Cetiedil

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

Cetiedil
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 InfoCard100.034.556
Chemical and physical data
FormulaC20H31NO2S
Molar mass349.53064 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 ☒N
  • Key:MMNICIJVQJJHHF-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Synthesis
Thieme Original patents:[2] Prepn and activity:[3] Revised synthesis:[4][5] Analogues:[6]

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).

References
  1. Alavi JB (May 1984). "Sickle cell anemia. Pathophysiology and treatment". The Medical Clinics of North America. 68 (3): 545–56. doi:10.1016/s0025-7125(16)31115-4. PMID 6205230.
  2. Pons, Robba, FR 1460571 and Pons et al., FR M5504 (1966, 1967, both to Innothera), C.A. 68, 59429d (1968); 71, 91286c (1969).
  3. Robba, LeGuen, Chim. Ther. 2, 120 (1967).
  4. Roxburgh, Craig J.; Ganellin, C. Robin; Shiner, Mark A. R.; Benton, David C. H.; Dunn, Philip M.; Ayalew, Yeshi; Jenkinson, Donald H. (1996). "The Synthesis and Some Pharmacological Actions of the Enantiomers of the K+-Channel Blocker Cetiedil". Journal of Pharmacy and Pharmacology. 48 (8): 851–859. doi:10.1111/j.2042-7158.1996.tb03986.x.
  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.


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