Selective muscarinic M1 antagonists: drug design and discovery

Widzowski, Dan; Wu, E. S. C.; Helander, Herbert F.

doi:10.1016/s1359-6446(97)01076-3

Cited by 12 publications

(12 citation statements)

References 59 publications

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“…However, the structures of these ligands are highly diverse, and they have been reviewed else where (Broadley and Kelly, 2001;Clader and Wang, 2005;Ishii and Kurachi, 2006;Widzowski et al, 1997). The structures of the methoxyflavones tested here differ from these known ligands for muscarinic receptors, for example, they clearly lack the nitrogen moiety.…”

Section: Resultsmentioning

confidence: 99%

Muscarinic receptor binding activity of polyoxygenated flavones from Melicope subunifoliolata

Chung¹,

Yap²,

Goh³

et al. 2008

Phytochemistry

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Section: Resultsmentioning

confidence: 99%

Muscarinic receptor binding activity of polyoxygenated flavones from Melicope subunifoliolata

Chung¹,

Yap²,

Goh³

et al. 2008

Phytochemistry

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“…Moreover, TAN1251A and B exhibit cholinergic activity and inhibit acetylcholine-induced contraction of the guinea-pig ileum with ED 50 values of 8.0 and 10.0 nM, respectively. 42) In the chiral synthesis of TAN 1251A, 38,39) we chose Ltyrosine and glycine as the starting materials, and aromatic oxidation of the secondary amine (53) with a hypervalent iodine reagent was employed, as the key reaction, to construct the desired spirocyclic carbon-nitrogen bond, as depicted in Chart 20.…”

Section: -40)mentioning

confidence: 99%

Investigation of Innovative Synthesis of Biologically Active Compounds on the Basis of Newly Developed Reactions

Honda

2012

Chem. Pharm. Bull.

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Synthesis of biologically active compounds, including natural products and pharmaceutical agents, is an important and interesting research area since the large structural diversity and complexity of bioactive compounds make them an important source of leads and scaffolds in drug discovery and development. Many structurally and also biologically interesting compounds, including marine natural products, have been isolated from nature and have also been prepared on the basis of a computational design for the purpose of developing medicinal chemistry. In order to obtain a wide variety of derivatives of biologically active compounds from the viewpoint of medicinal chemistry, it is essential to establish efficient synthetic procedures for desired targets. Newly developed reactions should also be used for efficient synthesis of desired compounds. Thus, recent progress in the synthesis of biologically active compounds by focusing on the development of new reactions is summarized in this review article.

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“…TAN1251A exhibits cholinergic activity and inhibits acetylcholine-induced contraction of the guinea-pig ileum. TAN1251A is also known as a selective muscarinic M 1 subtype receptor antagonist [5]. Due to its intriguing structural features and attractive biological activity, several total syntheses have appeared in the past few years.…”

Section: Synthesis Of Tan1251a Tan1251c and Tan1251dmentioning

confidence: 99%

“…Some of those natural products exhibit various interesting biological activities, although a spirocyclic ring system does not seem to be essential to elicit the activities. The well-known spirocyclic bioactive natural products are [5,5]-, [5,6]-, and [6,6]-spiroacetals, which have a wide range of structural features and biological activities. Spirocyclic frameworks have also been found in bioactive alkaloids.…”

Section: Introductionmentioning

confidence: 99%

Development of an efficient synthetic strategy for bioactive alkaloids possessing a spirocyclic ring system

Honda

2010

Pure and Applied Chemistry

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Efficient synthetic strategies for several bioactive alkaloids bearing a spirocyclic ring system have been developed. By application of an intramolecular aromatic oxidation of a phenolic intermediate, derived from L-tyrosine and glycine, with hypervalent iodine reagents, TAN1251A, isolated from Penicillium thomii RA-89, was synthesized in an optically pure form. Similarly, a novel synthetic path to TAN1251C and TAN1251D was established by employing an L-tyrosine dimer as a common starting material. Moreover, an enamide-phenol oxidative coupling reaction was applied to the synthesis of spirocyclic isoquinoline alkaloids, stepharine and annosqualine. Finally, stereoselective syntheses of securinine and viroallosecurinine in optically active forms were established by using a tandem ring-closing metathesis (RCM) of the enyne as a key reaction.

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Selective muscarinic M1 antagonists: drug design and discovery

Cited by 12 publications

References 59 publications

Muscarinic receptor binding activity of polyoxygenated flavones from Melicope subunifoliolata

Muscarinic receptor binding activity of polyoxygenated flavones from Melicope subunifoliolata

Investigation of Innovative Synthesis of Biologically Active Compounds on the Basis of Newly Developed Reactions

Development of an efficient synthetic strategy for bioactive alkaloids possessing a spirocyclic ring system

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