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Antipsychotic
Mazapertine
Другие языки:

Mazapertine

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Mazapertine
Mazapertine.svg
Names
Preferred IUPAC name
(Piperidin-1-yl){3-[(4-{2-[(propan-2-yl)oxy]phenyl}piperazin-1-yl)methyl]phenyl}methanone
Other names
RWJ-37796
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C26H35N3O2/c1-21(2)31-25-12-5-4-11-24(25)28-17-15-27(16-18-28)20-22-9-8-10-23(19-22)26(30)29-13-6-3-7-14-29/h4-5,8-12,19,21H,3,6-7,13-18,20H2,1-2H3
    Key: ZKZFPRUSWCYSGT-UHFFFAOYSA-N
  • O=C(N1CCCCC1)c2cc(ccc2)CN4CCN(c3ccccc3OC(C)C)CC4
Properties
C26H35N3O2
Molar mass 421.585 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Mazapertine (RWJ-37796) is an antipsychotic agent that was developed by Johnson & Johnson but never marketed. It exerts its pharmacological effect through affinity for dopamine D2, serotonin 5-HT1A, and α1-adrenergic receptors.

Mazapertine is safe and well tolerated when administered orally.

Analogs of mazapertine with conformational restriction have been prepared and have greater affinity for the 5-HT1A receptor.

Synthesis

Synthesis: Patent:

Alkylation of 2-Nitrophenol [88-75-5] (1) with isopropyl bromide gives 2-isopropoxynitrobenzene [38753-50-3] (2). Catalytic hydrogenation of nitro group gives 2-isopropoxyaniline [29026-74-2] (3). Intermolecular ring formation of this aniline with nornitrogen mustard [334-22-5] yields 1-(2-isopropoxyphenyl)piperazine [54013-91-1] (4).

Amide formation of 3-(chloromethyl)benzoyl chloride [63024-77-1] (5) with piperidine gives 1-[3-(chloromethyl)benzoyl]piperidine [148583-64-6] (6).

Ex 1: The last step is the convergent synthesis between the above two arms of the synthesis to afford the alkylation product mazapertine (7).



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