Torres Gómez, Héctor Manuel; Torres-Gómez, Héctor Manuel; Gómez, Héctor Manuel Torres; Daniliuc, Constantin Gabriel; Daniliuc, Constantin G.; Daniliuc, Constantin; Daniliuc, C. G.; Schepmann, Dirk; Laurini, Erik; Pricl, Sabrina; Wünsch, Bernhard: Propellanes as Rigid Scaffolds for the Stereodefined Attachment of σ-Pharmacophoric Structural Elements to Achieve σ Affinity
Inhalt
- Chemistry
- Computational Studies
- Conclusions
- Experimental
- Chemistry, General Methods
- General Procedure A for the Synthesis of Carbamates and Ureas
- Synthetic Procedures
- (anti-11-Oxo[4.3.3]propellan-8-yl) N-(2-methoxy-5-methylphenyl)carbamate (anti-7) and (syn-11-Oxo[4.3.3]propellan-8-yl) N-(2-methoxy-5-methylphenyl)carbamate (syn-7)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(3,4-Dimethoxbenzylamino)[4.3.3] propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4b)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(4-Chlorobenzylamino)[4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4c)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(3,4-Dichlorobenzylamino)[4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4d)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(2,4-Dimethylbenzylamino)[4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4e)
- [(8-anti-11-anti and 8-anti-11-syn)-11-[(3,5-Bis(trifluoromethyl)benzylamino]-[4.3.3] propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4f)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(4-Nitrobenzylamino)[4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4g)
- [(8-anti-11-anti and 8-anti-11-syn)-11-[(4-Dimethylamino)benzylamino]-[4.3.3] propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4h)
- [(8-anti-11-anti and 8-anti-11-syn)-11-[(Furan-2-yl-mehtyl)amino][4.3.3] propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4i)
- [(8-syn-11-syn and 8-syn-11-anti)-11-[(Furan-2-yl-mehtyl)amino][4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-syn-4i)
- [(8-anti-11-anti and 8-anti-11-syn)-11-[2-(Indol-3-yl)ethylamino][4.3.3] propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4k)
- [(8-syn-11-syn and 8-syn-11-anti)-11-[(2-(Indol-3-yl)ethylamino][4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-syn-4k)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(Phenylamino)[4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4l)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(4-Methoxyphenylamino)[4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4m)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(3-Chloro-4-methoxyphenylamino)-[4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4n)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(4-Aminophenylamino)[4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4o)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(Phenethylamino)[4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4p)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(3-Phenylpropylamino)[4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4q)
- [(8-anti-11-anti and 8-anti-11-syn)-11-[(3-Aminopropyl)amino][4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4r)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(2-Hydroxyethyl-1-amino)[4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4s)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(5-Hydroxypentylamino)[4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4t)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(Isobutylamino)[4.3.3]propellan-8-yl] N-(2-methoxy-5-methylphenyl)carbamate (8-anti-4u)
- [(8-anti-11-anti and 8-anti-11-syn)-11-(Benzylamino)[4.3.3]propellan-8-ol (11-anti-13)
- [(8-syn-11-syn and 8-syn-11-anti)-11-(Benzylamino)[4.3.3]propellan-8-ol (11-syn-13)
- (11'-anti)-Spiro-([1,3]dioxolane-2,8'-(N-benzyl[4.3.3]propellan))-11'-amine (anti-14) and (11'-syn)-spiro-([1,3-dioxolane-2,8'-(N-benzyl[4.3.3]propellan))-11'-amine (syn-14)
- syn- and anti-N-[2-(Indol-3-yl)ethyl]-[4.3.3]propellan-8-amine (15)
- syn- and anti-N-(4-(Dimethylaminobenzyl)-[4.3.3]propellan-8-amine (17)
- syn- and anti-N-Cyclohexylmethyl[4.3.3]propellan-8-amine (18)
- 11-syn-11-Benzylamino[4.3.3]propellan-11-one (syn-20) and 11-anti-11-Benzylamino[4.3.3]propellan-8-one (anti-20)
- 1 -Benzyl-3-(2-methoxy-5-methylphenyl)-1-(syn-11-oxo-[4.3.3]propellan-8-yl)urea (syn-21)
- 1 -Benzyl-3-(2-methoxy-5-methylphenyl)-1-(anti-11-oxo-[4.3.3]propellan-8-yl)urea (anti-21)
- 1 -Benzyl-1-{(8-syn,11-anti)-11-hydroxy[4.3.3]propellan-8-yl}-3-(2-methoxy-5-methylphenyl)urea (syn,anti-22) and 1-benzyl-1-{(8-syn,11-syn)-11-hydroxy[4.3.3] propellan-8-yl}-3-(2-methoxy-5-methylphenyl)urea (syn,syn-22)
- 1 -Benzyl-1-{(8-anti,11-anti)-11-hydroxy[4.3.3]propellan-8-yl}-3-(2-methoxy-5-methylphenyl)urea (anti,anti-22) and 1-benzyl-1-{(8-anti,11-syn)-11-hydroxy[4.3.3] propellan-8-yl}-3-(2-methoxy-5-methylphenyl)urea (anti,syn-22)
- 1 -Phenyl-3-(syn- and anti-[4.3.3]propellan-8-yl)urea (23a)
- 1 -Cyclohexyl-3-(syn- and anti-[4.3.3]propellan-8-yl)urea (23b)
- 1 -(2-Methoxy-5-methylphenyl)-3-(syn- and anti-[4.3.3]propellan-8-yl)urea (23c)
- 1 -(3,4-Difluorophenyl)-3-(syn- and anti-[4.3.3]propellan-8-yl)urea (23d)
- (11'-syn and 11'-anti)-Spiro ([1,3]dioxolane-2,8'-[4.3.3]propellan)-11'-amine (24)
- 1 -(3,4-Difluorophenyl)-3-(syn- and anti-spiro[1,3]dioxolane-2,8’-[4.3.3] propellan-11’-yl)urea
- 1-(3,4-. Difluorophenyl)-3-(8-syn-11-oxo[4.3.3]propellan-8-yl)urea (syn-25) and 1-(3,4-Difluorophenyl)-3-(8-anti-11-oxo[4.3.3]propellan-8-yl)urea (anti-25)
- 1 -(3,4-Difluorophenyl)-3-(8-syn-11-syn- and 8-syn-11-anti-11-hydroxy[4.3.3]-propellan-8-yl)urea (syn,syn-26 and syn,anti-26)
- 1 -(3,4-Difluorophenyl)-3-(8-anti-11-anti-11-hydroxy[4.3.3]propellan-8-yl)urea (anti,anti-26) and 1-(3,4-Difluorophenyl)-3-(8-anti-11-syn-11-hydroxy[4.3.3] propellan-8-yl)urea (anti,syn-26)
- Computational Details
- X-ray Diffraction
- General
- X-ray Crystal Structure Analysis of syn-7
- X-ray Crystal Structure Analysis of anti-21
- X-ray Crystal Structure Analysis of syn,anti-22
- X-ray Crystal Structure Analysis of anti,syn-22
- X-ray Crystal Structure Analysis of syn-25
- Receptor Binding Studies
- References