Guanochlor

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Guanochlor
Guanoclor.png
ATC code C02CC05 (WHO)
Identifiers
Systematic (IUPAC) name: 2-{[2-(2,6-dichlorophenoxy)ethyl]amino}guanidine
CAS Number 5001-32-1
PubChem (CID) 71835
ChemSpider 64857
Chemical and physical data
Formula C9H12Cl2N4O
Molar mass 263.12 g/mol
3D model (Jmol) Interactive image
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Guanoclor is a sympatholytic drug. It is known to bind to non-adrenergic sites in pig kidney membranes.[1]

Synthesis[edit]

Guanochlor synthesis:[2][3]

When β-(2,6-dichlorophenoxy)ethyl bromide (1) is reacted with hydrazine to give 2, and this is reacted with S-methylthiourea, guanochlor (3) results.

Guanoxyfen[edit]

Guanoxyfen synthesis:[4] (based on Dan's book)

Guanoxyfen is synthesized by base-catalyzed condensation of phenol with chloroacetonitrile, followed by hydride reduction to amine 2. The guanido function is introduced by reaction with S-methylthiourea to give guanoxyfen (3).

References[edit]

  1. ^ Vigne, Paul; Michael Lazdunski; Christian Frelin (31 January 1989). "Guanabenz, guanochlor, guanoxan and idazoxan bind with high affinity to non-adrenergic sites in pig kidney membranes". European Journal of Pharmacology. 160 (2): 295–298. doi:10.1016/0014-2999(89)90503-7. PMID 2527160. 
  2. ^ Durant, G. J.; Smith, G. M.; Spickett, R. G. W.; Wright, S. H. B. (1966). "Biologically Active Guanidines and Related Compounds. II. Some Antiinflammatory Aminoguanidines1". Journal of Medicinal Chemistry. 9 (1): 22–7. doi:10.1021/jm00319a005. PMID 5958955. 
  3. ^ Prepn of free base and sulfate: BE 629613  (1963 to Pfizer), C.A. 60, 14437d (1964).
  4. ^ Barron, D. I.; Bavin, P. M. G.; Durant, G. J.; Natoff, I. L.; Spickett, R. G. W.; Vallance, D. K. (1963). "Potential Antihypertensive Agents. Some Guanidine Derivatives". Journal of Medicinal Chemistry. 6 (6): 705. doi:10.1021/jm00342a017.