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Aganodine ,ZYF Pharm Chemical

Aganodine is a guanidine that activates presynaptic imidazoline receptors and can inhibit electrically evoked [3H]-norepinephrine release[1][2][3].

The solution of 3,6-dichlorophthalic anhydride in 300 ml of N,Ndimethylformamide are heated to the boiling point over 15 min with tbutylcarbazate. Subsequent to evaporation of the solvent, N-(tbutyloxycarbonylamino)- 3,6-dichlorophthalimide is obtained from ethanol.
The solution of N-(t-butyloxycarbonylamino)-3,6-dichlorophthalimide in 400 ml of absolute tetrahydrofuran are slowly dripped into a suspension of aluminum lithium hydride in absolute tetrahydrofuran. The mixture is heated to the boiling point. Conventional processing yields N-(t-butyloxycarbonylamino)-4,7- dichloroisoindoline.
N-(t-Butyloxycarbonylamino)-4,7-dichloroisoindoline are introduced into concentrated hydrochloric acid and stirred at room temperature. The hydrochloride of 2-amino-4,7-dichloroisoindoline precipitates in the form of crystals is obtained, melting point 230°-232°C.
2-Amino-4,7-dichloroisoindoline hydrochloride and cyanamide are heated over 2 h to the boiling point in n-amyl alcohol. The solvent is evaporated off and the residue recrystallized from isopropyl alcohol and ethyl ether, yielding the (4,7-dichloroisoindolin-2-yl)guanidine in the form of hydrochloride, melting point 235°-237°C.
To obtained the base (4,7-dichloroisoindolin-2-yl)guanidine the salt (4,7- dichloroisoindolin-2-yl)guanidine hydrochloride is treated with sodium bicarbonicum.

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[1] Molderings G J, et al. Presynaptic imidazoline receptors and non‐adrenoceptor [3H]‐idazoxan binding sites in human cardiovascular tissues[J]. British journal of pharmacology, 1997, 122(1): 43-50.
[2] G?thert M, et al. α2‐Adrenoceptor‐independent inhibition by imidazolines and guanidines of noradrenaline release from peripheral, but not central noradrenergic neurons[J]. Annals of the New York Academy of Sciences, 1995, 763(1): 405-419.
[3] Schlicker E, et al. Effects of imidazolines in noradrenaline release in brain: An investigation into their relationship to imidazoline, α2 and H3 receptors[J]. Neurochemistry international, 1997, 30(1): 73-83. DOI:10.1016/s0197-0186(96)00045-9