening of dihydrodibenzothiepine and dihydrodinaphtho-oxepine and -thiepine." Tetrahedron 61, no. 38 (September 2005): 9082–96. http://dx.doi.org/10.1016/j.tet.2005.07.042.

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7

Edwards, David J., Robin G. Pritchard, and Timothy W. Wallace. "Fine-tuning of biaryl dihedral angles: structural characterization of five homologous three-atom bridged biphenyls by X-ray crystallography." Acta Crystallographica Section B Structural Science 61, no. 3 (May 13, 2005): 335–45. http://dx.doi.org/10.1107/s0108768105006713.

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The homologous series of three-atom bridged biaryls comprising 5,7-dihydro-1,2,3,9,10,11-hexamethoxydibenzo[c,e]oxepine, 6,7-dihydro-1,2,3,9,10,11-hexamethoxy-6-methyl-5H-dibenzo[c,e]azepinium chloride, 5,7-dihydro-1,2,3,9,10,11-hexamethoxydibenzo[c,e]thiepine, and the 6-oxide and 6,6-dioxide derivatives of the latter have been characterized by X-ray crystal structure analysis. Within this series the endocyclic and exocyclic biaryl dihedral angles vary over 10° ranges, reflecting the changing balance of intramolecular (steric, geometric) and intermolecular (crystal packing) forces, the former being potential control elements for fine-tuning the helicity of the biaryl system.

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8

Higashi, Y., Y. Momotani, E. Suzuki, and T. Kaku. "Clinical and EEG Studies of Zotepine, a Thiepine Neuroleptic, on Schizophrenic Patients." Pharmacopsychiatry 20, S 1 (February 1987): 8–11. http://dx.doi.org/10.1055/s-2007-1017124.

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9

Foubelo, Francisco, Benjamín Moreno, and Miguel Yus. "Reductive opening of 2,7-dihydrodinaphthoxepine and thiepine: easy regioselective preparation of 2,2′-difunctionalised binaphthyls." Tetrahedron Letters 45, no. 49 (November 2004): 8983–86. http://dx.doi.org/10.1016/j.tetlet.2004.10.041.

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10

Bøgesø, Klaus P., and Michael Bech Sommer. "The effect of aromatic substitution on neuroleptic activity in 1-piperazino-3-phenylindans. A comparison based on a new D-2 receptor model with corresponding 10-piperazino-10,11-dihydrodibenzo[b,f]thiepins." Collection of Czechoslovak Chemical Communications 56, no. 11 (1991): 2456–67. http://dx.doi.org/10.1135/cccc19912456.

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The validity of a new dopamine D-2 receptor interaction model based on conformational analysis and least-squares superimposition studies of the indan derivative tefludazine and the thiepin derivative octoclothepin was further tested by comparison of the effect of aromatic substitution on D-2 antagonistic activity in two series of indan and thiepin derivatives. The indan series include new derivatives substituted in the 4-, 7-, 2’- and 3’-position. The substitution effects were largely parallel with one important exception: Only 6-substituted indans have significant neuroleptic activity while both 8- and 7-substituted thiepin derivatives have neuroleptic activity. In indans additional fluorination in the 2’- or 4’-position is demanded to give potent neuroleptic activity, while a 3’-fluoro-substituted derivative was inactive. Fluorination is not necessary in thiepins although 3-fluoro derivatives have a significant prolonged duration of action. Considering the differences in physico-chemical properties, metabolism and pharmacokinetics between the two series, the largely parallel substitution effects support the new D-2 receptor model.

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11

Blaton, N. M., O. M. Peeters, and C. J. De Ranter. "2-Methylthio-10,11-dihydro-11-(4-methylpiperazin-1-yl)dibenzo[b,f]thiepine Maleic Acid (Metitepine Maleate)." Acta Crystallographica Section C Crystal Structure Communications 51, no. 4 (April 15, 1995): 777–80. http://dx.doi.org/10.1107/s0108270194011637.

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12

Šindelář, Karel, Jiří Holoubek, Emil Svátek, Jan Metyš, Hana Blehová, and Zdeněk Polívka. "Potential antihistaminics: Tricyclic carboxylic acids derived from 6,11-dihydrodibenzo[b,e]thiepine and 4,9-dihydrothieno[2,3-c]-2-benzothiepine." Collection of Czechoslovak Chemical Communications 56, no. 11 (1991): 2482–93. http://dx.doi.org/10.1135/cccc19912482.

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Reaction of nitrile IVa with the Grignard’s reagent 1-methyl-4-piperidylmagnesium chloride gave carbinol XIb as product. Carbinols XIa and XIb were dehydrated and hydrolysed with dilute hydrochloric acid to give hydrochlorides of the tricyclic amino acids Vb and Vc. Isomeric compounds with a carboxyl group in position 9 of the tricyclic skeleton were obtained either by hydrolysis of the formely prepared nitrile VIIb (compound VIIIb) or on reaction of bromoketone VIa with 1-methyl-4-piperidylmagnesium chloride, nucleophilic substitution of the bromine atom by the cyano group at the stage of carbinol XIIIb, and subsequent dehydration and hydrolysis of the cyano group, to give amino acid VIIIc. In the first case the synthesis of thiophene analogues XVIIIb and XVIIIc started from ketone XVa, which was brominated with bromine in acetic acid into position 2 of the tricyclic skeleton, followed by Grignard’s reaction with 3-dimethylaminopropylmagnesium chloride in tetrahydrofuran and hydrolysis to bromo derivative XVIb. In the second case derivative XVIc was obtained directly by bromination of hydrochloride XVc. Basic bromo derivatives XVIb and XVIc were reacted with butyllithium in tetrahydrofuran at –60°C to afford corresponding organometallic reagents which, when reacted with solid carbon dioxide, afforded the required amino acids XVIIIb and XVIIIc. Further, some other tricyclic nitriles were synthesized as potential intermediates. The prepared tricyclic amino acids Vb, Vc, VIIIb, VIIIc, XVIIIb and XVIIIc were tested both on animals and in assays of biochemical pharmacology. Some of them displayed considerable antihistaminic activity. The most interesting compound of this series, hydrochloride Vc (VUFB-17689) is a strong antihistaminic with distinctly suppressed sedative effects and it was therefore selected for a more detailed pharmacological testing.

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13

SINDELAR, K., J. HOLUBEK, E. SVATEK, J. METYS, H. BLEHOVA, and Z. POLIVKA. "ChemInform Abstract: Potential Antihistaminics: Tricyclic Carboxylic Acids Derived from 6, 11-Dihydrodibenzo(b,e)thiepine and 4,9-Dihydrothieno(2,3-c)-2- benzothiepine." ChemInform 23, no. 9 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199209243.

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14

Jílek, Jiří, Jiří Holubek, Emil Svátek, Jiřina Metyšová, Josef Pomykáček, Zdeněk Šedivý, and Miroslav Protiva. "Potential metabolites of the neuroleptic agents belonging to the 8-methylthio-10-piperazino-10,11-dihydrodibenzo[b,f]thiepin series; Synthesis of 2-hydroxy and 3-hydroxy derivatives." Collection of Czechoslovak Chemical Communications 50, no. 10 (1985): 2179–90. http://dx.doi.org/10.1135/cccc19852179.

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The acid VI, prepared by reaction of potassium salts of (2-iodo-5-methoxyphenyl)acetic acid and 4-(methylthio)thiophenol in the presence of copper, was transformed via intermediates VII-IX to 2-methoxy-8-methylthio-10-piperazino-10,11-dihydrodibenzo[b,f]thiepins X and XI. Their demethylation with boron tribromide afforded 2-hydroxy derivatives of the neuroleptic agents methiothepin and oxyprothepin I and II. 11-Chloro-7-methoxy-2-methylthio-10,11-dihydrodibenzo[b,f]thiepin was subjected to substitution reactions with 1-methylpiperazine and 1-(ethoxycarbonyl)piperazine and gave piperazine derivatives XIII and XIV, out of which the latter gave the secondary amine XV by alkaline hydrolysis. The ethers XIII and XV were also cleaved with boron tribromide and gave 3-hydroxy derivatives of methiothepin (III) and its demethyl derivative IV. The phenols I, II, and IV are potential metabolites of the mentioned neuroleptic agents; compound III, which already was identified as a metabolite, disclosed properties of a strong and cataleptic neuroleptic agent with prolonged duration of the effects. The methoxy compounds X, XI, and XIII are practically devoid of the neuroleptic activity.

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15

Shirani, Hamid, and Tomasz Janosik. "A New Concise Strategy for Synthesis of Dibenzo[b,f]thiepins and Related Fused Symmetrical Thiepin Derivatives." Journal of Organic Chemistry 72, no. 23 (November 2007): 8984–86. http://dx.doi.org/10.1021/jo701627g.

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16

Chihab-Eddine, Abderrahim, Adam Daı̈ch, Abderrahim Jilale, and Bernard Decroix. "Synthesis and reactivity of (1S)-N-(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[d]thiepine based on π-cationic cyclization." Tetrahedron Letters 42, no. 4 (January 2001): 573–76. http://dx.doi.org/10.1016/s0040-4039(00)02037-2.

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17

Valenta, Vladimír, Marie Vlková, Jiří Holubek, Jiřina Metyšová, and Miroslav Protiva. "Potential antidepressants: 10-Amino-2-chloro-10,11-dihydrodibenzo[b,f]thiepins." Collection of Czechoslovak Chemical Communications 54, no. 7 (1989): 1979–94. http://dx.doi.org/10.1135/cccc19891979.

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Reduction of N-(2-chloro-10,11-dihydrodibenzo[b,f]thiepin-10-yl)formamide with lithium aluminium hydride resulted in the methylamino compound IV. The dimethylamino compound V was obtained by methylation of 10-amino-2-chloro-10,11-dihydrodibenzo[b,f]thiepin with formic acid and aqueous formaldehyde. Substitution reactions of 2,10-dichloro-10,11-dihydrodibenzo[b,f]thiepin with a series of primary and secondary amines afforded the title compounds VI to XXVIII. The bases were transformed to salts and pharmacologically tested. Only the pyrrolidino compound IX (hydrogen succinate VÚFB-15 551) showed a clear pharmacological profile of a potential antidepressant.

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18

Valenta, Vladimír, Hana Hulinská, Jiří Holubek, Antonín Dlabač, Jan Metyš, Hana Frycová, and Miroslav Protiva. "N-substituted derivatives of 6,11-dihydrodibenzo[b,e]thiepin-11-amine and related compounds; Synthesis and pharmacological screening." Collection of Czechoslovak Chemical Communications 53, no. 4 (1988): 860–69. http://dx.doi.org/10.1135/cccc19880860.

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Reactions of N-(6,11-dihydrodibenzo[b,e]thiepin-11-yl)chloroacetamide (II) with dimethylamine, morpholine, and 2-(1-piperazinyl)ethanol afforded the amino amides III-V. Substitution reactions of 11-chloro-6,11-dihydrodibenzo[b,e]thiepin with ethylenediamine and N,N-dimethylethylenediamine gave the diamines VI and VII. 6,11-Dihydrodibenzo[b,e]thiepin-11-amine (I) was treated with ethyl chloroacetate and ethyl 2-bromopropionate to give the amino esters X and XI which were transformed on the one hand to the acids VIII and IX, and to the amides XII and XIII on the other. (6,11-Dihydrodibenzo[b,e]thiepin -11-yl)methylamine (XVIa) and (10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-yl)methylamine (XVIb) were transformed via the chloroacetamides XVIIa and XVIIb to the (4-methyl-1-piperazinyl)acetamides XVa and XVb. Compound V showed local anaesthetic and antiarrhythmic activity, the diamine VII had antihistamine and antireserpine effects, the amide XII was found to be an anticonvulsant, and the piperazines XVa and XVb inhibited effectively the formation of the indomethacin-induced gastric ulcers in rats.

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19

Šindelář, Karel, Miloš Buděšínský, Tomáš Vaněk, Jiří Holubek, Emil Svátek, Oluše Matoušová, Charles Wayne Rees, and Miroslav Protiva. "Reaction of 6,11-dihydrodibenzo[b,e]thiepin-11-carbonitrile with 1,2-dibromoethane, a reinvestigation. Formation of 11,12-dihydro-6H-6,12-methanodibenzo[b,f]thiocin-12-carbonitrile." Collection of Czechoslovak Chemical Communications 52, no. 9 (1987): 2281–94. http://dx.doi.org/10.1135/cccc19872281.

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Reinvestigation of the minor product of reaction of 6,11-dihydrodibenzo[b,e]thiepin-11-carbonitrile (I) with 1,2-dibromoethane in the presence of tetrabutylammonium bromide or benzyltriethylammonium chloride and 50% sodium hydroxide by means of 1H and 13C NMR spectroscopy led to the formula XI named in the title, which was confirmed by X-ray crystallographic analysis. The product of a similar reaction, carried out in dimethyl sulfoxide in the presence of potassium carbonate at 100 °C was identified as the stereoisomeric mixture of 11,11'-ethylenebis(6,11-dihydrodibenzo[b,e]thiepin-11-carbonitriles) (XII) which was separated to the components by preparative HPLC. The title compound XI was oxidized to the sulfoxide XIII and the sulfone XIV, and was transformed by reduction and the following methylation to amines XV and XVI. The reduction of the vinyl nitrile III with lithium aluminium hydride is complicated on the one hand by allylic rearrangement, and with cyanide anion abstraction on the other, the products being (E,Z)-mixture of 3-(6,11-dihydrodibenzo[b,e]thiepin-11-ylidene)propylamines (XVII) and 11-vinyl-6,11-dihydrodibenzo[b,e]thiepin (X). The amine XVI is devoid of thymoleptic activity.

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20

Polívka, Zdeněk, Jan Metyš, and Miroslav Protiva. "6,11-Dihydrodibenzo[b,e]thiepin-11-yl 3-quinuclidinyl ethers: New potential intidepressants and antihistamine agents." Collection of Czechoslovak Chemical Communications 53, no. 8 (1988): 1806–11. http://dx.doi.org/10.1135/cccc19881806.

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Reactions of 11-chloro-6,11-dihydrodibenzo[b,e]thiepin and its 2-methyl derivative, and further of the methanesulfonates of 2-chloro- and 2-bromo-6,11-dihydrodibenzo[b,e]thiepin-11-ol with 3-quinuclidinol afforded the title ethers I-IV. The 2-methyl compound II (VÚFB-17 088) showed significant antihistamine activity and the 2-chloro compound III (VÚFB-17 089), having antireserpine and anticataleptic activity, proved a potential antidepressant agent.

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21

Polívka, Zdeněk, Jan Metyš, and Miroslav Protiva. "Heterocyclic ethers derived from 6,11-dihydrodibenzo[b,e]thiepin-11-ols and 4,9-dihydrothieno[2,3-c]-2-benzothiepin-4-ol; A new series of potential antidepressants and antihistamine agents." Collection of Czechoslovak Chemical Communications 51, no. 9 (1986): 2034–49. http://dx.doi.org/10.1135/cccc19862034.

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Reactions of 11-chloro-6,11-dihydrodibenzo[b,e]thiepin and methanesulfonates of 6,11-dihydrodibenzo[b,e]thiepin-11-ol (I), its 2-methyl derivative II and 4,9-dihydrothieno[2,3-c]-2-benzothiepin-4-ol (III) with 1-methylpiperidin-4-ol, 1-methylperhydroazepin-4-ol (XIX), and tropine gave the ethers V-X. Their methanesulfonates were pharmacologically tested and showed antireserpine, anticataleptic, and antihistamine activities of various degree. The most active compounds were the ethers V and VI.

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22

Stachel, Hans-Dietrich, and Josef Schachtner. "Synthese von Heteroanaloga der Penicillsäure / Synthesis of Hetero Analogues of Penicillic Acid." Zeitschrift für Naturforschung B 51, no. 9 (September 1, 1996): 1334–38. http://dx.doi.org/10.1515/znb-1996-0919.

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23

Šindelář, Karel, Jiří Jílek, Josef Pomykáček, Vladimír Valenta, Marta Hrubantová, Marie Vlková, Jiří Holubek, et al. "Tricyclic neuroleptics: Synthesis of metabolites of isofloxythepin and some related compounds." Collection of Czechoslovak Chemical Communications 55, no. 9 (1990): 2282–303. http://dx.doi.org/10.1135/cccc19902282.

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The isofloxythepin (I) metabolite IV was synthesized via the acids IX and XI and the esters X and XII. The enamine VIII was prepared from 3-fluoro-8-(2-propyl)dibenzo[b,f]thiepin-10(11H)-one by two methods and was reduced to I. Cloflumide (II) was obtained by reaction of 2,10-dichloro-7-fluoro-10,11-dihydrodibenzo[b,f]thiepin with 3-(1-piperazinyl)propionamide and was oxidized to the sulfoxide XVI. The unsaturated analogue XVII of clopithepin (III) was prepared from 2-chlorodibenzo[b,f]thiepin-10(11H)-one by reaction with 2-bromoethanol in the presence of 4-toluenesulfonic acid in boiling benzene and by the following substitution reaction with 2-(1-piperazinyl)ethanol. An improved synthesis of 6-methyldibenzo[b,f]thiepin-10(11H)-one (XIX) was elaborated. The acid XXVII was synthesized and cyclized with polyphosphate ester. A mixture of compounds was formed from which the ketone XXXVI was isolated and processed by reaction with formamide and formic acid at 200 °C. One of the products was characterized as the formamide XXXIII and was reduced with lithium aluminium hydride to a basic product supposed to be XXXIV. A series of by-products was isolated and characterized. The enamine VIII (V⁄FB-17 156) was found to be a strong neuroleptic agent, similar to isofloxythepin (I). The enol ether XVII (V⁄FB-17 733) was characterized as a mild, practically noncataleptic neuroleptic agent.

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24

Kakehi, Akikazu, Hidetoshi Isawa, and Hiroyuki Suga. "First Formation of Thiepino[2,3-b]- and Thiepino[3,2-a]indolizine Derivatives." HETEROCYCLES 78, no. 2 (2009): 319. http://dx.doi.org/10.3987/com-08-11536.

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25

Kassaee, M. Z., S. M. Musavi, M. Majdi, A. Cheshmehkani, E. Motamedi, and A. Aghaee. "Beyond benzene sulfides and thiepins: Tautomerizations and thiepins inversions at theoretical levels." Journal of Molecular Structure: THEOCHEM 848, no. 1-3 (January 2008): 67–73. http://dx.doi.org/10.1016/j.theochem.2007.09.012.

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26

Wyatt, Dorothy K., Nina Matheny Roscher, and Lee T. Grady. "Carbon13 NMR Shift Assignments for E- and Z-Dothiepin Hydrochloride and 6H-Dibenzo[b,e]thiepin-11-One." Applied Spectroscopy 40, no. 3 (March 1986): 369–73. http://dx.doi.org/10.1366/0003702864509079.

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Carbon13 chemical shift assignments are reported for Z- and E-dothiepin hydrochloride (N,N-dimethyldibenzo[b,e]thiepin- delta-11(6H)′, gamma-propylamine hydrochloride). The commercial product, a mixture of approximately 95% E-isomer, is of clinical importance as an antidepressant drug. The precursor and degradation product, 6H-dibenzo[b,e]thiepin-11-one, and related model compounds were also studied. Homo- and heteronuclear shift-correlated 2D NMR, selective INEPT, selective and off-resonance decoupling, and inversion-recovery ( T1) experiments as well as model compound comparisons were used in assignments.

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27

Polívka, Zdeněk, Irena Lichá, Petr Taufmann, Emil Svátek, Jiří Holubek, and Miroslav Protiva. "Synthesis of 3-(6,11-dihydrodibenzo[b,e]thiepin-11-ylidene)propanoic acid and related compounds." Collection of Czechoslovak Chemical Communications 52, no. 6 (1987): 1566–82. http://dx.doi.org/10.1135/cccc19871566.

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The alcohol XIa, obtained by reaction of dibenzo[b,e]thiepin-11(6H)-one with vinylmagnesium bromide, was transformed by treatment with hydrogen bromide in acetic acid to the bromo compound XIIa which was converted via the nitrile XIIIa to the title acid VIIIa. The pure (E)-isomer was prepared and correlated via the dimethylamide XVIIIa with (E)-prothiadene (Ia). Similar procedures in the 2-methyl-6,11-dihydrodibenzo[b,e]thiepin and 10,11-dihydrodibenzo[a,d]cycloheptene series afforded the acids VIIIb and IV. The acids VIIIab were oxidized with hydrogen peroxide to the sulfoxides IXab and to the sulfones Xab. The acid IV is the suggested metabolite of the antidepressant amitriptyline (II) and the acids VIIIab-Xab are potential metabolites of the antidepressant prothiadene (Ia) and the antihistamine agent methiadene (Ib). The amides VII and XVIab were prepared from the acids via the acid chlorides. The (Z)-isomer of prothiadene (XXII) was prepared from dibenzo[b,e]thiepin-11(6H)-one by the Wittig reaction. The acids IV, VIIIab and IXab showed some antiinflammatory activity.

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28

Song, Changsik, and Timothy M. Swager. "Reactive Conducting Thiepin Polymers." Journal of Organic Chemistry 75, no. 4 (February 19, 2010): 999–1005. http://dx.doi.org/10.1021/jo902079j.

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29

Šindelář, Karel, Vladimír Valenta, Jiří Holubek, Oluše Matoušová, and Miroslav Protiva. "Potential antidepressants. Synthesis of 6,11-dihydrodibenzo[b,e]thiepin-11-yl (dimethylaminomethyl)phenyl ethers, sulfides, amines and some related compounds." Collection of Czechoslovak Chemical Communications 55, no. 1 (1990): 282–95. http://dx.doi.org/10.1135/cccc19900282.

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Reactions of 11-chloro-6,11-dihydrodibenzo[b,e]thiepin and its 2-bromo derivative with the isomeric (dimethylaminomethyl)phenols, (dimethylaminomethyl)thiophenols, and (dimethylaminomethyl)anilines in toluene afforded the title compounds IIIb,c, Va, VIIIa,b,c, and Xa,b,c. Reactions of 11-chloro-6,11-dihydrodibenzo[b,e]thiepin and its 2-chloro and 2-methyl derivatives with N,N-dimethyl-2-(4-aminophenoxy)ethylamine and N,N-dimethyl-3-(4-aminophenoxy)propylamine by heating in dimethylformamide in the presence of sodium carbonate gave the diamino ethers XI-XIV. The compounds showed only indications of the antidepressant agents profile and some antimicrobial effects in vitro.

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30

Šindelář, Karel, Jan Metyš, and Miroslav Protiva. "Potential antidiarrheal agents: 1-(11-Cyano-6,11-dihydrodibenzo[b,e]thiepin-11-yl-alkyl)- and 1-(10-cyano-10,11-dihydrodibenzo[b,f]thiepin-10-yl-alkyl)-4-substituted piperidines." Collection of Czechoslovak Chemical Communications 50, no. 5 (1985): 1089–96. http://dx.doi.org/10.1135/cccc19851089.

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Substitution reactions of 11-(2-bromoethyl)- and 11-(3-bromopropyl)-6,11-dihydrodibenzo[b,e]thiepin-11-carbonitrile and further of 10-(2-bromoethyl)- and 10-(3-bromopropyl)-10,11-dihydrodibenzo[b,f]thiepin-10-carbonitrile with ethyl 4-phenylpiperidine-4-carboxylate, 4-phenylpiperidin-4-ol, 4-(2-tolyl)piperidin-4-ol, 4-(4-fluorophenyl)piperidin-4-ol, 4-(2-oxobenzimidazolin-1-yl)-piperidine and 1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one afforded the tricyclic piperidinoalkyl nitriles IV-XIII which are cyclic analogues of the antidiarrheal agents diphenoxylate (I) and loperamide (III). Out of the compounds prepared only IV and XI showed a significant inhibitory effect towards diarrhea elicited by intravenously administered serotonin in mice.

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31

Jílek, Jiří, Jiří Holubek, Emil Svátek, Jan Metyš, Hana Frycová, Josef Pomykáček, and Miroslav Protiva. "Tricyclic analogues of the antiallergic agent oxatomide: 1-(3-(4-(10,11-Dihydro-5H-dibenzo[a,d]cycloheptene-5-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one and the related 6,11-dihydrodibenzo[b,e]thiepin, 4,9-dihydrothieno[2,3-c]-2-benzothiepin, and 10,11-dihydrodibenzo[b,f]thiepin derivatives." Collection of Czechoslovak Chemical Communications 53, no. 4 (1988): 870–83. http://dx.doi.org/10.1135/cccc19880870.

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11-Chloro-6,11-dihydrodibenzo[b,e]thiepin and its 2-methyl derivative VI were transformed via the 11-(4-ethoxycarbonyl)-1-piperazinyl) compounds IVc and Vc to 11-(1-piperazinyl)compounds IVb and Vb. Their reactions with 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one (II) afforded the title compounds IVa and IVb. Similar reactions and sequences in the series of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene, 4,9-dihydrothieno[2,3-c]-2-benzothiepin, and 10,11-dihydrodibenzo[b,f]thiepin led to further oxatomide (Ia) analogues IIIa and VIIa-XIa. In the test of passive cutaneous anaphylaxis in rats, compound VIIIa was more active than Ia, and IVa had similar activity like Ia.

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32

Ābele, E., R. Ābele, Ļ. Golomba, J. Višņevska, T. Beresņeva, and K. Rubina. "Oximes of Seven-Membered Heterocyclic Compounds Containing One Heteroatom." Latvian Journal of Chemistry 50, no. 3-4 (January 1, 2011): 205–22. http://dx.doi.org/10.2478/v10161-011-0071-7.

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Oximes of Seven-Membered Heterocyclic Compounds Containing One Heteroatom Literature data on the synthesis and structure of azepane, oxepane and thiepane oximes were reviewed. Synthesis of novel heterocycles from oximes of seven-membered heterocycles containing one heteroatom were described. Biological activity of oximes of seven-membered heterocycles with one heteroatom was also reviewed.

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33

Polívka, Zdeněk, Jiří Holubek, Miloš Buděšínský, Oluše Matoušová, Emil Svátek, Jan Metyš, and Miroslav Protiva. "Potential antihistamine agents: 4-(6,11-Dihydrodibenzo[b,e]thiepin-11-ylidene)-1-methyltetrahydrothiopyranium iodide and similar sulfonium salts derived from related tricyclic systems." Collection of Czechoslovak Chemical Communications 52, no. 11 (1987): 2758–74. http://dx.doi.org/10.1135/cccc19872758.

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Thioxanthone, 10,11-dihydrodibenzo[a,d]cyclohepten-5-one, dibenzo[b,e]thiepin-11(6H)-one, its 2-methyl derivative, and thieno[2,3-c]-2-benzothiepin-4(9H)-one were reacted with 4-tetrahydrothiopyranylmagnesium bromide and the obtained tertiary alcohols IVabc, VIc, and XIX were dehydrated to the olefinic sulfides IXabc, Xc, and XXI. Addition of methyl iodide afforded the title compounds XIabc, XIIc, and XXII. The Grignard reactions were accompanied by the 1,6-addition giving the ketones XVI-XVIII as by-products. The reductive properties of tetrahydrothiopyranylmagnesium bromide were most striking in the case of reaction with 2-chlorothioxanthone; the isolation of thioxanthene and thioxanthone showed that nuclear dehalogenation took also place. Reactions of 11-chloro-6,11-dihydrodibenzo[b,e]thiepin and benzhydryl chloride with tetrahydrothiopyran-4-ol gave the sulfides XXV and XXVIII; whereas the latter reacted with methyl iodide under the formation of sulfonium salt XXIX, the former was cleaved and gave 4-hydroxyl-1-methyltetrahydrothiopyranium iodide (XXVI). The sulfonium salts are free of the central effects but their antihistamine activity is rather low.

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34

Valenta, Vladimír, Marie Vlková, and Miroslav Protiva. "Potential neurotropic and antiinflammatory agents: 2-Chloro-10,11-dihydrodibenzo[b,f]thiepin-10-yl sulfides." Collection of Czechoslovak Chemical Communications 54, no. 5 (1989): 1403–21. http://dx.doi.org/10.1135/cccc19891403.

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2-Chloro-10,11-dihydrodibenzo[b,f]thiepin-10-thiol (VII) was synthesized from 2,10-dichloro-10,11-dihydrodibenzo[b,f]thiepin (IV) and was alkylated with a series of aminoalkyl chlorides which led to amino sulfides IX, XII, XIII, and XVI-XX. The primary amine IXa was transformed by treatment with ethyl chloroformate to the carbamate Xa which was reduced to the methylamino compound XIa. The carbamate XX was similarly reduced to compound XXI. Alkylation of VII with 2-bromoethanol gave the alcohol XIVa which was transformed to the crude tosylate XVa. Its reactions with the corresponding piperazines gave compounds XXII to XXIV. The alcohol XXII was esterified to the decanoate XXV. Reactions of the sodium salt of VII with ethyl chloroacetate, ethyl 2-chloropropionate and ethyl 4-chlorobutyrate gave the corresponding esters which were saponified to acids XXVIb-XXVIIIb. Their amides XXVId to XXVIIId and XXVIe were prepared either via the acid chlorides or via the esters. Out of the compounds prepared only XIa showed a clear profile of a potential antidepressant. The other compounds showed indications of thymoleptic, antiinflammatory and antimicrobial activities.

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35

Ke, Jia, Qi Lu, Xin Wang, Rui Sun, Zhe Jin, Xiaoyi Zhan, Jianshu Hu, David Wan, and Chun Hu. "Discovery of 4,5-Dihydro-1H-thieno[2′,3′:2,3]thiepino [4,5-c]pyrazole-3-carboxamide Derivatives as the Potential Epidermal Growth Factor Receptors for Tyrosine Kinase Inhibitors." Molecules 23, no. 8 (August 8, 2018): 1980. http://dx.doi.org/10.3390/molecules23081980.

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The epidermal growth factor receptors (EGFRs), in which overexpression (known as upregulation) or overactivity have been associated with a number of cancers, has become an attractive molecular target for the treatment of selective cancers. We report here the design and synthesis of a novel series of 4,5-dihydro-1H-thieno [2′,3′:2,3]thiepino[4,5-c]pyrazole-3-carboxamide derivatives and the screening for their inhibitory activity on the EGFR high-expressing human A549 cell line using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). A Docking simulation was performed to fit compound 6g and gifitinib into the EGFR to determine the probable binding models, and the binding sites and modes conformation of 6g and gifitinib were exactly similar, the two compounds were stabilized by hydrogen bond interactions with MET769. Combining with the biological activity evaluation, compound 6g demonstrated the most potent inhibitory activity (IC50 = 9.68 ± 1.95 μmol·L–1 for A549). Conclusively, 4,5-dihydro-1H-thieno[2′,3′:2,3]thiepino[4,5-c]pyrazole-3-carboxamide derivatives as the EGFR tyrosine kinase inhibitors were discovered, and could be used as potential lead compounds against cancer cells.

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36

Jasinski, Jerry P., Q. N. M. Hakim Al-arique, Ray J. Butcher, H. S. Yathirajan, and B. Narayana. "Dibenzo[b,e]thiepin-11(6H)-one." Acta Crystallographica Section E Structure Reports Online 66, no. 2 (January 13, 2010): o350. http://dx.doi.org/10.1107/s1600536810000796.

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37

Šindelář, Karel, Jiřina Metyšová, and Miroslav Protiva. "Potential antidepressants: 2-(6,11-Dihydrodibenzo[b,e]thiepin-11-yl)-4,5-dihydroimidazoles." Collection of Czechoslovak Chemical Communications 54, no. 1 (1989): 229–34. http://dx.doi.org/10.1135/cccc19890229.

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Reactions of 2-substituted 11-chloro-6,11-dihydrodibenzo[b,e]thiepins with trimethylsilyl cyanide in dichloromethane in the presence of stannic chloride afforded nitriles IIb-IId in high yields. Heating of IIa-IId with 2-aminoethylammonium toluene-4-sulfonate to 200 °C gave the title compounds Ia-Id which were transformed to hydrogen maleates. Compound Ic (hydrogen maleate VÚFB-17 092) showed in several tests a clear thymoleptic (potential antidepressant) character.

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38

Waisser, Karel, and Jana Bořková. "Relations between structure and antituberculotic activity in a group of 10-piperazino-10,11-dihydrodibenzo[b,f]thiepins." Collection of Czechoslovak Chemical Communications 56, no. 11 (1991): 2395–401. http://dx.doi.org/10.1135/cccc19912395.

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Relations between chemical structure and activity to Mycobacterium tuberculosis have been looked for within a group of the derivatives of 10-piperazino-10,11-dihydrodibenzo[b,f]thiepins prepared by Protiva et al. It has been found that the most reliable results are obtained with application of the model by Free and Wilson. The activity can be considered additive with regard to the contributions of the molecular segments varied.

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39

Jursic, Branko S. "Theoretical study of thieno[3,4-d]thiepin and furo[3,4-d]thiepin as dienes in the diels-alder reaction." Journal of Heterocyclic Chemistry 32, no. 5 (September 1995): 1499–508. http://dx.doi.org/10.1002/jhet.5570320515.

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40

Šindelář, Karel, Jiří Holubek, Miroslav Ryska, Ivan Koruna, and Miroslav Protiva. "5-Substituted and 5,7-disubstituted 5,7-dihydrodibenzo[c,e]thiepins and the corresponding S-oxygenated compounds: Alkylamines, carboxylic acids, and carboxamides; synthesis and pharmacological screening." Collection of Czechoslovak Chemical Communications 51, no. 12 (1986): 2848–68. http://dx.doi.org/10.1135/cccc19862848.

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Reaction of 5,7-dihydrodibenzo[c,e]thiepin (I) with n-butyllithium resulted in the partial sulfur extrusion and in the formation of the 9,10-dihydrophenanthrene-9-thiolate anion (B). Its further transformations (by hydrolysis, aminoalkylation and spontaneous dehydrogenation) led to phenanthrene-9-thiol (IX), the corresponding disulfide X, and the S-(2-dimethylaminoethyl) derivatives XI and XIV. Reactions of 5-chloro-5,7-dihydrodibenzo[c,e]thiepin (II) with the corresponding Grignard reagents were only a poor source of the amines III and IV. Reaction of the sulfoxide XVIII with n-butyllithium or with sodium hydride and the following treatment with 2-dimethylaminoethyl chloride gave the amine XIX in a low yield. Only the sulfone X was found more useful for preparing the 5- and 5,7-substituted derivatives. Treatment with n-butyllithium and following carbonation afforded mixtures of the monocarboxylic acid XXI and dicarboxylic acid XXVIII. Via acid chlorides they were transformed to the methylamides XXII and XXIX, and to the dimethylamides XXIII and XXX. The amide XXIII was reduced to the 5-(dimethylaminomethyl) compound XXV. Lithiation of the sulfone XX or treatment with sodium hydride, and the following action of 2-dimethylaminoethyl chloride and 3-dimethylaminopropyl chloride gave the amines XXVI, XXVII, and XXXI. Only the phenanthrene derivatives XI and XIV, and the amino sulfone XXVII showed clear indications of thymoleptic activity as potential antidepressants.

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41

Hudson, Andrew, A. Guy Orpen, Hirihattaya Phetmung, and Paul Wyatt. "Synthesis of novel C2 symmetrical and enantiomerically pure thiepines." Tetrahedron Letters 40, no. 4 (January 1999): 813–16. http://dx.doi.org/10.1016/s0040-4039(98)02460-5.

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42

Shirani, Hamid, Jan Bergman, and Tomasz Janosik. "New syntheses of unsymmetrical thiepins and their selenium analogues." Tetrahedron 65, no. 40 (October 2009): 8350–53. http://dx.doi.org/10.1016/j.tet.2009.08.014.

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43

Reinhoudt, D. N. "Thiepins and benzothiepins; the conquest of elusive sulfur heterocycles." Recueil des Travaux Chimiques des Pays-Bas 101, no. 9 (September 2, 2010): 277–87. http://dx.doi.org/10.1002/recl.19821010901.

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44

Červená, Irena, Jiří Holubek, Emil Svátek, Miroslav Ryska, and Miroslav Protiva. "Potential antidepressants: 6-(Aminoalkoxy)dibenzo[b,f]thiepin-10(11H)-ones and 6-(aminoalkoxy)-10,11-dihydrodibenzo[b,f]thiepin-10-ols." Collection of Czechoslovak Chemical Communications 54, no. 7 (1989): 1955–65. http://dx.doi.org/10.1135/cccc19891955.

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Sodium salts of 6-hydroxydibenzo[b,f]thiepin-10(11H)-one and its 2-chloro derivative were reacted with hydrochlorides of 2-dimethylaminoethyl chloride, 2-(piperidino)ethyl chloride, 3-dimethylaminopropyl chloride, and 3-(piperidino)propyl chloride in ethanol in the presence of sodium ethoxide which resulted in the title compounds IIa, IIb, IVa, Va, Vb, and VIIa. The tertiary amines IIa, IIb, and Va were partially demethylated via the carbamates VIIIa, VIIIb, and IXa to the secondary amines IIIa, IIIb, and VIa. The amino ketones IIa and Va were reduced to the amino alcohols XII and XIII. With the exception of compound Va (hydrochloride VÚFB-15 515), the products lacked completely the expected pharmacological profile of potential antidepressants.

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45

JURSIC, B. S. "ChemInform Abstract: Theoretical Study of Thieno(3,4-d)thiepin and Furo(3,4-d)thiepin as Dienes in the Diels-Alder Reaction." ChemInform 27, no. 13 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199613062.

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46

Jílek, Jiří, Martin Valchář, Josef Pomykáček, Antonín Dlabač, and Miroslav Protiva. "Noncataleptic neuroleptic agents: Synthesis of some esters of 2-chloro-10-(4-(2-hydroxyethyl)piperazino)-10,11-dihydrodibenzo[b,f]thiepin." Collection of Czechoslovak Chemical Communications 51, no. 7 (1986): 1503–8. http://dx.doi.org/10.1135/cccc19861503.

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Reactions of 2-chloro-10-(4-(2-hydroxyethyl)piperazino)-10,11-dihydrodibenzo[b,f]thiepin (I) with phenylacetic, methoxyacetic, methylthioacetic, phenoxyacetic and morpholinoacetic acid in dichloromethane and in the presence of N,N'-carbonyldiimidazole gave the title esters II - VI. Reaction of I with succinic anhydride afforded the hemisuccinate VII. The esters prepared elicited ataxia in low doses, were low-cataleptic, but only II, IV, and VII proved some antidopaminergic activity in the test using the affecting dopamine metabolism in rat brain striatum.

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47

Červená, Irena, Jiří Holubek, Emil Svátek, Jiřina Metyšová, Martin Valchář, Antonín Dlabač, Stanislav Wildt, and Miroslav Protiva. "6-Substituted and 2-chloro-6-substituted 10-piperazino-10,11-dihydrodibenzo[b,f]thiepins as potential antidepressants; Synthesis and pharmacology." Collection of Czechoslovak Chemical Communications 51, no. 1 (1986): 141–55. http://dx.doi.org/10.1135/cccc19860141.

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6-Substituted and 2-chloro-6-substituted 10-chloro-10,11-dihydrodibenzo[b,f]thiepins XIIIa - f were reacted with 1-(ethoxycarbonyl)piperazine and the carbamates IIIa - f obtained were hydrolyzed to the title compounds Ia -f. The new chlorides XIIIa - c were obtained from 2-(2-aryl-thiophenyl)acetic acids VIIIa - c via ketones XIa - c and alcohols XIIa - c. Reactions of the chlorides XIIIa and XIIIc with 1-methylpiperazine afforded compounds IIa and IIc. All compounds I are devoid of antireserpine and cataleptic activity; they are neither typical antidepressants nor neuroleptics.

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48

Jílek, Jiří, Martin Valchář, Jiří Holubek, Nataša Dlohožková, Josef Pomykáček, Oluše Matoušová, Jiřina Metyšová, and Miroslav Protiva. "Noncataleptic neuroleptic agents: 2-(4-(2-(2-Chloro-10,11-dihydrodibenzo[b,f]thiepin-10-yloxy)ethyl)piperazine-1-yl)ethanol and some related compounds." Collection of Czechoslovak Chemical Communications 53, no. 11 (1988): 2731–41. http://dx.doi.org/10.1135/cccc19882731.

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10-(2-Bromoethoxy)-2-chloro-10,11-dihydrodibenzo[b,f]thiepin (X), prepared by two methods, was subjected to substitution reactions with 2-(1-piperazinyl)ethanol, 3-(1-piperazinyl)propanol, 1-methylpiperazine, 3-(1-piperazinyl)propionamide, piperazine, and 1-(ethoxycarbonyl)piperazine and gave the title compounds II-VII. The alcohol II was esterified by treatment with acid chlorides to compounds VIII and IX. Compounds II, V, and VIII proved to be noncataleptic neuroleptic agents and II (clopithepin, VÚFB-17 076) was selected for preclinical studies.

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49

Červená, Irena, Jiří Holubek, Emil Svátek, Jan Metyš, Martin Valchář, and Miroslav Protiva. "Potential antidepressants: Synthesis of two 4-(aminoalkoxy)dibenzo[b,e]thiepin-11(6H)-ones." Collection of Czechoslovak Chemical Communications 54, no. 1 (1989): 225–28. http://dx.doi.org/10.1135/cccc19890225.

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Heating of 4-methoxydibenzo[b,e]thiepin-11(6H)-one with pyridine hydrochloride to 225 to 235 °C effected demethylation and gave IV. Its sodium salt reacted with 3-dimethylaminopropyl chloride in ethanol and afforded the 4-(3-dimethylaminopropoxy) compound II. The isomeric ether III was prepared via the 4-(4-bromobutoxy) compound V. Hydrochloride of II (VÚFB-17 033) inhibited mildly the binding of [3H]desipramine in rat hypothalamus, had antireserpine activity in rats, mild anticonvulsant effect, and antihypoxic effect in the test of nitrogen anoxia in mice.

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50

Gleiter, Rolf, Gerhard Krennrich, Dieter Cremer, Kagetoshi Yamamoto, and Ichiro Murata. "Electronic structure and thermal stability of thiepins. Photoelectron spectroscopic investigations." Journal of the American Chemical Society 107, no. 24 (November 1985): 6874–79. http://dx.doi.org/10.1021/ja00310a022.

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