Discovery and stereoselective synthesis of the novel isochroman neurokinin-1 receptor antagonist ‘CJ-17,493’

Shishido, Yuji; Wakabayashi, Hisatsugu; Koike, Hiroshi; Ueno, Naomi; Nukui, Seiji; Yamagishi, Tatsuya; Murata, Yoshinori; Naganeo, Fumiharu; Mizutani, Masami; Shimada, Kaoru; Fujiwara, Yuzuru; Sakakibara, Ayano; Suga, Osamu; Kusano, Rinko; Ueda, Shunsaku; Kanai, Yoshihito; Tsuchiya, Megumi; Satake, Kenichi

doi:10.1016/j.bmc.2008.06.047

Cited by 59 publications

(20 citation statements)

References 15 publications

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“…[2] Numerous efforts have been made to develop methods to preparei sochromene and related cyclic ether structures, [3] but available approaches suffer from low yield or requirecomplex starting materials.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of 4‐(Trifluoromethyl)‐1 H‐isochromenes from Alkynols

Siyang

Liu

et al. 2015

Asian J Org Chem

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Isochromene derivatives are important structural motifs found in various biologically activec ompounds as well as important natural products. Am ethod to generate CF 3 -containing isochromene derivatives has been developed, which gives moderate to good yields by using To gni's reagent as the trifluoromethyl source. The key step involves alkynol cyclization and subsequent trapping by ar eactive electrophilic trifluoromethyl species generated in situ from To gni's reagent.

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Section: Introductionmentioning

confidence: 99%

Facile Synthesis of 4‐(Trifluoromethyl)‐1 H‐isochromenes from Alkynols

Siyang

Liu

et al. 2015

Asian J Org Chem

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“…On the other hand, synthetic isochromans are exemplified by the apoptosis inhibitor of vascular endothelial cells ISO-09 (6), [6] the anti-migraine drug PNU-142633 (7), [7] the commercial fragrance galaxolide (8) [8] and the novel neurokinin-1 receptor antagonist CJ-17,493 (9), [9] while the non-steroidal anti-inflammatory drug etodolac (10) [10] is an example of a synthetic commercial aryl pyran other than a benzo-fused heterocyclic derivative.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Oxacycles Employing the Oxa‐Pictet–Spengler Reaction: Recent Developments and New Prospects

2011

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The oxa‐Pictet–Spengler cyclization is the oxygen variation of the Pictet–Spengler reaction, in which an aromatic alcohol component (generally a β‐arylethyl alcohol) reacts with acarbonyl component (aldehyde, ketone or their masked derivatives), to yield a 1‐substituted (or 1,1′‐disubstituted)pyran fused to the aromatic ring system found in the starting alcohol. The transformation is usually promoted by Brønsted and Lewis acids. Intramolecular versions of the reaction are also known, where both components are mutually masked as an acetal. Discussed here are aspects concerning the most recent developments and new applications of this useful reaction, including the scope and limitations of new promoters, and new mechanistic pictures of this transformation. The use of novel stereochemical control strategies and the application of the reaction to the synthesis of natural products and their analogs, as well as to accessing fully synthetic bioactive compounds and new ring systems are presented, and chiral versions of the oxa‐Pictet–Spengler are also analyzed.

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“…7 Synthetic isochromans include the isochroman-6-carboxamides PNU-109291 ( 7 ) and PNU-142633 ( 8 ), both selective 5-HT 1D agonists and anti-migraine agents, 8-10 and CJ-17,493 ( 9 ) a neurokinin-1 receptor antagonist with antiemetic properties. 11,12 …”

Section: Introductionmentioning

confidence: 99%

Facile synthesis of 4,5,6a,7-tetrahydrodibenzo[de,g]chromene heterocycles and their transformation to phenanthrene alkaloids

Kapadia

Harding

2013

Tetrahedron

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Oxa-Pictet-Spengler cyclization and microwave-assisted C-H arylation have been implemented as key steps in the synthesis of new isochroman heterocycles containing a 4,5,6a,7-tetrahydrodibenzo[de,g]chromene motif. These isochromans may be easily transformed to phenanthrene alkaloids via acidic cleavage of the isochroman ring and standard synthetic manipulations thereafter. The route described is attractive in that it provides access to two biologically interesting scaffolds in simple and high yielding synthetic steps.

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Discovery and stereoselective synthesis of the novel isochroman neurokinin-1 receptor antagonist ‘CJ-17,493’

Cited by 59 publications

References 15 publications

Facile Synthesis of 4‐(Trifluoromethyl)‐1 H‐isochromenes from Alkynols

Facile Synthesis of 4‐(Trifluoromethyl)‐1 H‐isochromenes from Alkynols

Synthesis of Oxacycles Employing the Oxa‐Pictet–Spengler Reaction: Recent Developments and New Prospects

Facile synthesis of 4,5,6a,7-tetrahydrodibenzo[de,g]chromene heterocycles and their transformation to phenanthrene alkaloids

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