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The benzofuranethanamines 3a and 3b were synthesized and pharmacologically tested to investigate structure-activity relationships with antiarrhythmic compounds. The key-step in the synthesis was the chemoselective reduction of the chloroacetyl-dihydrobenzofurane 5 to chloroethylbenzofurane 9 using triethylsilane/BF3.Et2O. Results of a series of further attempts to reduce 5 are also described. Pharmacological investigations on isolated guinea pig heart muscle preparations showed that 3a exhibits similar negative inotropic and negative chronotropic action in comparison to propafenone and the conformationally restricted benzofurane 1a. In contrast to these substances, however, 3a shows no beta 1-adrenoreceptor blocking activity.
G Ecker, and
T Helml, and
W Fleischhacker, and
C R Noe, and
C Studenik, and
B Schade, and
P Heistracher
December 2012,
Bioorganic & medicinal chemistry,
G Ecker, and
T Helml, and
W Fleischhacker, and
C R Noe, and
C Studenik, and
B Schade, and
P Heistracher
February 1994,
Drug design and discovery,
G Ecker, and
T Helml, and
W Fleischhacker, and
C R Noe, and
C Studenik, and
B Schade, and
P Heistracher
February 2009,
Acta crystallographica. Section E, Structure reports online,
G Ecker, and
T Helml, and
W Fleischhacker, and
C R Noe, and
C Studenik, and
B Schade, and
P Heistracher
December 2008,
Acta crystallographica. Section E, Structure reports online,
G Ecker, and
T Helml, and
W Fleischhacker, and
C R Noe, and
C Studenik, and
B Schade, and
P Heistracher
April 2009,
Acta crystallographica. Section E, Structure reports online,
G Ecker, and
T Helml, and
W Fleischhacker, and
C R Noe, and
C Studenik, and
B Schade, and
P Heistracher
February 2009,
Acta crystallographica. Section E, Structure reports online,
G Ecker, and
T Helml, and
W Fleischhacker, and
C R Noe, and
C Studenik, and
B Schade, and
P Heistracher
March 2013,
Medicinal chemistry (Shariqah (United Arab Emirates)),
G Ecker, and
T Helml, and
W Fleischhacker, and
C R Noe, and
C Studenik, and
B Schade, and
P Heistracher
April 2007,
Bioorganic & medicinal chemistry,
G Ecker, and
T Helml, and
W Fleischhacker, and
C R Noe, and
C Studenik, and
B Schade, and
P Heistracher
July 2010,
Bioorganic & medicinal chemistry,
G Ecker, and
T Helml, and
W Fleischhacker, and
C R Noe, and
C Studenik, and
B Schade, and
P Heistracher
October 2012,
Acta crystallographica. Section E, Structure reports online,
