Two intermediates in the synthesis of decahydroisoquinolines with NMDA and AMPA receptor antagonist activity.
In 6-methyl-N-(4-nitrobenzoyl)-5,6-dihydropyridin-2(1H)-one, C(13)H(12)N(2)O(4), (I), the piperidone ring is in a distorted half-chair conformation. In 8-methoxy-3-methyl-N-(4-nitrobenzoyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline-1,6-dione, C(18)H(20)N(2)O(6), (II), the heterocyclic ring is in a slightly distorted half-boat conformation, while the other six-membered ring is in a distorted chair conformation. Compound (II) presents a strong intramolecular C-H...O hydrogen bond. In both (I) and (II), the molecules interact through C-H...O interactions.
Zukerman-Schpector
J
J
Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil. julio@power.ufscar.br
Vega
M
M
Caracelli
I
I
Dias
L C
LC
Fernandes
A M
AM
D018360:Crystallography, X-Ray; D018691:Excitatory Amino Acid Antagonists / Q000138:chemical synthesis / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D018091:Receptors, AMPA / Q000037:antagonists & inhibitors*; D016194:Receptors, N-Methyl-D-Aspartate / Q000037:antagonists & inhibitors*
C438126:6-methyl-N-(4-nitrobenzoyl)-5,6-dihydropyridin-2(1H)-one; C438128:8-methoxy-3-methyl-N-(4-nitrobenzoyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline-1,6-dione; D018691:Excitatory Amino Acid Antagonists; D007546:Isoquinolines; D009574:Nitro Compounds; D011725:Pyridines; D011804:Quinolines; D018091:Receptors, AMPA; D016194:Receptors, N-Methyl-D-Aspartate