OJMC  Vol.2 No.3 , September 2012
Synthesis and Biological Evaluation of Cyclic Imides with Coumarins and Azacoumarins
Abstract: A series of new N-substituted cyclic imides of coumarins and azacoumarins have been synthesized. All the compounds were screened for their antibacterial and antifungal activities. α-Amylase enzyme inhibition activities of some N-substituted phthalimide derivatives have been explored. All the compounds were characterized by IR, 1H-NMR, and GC-MS.
Cite this paper: nullR. Marulasiddaiah, R. Kalkhambkar and M. Kulkarni, "Synthesis and Biological Evaluation of Cyclic Imides with Coumarins and Azacoumarins," Open Journal of Medicinal Chemistry, Vol. 2 No. 3, 2012, pp. 89-97. doi: 10.4236/ojmc.2012.23011.

[1]   C. Lipinski and A. Hopkins. “Navigating Chemical Space for Biology and Medicine”, Nature, Vol. 432, 2004, pp. 855-861. (b) S. L. Schreiber, “Target-Oriented and Diversity-Oriented Organic Synthesis in Drug Discovery,” Science, Vol. 287, No. 5460, 2000, pp. 1964-1969. doi:10.1126/science.287.5460.1964

[2]   R. Dua, S. Shrivastava, S. K. Sonawane and S. K. Srivastava, “Pharmacological Significance of Synthetic Heterocycles Scaffold: A Review,” Advances in Biological Research, Vol. 5, No. 3, 2011, pp. 120-144.

[3]   P. M. Chauhan and S. K. Srivastava, “Recent Developments in the Combinatorial Synthesis of Nitrogen Heterocycles Using Solid Phase Technology,” Combinatorial Chemistry & High Throughput Screening, Vol. 4, No. 1, 2001, pp. 35-51.

[4]   B. Teng, J. Zheng, H. Huang and P. Huang, “Enantioselective Synthesis of Glutarimide Alkaloids,” Chinese Journal of Chemistry, Vol. 29, No. 7, 2011, pp. 13121318. doi:10.1002/cjoc.201180248

[5]   A. F. M. Fahmy, “Heterocycles as Versatile Building Blocks in Different Synthetic Strategies,” Archive for Organic Chemistry, Vol. 7, 2006, pp. 395-415.

[6]   M. K. Haergreeves, J. G. Prtichard and H. R. Dav, “Cyclic Carboxylic Monoimides,” Chemical Reviews, Vol. 70, No. 4, 1970, pp. 439-469. doi:10.1021/cr60266a001

[7]   V. C. Filho, R. Correa, Z. Vaz, J. B. Calixto, R. J. Nunes, A. D. Andricopulo and R. A. Yunes, “Further Studies on Analgesic Activity of Cyclic Imides II,” Farmaco, Vol. 53, No. 1,1998, pp. 55-57. doi:10.1016/S0014-827X(97)00006-2

[8]   D. E. Butler, J. D. Leonard, B. W. Caprathe, Y. J. Litalien, M. R. Pavia, F. M. Hershenson, P. H. Poschel and J. G. Marriott, “Amnesia-Reversal Activity of a Series of Cyclic Imides,” Journal of Medicinal chemistry, Vol. 30, No. 3, 1987, pp. 498-503.

[9]   A. D. Andricopulo, L. A. Muller, V. C. Filho, G. S. Cani, J. F. Roos, A. R. Santos, R. J. Nunes, R. A. Yunes and Farmaco, “Analgesic Activity of Cyclic Imides: 1,8Naphthalimide and 1,4,5,8-Naphthalenediimide Derivatives,” Farmaco, Vol. 55, No. 4, 2000, pp. 319-321. doi:10.1016/S0014-827X(00)00027-6

[10]   K. N. de Oliveira, L. D. Chiaradia, P. G. A. Martins, A. Mascarello, M. N. S.Cordeiro, R.V. C. Guido, A. D. Andricopulo, R. A. Yunes, R. J. Nunes, J. Vernalb and H. Terenzi, “Sulfonyl-Hydrazones of Cyclic Imides Derivatives as Potent Inhibitors of the Mycobacterium tuberculosis Protein Tyrosine Phosphatase B (PtpB),” Medicinal Chemistry Communication, Vol. 2, No. 3, 2011, pp. 500504.

[11]   S. M. Sondhi, R. Rani, A. D. Dwiwedi and P. Roy, “Synthesis of Some Heterocyclic Imides and Azomethine Derivatives under Solvent Free Condition and Their Anti-Inflammatory Activity Evaluation,” Journal of Heterocyclic Chemistry, Vol. 46, No. 6, 2009, pp. 13691374. doi:10.1002/jhet.249

[12]   S. M. Sondhi, R. Rani, P. Roy, S. K. Agrawal and A. K. Saxena, “ChemInform Abstract: Microwave-Assisted Synthesis of N-Substituted Cyclic Imides and Their Evaluation for Anticancer and Anti-inflammatory Activities,” Bioorganic Medicinal Chemistry Letters, Vol. 19, No. 7, 2009, pp. 1534-1538. doi:10.1016/j.bmcl.2008.07.048

[13]   Q. Li, H.Fang, X. Wang and W. Xu, “Novel Cyclic-Imides Peptidomimetics as Amino Peptidase N Inhibitors,” European Journal of Medicinal Chemistry, Vol. 45, No. 4, 2010, pp. 1618-1626. doi:10.1016/j.ejmech.2009.12.071

[14]   Q. Li, H. Fang, X. Wang, L. Hu and W. Xu, “Novel Cyclic-Imide Peptidomimetics as Amino Peptidase N Inhibitors. Design, Chemistry and Activity Evaluation. Part I,” European Journal of Medicinal Chemistry, Vol. 44, No. 12, 2009, pp. 4815-4825. doi:10.1016/j.ejmech.2009.07.022

[15]   J. Zhang, M. Senthilkumar, S. C. Ghosh and S. H. Hong, “Synthesis of Cyclic Imides from Simple Diols,” Angewandte Chemie International Edition, Vol. 49, No. 36, 2010, pp. 6391-6395. doi:10.1002/anie.201002136

[16]   Y. M. Hiji and B. Ellis, “Efficient Microwave Assisted Syntheses of Unsubstituted Cyclic Imides,” Heterocycles, Vol. 68, No. 11, 2006, pp. 2259-2267. doi:10.3987/COM-06-10841

[17]   E. Benjamin and Y. Hijji, “The Synthesis of Unsubstituted Cyclic Imides Using Hydroxylamine under Microwave Irradiation,” Molecules, Vol. 13, No. 1, 2008, pp. 157-169.

[18]   A. Kato and Y. Minoshima, “Protective Effects of Dietary Chamomile Tea on Diabetic Complications,” Journal of Agricultural Food Chemistry, Vol. 56, No. 17, 2008, pp. 8206-8211. doi:10.1021/jf8014365

[19]   M. Najafian, A. Ebrahim-Habibi, N. Hezareh, P. Yaghmaei, K. Parivar and B. Larijani, “Trans-Chalcone: A Novel Small Molecule Inhibitor of Mammalian Alpha-Amylase,” Molecular Biology Reports, Vol. 38, No. 3, 2010, pp. 1617-1620.

[20]   M. V. Kulkarni, G. M. Kulkarni, C.-H. Lin and C.-M. Sun, “Recent Advances in Coumarins and 1-Aza Coumarins as Versatile Biodynamic Agents,” Current Medicinal Chemistry, Vol. 13, No. 23, 2006, pp. 2795-2889. doi:10.2174/092986706778521968

[21]   H. Higashi, K. Sato, A. Ohtake, A. Omori, S. Yoshida and Y. Kudo, “Imaging of cAMP-Dependent Protein Kinase Activity in Living Neural Cells Using a Novel Fluorescent Substrate,” FEBS Letters, Vol. 414, No. 7, 1997, pp. 55-60. doi:10.1016/S0014-5793(97)00970-8

[22]   M. D Ghate, M. V. Kulkarni, R. Shobha and S. Y. Kattimani, “Synthesis of Vanillin Ethers from 4-(Bromomethyl) Coumarins as Anti-Inflammatory Agents,” European Journal of Medicinal Chemistry, Vol. 38, No. 3, 2003, pp. 297-302. doi:10.1016/S0223-5234(03)00016-3

[23]   L. A. Shastri, K. Shivashankar and M. V. Kulkarni, “Facile Synthesis of Some Novel 4-{3-Aryl-3,4-Dihydro2H-Benzo[b][1,4] Thiazin-2-yl}-2H-Chromen-2-One Derivatives,” Journal of Sulfur Chemistry, Vol. 28, No. 6, 2007, pp. 625-630. doi:10.1080/17415990701591286

[24]   G. M. Kulkarni, M. V. Kulkarni and V. D. Patil, “Heterocycles with Bridgehead Nitrogen: Synthesis, High Resolution NMR and Mass Spectra of 5 Aryloxymethyltetrazolo[1,5-a]Quinolines,” Journal of Indian Chemical Society, Vol. 74,1997, pp. 502-503.

[25]   R. G. Kalkhambkara, G. M. Kulkarni, et al., “Synthetic and Biological Studies on Monoand Bis-MethyleneBridged Heterocyclic Sulfides and Sulfones of Carbostyrils,” Journal of Sulfur Chemistry, Vol. 30, No. 6, 2009, pp. 596-610. doi:10.1080/17415990903191745

[26]   R. G. Kalkhambkar, G. M. Kulkarni and C. M. Kamanavalli, “Synthesis and Biological Activities of Some New Fluorinated Coumarins and 1-Aza Coumarins,” European Journal of Medicinal Chemistry, Vol. 43, No. 10, 2008, pp. 2178-2188. doi:10.1016/j.ejmech.2007.08.007

[27]   M. V. Kulkarni and V. D. Patil, “Synthesis and Biological Properties of Some 3-Heterocyclic Coumarins,” Archiv der Pharmazie (Weinheim), Vo1. 314, No. 5, 1981, 435439.

[28]   E. J. Threlfall, I. S. T. Fisher, l. R. Ward, H. Tsch?pe and P. Gerner-Smidt, “Harmonization of Antibiotic Susceptibility Testing for Salmonella,” Microbial Drug Resistance, Vol. 5, No. 3, 1999, pp. 195-199. doi:10.1089/mdr.1999.5.195

[29]   W. B. Hugo, A. B. Russel, S. P. Denyer, N. A. Hodges and S. P. German, “Pharmaceutical Microbiology,” Blackwell Scientific Publication, 1987, pp. 187-202.

[30]   S. Sadasivam and A. Manickam, “Biochemical Methods,” New Age International (P) Limited, New Delhi, Vol. 2. 1996, pp. 124-126.

[31]   M. V. Kulkarni, B. G. Pujar and V. D. Patil, “Studies on Coumarins II,” Archiv der Pharmazie (Weinheim), Vol. 316, No. 1, 1983, pp. 15-17. doi:10.1002/ardp.19833160106

[32]   M. Hasegawa, “Synthesis of 4-Bromomethyl Carbostyrils,” Pharmaceutical Bulletin Japan, Vol. 1, 1953, pp. 1-3.

[33]   R. Marulasiddaiah, M. V. Kulkarni, D. Sharma and V. K. Gupta, “Crystal Structure of 1-(7,8-Dimethyl-2-oxo-2HChromen-4-ylmethyl)-PYRROLIDINE-2,5-Dione,” X-Ray Structure Analysis Online ,Vol. 27, 2011, pp. 41-42. doi:10.2116/xraystruct.27.41

[34]   F. M. Lajolo and F. F. Filho, “Partial Characterization of the Amylase Inhibitor of Black Beans (Phaseolus Vulgaris) Variety Rico 23,” Journal of Agricultural Food Chemistry, Vol. 33, No. 1, 1985, pp. 132-138. doi:10.1021/jf00061a038

[35]   B. Gibbs and I. Alli, “Characterization of a Purified α-Amylase Inhibitor from White Kidney Beans (Phaseolus Vulgaris),” Food Research International, Vol. 31, No. 3, 1998, pp. 217-225. doi:10.1016/S0963-9969(98)00074-X