Cinepazet

Cinepazet is a vasodilator and is an ethyl ester derivative of cinepazic acid.[1]

Cinepazet
Clinical data
ATC code
Identifiers
IUPAC name
  • Ethyl 2-{4-[(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]piperazin-1-yl}acetate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.041.738
Chemical and physical data
FormulaC20H28N2O6
Molar mass392.452 g·mol−1
3D model (JSmol)
Density1.172 g/cm3
SMILES
  • CCOC(=O)CN1CCN(CC1)C(=O)\C=C\c2cc(OC)c(OC)c(OC)c2
InChI
  • InChI=1S/C20H28N2O6/c1-5-28-19(24)14-21-8-10-22(11-9-21)18(23)7-6-15-12-16(25-2)20(27-4)17(13-15)26-3/h6-7,12-13H,5,8-11,14H2,1-4H3/b7-6+
  • Key:XDUOTWNXVDBCDY-VOTSOKGWSA-N

Synthesis
Thieme Patents:[2][3]

The alkylation between benzylpiperazine (1) and ethyl chloroacetate (2) gives ethyl 2-(4-benzylpiperazin-1-yl)acetate [23173-76-4] (3). The benzyl protecting group is easily cleaved by catalytic hydrogenation giving ethyl 2-(piperazin-1-yl)acetate [40004-08-8] (4). The Schotten-Baumann reaction with 3,4,5-trimethoxycinnamoyl chloride [4521-61-3] (5) gives the amide, and hence completing the synthesis of Cinepazet (6).

References
  1. Morton IK, Hall JM (1999). "Cinepazet". Concise Dictionary of Pharmacological Agents : Properties and Synonyms. Dordrecht: Springer Netherlands. p. 77. ISBN 9789401144391.
  2. Raynaud, G.; Pourias, B.; Fauran, F.; Turin, M.; 1977, U.S. Patent 4,029,650 (1977 to Delalande S. A.).
  3. GB1168108 idem Claude Fauran, Gerard Huguet, Guy Raynaud, Bernard Pourrias, Michel Turin, U.S. Patent 3,590,034 (1971 to Delalande Sa).
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