Cetiedil

Last updated
Cetiedil
Cetiedil small.png
Cetiedil-3D-balls.png
Clinical data
ATC code
Identifiers
  • 2-(azepan-1-yl)ethyl 2-cyclohexyl-2-(thiophen-3-yl)acetate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard 100.034.556 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H31NO2S
Molar mass 349.53064 g·mol−1
3D model (JSmol)
  • O=C(OCCN1CCCCCC1)C(c2ccsc2)C3CCCCC3
  • InChI=1S/C20H31NO2S/c22-20(23-14-13-21-11-6-1-2-7-12-21)19(18-10-15-24-16-18)17-8-4-3-5-9-17/h10,15-17,19H,1-9,11-14H2 X mark.svgN
  • Key:MMNICIJVQJJHHF-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Cetiedil is a vasodilator and an anti-sickling agent. [1]

Synthesis

Thieme Original patents: Prepn and activity: Revised synthesis: Analogues: Cetiedil synthesis.svg
Thieme Original patents: Prepn and activity: Revised synthesis: Analogues:

The Clemmensen reduction of 3-thienylcyclohexyl-glycolic acid, CID:11064522 (1) gives cyclohexyl(thiophen-3-yl)acetic acid [16199-74-9] (2). Esterification of the sodium salt of the resulting acid with 1-(2-chloroethyl)azepane [2205-31-4] (3) produces cetiedil (4).

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References

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  5. Charles Pigerol, et al. U.S. Patent 4,108,865 (1978 to Labaz SA).
  6. Roxburgh, Craig J.; Ganellin, C. Robin; Athmani, Salah; Bisi, Alessandra; Quaglia, Wilma; Benton, David C. H.; Shiner, Mark A. R.; Malik-Hall, Misbah; Haylett, Dennis G.; Jenkinson, Donald H. (2001). "Synthesis and Structure−Activity Relationships of Cetiedil Analogues as Blockers of the Ca2+-Activated K+Permeability of Erythrocytes†". Journal of Medicinal Chemistry. 44 (20): 3244–3253. doi:10.1021/jm001113w.