Cloricromen
{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name = Ethyl 2-(8-chloro-3-(2-(diethylamino)ethyl)-4-methyl-2-oxo-2H-chromen-7-yloxy)acetate
| image = Cloricromen.svg
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| CAS_number = 68206-94-0
| ATC_prefix = B01
| ATC_suffix = AC02
| PubChem = 68876
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 62108
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = B9454PE93C
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07139
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 255066
| C=20 | H=26 | Cl=1 | N=1 | O=5
| smiles = O=C(OCC)COc2ccc\1c(OC(=O)/C(=C/1C)CCN(CC)CC)c2Cl
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H26ClNO5/c1-5-22(6-2)11-10-15-13(4)14-8-9-16(26-12-17(23)25-7-3)18(21)19(14)27-20(15)24/h8-9H,5-7,10-12H2,1-4H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GYNNRVJJLAVVTQ-UHFFFAOYSA-N
}}
Cloricromen is a platelet aggregation inhibitor.{{cite journal | vauthors = Orefice G, Grasso A, Fazio N, Del Vecchio G, Volpe G, Coppola M, D'Alessio A, Carrieri PB | title = No effect of cloricromen on some coagulation parameters in patients with ischaemic cerebrovascular disease | journal = The Journal of International Medical Research | volume = 22 | issue = 5 | pages = 287–91 | date = 1994 | pmid = 7867874 | doi = 10.1177/030006059402200506 | s2cid = 36081514 }} Coronary vasodilator.
Synthesis
Base catalyzed alkylation of ethyl acetoacetate (1) with 2-chlorotriethylamine (2) gives compound (3). Separately, disulfonation of resorcinol (4) with 96% sulfuric acid gives the disulfonic acid (5). This is chlorinated with potassium chlorate to give 5-chloro-4,6-dihydroxybenzene-1,3-disulfonic acid (6). Removal of the sulfonate groups in dilute acid then gives 2-chlororesorcinol (7).{{cite book |doi=10.1007/978-1-4684-7218-9_1 |chapter=Protection of C-H Bonds |title=Protective Groups in Organic Chemistry |page=14 |date=1973 |last1=Walton |first1=D. R. M. |isbn=978-1-4684-7220-2 }} An acid-catalyzed condensation reaction between (3) and (7) produces the intermediate (8). Ether formation at its phenolic hydroxyl group with ethyl bromoacetate (9) completes the synthesis of cloricromen.Francesco Della Valle, {{US patent|4452811}} (1984 to Fidia S.P.A.).{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-03-0223 |title=Cloricromen |publisher=Thieme}}
See also
- Carbocromen is the analogue without the chlorine substituent