A review on chemical and pharmacological interest of morpholine and pyrans derivatives

Document Type : Review Article

Authors

1 Department of Pharmaceutical chemistry, Himalayan Institute of Pharmacy Research, Dehradun, (Uttarakhand), 248009, India.

2 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Northern Border University, Rafha 91911, PO Box 840, Saudi Arabia.

Abstract

Morpholine is a six-membered aromatic organic heterocycle that possesses one nitrogen atom and one oxygen atom their ring structure. Morpholine ring is present in various organic compounds those were developed by chemical designing for diverse pharmacologically activities. In recent years, scientists have explored this moiety. This review summarizes the broad spectrum of pharmacological profile of morpholine derivatives. Six-membered heterocyclic compounds containing oxygen like 2H-pyran and 4H-pyrans constitute an important class of biologically active compounds, playing an essential role in biochemistry and continuing to attract interest. Pyrans and its analogues engage prime position due to their diverse applications. In this review, up to date information about the developments and exploration of methodologies of morpholine and pyran analogues were discussed. This review shows current tendency in the morpholine and pyran analogues and reveals their potent pharmacophoric activities. This article will support to the researcher in future to design and synthesized novel morpholine and pyran derivatives.

Keywords

Main Subjects


[1]    Review of morpholine and its derivatives, Merck Index, 12th ed. published by Merck & co, Whitehouse Station, NJ, 1996, 1074-5.
[2]    M Pushpak, M Bekington. Tetrahedron Lett. 2006, 47(44):7823-7826.
[3]    G Zhou, N Zorn, P Ting, R Aslanian, M Lin, C John. Med. Chem. Lett. 2014, 5(5): 544-549.
[4]    B Achari, BM Sukhendu, P Dutta, C Chowdhury. Synlett. 2004, 14:2449-2467.
[5]    P Panneerselvam, RV Pradeepchandran, SK Sreedhar. Indian J. pharm. Sci. 2003, 65(3): 268-273.
[6]    GR Brown, AJ Foubister, D Stribling J. Chem. Soc. Perkin Trans. 1987, 1: 547.
[7]    AH El-masry, HH Fahmy, ASH Abdelwahed. Molecules. 2000, 12:1429.
[8]    V Duhalde, B Lahillie, F Camou, S Pedeboscq, JP Pometan, Pathologie. Biologie. 2007, 55(10): 478-481.
[9]    C Marireau, M Guilloton, F Kartst. Antimicrob Agents Chemother. 1990, 34(6): 989-993.
[10] SP Sawargave, AS Kudale, JV Deore, DS Bhosale, JM Divse, SP Chavan, HB Borate. Tetrahedron Lett 2011, 52: 5491.
[11] F Segat-Dioury, O Lingibé, B Graffe, M-C Sacquet, G Lhommet. Tetrahedron 2000, 56: 233-248.
[12] A Trabocchi, A Krachmalnicoff, G Menchi, A Guarna. Tetrahedron, 2012, 68: 9701.
[13] DP Walker, BM Eklov, MW Bedore. Synthesis, 2012, 44: 2859.
[14] T. Moriguchi, H. Matsuura, Y. Itakura, H. Katsuki, H. Saito, N. Nishiyama. Life Sci, 1997, 61, 1420.
[15] G.H. Abou El-Fotooh, Osama I Abd El-Salam, M.M. Ashraf, A.H. Nagla. Ind. J. Chem, 2005, 44B, 1893.
[16]    D. Armesto, W.M. Horspool, N. Martin, A. Ramos, C. Seoane. J. Org. Chem, 1989, 54, 3069.
[17]    J.A. Rideout, I.R. Smith, M.D. Sutherland. Aust. J. Chem, 1976, 29(5), 1087.
[18]    D. Kumar, V.B. Reddy, S. Sharad, U. Dube, K A. Suman. Eur. J. Med. Chem, 2009, 44, 3805.
[19]    Yong Rok Lee, Xue Wang, Likai Xia. Molecules, 2007, 12, 1420.
[20]    H. Junek, H. Aigner. Chem. Ber, 1973, 106, 921.
[21]    H.H. Otto. Arch. Pharm, 1974, 307, 444.
[22]    V. Colatta, D. Catarzi, F. Varano, F. Melani, G. Filacchioni, L. Cecci, L. Trincavelli, C. Martini, A. Lucacchini. Il Farmaco.1998, 53, 189.
[23]    G Tosi, F Zironi, E Caselli, A Forni, F Prati. Synthesis, 2004, 1625.
[24]    OL Shvaika. Osnovisintezulіkars’ kikhrechovin (Principles of Synthesis of Medicines), Donets’K: Skhіdnii Vidavn. Dіm, 2002.
[25]    G Assaf, G Cansell, D Critcher, S Field, S Hayes, S Mathew, A Pettman. Tetrahedron Lett, 2010, 51: 5048.
[26]    SP Hanlon, A Camattari, S Abad, A Glieder, M Kittelmann, S Lütz, B Wirz, M Winkler. Chem. Commun, 2012, 48: 6001.
[27]    Tatsumi Y, Yokoo M, Senda H, Kakehi K. Antimicrob. Agents Chemother, 2002, 46: 3797.
[28]    D.S. Li, Eds, Hoboken, N.J. The Art of Drug Synthesis, Johnson: Wiley, Canada, 2007, 71-81.
[29]    Q Yang, LG Ulysse, MD McLaws, DK Keefe, BP Haney, C Zha, PR Guzzo, S Liu. Org. Process Res. Dev, 2012, 16: 499.
[30]    PA Burland, HMI Osborn, A Turkson. Bioorg. Med. Chem, 2011, 19: 5679.
[31]    J Keldenich, C Michon, A Nowicki, FA Niedercorn. Syn lett, 2011, 2939.
[32]    T-X Meìtro, A Cochi, DG Pardo, J CossyJ. J. Org. Chem, 2011, 76: 2594.
[33]    RJ Lukas, AZ Muresan, MI Damaj, BE Blough, X Huang, HA Navarro, SW Mascarella, JB Eaton, SK Marxer-Miller, FI Carroll. J. Med. Chem, 2010, 53: 4731.
[34]    X Sun, L Niu, X Li, X Lu,FJ  Li. J. Pharm. Biomed. Anal, 2009, 50: 27.
[35]    R Dave, NA Sasaki. Tetrahedron: Asymmetry, 2006, 17: 388.
[36]    DEA Raup, B Cardinal-David, D Holte, KA Scheidt. Nat. Chem, 2010, 2: 766.
[37]    R.M, An introduction to the chemistry of heterocyclic compound 2ndedn. John Wiley & Sons, Inc compounds. 1976, 348.
[38]    AKC Schmidt, CBW Stark. Org. Lett, 2011, 13: 5788.
[39]    W Xiao-Meng J Xu, M-H Xin, S-M Lu, S-Q Zhan. Bioorg. Med. Chem. Letts, 2015, 25, 1730–1735.
[40]    X-M Wang, M-H, Xin, J Xu, B-R, Kang, Y Li, S-M Lu, S-Q Zhang. Eur. J. Med. Chem, 2015, 96, 382-395.
[41]    R Kishna, Senwar, P Sharma, T. S Reddy, MK Jeengar, V. L Nayak, V.G.M. Naidu, A Kamal, N Shankaraiah. Eur. J. Med. Chem. 2015, 102, 413-424.
[42]    AI Marwa, SM Abou-Seri, MM Hanna, MM Abdalla, NEl Sayed. Eur. J. Med. Chem, 2015, 99, 1-13.
[43]    W Zhu, C Sun, S Xu, C Wua, J Wua, M Xu, H Zhao, L Chen, W Zeng, P Zheng. Bioorg. Med. Chem, 2014, 22, 6746–6754.
[44]    GW. Rewcastle, SA. Gamage, J U. Flanagan, J D. Kendall, W A. Denny, B C. Baguley, CM. Buchanan, M Chao, P Kestell, S Kolekar, W-J, Lee, CL, Lill, A Malik, R Singh, SMF, Jamieson, P R, Shepherd. Eur. J. Med. Chem, 2013, 64, 137-147.
[45]    W Zhu, Y Liu, X Zhai, X Wang, Y Zhu, D Wua, H Zhou, P Gong, Y Zhao. Eur. J. Med. Chem, 2012, 57, 162-175.
[46]    W Zhu, X Zhai, Q Fu, F Guo, M Bai, J Wang, H Wang, P Gong. Chem. Pharm. Bull. 2012, 60, 1037–1045.
[47]    Y-J Zhu, J-D Huang, X-J Jiang, J-C Sun. Inorg. Chem. Comm, 2006, 9, 473–477.
[48]    D Yancheva, L Daskalova, E Cherneva, B Mikhova, A Djordjevic, Z Smelcerovic, A Smelcerovic. J. Mol. Str, 2012, 1016, 147–154.
[49]    P Panneerselvam, RR, Nair, G Vijayalakshmi, E H, Subramanian, S K Sridhar. Eur. J. Med. Chem, 2005, 40, 225–229.
[50]    K Araki, T Kuroda, S Uemori, A Moriguchi, Y Ikeda, F Hirayama, Y Yokoyama, T Kushiji. J. Med. Chem, 1993, 36, 1356-1363.
[51]    A Smelcerovic, M Rangelov, Z Smelcerovic, A Veljkovic, E Cherneva, D Yancheva, GM Nikolic, Z Petronijevic, G Kocic. Food Chem. Toxicol, 2013, 55, 493–497.
[52]    SA Khanum, BA Begum, V Giris, K N Fatima. Int. J. Biomed. Sci, 2010, 6(1), 60-65.
[53]    M Takaya, M Sato, K Terashima, H Tanizawa. J. Med. Chem, 1979, 22(1), 53-58.
[54]    HB Donahoer, RJ Seiwald, SM Marguerite, CBVM Neumann, K Kimura. J. Med. Pharm. Chem, 1961, 3, 3.
[55]    S Kuettel, A Zambon, M Kaiser, R Brun, L Scapozza, R Perozzo. J. Med. Chem, 2007, 50, 5833-5839.
[56]    JJ Hale, SG Mills, M MacCoss, CP Dorn, PE Finke, RJ Budhu, RA Reamer, SEW Huskey, D Luffer-Atlas, BJ Dean, EM McGowan, WP Feeney, SHL Chiu, MA Cascieri, GG Chicchi, MM Kurtz, S Sadowski, E Ber, FD Tattersall, NMJ Rupniak, AR Williams, W Rycroft, R Hargreaves, JM Metzger, DE MacIntyre. J. Med. Chem. 2000, 43, 1234-1241.
[57]    EM Ladopoulou, AN Matralis, A, Nikitakis, AP Kourounakis. Bioorg. Med. Chem, 2015, 23, 7015–7023.
[58]    MC Chrysselis, EA Rekka, PN Kourounakis. J. Med. Chem, 2000, 43, 609-612.
[59]      S Kato, T Morie, K Hino, T Kon, S Naruto, N Yoshida, T Karasawa, J-I Matsumoto.  J. Med. Chem, 1990, 33, 1406-1413.
[60]      H Hamidian, S Azizi. Bio. Org. Med. Chem. 2015, 23, 7089–7094
[61]      PM Andrey, VD Aleksadr, OG Oleksandr, AT Andrey. Arkivoc, 2012, 8, 226.
[62]      U Das, C-H Huang, W Lin. Chem. Commun, 2012, 48, 5590.
[63]      T Wang, J Liu, H Zhong, H Chen, Zhiliang Lv, Y Zhang, M Zhang, D Geng, C Niu, Y Li, K Li. Bioorg. Med. Chem. Lett, 2011, 21, 3381.
[64]      D-C Wanga, Y-M Xie, C Fan, S Yao, H Song. Chin. Chem. Lett, 2014, 25, 1011.
[65]      RM Mohareb, F Al-Omran, RA Azzam. Steroids. 2014, 84, 46.
[66]      A Shamsuzzaman, H Mashrai, H Khanam, M Asif, A Ali, A Sherwani, M Owais. J. King Saud Univ. Sci, 2015, 27, 1.
[67]      J. Madda, A Venkatesham, NK Bejjanki, N Kommu, S Pombala, CG Kumar, TP Rao, JB Nanubolu. Bioorg. Med. Chem. Lett, 2014, 24, 4428.
[68]      S Debnath, V Mallareddy, SY Manjunath, MF Saleshier, Int. J. Pharm. Sci. Nanotech, 2010, 3, 1157.
[69]      DK Reddy, V Shekhar, P Prabhakar, BC Babu, B Siddhardha, USN Murthy, Y Venkateswarlu. Eur. J. Med. Chem, 2010, 45, 4657.
[70]      AR. Saundane, K Vijaykumar, A.V Vaijinath. Bioorg. Med. Chem. Lett, 2013, 23, 1978.
[71]      RM. Mohareb, MY. Zaki, NS. Abbas. Steroids, 2015, 98, 80.
[72]      Q Chong, C Wang, D Wang, H Wang, F Wu, X Xin, B Wan. Tetrahedron Lett, 2015, 56, 401.
[73]      P Das, A Dutta, A Bhaumik, C Mukhopadhyay. Green Chem, 2014, 16, 1426.
[74]      AJ Kumar, N Renuka, GV Kumar, DM Lokeshwari. J Chem & Pharm Res, 2015, 7(11):693-700.
[75]      MJ Naim, O Alam, MJ Alam, P Alam, N Shrivastava. Inter. J. Pharmacol. Pharm. Sci. 2015, 3(1), 40-51.