Monatepil

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Monatepil
Chemical structure of 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
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KEGG
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • 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) checkY
    Key: WFNRNNUZFPVBSM-UHFFFAOYSA-N checkY
  • 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).

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

Synthesis

[edit | edit source]

The synthesis of monatepil was first disclosed in patents filed by Dainippon Pharmaceutical.[2]

The amino group of the dihydrodibenzothiepin (1) is first reacted with the acid chloride of 4-chlorobutyric acid, to give the amide (3). This is then used to alkylate para-fluorophenylpiperazine (4) to yield monatepil.[2][3]

References

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  2. ^ a b US patent 4749703, Hitoshi Uno, et al., "Calcium antagonist piperazine derivatives, and compositions therefor", issued Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Dainippon Pharmaceutical Co Ltd 
  3. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).


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