Probes for narcotic receptor mediated phenomena. 39. Enantiomeric N-substituted benzofuro[2,3-c]pyridin-6-ols: synthesis and topological relationship to oxide-bridged phenylmorphans.
نویسندگان
چکیده
Enantiomers of N-substituted benzofuro[2,3-c]pyridin-6-ols have been synthesized, and the subnanomolar affinity and potent agonist activity of the known racemic N-phenethyl substituted benzofuro[2,3-c]pyridin-6-ol can now be ascribed to the 4aS,9aR enantiomer. The energy-minimized structures suggest that the active enantiomer bears a greater three-dimensional resemblance to morphine than to an ostensibly structurally similar oxide-bridged phenylmorphan. Structural features of the conformers of N-substituted benzofuro[2,3-c]pyridin-6-ols were compared to provide the rationale for their binding affinity.
منابع مشابه
Synthesis and pharmacological effects of the enantiomers of the N-phenethyl analogues of the ortho and para e- and f-oxide-bridged phenylmorphans.
The N-phenethyl analogues of (1R*,4aR*,9aS*)-2-phenethyl-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridin-6-ol and 8-ol and (1R*,4aR*,9aR*)-2-phenethyl-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2.3-c]pyridin-6-ol and 8-ol, the ortho- (43) and para-hydroxy e- (20), and f-oxide-bridged 5-phenylmorphans (53 and 26) were prepared in racemic and enantiomerically pure forms from a common...
متن کاملSynthesis, Characterization and Study of Some N-Substituted Aryl-2- ({4-[(Substituted Aryl Carbamoyl) Methyl]-5-(Pyridin-4-yl)-4H-1, 2, 4-Triazol-3-yl} Sulfanyl) Acetamide
Pathogenic infections and inflammation are very common ailments humans suffer. Upsurge of resistant pathogens has impeded the antimicrobial drug development process in recent years and the search of new antimicrobial agents is clearly evident from the literature. In line with these developments the synthesis of N-substituted aryl-2-({4-[(substituted aryl carbamoyl) methyl]-5-(pyridin-4-yl)-4H-1...
متن کاملCholine chloride: 2 ZnCl2 catalyzed efficient one-pot regioselective synthesis of dihydrobenzofuro[2,3-b]benzofuran
The reaction of 2-naphthol and also para-substituted phenols with glyoxal in presence of choline chloride: 2 ZnCl2 [ChCl: 2ZnCl2], a deep eutectic solvent (DES), as a green catalyst was studied. The amount of catalyst, solvent type, temperature, and time on the yield of reaction were investigated. It was found that the optimal condition included 10% mol ratio of catalyst (mol percentage of DES ...
متن کاملA Clean and Highly Efficient Synthesis of Oxindole Substituted Pyrrolo[2,3-d]Pyrimidines under Ultrasound Irradiation
A practical and new method for the synthesis oxindole substituted pyrrolo[2,3-d]pyrimidines by the condensation of isatin, acetophenone and 6-amino-uracil under ultrasound irradiation conditions at 60 °C was described. The reaction was developed via a sequential tandem process to afford the oxindole substituted pyrrolo[2,3-d]pyrimidines in good to excellent yields. All reactions performed effic...
متن کاملSynthesis of Enantiopure 10-Nornaltrexones in the Search for Toll-like Receptor 4 Antagonists and Opioid Ligands
10-Nornaltrexones (3-(cyclopropylmethyl)-4a,9-dihydroxy-2,3,4,4a,5,6-hexahydro-1H-benzofuro[3,2-e]isoquinolin-7(7aH)-one, 1) have been underexploited in the search for better opioid ligands, and their enantiomers have been unexplored. The synthesis of trans-isoquinolinone 2 (4-aH, 9-O-trans-9-methoxy-3-methyl-2,3,4,4a,5,6-hexahydro-1H-benzofuro[3,2-e]isoquinolin-7(7aH)-one) was achieved through...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Journal of medicinal chemistry
دوره 52 23 شماره
صفحات -
تاریخ انتشار 2009