Guanochlor

Guanochlor

Systematic (IUPAC) name
2-{[2-(2,6-dichlorophenoxy)ethyl]amino}guanidine
Identifiers
CAS Number	5001-32-1
ATC code	C02CC05 (WHO)
PubChem	CID 71835
ChemSpider	64857
Chemical data
Formula	C9H12Cl2N4O
Molar mass	263.12 g/mol
SMILES C1=CC(=C(C(=C1)Cl)OCCNNC(=N)N)Cl
InChI InChI=1S/C9H12Cl2N4O/c10-6-2-1-3-7(11)8(6)16-5-4-14-15-9(12)13/h1-3,14H,4-5H2,(H4,12,13,15) Key:XIHXRRMCNSMUET-UHFFFAOYSA-N
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Guanoclor is a sympatholytic drug. It is known to bind to non-adrenergic sites in pig kidney membranes.^[1]

Synthesis

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

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

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.