Suritozole

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Suritozole
File:Suritozole.svg
Clinical data
ATC code
  • none
Identifiers
  • 5-(3-fluorophenyl)-2,4-dimethyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC10H10FN3S
Molar mass223.27 g·mol−1
3D model (JSmol)
  • Cn1c(=S)n(C)nc1-c2cccc(F)c2
  • InChI=1S/C10H10FN3S/c1-13-9(12-14(2)10(13)15)7-4-3-5-8(11)6-7/h3-6H,1-2H3 ☒N
  • Key:IWDUZEHNLHFBRZ-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Suritozole (MDL 26,479) is an investigational cognition enhancer. It acts as a partial inverse agonist at the benzodiazepine receptor site on the GABAA ion channel complex, but does not have either anxiogenic or convulsant effects, unlike other BZD inverse agonists such as DMCM.[1] It was investigated for the treatment of depression and Alzheimer's disease in the 90s,[2] but clinical development seems to have been discontinued.

Synthesis

[edit | edit source]
File:Suritozole synthesis.svg
Synthesis:[3][4] ~85%:[5] Patents:[6][7] etc

The reaction between monomethylhydrazine [60-34-4] (1) and methyl isothiocyanate (Trapex) [556-61-6] (2) gave 2,4-dimethylthiosemicarbazide [6621-75-6] (3). Amide formation with 3-fluorobenzoyl chloride [1711-07-5] (4) yielded 1-(3-fluorobenzoyl)-2,4-dimethylthiosemicarbazide [110623-52-4] (5). Cyclization to Suritozole (6).

See also

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References

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  6. ^ US5856350 idem Christopher Robin Dalton, John Michael Kane, John Herr Kehne, WO 1996033177  (1999 to Hoechst Marion Roussel, Inc.).
  7. ^ US5723624 idem Sandra K. Stolz-Dunn, David H. Louks, Yolanda M. Puga, Christian T. Goralski, WO 1996001812  (1998 to Merrell Pharmaceuticals Inc).
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