Clemeprol

Clemeprol
Clinical data
Other namesBRL 14342
Identifiers
IUPAC name
  • 1-(3-chlorophenyl)-3-(dimethylamino)-1-phenylpropan-2-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H20ClNO
Molar mass289.80 g·mol−1
3D model (JSmol)
SMILES
  • CN(C)CC(C(C1=CC=CC=C1)C2=CC(=CC=C2)Cl)O
InChI
  • InChI=InChI=1S/C17H20ClNO/c1-19(2)12-16(20)17(13-7-4-3-5-8-13)14-9-6-10-15(18)11-14/h3-11,16-17,20H,12H2,1-2H3
  • Key:KGSABFQIAANNPS-UHFFFAOYSA-N

Clemeprol is an serotonin–norepinephrine reuptake inhibitor (SNRI) antidepressant and anticholinergic agent.[1]

It is an enantiomeric mixture of R and S isomers. Both isomers show similar pharmacological activity.[2][3]

Synthesis

A synthetic pathway for clemeprol is disclosed: [4][5][6][7][8]

Clemeprol synthesis
Clemeprol synthesis

The Corey-Chaykovsky epoxidation between 3-chlorobenzophenone [1016-78-0] (1) and dimethylsulfoxonium methylide (Corey's reagent) [5367-24-8], gives 2-(3-chlorophenyl)-2-phenyloxirane [71827-53-7] (2). Further reaction with boron trifluoride etherate [109-63-7] gives m-chlorophenyl-phenylacetaldehyde, PC12549135 (3). A second Corey-Chaykovsky epoxidation gives 2-[(3-chlorophenyl)-phenylmethyl]oxirane, PC12549073 (4). Quenching with dimethylamine completes the synthesis of clemeprol (5).

See also

References

  1. ↑ Dictionary of Pharmacological Agents By C.R. Ganellin, David J. Triggle.
  2. ↑ Clark MS, Johnson AM, McClelland GR, Nelson DR (December 1980). "Pharmacological and biochemical properties of BRL 14342, a novel potential antidepressant drug". Neuropharmacology. 19 (12): 1207–8. doi:10.1016/0028-3908(80)90203-8. PMID 7442949.
  3. ↑ Koch, H., Drugs Future, 1983,8, 194.
  4. ↑ Clark JA, Clark MS, Gardner DV, Gaster LM, Hadley MS, Miller D, et al. (November 1979). "Substituted 3-amino-1,1-diaryl-2-propanols as potential antidepressant agents". Journal of Medicinal Chemistry. 22 (11): 1373–9. doi:10.1021/jm00197a018. PMID 533885.
  5. ↑ Anon., GB1448437 (1976-09-08 to Beecham Group Ltd).
  6. ↑ Judith Ann Clark, US4101676 & US4113972 (1978 to Beecham Group PLC).
  7. ↑ Judith Ann Clark, US4056630 (1977 to Beecham Group PLC).
  8. ↑ CA1049530 idem Judith Ann Clark, US4028415 (1977 to Beecham Group PLC).
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