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Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Suproclone: Difference between pages

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Saving copy of the {{drugbox}} taken from revid 447927139 of page Suproclone for the Chem/Drugbox validation project (updated: 'CAS_number').
 
→Synthesis: Notes
 
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{{Short description|Drug}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Suproclone|oldid=447927139}} 447927139] of page [[Suproclone]] with values updated to verified values.}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
⚫
| verifiedrevid = 443212429
| Watchedfields = changed
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| IUPAC_name = [6-(7-chloro-1,8-naphthyridin-2-yl)-5-oxo-3,7- dihydro-2H-[1,4]dithiino[2,3-c]pyrrol-7-yl]-4-propanoylpiperazine-1-carboxylate
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| verifiedrevid = 470475028
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| image = Suproclone-2d-skeletal.svg
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| IUPAC_name = [6-(7-chloro-1,8-naphthyridin-2-yl)-5-oxo-3,7-dihydro-2''H''-[1,4]dithiino[2,3-c]pyrrol-7-yl] 4-propanoylpiperazine-1-carboxylate
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| width = 180px
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| image = Suproclone.svg
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| width = 200


<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =
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<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = <!-- blanked - oldvalue: 77590-92-2 -->
| CAS_number = 76535-71-2
| ATC_prefix = none
| ATC_prefix = none
| ATC_suffix =
| ATC_suffix =
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| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D05975
| KEGG = D05975
| ChEMBL = 2105531


<!--Chemical data-->
<!--Chemical data-->
| C=22 | H=22 | Cl=1 | N=5 | O=4 | S=2
| C=22 | H=22 | Cl=1 | N=5 | O=4 | S=2
| molecular_weight = 520.024 g/mol
| smiles = O=C(N5CCN(C(=O)OC4C=1SCCSC=1C(=O)N4c2nc3nc(Cl)ccc3cc2)CC5)CC
| smiles = O=C(N5CCN(C(=O)OC4C=1SCCSC=1C(=O)N4c2nc3nc(Cl)ccc3cc2)CC5)CC
| InChI = 1/C22H22ClN5O4S2/c1-2-16(29)26-7-9-27(10-8-26)22(31)32-21-18-17(33-11-12-34-18)20(30)28(21)15-6-4-13-3-5-14(23)24-19(13)25-15/h3-6,21H,2,7-12H2,1H3
| InChIKey = IBAUKGNDWVSETP-UHFFFAOYAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C22H22ClN5O4S2/c1-2-16(29)26-7-9-27(10-8-26)22(31)32-21-18-17(33-11-12-34-18)20(30)28(21)15-6-4-13-3-5-14(23)24-19(13)25-15/h3-6,21H,2,7-12H2,1H3
| StdInChI = 1S/C22H22ClN5O4S2/c1-2-16(29)26-7-9-27(10-8-26)22(31)32-21-18-17(33-11-12-34-18)20(30)28(21)15-6-4-13-3-5-14(23)24-19(13)25-15/h3-6,21H,2,7-12H2,1H3
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| StdInChIKey = IBAUKGNDWVSETP-UHFFFAOYSA-N
| StdInChIKey = IBAUKGNDWVSETP-UHFFFAOYSA-N
}}
}}

'''Suproclone''' is a [[sedative]] and [[anxiolytic]] drug in the [[cyclopyrrolone]] family of drugs, developed by the French pharmaceutical company Rhône-Poulenc.<ref>{{cite web |author=Psychotropics.dk |title=suproclone |url=http://www.psychotropics.dk/moleculeView/default.aspx?ID=1532&Catalogtype=A&ChapterID=9&Thissortorder=1 |access-date=24 August 2009}}</ref> Other cyclopyrrolone drugs include [[zopiclone]], [[pagoclone]] and [[suriclone]].

Suproclone is very similar in structure to the related drug [[suriclone]], but little information has been published about it specifically. However it can be expected that the mechanism of action by which suproclone produces its sedative and anxiolytic effects is by modulating benzodiazepine receptors (resulting in an increased response to endogenous [[GABA]]), in a similar manner to other drugs of this class.<ref>{{cite journal | vauthors = Gardner CR | title = Pharmacological profiles in vivo of benzodiazepine receptor ligands. | journal = Drug Development Research | date = 1988 | volume = 12 | issue = 1 | pages = 1–28 | doi = 10.1002/ddr.430120102 | s2cid = 85573551 }}</ref><ref>{{cite book | vauthors = Doble A, Martin I, Nutt D | title = Calming the brain: benzodiazepines and related drugs from laboratory to clinic. | date = 23 October 2003 | publisher = Informa Healthcare | isbn = 1-84184-052-1 }}</ref>
==Synthesis==
[[File:Suproclone synthesis.svg|thumb|center|500px|[https://www.chemdrug.com/article/8/3284/16419747.html ChemDrug] Synthesis:<ref>Serradell, MN; Castaer, J.; Suproclone. Drugs Fut 1985, 10, 1, 45.</ref> Patent (Ex 1/15):<ref>Claude Cotrel, Claude Jeanmart, Mayer N. Messer, Cornel Crisan, {{US patent|4220646}} (1980 to Rhone-Poulenc Industries).</ref>]]
The condensation between 2,3-Dihydro-1,4-dithiino[2,3-c]furan-5,7-dione [10489-75-5] (1) and 7-Chloro-1,8-naphthyridin-2-amine [15944-33-9] (2) gives PC23343647 (3). Halogenation with phosphoryl chloride leads to PC23343652 (4). Reductino with potassium borohydride afforded [53788-25-3] (5). Treatment with phenyl chloroformate [1885-14-9] (6) resulted in 2-(7-chloro-1,8-naphthyridin-2-yl)-3-phenoxycarbonyloxy-isoindolin-1-one, PC23343637 (7). Reaction with piperazine [110-85-0] (8) afforded (9). Acylation with propionyl chloride completed the synthesis of Suproclone (10).

==References==
{{Reflist}}

{{Hypnotics and sedatives}}
{{GABAAR PAMs}}

[[Category:Carbamates]]
[[Category:Chloroarenes]]
[[Category:Cyclopyrrolones]]
[[Category:GABAA receptor positive allosteric modulators]]
[[Category:Lactams]]
[[Category:Naphthyridines]]
[[Category:Sedatives]]
[[Category:Dithianes]]
[[Category:Piperazines]]
[[Category:Nitrogen heterocycles]]
[[Category:Heterocyclic compounds with 2 rings]]
[[Category:Sulfur heterocycles]]

{{sedative-stub}}
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