Mazapertine

Source: Wikipedia, the free encyclopedia.
Mazapertine
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
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.[1]

Mazapertine is safe and well tolerated when administered orally.[2]

Analogs of mazapertine with conformational restriction have been prepared and have greater affinity for the 5-HT1A receptor.[3]

Synthesis

The laboratory synthesis of mazapertine has been reported.

Catalytic hydrogenation
of nitro group gives 2-isopropoxyaniline (3). Intermolecular ring formation of this aniline with bis(2-chloroethyl)amine yields 1-(2-isopropoxyphenyl)piperazine (4). Separately, amide formation of 3-(chloromethyl)benzoyl chloride (5) with piperidine gives 1-[3-(chloromethyl)benzoyl]piperidine (6). The last step is the convergent synthesis between the above two arms of the synthesis to afford the alkylation product mazapertine (7).

Synthesis of mazapertine

References

  1. PMID 9622541
    .
  2. S2CID 45947831
    .
  3. doi:10.1016/S0960-894X(97)00074-7
    .
  4. PMID 7909336
    .
  5. PMID 9622541
    .
  6. ^ Allen B. Reitz, U.S. patent 5,569,659 (1996 to Ortho McNeil Pharmaceutical Inc)
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