Monatepil

In today's world, Monatepil has become a topic of great relevance and interest to a wide spectrum of people. Whether due to its impact on society, its historical relevance or its influence on popular culture, Monatepil continues to capture the attention of millions of individuals around the world. With a history dating back centuries, Monatepil has evolved and adapted to the changes and advancements of modern society. In this article, we will explore in depth everything related to Monatepil, from its origins to its current impact on different aspects of everyday life.

Monatepil
Chemical structure of monatepil
Chemical structure of monatepil
Names
Preferred IUPAC name
N-(6,11-Dihydrodibenzothiepin-11-yl)-4-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) 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 , 100 kPa).

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

Synthesis

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

  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. ^ a b US patent 4749703, Hitoshi Uno, et al., "Calcium antagonist piperazine derivatives, and compositions therefor", issued 1988-06-07, assigned to Dainippon Pharmaceutical Co Ltd 
  3. ^ Kurokawa, Mikio; Sato, Fuminori; Fujiwara, Iwao; et al. (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.


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