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Dilazep

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Dilazep
Clinical data
Trade namesComelian Kowa
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 3-(4-{3-[(3,4,5-Trimethoxyphenyl)carbonyloxy]propyl}-1,4-diazepan-1-yl)propyl 3,4,5-trimethoxybenzoate
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC31H44N2O10
Molar mass604.697 g·mol−1
3D model (JSmol)
  • O=C(OCCCN2CCCN(CCCOC(=O)c1cc(OC)c(OC)c(OC)c1)CC2)c3cc(OC)c(OC)c(OC)c3
  • InChI=1S/C31H44N2O10/c1-36-24-18-22(19-25(37-2)28(24)40-5)30(34)42-16-8-12-32-10-7-11-33(15-14-32)13-9-17-43-31(35)23-20-26(38-3)29(41-6)27(21-23)39-4/h18-21H,7-17H2,1-6H3 checkY
  • Key:QVZCXCJXTMIDME-UHFFFAOYSA-N checkY
  (verify)

Dilazep is avasodilator that acts as anadenosine reuptake inhibitor.[1][2]

It is used for the treatment ofcardiopathy andrenal disorders.[3]

Synthesis

[edit]

The reaction of bis(3-hydroxypropyl)ethylene diamine (1) with1-bromo-3-chloropropane (2) gives thehomopiperazine derivative3. Esterification by reaction with 3,4,5-trimethoxybenzoyl chloride (4) completes the synthesis of dilazep (5).[4][5][6]

Synthesis of dilazep

See also

[edit]

References

[edit]
  1. ^Deguchi H, Takeya H, Wada H, Gabazza EC, Hayashi N, Urano H, Suzuki K (September 1997)."Dilazep, an antiplatelet agent, inhibits tissue factor expression in endothelial cells and monocytes".Blood.90 (6):2345–56.doi:10.1182/blood.V90.6.2345.PMID 9310485.
  2. ^PubChem."Dilazep".pubchem.ncbi.nlm.nih.gov. Retrieved2021-08-18.
  3. ^"Pharmaceuticals". Kowa Company Ltd.
  4. ^Thieme
  5. ^GB1107470 idem Herbert Arnold, Kurt Pahls, Rolf Rebling,Norbert Brock, Hans-Dieter Lenke,U.S. patent 3,532,685 (1970 to Asta Werke Ag Chem Fab)
  6. ^Schlögl, K., Schlögl, R. (1964). "Über pharmakodynamisch wirksame 3,4,5-Trimethoxybenzoate und verwandte Ester von symmetrischen Bis-hydroxyalkylpiperazinen und-dialkylpolymethylendiaminen".Monatshefte für Chemie.95 (3):922–941.doi:10.1007/BF00908805.
Nitrovasodilators
Quinolone vasodilators
Others
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others
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