Biology- and Diversity-Oriented Domino Reactions for Synthesis of AMPA Receptor Antagonist IKM-159 and Analogues

Masato Oikawa; Yuuki Kasori; Lisa Katayama; Etsuko Murakami; Yuya Oikawa; Yuichi Ishikawa

doi:10.1055/s-0033-1338543

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(22): 3106-3117
DOI: 10.1055/s-0033-1338543

paper

Biology- and Diversity-Oriented Domino Reactions for Synthesis of AMPA Receptor Antagonist IKM-159 and Analogues

Masato Oikawa*

Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan Fax: +81(45)7872403 eMail: moikawa@yokohama-cu.ac.jp

,

Yuuki Kasori

Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan Fax: +81(45)7872403 eMail: moikawa@yokohama-cu.ac.jp

,

Lisa Katayama

Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan Fax: +81(45)7872403 eMail: moikawa@yokohama-cu.ac.jp

,

Etsuko Murakami

Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan Fax: +81(45)7872403 eMail: moikawa@yokohama-cu.ac.jp

,

Yuya Oikawa

Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan Fax: +81(45)7872403 eMail: moikawa@yokohama-cu.ac.jp

,

Yuichi Ishikawa

Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan Fax: +81(45)7872403 eMail: moikawa@yokohama-cu.ac.jp

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

By natural product inspired diversity-oriented synthesis, we had developed a new class of selective antagonist, IKM-159, for the AMPA receptor. Here, we report syntheses of IKM-159 and skeletally diverse five analogues in racemic forms, two of which are heterotricycles and the other three compounds are truncated analogues, to study the structure–activity relationships. The key reactions are two domino reactions including Ugi/Diels–Alder reaction and domino metathesis reaction. An exceptionally high level of regiocontrol in the cross metathesis reaction is also reported.

Key words

domino reaction - heterocycles - medicinal chemistry - metathesis - multicomponent reaction

Volltext

Referenzen

References

1a Mitchison TJ. Chem. Biol. 1994; 1: 3
1b Schreiber SL. Bioorg. Med. Chem. 1998; 6: 1127

2 Schreiber SL. Science 2000; 287: 1964
3 Burke MD, Schreiber SL. Angew. Chem. Int. Ed. 2004; 43: 46
4 Nielsen TE, Schreiber SL. Angew. Chem. Int. Ed. 2008; 47: 48
5 Nören-Müller A, Reis-Corrêa I, Prinz H, Rosenbaum C, Saxena K, Schwalbe HJ, Vestweber D, Cagna G, Schunk S, Schwarz O, Schiewe H, Waldmann H. Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 10606

For recent reviews, see:

6a de Graaff C, Ruijter E, Orru RV. A. Chem. Soc. Rev. 2012; 41: 3969
6b Shiri M. Chem. Rev. 2012; 112: 3508
6c van Berkel SS, Bögels BG. M, Wijdeven MA, Westermann B, Rutjes FP. J. T. Eur. J. Org. Chem. 2012; 3543

For recent reviews, see:

7a Nicolaou KC, Chen JS. Chem. Soc. Rev. 2009; 38: 2993
7b Núñez MG, García P, Moro RF, Díez D. Tetrahedron 2010; 66: 2089
7c Grossmann A, Enders D. Angew. Chem. Int. Ed. 2012; 51: 314
7d Lu L.-Q, Chen J.-R, Xiao W.-J. Acc. Chem. Res. 2012; 45: 1278

8 Robinson R. J. Chem. Soc., Trans. 1917; 111: 762
9 Tietze LF. Chem. Rev. 1996; 96: 115
10 Oh CH, Karmakar S, Park H, Ahn Y, Kim JW. J. Am. Chem. Soc. 2010; 132: 1792
11 Dückert H, Pries V, Khedkar V, Menninger S, Bruss H, Bird AW, Maliga Z, Brockmeyer A, Janning P, Hyman A, Grimme S, Schürmann M, Preut H, Hübel K, Ziegler S, Kumar K, Waldmann H. Nat. Chem. Biol. 2012; 8: 179
12 Aydillo C, Jiménez-Osés G, Avenoza A, Busto JH, Peregrina JM, Zurbano MM. J. Org. Chem. 2011; 76: 6990
13 Hong B.-C, Nimje RY, Lin C.-W, Liao J.-H. Org. Lett. 2011; 13: 1278
14 Barluenga J, Mendoza A, Rodríguez F, Fañanás FJ. Angew. Chem. Int. Ed. 2008; 120: 7152
15 Hong B.-C, Kotame P, Tsai C.-W, Liao J.-H. Org. Lett. 2010; 12: 776

16a Ugi I. Angew. Chem. 1959; 71: 386
16b Ugi I, Steinbruckner C. Angew. Chem. 1960; 72: 267

17 Akritopoulou-Zanze I, Djuric SW. Heterocycles 2007; 73: 125
18 Paulvannan K. Tetrahedron Lett. 1999; 40: 1851
19 Lee DS, Sello JK, Schreiber SL. Org. Lett. 2000; 2: 709

20a Oikawa M, Ikoma M, Sasaki M. Tetrahedron Lett. 2005; 46: 5863
20b Oikawa M, Ikoma M, Sasaki M. Tetrahedron Lett. 2005; 46: 415
20c Ikoma M, Oikawa M, Sasaki M. Tetrahedron 2008; 64: 2740
20d Ikoma M, Oikawa M, Sasaki M. Eur. J. Org. Chem. 2009; 72

21a Sakai R, Kamiya H, Murata M, Shimamoto K. J. Am. Chem. Soc. 1997; 119: 4112
21b Sakai R, Koike T, Sasaki M, Shimamoto K, Oiwa C, Yano A, Suzuki K, Tachibana K, Kamiya H. Org. Lett. 2001; 3: 1479

22 Parsons AF. Tetrahedron 1996; 52: 4149

23a Ikoma M, Oikawa M, Gill MB, Swanson GT, Sakai R, Shimamoto K, Sasaki M. Eur. J. Org. Chem. 2008; 5215
23b Oikawa M, Ikoma M, Sasaki M, Gill MB, Swanson GT, Shimamoto K, Sakai R. Eur. J. Org. Chem. 2009; 5531
23c Oikawa M, Ikoma M, Sasaki M, Gill MB, Swanson GT, Shimamoto K, Sakai R. Bioorg. Med. Chem. 2010; 18: 3795

24 Gill MB, Frausto S, Ikoma M, Sasaki M, Oikawa M, Sakai R, Swanson GT. Br. J. Pharmacol. 2010; 160: 1417
25 Juknaitė L, Sugamata Y, Tokiwa K, Ishikawa Y, Takamizawa S, Eng A, Sakai R, Pickering DS, Frydenvang K, Swanson GT, Kastrup JS, Oikawa M. J. Med. Chem. 2013; 56: 2283

26a Fukuyama T, Jow CK, Cheung M. Tetrahedron Lett. 1995; 36: 6373
26b Kan T, Fukuyama T. Chem. Commun. 2004; 353

27 Francais A, Bedel O, Haudrechy A. Tetrahedron 2008; 64: 2495
28 Takeuchi R, Tanabe K, Tanaka S. J. Org. Chem. 2000; 65: 1558
29 Garber SB, Kingsbury JS, Gray BL, Hoveyda AH. J. Am. Chem. Soc. 2000; 122: 8168

30a Weeresakare GM, Liu Z, Rainier JD. Org. Lett. 2004; 6: 1625
30b Liu Z, Rainier JD. Org. Lett. 2005; 7: 131

31a Kraus GA, Taschner MJ. J. Org. Chem. 1980; 45: 1175
31b Bal BS, Childers Jr WE, Pinnick HW. Tetrahedron 1981; 37: 2091
31c Dalcanale E, Montanari F. J. Org. Chem. 1986; 51: 567

32 Brown HC, Liu K.-T. J. Am. Chem. Soc. 1970; 92: 3502
33 Sakai, R., personal communication.

Zusatzmaterial

Supporting Information