6187-58-2Relevant academic research and scientific papers
PROCESS FOR PRODUCING DIHYDROISOQUINOLINE ZWITTERIONS
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Page/Page column 16, (2008/06/13)
This invention relates to a preparation of zwitterionic sulfates of substituted or unsubstituted 3, 4-dihydroisoquinoline.
OXIDATION OF 1,2,3,4-TETRAHYDROISOQUINOLINES TO 3,4-DIHYDROISOQUINOLINES WITH MOLECULAR OXYGEN CATALYZED BY COPPER(II) CHLORIDE
Shimizu, Masao,Orita, Hideo,Hayakawa, Takashi,Suzuki, Kunio,Takehira, Katsuomi
, p. 773 - 780 (2007/10/02)
A catalytic oxidation system, a CuCl2-O2 system, was efficient for dehydrogenation of 1,2,3,4-tetrahydroisoquinolines to 3,4-dihydroquinolines.Oxidation of 1,2,3,4-tetrahydroquinoline was also carried out.
Synthesis and Antihypertensive Activity of a Series of Spiroquinolizine-2,5'-oxazolidin-2'-one>s
Caroon, Joan M.,Clark, Robin D.,Kluge, Arthur F.,Lee, Chi-Ho,Strosberg, Arthur M.
, p. 1426 - 1433 (2007/10/02)
The 2R*,11bS* and 2S*,11bS* diastereoisomers of the spiroquinolizine-2,5'-oxazolidin-2'-one> system were prepared by stereoselective methods.Evaluation of these compounds for antihypertensive activity by oral administration to the spontaneously hypertensive rat showed the 2S*,11bS* series was the more potent.Within that series it was found that small alkyl substituents at positions 3 and 4' enhanced antihypertensive activity and that methoxyl substitution at positions 9 and 10 was optical. (2S,3S,11bS)-Spiroquinolizine-2,5'-oxazolidin-2'-one> was one of the most efficacious compounds of this series, while its antipode, (+)-9e, was inactive.Selected compounds in this series were shown to be α-adrenoceptor antagonists.
Synthesis and Stereochemistry of 7-Phenyl-2-propionanilidobenzoquinolizidine Derivatives. Structural Probes of Fentanyl Analgesics
Maryanoff, Bruce E.,McComsey, David F.,Taylor, Russell J.,Gardocki, Joseph F.
, p. 79 - 88 (2007/10/02)
The four diastereomers of N-(1,3,4,6,7,11b-hexahydro-7-phenyl-2H-benzoquinolizin-2-yl)-N-phenylpropanamide (7c, 7d, 9c, and 9d), which are conformationally restricted analogues of fentanyl, were synthesized and seperately tested for analgesic activity and affinity for the opiate receptor of rat brain.Stereochemical assignments for 7c, 7d, 9c, and 9d were deduced from NMR spectral analyses.Conformational analysis revealed that the 2α isomers (7d and 9d) exist in solution as mixtures of cis- and trans-fused conformers with ca. 90 and 45percent cis form, respectively.Other compounds (12a, 12b, and 14) related to these propionanilides were also prepared, stereochemically characterized, and tested.Weak analgesic activity was observed for 7d, and both 7d and 9d bound to the opiate receptor with an I50 of ca. 1100 and 1500 nM, respectively (ca. 0.5percent of fentanyl and 2percent of morphine).The analgesic activity of 7d was abolished by the opiate antagonist naloxone.
