Literature DB >> 26663991

Synthesis of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one.

Shobanbabu Bommagani1, Na-Ra Lee2, Xuan Zhang1, Linda P Dwoskin2, Guangrong Zheng1.   

Abstract

Efficient syntheses of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one are presented. The O-alkylated analogues were synthesized through a reduction-cyclization cascade and a selective O-alkylation reaction; whereas the N-alkylated analogues were obtained through a key Buchwald coupling.

Entities:  

Keywords:  1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one; Buchwald coupling; Muscarinic acetylcholine receptors; Reduction-cyclization cascade; Suzuki coupling

Year:  2015        PMID： 26663991      PMCID： PMC4671082          DOI： 10.1016/j.tetlet.2015.09.156

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  12 in total

1.  The development of efficient protocols for the palladium-catalyzed cyclization reactions of secondary amides and carbamates.

Authors:  B H Yang; S L Buchwald
Journal:  Org Lett       Date:  1999-07-15       Impact factor: 6.005

Review 2.  Muscarinic receptors--characterization, coupling and function.

Authors:  M P Caulfield
Journal:  Pharmacol Ther       Date:  1993-06       Impact factor: 12.310

Review 3.  International Union of Pharmacology. XVII. Classification of muscarinic acetylcholine receptors.

Authors:  M P Caulfield; N J Birdsall
Journal:  Pharmacol Rev       Date:  1998-06       Impact factor: 25.468

Review 4.  Muscarinic acetylcholine receptors: novel opportunities for drug development.

Authors:  Andrew C Kruse; Brian K Kobilka; Dinesh Gautam; Patrick M Sexton; Arthur Christopoulos; Jürgen Wess
Journal:  Nat Rev Drug Discov       Date:  2014-06-06       Impact factor: 84.694

5.  Loss of M5 muscarinic acetylcholine receptors leads to cerebrovascular and neuronal abnormalities and cognitive deficits in mice.

Authors:  Runa Araya; Takanori Noguchi; Munehiro Yuhki; Naohito Kitamura; Makoto Higuchi; Takaomi C Saido; Kenjiro Seki; Shigeyoshi Itohara; Masako Kawano; Kentaro Tanemura; Akihiko Takashima; Kazuyuki Yamada; Yasushi Kondoh; Iwao Kanno; Jürgen Wess; Masahisa Yamada
Journal:  Neurobiol Dis       Date:  2006-09-07       Impact factor: 5.996

Review 6.  Muscarinic acetylcholine receptors: mutant mice provide new insights for drug development.

Authors:  Jürgen Wess; Richard M Eglen; Dinesh Gautam
Journal:  Nat Rev Drug Discov       Date:  2007-09       Impact factor: 84.694

7.  Structural modifications to tetrahydropyridine-3-carboxylate esters en route to the discovery of M5-preferring muscarinic receptor orthosteric antagonists.

Authors:  Guangrong Zheng; Andrew M Smith; Xiaoqin Huang; Karunai L Subramanian; Kiran B Siripurapu; Agripina Deaciuc; Chang-Guo Zhan; Linda P Dwoskin
Journal:  J Med Chem       Date:  2013-02-18       Impact factor: 7.446

Review 8.  Muscarinic acetylcholine receptor knockout mice: novel phenotypes and clinical implications.

Authors:  Jürgen Wess
Journal:  Annu Rev Pharmacol Toxicol       Date:  2004       Impact factor: 13.820

9.  Deletion of the M5 muscarinic acetylcholine receptor attenuates morphine reinforcement and withdrawal but not morphine analgesia.

Authors:  Anthony S Basile; Irina Fedorova; Agustin Zapata; Xiaoguang Liu; Toni Shippenberg; Alokesh Duttaroy; Masahisa Yamada; Jurgen Wess
Journal:  Proc Natl Acad Sci U S A       Date:  2002-08-01       Impact factor: 11.205

10.  Decreased prepulse inhibition and increased sensitivity to muscarinic, but not dopaminergic drugs in M5 muscarinic acetylcholine receptor knockout mice.

Authors:  Morgane Thomsen; Gitta Wörtwein; Anders Fink-Jensen; David P D Woldbye; Jürgen Wess; S Barak Caine
Journal:  Psychopharmacology (Berl)       Date:  2007-02-20       Impact factor: 4.415
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  1 in total

1.  Structure-Based Design and Synthesis of an Isozyme-Selective MTHFD2 Inhibitor with a Tricyclic Coumarin Scaffold.

Authors:  Junya Kawai; Masahiro Ota; Hitoshi Ohki; Tadashi Toki; Makoto Suzuki; Takashi Shimada; Satoshi Matsui; Hidekazu Inoue; Chika Sugihara; Norikazu Matsuhashi; Yumi Matsui; Sachiko Takaishi; Kiyoshi Nakayama
Journal:  ACS Med Chem Lett       Date:  2019-05-24       Impact factor: 4.345
  1 in total

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