Cloricromen

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Cloricromen
Clinical data
ATC code
Identifiers
  • Ethyl 2-(8-chloro-3-(2-(diethylamino)ethyl)-4-methyl-2-oxo-2H-chromen-7-yloxy)acetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.164.003 Edit this at Wikidata
Chemical and physical data
FormulaC20H26ClNO5
Molar mass395.88 g·mol−1
3D model (JSmol)
  • O=C(OCC)COc2ccc\1c(OC(=O)/C(=C/1C)CCN(CC)CC)c2Cl
  • InChI=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 checkY
  • Key:GYNNRVJJLAVVTQ-UHFFFAOYSA-N checkY

Cloricromen is a platelet aggregation inhibitor.[1] 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).[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.[3][4]

See also

  • Carbocromen is the analogue without the chlorine substituent

References

  1. ^ Orefice G, Grasso A, Fazio N, Del Vecchio G, Volpe G, Coppola M, D'Alessio A, Carrieri PB (1994). "No effect of cloricromen on some coagulation parameters in patients with ischaemic cerebrovascular disease". The Journal of International Medical Research. 22 (5): 287–91. doi:10.1177/030006059402200506. PMID 7867874. S2CID 36081514.
  2. ^ Walton, D. R. M. (1973). "Protection of C-H Bonds". Protective Groups in Organic Chemistry. p. 14. doi:10.1007/978-1-4684-7218-9_1. ISBN 978-1-4684-7220-2.
  3. ^ Francesco Della Valle, U.S. patent 4,452,811 (1984 to Fidia S.P.A.).
  4. ^ "Cloricromen". Thieme.


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