Cloricromen

Last updated
Cloricromen
Cloricromen.svg
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 InfoCard 100.164.003 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H26ClNO5
Molar mass 395.88 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 Yes check.svgY
  • Key:GYNNRVJJLAVVTQ-UHFFFAOYSA-N Yes check.svgY

Cloricromen is a platelet aggregation inhibitor. [1] Coronary vasodilator.

Contents

Synthesis

Cloricromen synthesis.svg

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

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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