Monatepil
Chemical structure of monatepil
Names
Preferred IUPAC name
N-(6,11-Dihydrodibenzo[b,e]thiepin-11-yl)-4-[4-(4-fluorophenyl)piperazin-1-yl]butanamide
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
  • InChI=1S/C28H30FN3OS/c29-22-11-13-23(14-12-22)32-18-16-31(17-19-32)15-5-10-27(33)30-28-24-7-2-1-6-21(24)20-34-26-9-4-3-8-25(26)28/h1-4,6-9,11-14,28H,5,10,15-20H2,(H,30,33) ☒N
    Key: WFNRNNUZFPVBSM-UHFFFAOYSA-N ☒N
  • InChI=1/C28H30FN3OS/c29-22-11-13-23(14-12-22)32-18-16-31(17-19-32)15-5-10-27(33)30-28-24-7-2-1-6-21(24)20-34-26-9-4-3-8-25(26)28/h1-4,6-9,11-14,28H,5,10,15-20H2,(H,30,33)
    Key: WFNRNNUZFPVBSM-UHFFFAOYAJ
  • C1CN(CCN1CCCC(=O)NC2C3=CC=CC=C3CSC4=CC=CC=C24)C5=CC=C(C=C5)F
Properties
C28H30FN3OS
Molar mass 475.63 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Monatepil is a calcium channel blocker and α1-adrenergic receptor antagonist used as an antihypertensive.[1]

Synthesis

Synthesis:[2] Patent:[3]
Synthesis:[2] Patent:[3]

Acylation of [1745-53-5] (1) with 4-chlorobutyryl chloride [4635-59-0] (2) then leads to the corresponding amide 4-Chloro-N-(5,11-dihydro-10-thia-dibenzo[a,d]cyclohepten-5-yl)-butyramide [103379-37-9] (3). Alkylation with para-Fluorophenylpiperazine [2252-63-3] (4) then completed the synthesis of monatepil (5).

References

  1. ^ Sugimoto T, Hosoki K, Karasawa T (July 1995). "Relative contribution of alpha 1-adrenoceptor blocking activity to the hypotensive effect of the novel calcium antagonist monatepil". Journal of Cardiovascular Pharmacology. 26 (1): 55–60. doi:10.1097/00005344-199507000-00009. PMID 7564365.
  2. ^ Kurokawa, M., Sato, F., Fujiwara, I., Hatano, N., Honda, Y., Yoshida, T., Naruto, S., Mastumoto, J., Uno, H. (March 1991). "A new class of calcium antagonists. 2. Synthesis and biological activity of 11-[4-[4-(4-fluorophenyl)-1-piperazinyl]butyryl]amino]-6,11-dihydrodibenzo[b,e]thiepin maleate and related compounds". Journal of Medicinal Chemistry. 34 (3): 927–934. doi:10.1021/jm00107a009.
  3. ^ Hitoshi Uno, et al. U.S. Patent 4,749,703 (1988 to Dainippon Pharmaceutical Co Ltd).