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Current Organocatalysis

Author(s): Biswa Mohan Sahoo* and Bimal Krishna Banik

DOI: 10.2174/2213337206666190405144423

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Organocatalysis: Trends of Drug Synthesis in Medicinal Chemistry

Page: [92 - 105] Pages: 14

  • * (Excluding Mailing and Handling)

Abstract

Background: The continuous increase in challenges associated with the effective treatment of life threatening diseases influences the development of drug therapies with suitable physicochemical properties, efficiency and selectivity. So, organocatalysis is a potential synthetic tool which is accelerating the development of new drug molecules.

Methods: Organocatalysis reactions can be carried out at lower temperatures and in milder pH conditions as compared to metal based catalysed reactions. Due to ready availability of catalysts, stability, purity, low toxicity and easy in handling of the chemical reactions, it has become an attractive technique to synthesise complex molecules with diverse structures. Here, the impact of various catalysts in organic synthesis with methods is discussed.

Results: Organic catalysts are used widely in various chemical reactions such as Michael Addition, aldol reaction, Diels-Alder reactions and Knoevenagal reactions. It was observed that the use of organocatalyst results in the formation of stereo active molecules with diverse biological activities.

Conclusion: This review also focuses on the various scopes and limitations of organocatalytic reactions in the production of medicinally useful drug molecules. Organocatalysts possess several advantages over traditional metal catalysts because they are non-toxic, readily available, stable, efficient, and easy to handle which involves environmentally friendly reaction.

Keywords: Chemistry, development, drug, organocatalysis, reaction, synthesis.

Graphical Abstract

[1]
McMillan, D.W.C. Commentary the advent and development of organocatalysis. Nature, 2008, 45(5), 304-308.
[2]
List, B.; Yang, J.W. The organic approach to asymmetric Organocatalysis. Science, 2006, 313(5793), 1584-1586.
[3]
Liebig, J.V. Ueber die Bildung des Oxamidsaus Cyan. Eur. J. Org. Chem., 1860, 113(2), 246-247.
[4]
Purkait, N.; Roymahapatra, G. Development in organocatalysis-The green chemistry aspect: A review update. Int. J. Hit. Transceccn., 2017, 3, 128-138.
[5]
Grondal, C.; Jeanty, M.; Enders, D. Organocatalytic cascade reactions as a new tool in total synthesis. Nat. Chem., 2010, 2(3), 167-178.
[6]
Dalko, P.I.; Moisan, L. Enantioselective organocatalysis. Angew. Chem. Int. Ed. Engl., 2001, 113, 3726-3748.
[7]
Mukherjee, S. Asymmetric enamine catalysis. Chem. Rev., 2007, 107(12), 5471-5569.
[8]
List, B.; Lerner, R.A.; Barbas, C.F. Proline-catalyzed direct asymmetric aldol reactions. J. Am. Chem. Soc., 2000, 122(10), 2395-2396.
[9]
Notz, W. Enamine-based organocatalysis with proline and diamines: The development of direct catalytic asymmetric aldol, mannich, michael, and Diels–alder reaction. Acc. Chem. Res., 2004, 37, 580-591.
[10]
Aleman, J.; Cabrera, S. Applications of asymmetric organocatalysis in medicinal chemistry. Chem. Soc. Rev., 2013, 42(2), 774-793.
[11]
Dalco, P.I. Enantioselective organocatalysis, 2007.Wiley-VCH..
[12]
Berkessel, A.; Gröger, H. Asymmetric Organocatalysis. , 2005. Wiley-VCH.
[13]
Feng, B. Total synthesis of natural and pharmaceutical products powered by organocatalytic reactions. Tetrahedron Lett., 2015, 56, 2133-2140.
[14]
Tian, S.K.; Deng, L. A highly enantioselective chiral lewis base catalyzed asymmetric cyanation of ketones. J. Am. Chem. Soc., 2001, 123(25), 6195-6196.
[15]
List, B. Proline-catalysed direct asymmetric aldol reactions. J. Am. Chem. Soc., 2000, 122, 2395-2396.
[16]
Enders, D.; Fronert, J.; Bisschops, T.; Boeck, F. Asymmetric total synthesis of Smyrindiol employing an organocatalytic aldol key step. Beilstein J. Org. Chem., 2012, 8, 1112-1117.
[17]
Chouthaiwale, P.V.; Kotkar, S.P.; Sudalai, A. Formal synthesis of (-)Anisomycin via organocatalysis. ARKIVOC, 2009, (ii), 88-94.
[18]
Wagh, S.J.; Chowdhury, R.; Ghosh, S.K. Pyrrolidinecatalyzed direct synthesis of 3,5-diarylcyclohexenones from acetone and chalcones. COCAT, 2014, 1(2), 71-78.
[19]
Hayashi, Y.; Ogasawara, S. Economical total synthesis of (−)-Oseltamivir. Org. Lett., 2016, 18(14), 3426-3429.
[20]
Valero, G.; Schimer, J.; Cisarova, I.; Vesely, J.; Moyano, A. Highly enantioselective organocatalytic synthesis of piperidines and formal synthesis of (-)-Paroxetine. Tetrahedron Lett., 2009, 50(17), 1943-1946.
[21]
Meyer, J.B.O.; Helmchen, G. Enantioselective syntheses of (-)-(R)-Rolipram, (-)-(R)-Baclofen and other GABA analogues via rhodium-catalyzed conjugate addition of arylboronic acids. Synthesis, 2003, 18, 2805-2810.
[22]
Zhao, G.L.; Lin, S.; Cordova, A. Asymmetric synthesis of maraviroc (UK-427,857). Advanced Synthesis & Catalysis., 2010, 13, 2291-2298.
[23]
Tian, J.; Zhong, J.; Li, Y.; Ma, D. Organocatalytic and scalable synthesis of the anti-influenza drugs zanamivir, laninamivir, and CS-8958. Angew. Chem. Int. Ed. Engl., 2014, 53(50), 13885-13888.
[24]
Bassas, O.; Huuskonen, J.; Rissanen, K.; Koskinen, A.M.P. A Simple organocatalytic enantioselective synthesis of Pregabalin. Eur. J. Org. Chem., 2009, 9, 1340-1351.
[25]
Figueiredo, R.M.; Christman, M. Organocatalytic synthesis of drugs and bioactive natural products. Eur. J. Org. Chem., 2007, 16, 2575-2600.
[26]
Hong, B.C.; Kotame, P.; Tsai, C.W.; Liao, J.H. Enantioselective total synthesis of (+)-conicol. Org. Lett., 2010, 12, 776-779.
[27]
Sharma, L.; Sharma, S.C. Studies in asymmetric epoxidation of chalcone using quaternary salts and nonionic surfactants based on 6-amino-6-deoxy-glucose as chiral phase transfer catalysts. Eur. J. Chem., 2011, 8(3), 1293-1297.
[28]
Gualtierotti, J.B.; Pasche, D.; Wang, Q.; Zhu, J.A. Phosphoric acid catalyzed desymmetrization of bicyclic bis-lactones bearing an all-carbon stereogenic center: Total syntheses of (-)-Rhazinilam. Chem. Int. Ed, 2014, 53, 9926-9930.
[29]
Evans, D.A.; Scheidt, K.A.; Wade, C. Synthesis of (-)-Epibatidine. Org. Lett., 2001, 3(19), 3009-3012.
[30]
Dolling, U.; Davis, P.; Edward, J.J. Efficient catalytic asymmetric alkylations: Enantioselective synthesis of (+)-indacrinone via chiral phase-transfer catalysis. J. Am. Chem. Soc., 1984, 106(2), 446-447.
[31]
Ricci, A. Asymmetric organocatalysis at the service of medicinal chemistry. ISRN Organic Chemistry, ID, 2014Article ID 531695,. , 1-29.
[32]
Dadas, Y.; Pelin, G. Synthesis and anticancer activity of some novel Tolmetin thiosemicarbazides. Marmara Pharm. J., 2015, 19, 259-267.
[33]
Benavent, L.; Puccetti, F.; Baeza, A.; Melania, G.M. Readily available chiral benzimidazoles derived guanidines as organocatalysts in the asymmetric amination of 1,3-dicarbonyl compounds. Molecules, 2017, 22(8), pii E1333.
[34]
Hazra, G.; Maity, S.; Bhowmick, S.; Ghorai, P. Organocatalytic, enantioselective synthesis of benzoxaboroles via Wittig/oxa-Michael reaction cascade of α-formyl boronic acids. Chem. Sci. , 2017, 8, 3026-3030.