3,4,5-trimethoxyphenol (aka Antiarol) [642-71-7] (1) is alkylated with epichlorohydrin (2) to give [(3,4,5-Trimethoxyphenoxy)methyl]oxirane [74760-14-8] (3). Opening of the epoxide with o-anisyl-piperazine [35386-24-4] (4) completes the synthesis of enciprazine (5).
^
abMatheson GK, Knowles A, Gage D, Michel C, Guthrie D, Bauer C, Blackbourne J, Weinzapfel D (1997). "Modification of hypothalamic-pituitary-adrenocortical activity by serotonergic agents in the rat". Pharmacology. 55 (2): 59–65.
doi:
10.1159/000139513.
PMID9323305.
^
abScatina JA, Lockhead SR, Cayen MN, Sisenwine SF (1991). "Metabolic disposition of enciprazine, a non-benzodiazepine anxiolytic drug, in rat, dog and man". Xenobiotica. 21 (12): 1591–604.
doi:
10.3109/00498259109044408.
PMID1686125.
^Linden M, Helmchen H, Müller-Oerlinghausen B (1988). "Early phase-II semi double-blind study of the new alkaline propanolamine derivative enciprazine (short communication)". Arzneimittelforschung. 38 (6): 814–6.
PMID3178922.
^Engel J, Fleischhauer I, Jakovlev V, Kleemann A, Kutscher B, Nickel B, Rauer H, Werner U, Szelenyi I, Johanson CE (November 1990). "Chemistry and pharmacology of the non-benzodiazepine anxiolytic enciprazine and related compounds". Journal of Medicinal Chemistry. 33 (11): 2976–81.
doi:
10.1021/jm00173a012.
PMID1977910.
^Banoth L, Narayan TK, Banerjee UC (September 2012). "New chemical and chemo-enzymatic routes for the synthesis of (RS)-and (S)-enciprazine". Tetrahedron: Asymmetry. 23 (17): 1272–1278.
doi:
10.1016/j.tetasy.2012.08.002.
^Narsaiah AV, Nagaiah B (August 2010). "A simple and efficient asymmetric synthesis of anxiolytic drug enciprazine". Synthesis. 2010 (16): 2705–2707.
doi:
10.1055/s-0030-1258173.
3,4,5-trimethoxyphenol (aka Antiarol) [642-71-7] (1) is alkylated with epichlorohydrin (2) to give [(3,4,5-Trimethoxyphenoxy)methyl]oxirane [74760-14-8] (3). Opening of the epoxide with o-anisyl-piperazine [35386-24-4] (4) completes the synthesis of enciprazine (5).
^
abMatheson GK, Knowles A, Gage D, Michel C, Guthrie D, Bauer C, Blackbourne J, Weinzapfel D (1997). "Modification of hypothalamic-pituitary-adrenocortical activity by serotonergic agents in the rat". Pharmacology. 55 (2): 59–65.
doi:
10.1159/000139513.
PMID9323305.
^
abScatina JA, Lockhead SR, Cayen MN, Sisenwine SF (1991). "Metabolic disposition of enciprazine, a non-benzodiazepine anxiolytic drug, in rat, dog and man". Xenobiotica. 21 (12): 1591–604.
doi:
10.3109/00498259109044408.
PMID1686125.
^Linden M, Helmchen H, Müller-Oerlinghausen B (1988). "Early phase-II semi double-blind study of the new alkaline propanolamine derivative enciprazine (short communication)". Arzneimittelforschung. 38 (6): 814–6.
PMID3178922.
^Engel J, Fleischhauer I, Jakovlev V, Kleemann A, Kutscher B, Nickel B, Rauer H, Werner U, Szelenyi I, Johanson CE (November 1990). "Chemistry and pharmacology of the non-benzodiazepine anxiolytic enciprazine and related compounds". Journal of Medicinal Chemistry. 33 (11): 2976–81.
doi:
10.1021/jm00173a012.
PMID1977910.
^Banoth L, Narayan TK, Banerjee UC (September 2012). "New chemical and chemo-enzymatic routes for the synthesis of (RS)-and (S)-enciprazine". Tetrahedron: Asymmetry. 23 (17): 1272–1278.
doi:
10.1016/j.tetasy.2012.08.002.
^Narsaiah AV, Nagaiah B (August 2010). "A simple and efficient asymmetric synthesis of anxiolytic drug enciprazine". Synthesis. 2010 (16): 2705–2707.
doi:
10.1055/s-0030-1258173.