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Arabian Journal for Science and Engineering
Published in: Arabian Journal for Science and Engineering 6/2020

14-03-2020 | Research Article-Chemistry

Synthesis of Pharmacologically Relevant New Derivatives of Maleimides via Ligand-Free Pd-Catalyzed Suzuki–Miyaura Cross-Coupling Reactions

Authors: Muhammad Sharif, Julita Opalach, Ralf Jackstell, Anahit Pews-Davtyan, Matthias Beller

Published in: Arabian Journal for Science and Engineering | Issue 6/2020

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Abstract

The Suzuki–Miyaura coupling reactions were applied for synthesis of pharmacological relevant derivatives of known 3,4-dibromo-1-methyl-1H-pyrrole-2,5-dione compound. Suzuki–Miyaura reactions of 3,4-dibromo-1-methyl-1H-pyrrole-2,5-dione with two equivalents of arylboronic acids gave vicinal diphenyl-substituted maleimide products. The reaction with one equivalent of arylboronic acid resulted in site-selective synthesis of N-methyl-2-aryl-3-bromomaleimide. The one-pot reaction of 3,4-dibromo-1-methyl-1H-pyrrole-2,5-dione with two different arylboronic acids afforded N-methyl-2-3-diaryl-maleimides containing two different aryl groups. Maleimide-resulting compounds have added a general interest in the fields of Pharmaceuticals, diagnostics, materials and catalysis. The synthesis of maleimide-substituted compounds via Suzuki–Miyaura cross-coupling protocols has increased extensive interest in the synthesis of heterocyclic compounds.
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Literature
1.
Bergman, J.; Koch, E.; Pelcman, B.: Coupling reactions of indole-3-acetic acid derivatives. Synthesis of arcyriaflavin A. J. Chem. Soc. Perkin Trans. 1, 2609–2614 (2000)CrossRef
2.
Ohkubo, M.; Nishimura, T.; Jona, H.; Honma, T.; Morishima, H.: Practical synthesis of indolopyrrolocarbazoles. Tetrahedron 52, 8099–8112 (1996)CrossRef
3.
Steglich, W.: Slime moulds (Myxomycetes) as a source of new biologically active metabolites. Pure Appl. Chem. 61, 281–288 (1989)CrossRef
4.
Friedmann, E.: Spectrophotometric investigation of the interaction of glutathione with maleimide and N-ethylmaleimide. Biochim. Biophys. Acta 9, 65–75 (1952)CrossRef
5.
Kajfež, T.; Kamenar, B.; Piližota, V.; Fleš, D.: Crystal and molecular structures of N-phenylmaleimide and N-phenyl-2,3-dimethylmaleimide. Croat. Chem. Acta 76(4), 343–346 (2003)
6.
Koniev, O.; Wagner, A.: Developments and recent advancements in the field of endogenous amino acid selective bond forming reactions for bioconjugation. Chem. Soc. Rev. 44, 5495–5551 (2015)CrossRef
7.
Beck, A.; Goetsch, L.; Dumontet, C.; Coravia, N.: Strategies and challenges for the next generation of antibody-drug conjugates. Nat. Rev. Drug Discov. 16, 315–337 (2017)CrossRef
8.
Ravasco, J.M.J.M.; Faustino, H.; Trindade, V.; Gois, P.M.P.: Bioconjugation with Maleimides: a useful tool for chemical biology. Chem. Eur. J. 25, 43–49 (2019)CrossRef
9.
Boutureira, O.; Bernardes, G.J.L.: Advances in chemical protein modification. Chem. Rev. 115, 2174–2195 (2015)CrossRef
10.
Liu, C.C.; Schultz, P.G.: Adding new chemistries to the genetic code. Annu. Rev. Biochem. 79, 413–444 (2010)CrossRef
11.
Kulkarni, S.S.; Sayers, J.; Premdjee, B.; Payne, R.J.: Rapid and efficient protein synthesis through expansion of the native chemical ligation concept. Nat. Rev. Chem. 2(0122), 1–17 (2018)
12.
Salmond, G.P.C.; Fineran, P.C.: A century of the phage: past, present and future. Nat. Rev. Microbiol. 13, 777–786 (2015)CrossRef
13.
Li, T.; Takeoka, S.: A novel application of maleimide for advanced drug delivery: in vitro and in vivo evaluation of maleimide-modified pH-sensitive liposomes. Int. J. Nanomed. 8, 3855–3866 (2013)
14.
Lyon, R.P.; Meyer, D.L.; Setter, J.R.; Senter, P.D.: Conjugation of anticancer drugs through endogenous monoclonal antibody cysteine residues. Methods Enzymol. 502, 123–138 (2012)CrossRef
15.
Ducry, L.; Stump, B.: Antibody—drug conjugates: linking cytotoxic payloads to monoclonal antibodies. Bioconjug. Chem. 21(1), 5–13 (2010)CrossRef
16.
Junutula, J.R.; Raab, H.; Clark, S.; Bhakta, D.; Leipold, D.D.; Weir, S.; Chen, Y.: Site-specific conjugation of a cytotoxic drug to an antibody improves the therapeutic index. Nat. Biotechnol. 26(8), 925–932 (2008)CrossRef
17.
Kalia, D.; Pawar, S.P.; Thopate, J.S.: Stable and rapid thiol bioconjugation by light-triggered thiomaleimide ring hydrolysis. Angew. Chem. Int. Ed. 56, 1885–1889 (2017)CrossRef
18.
Gray, N.; Detivaud, L.; Doering, C.; Meijer, L.: ATP-site directed inhibitors of cyclin-dependent kinases. Curr. Med. Chem. 6, 859–875 (1999)
19.
Goekjian, P.G.; Jirousek, M.R.: The specificity of the protein kinase C α, βII and γ isoforms as assessed by an unnatural alcohol-appended peptide library. Curr. Med. Chem. 6, 877–903 (1999)
20.
Brennführer, A.; Neumann, H.; Pews-Davtyan, A.; Beller, M.: Catalytic and stoichiometric synthesis of novel 3-aminocarbonyl-, 3-alkoxycarbonyl-, and 3-amino-4-indolylmaleimides. Eur. J. Org. Chem. 2009, 38–42 (2009)CrossRef
21.
Pews-Davtyan, A.; Tillack, A.; Ortinau, S.; Rolfs, A.; Beller, M.: Efficient palladium-catalyzed synthesis of 3-indolyl-4-aryl-maleimides. Org. Biomol. Chem. 6, 992–997 (2008)CrossRef
22.
Furusaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Omura, S.: A new concise synthesis of arcyriacyanin a and its unique inhibitory activity against a panel of human cancer cell line. Bull. Chem. Soc. Jpn. 55, 3681–3685 (1982)CrossRef
23.
Furusaki, A.; Hashiba, N.; Matsumoto, T.: X-ray crystal structure of staurosporine: a new alkaloid from a Streptomyces strain. J. Chem. Soc. Chem. Commun. 18, 800–801 (1978)CrossRef
24.
Omura, S.; Iwai, Y.; Nakayawa, A.; Awaya, J.; Tsuchiya, T.; Takahashi, Y.; Masuma, R.: A new alkaloid AM-2282 OF streptomyces origin. Taxonomy, fermentation, isolation and preliminary characterization. J. Antibiot. 30, 275–282 (1977)CrossRef
25.
Lin, K.F.; Lin, J.S.; Cheng, C.H.: High temperature resins based on allylamine/bismaleimides. Polymer 37, 4729–4737 (1996)CrossRef
26.
Mahboobi, S.; Eichhorn, E.; Popp, A.; Sellmer, A.; Elz, S.; Moellmann, U.: 3-Bromo-4-(1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione derivatives as new lead compounds for antibacterially active substances. Eur. J. Med. Chem. 41, 176–191 (2006)CrossRef
27.
Gingerich, D.E.; Reddy, D.R.; Iqbal, M.A.; Singh, J.; Aimone, L.D.; Angeles, T.S.; Albom, M.; Yang, S.; Ator, M.A.; Meyer, S.L.; Robinson, C.; Ruggeri, B.A.; Dionne, C.A.; Vaught, J.L.; Mallamo, J.P.; Hudkins, R.L.: A new class of potent vascular endothelial growth factor receptor tyrosine kinase inhibitors: structure—activity relationships for a series of 9-alkoxymethyl-12-(3-hydroxypropyl)indeno[2,1-a]pyrrolo[3,4-c]carbazole-5-ones and the Identification of CEP-5214 and its dimethylglycine ester prodrug clinical candidate CEP-7055. J. Med. Chem. 46, 5375–5388 (2003)CrossRef
28.
Gschwendt, M.; Dieterich, S.; Rennecke, J.; Kittstein, W.; Mueller, H.J.; Johannes, F.J.: Inhibition of protein kinase C μ by various inhibitors. Inhibition from protein kinase c isoenzymes. FEBS Lett. 392, 77–80 (1996)CrossRef
29.
Panov, A.A.; Simonove, A.Y.; Lavrnov, S.N.; Lakatosh, S.A.; Trenin, A.S.: 3,4-Disubstituted maleimides: synthesis and biological activity. Chem. Heterocycl. Comp. 54(2), 103–113 (2018)CrossRef
30.
Deore, P.S.; Argade, N.P.: Metal-catalyzed cross-coupling reactions of halomaleic anhydrides and halomaleimides: synthesis of structurally interesting and biologically important natural and unnatural products. Synthesis 46(3), 281–289 (2014)CrossRef
31.
Capretta, A.; Awuha, E.: Development of methods for the synthesis of libraries of substituted maleimides and r, β-unsaturated-γ-butyrolactams. J. Org. Chem. 46, 3122–3130 (2011)
32.
Dyachenko, V.D.; Tkachev, R.P.: Functionally-substituted alkoxyethylenes in reactions with nucleophiles: Part 2. Synthesis of noncyclic structures, benzene derivatives, 5-, 7-membered, and macroheterocycles. Russ. J. Org. Chem. 42, 149–171 (2006)CrossRef
33.
Sharif, M.; Shoaib, K.; Ahmed, S.; Iqbal, J.; Abilov, Z.A.; Spannenberg, A.; Langer, P.: Suzuki–Miyaura reactions of 3,5-dichloro-2,4,6-trifluoropyridines. Tetrahedron Lett. 57, 3060–3062 (2016)CrossRef
34.
Reimann, S.; Parpart, P.; Ehlers, P.; Sharif, M.; Spannenberg, A.; Langer, P.: Synthesis of tetraarylpyridines by chemo-selective Suzuki–Miyaura reactions. Org. Biomol. Chem. 13, 6832–6838 (2015)CrossRef
35.
Sharif, M.; He, L.; Neumann, H.; Beller, M.; Wu, X.-F.: A novel and convenient palladium-catalyzed synthesis of 4(3H)-quinazolinones from 2-bromoformanilides and organo nitros with Mo(CO)6 as a multiple promoter. Green Chem. 16, 3763–3767 (2014)CrossRef
36.
Sharif, M.; Pews-Devtyan, A.; Langer, P.; Rolfs, A.; Beller, M.: First palladium-catalyzed Suzuki–Miyaura coupling reactions of bromohexine and ambroxol. Tetrahedron 70, 5128–5135 (2014)CrossRef
37.
Sharif, M.; Pews-Davtyan, A.; Lukas, J.; Schrank, J.; Langer, P.; Rolfs, A.; Beller, M.: Palladium-catalysed carbonylative transformations of bromhexine to new bioactive compounds as glucocerebrosidase ınhibitors. Eur. J. Org. Chem. 2014, 222–230 (2014)CrossRef
38.
Sharif, M.; Opalach, J.; Langer, P.; Beller, M.; Wu, X.-F.: Oxidative synthesis of quinazolinones and benzothiadiazine 1,1-dioxides from 2-aminobenzamide and 2-aminobenzenesulfonamide with benzyl alcohols and aldehydes. RSC Adv. 15, 1956–1961 (2014)
39.
Reimann, S.; Ehlers, P.; Sharif, M.; Spannenberg, A.; Langer, P.: A general protocol for the efficient synthesis of polyarylated benzenes by multiple Suzuki–Miyaura reactions of polychlorinated benzenes. Tetrahedron 72, 1083–1094 (2016)CrossRef
40.
Maalik, A.; Sharif, M.; Abbass, N.; Spannenberg, A.; Villinger, A.; Langer, P.: Synthesis of tetra and pentaaryl fluorobenzenes by Suzuki–Miyaura coupling reactions and their photophysical properties. Tetrahedron 72, 1076–1082 (2016)CrossRef
41.
Sharif, M.; Wu, X.-F.: Palladium-catalyzed synthesis of primary benzamides from ary bromides via cyanation and hydration sequence. RSC Adv. 5, 21001–21004 (2015)CrossRef
42.
Sharif, M.; Maalik, A.; Reimann, S.; Iqbal, J.; Patonay, T.; Villinger, A.; Spannenberg, A.; Langer, P.: Synthesis and photophysical properties of tetra- and pentaalkynyl fluorobenzenes. Tetrahedron 69, 174–183 (2013)CrossRef
43.
Wu, X.-F.; Sharif, M.; Shoaib, K.; Neumann, H.; Pews-Davtyan, A.; Langer, P.; Beller, M.: A convenient palladium-catalyzed carbonylative synthesis of 2-aminbenzoxazinones from 2-bromoanilines and isocyanates. Chem. Eur. J. 19, 6230–6233 (2013)CrossRef
44.
Sharif, M.; Maalik, A.; Reimann, S.; Iqbal, J.; Patonay, T.; Villinger, A.; Langer, P.: Synthesis of functionalized fluorinated terphenyls by site-selective Suzuki–Miyaura cross-coupling reactions of dibrominated fluorbenzenes. J. Fluor. Chem. 146, 19–36 (2013)CrossRef
Metadata
Title
Synthesis of Pharmacologically Relevant New Derivatives of Maleimides via Ligand-Free Pd-Catalyzed Suzuki–Miyaura Cross-Coupling Reactions
Authors
Muhammad Sharif
Julita Opalach
Ralf Jackstell
Anahit Pews-Davtyan
Matthias Beller
Publication date
14-03-2020
Publisher
Springer Berlin Heidelberg
Published in
Arabian Journal for Science and Engineering / Issue 6/2020
Print ISSN: 2193-567X
Electronic ISSN: 2191-4281
DOI
https://doi.org/10.1007/s13369-020-04450-5

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