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tametraline : ウィキペディア英語版
tametraline

Tametraline (CP-24,441) is the parent of a series of chemical compounds investigated at Pfizer that eventually led to the development of sertraline (CP-51,974-1).
Sertraline has been called "3,4-dichloro tametraline". This is correct but it is an oversimplification in the sense that sertraline is the ''SS ''isomer whereas tametraline is the ''1R'',''4S ''stereoisomer.
''1R''-Methylamino-''4S''-phenyl-tetralin is a potent inhibitor of norepinephrine uptake in rat brain synaptosomes, reverses reserpine induced hypothermia in mice, and blocks uptake of () into rat heart.
Tametraline is a norepinephrine-dopamine reuptake inhibitor.
Indatraline is an indanamine homolog of tetralin-based tametraline, although in the case of indatraline the product is pm-dichlorinated.
==Chemistry==
Two routes have been previously described, one for aryl moieties containing electron withdrawing groups, and one for electron donating groups:
"As expected, Friedel-Crafts cyclization of the diarylbutyric acid derivatives # to the most reactive ring was observed with little or none of the alternative isomer being detected."
"The KMnO4 oxidation of the 1-aryl-tetralins # was observed to give 4-hydroxy-4-aryltetralones # instead of the expected tetralone # previously reported.〔 As a result of this finding, direct oxidation of Grignard reaction product # was attempted and found to be a more efficient route."
See also: (and refs therein: )

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
ウィキペディアで「tametraline」の詳細全文を読む



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