Monatepil

Monatepil is a calcium channel blocker and α1-adrenergic receptor antagonist used as an antihypertensive.[1]

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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Infobox references

Synthesis
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. S2CID 1548014.
  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. PMID 2002473.
  3. Hitoshi Uno, et al. U.S. Patent 4,749,703 (1988 to Dainippon Pharmaceutical Co Ltd).


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