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CAL-B accelerated novel synthetic protocols for 3,3’-arylidenebis-4-hydroxycoumarins and dimethyl ((substituted phenyl) (phenylamino)methyl) phosphonates

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Abstract

Green protocols for the syntheses of 3,3′-arylidenebis-4-hydroxycoumarins and dimethyl ((substituted phenyl) (phenylamino)methyl) phosphonates have been first time developed using biocatalyst, CAL-B (lipase). These are carried at room temperature under stirring and are convenient and cost effective. The developed protocols are environmentally acceptable and are giving better to excellent yields of the titled products.

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References

  1. J. Hinman, H. Hoeksema, E.L. Caron, W.G. Jackson, J. Am. Chem. Soc. 78, 1072 (1956)

    Article  CAS  Google Scholar 

  2. H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 7, 890 (2010)

    Article  CAS  Google Scholar 

  3. E.A. Abu-Gharib, R.M. EL-Khatib, L.A.E. Nassr, A.M. Abu-Dief, J. Kore. Chem. Soc. 55(3), 346 (2011)

    Article  CAS  Google Scholar 

  4. E.A. Abu-Gharib, R.M. El-Khatib, L.A.E. Nassr, A.M.R. Abu-Dief, J. Gen. Chem. 84(3), 578 (2014)

    Article  CAS  Google Scholar 

  5. E.A. Abu-Gharib, R.M. EL-Khatib, L.A.E. Nassr, A.M. Abu-Dief, J. King Saud Univ-Sci. 27(1), 54 (2015)

    Article  Google Scholar 

  6. J. Li, Y.P. Sui, J.J. Xin, X.L. Du, J.T. Li, H.R. Huo, H. Ma, W.H. Wang, H. Zhou, Y.H.D. Zhan, Z.J. Wang, C. Li, F. Sui, X. Li, Bioorg. Med. Chem. Lett. 25, 5520 (2015)

    Article  CAS  PubMed  Google Scholar 

  7. J. Li, Z. Hou, F. Li, Z.D. Zhang, Y. Zhou, X. Luo, X.M.K. Li, J. Mol. Struct. 107531, 509 (2014)

    Article  CAS  Google Scholar 

  8. Y.P. Sui, H.R. Huo, J.J. Xin, J. Li, X. Li, J.X.L. Du, H. Ma, H.Y. Zhou, H.D. Zhan, Z.J. Wang, C. Li, F. Sui, M.K. Li, Molecules 20, 17614 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. J.J. Xin, J. Li, Z.D. Zhang, X.B. Hu, M.K. Li, J. Mol. Struct. 1084, 200 (2015)

    Article  CAS  Google Scholar 

  10. K.M. Khan, S. Iqbal, M.A. Lodhi, G.M. Maharvi, Z. Ullah, M.I. Choudhary, A. Rahman, S. Perveen, Bioorg. Med. Chem. 12, 1963 (2004)

    Article  CAS  PubMed  Google Scholar 

  11. K.M. Khan, F. Rahim, A. Wadood, N. Kosar, M. Taha, S. Lalani, A. Khan, M.I. Fakhri, M. Junaid, W. Rehman, M. Khan, S. Perveen, M. Sajid, M.I. Choudhary, Eur. J. Med. Chem. 81, 245 (2014)

    Article  CAS  PubMed  Google Scholar 

  12. Z.N. Siddiqui, M.T.N. Musthafa, A. Ahmad, A.U. Khan, Arch. Pharm. 344, 394 (2011)

    Article  CAS  Google Scholar 

  13. I. Kostova, G. Momekov, Eur. J. Med. Chem. 41, 717 (2006)

    Article  CAS  PubMed  Google Scholar 

  14. M. Kidwai, V. Bansal, P. Mothsra, S. Saxena, R.K. Somvanshi, S. Dey, T.P. Singh, J. Mol. Cat. A Chem. 268, 76 (2007)

    Article  CAS  Google Scholar 

  15. V. Padalkara, K. Phatangarea, S. Takaleb, R. Pisalb, A. Chaskar, J. Saudi. Chem. Soc. 19, 42 (2015)

    Article  Google Scholar 

  16. J.M. Khurana, S. Kumar, Monatsh. Chem. 141, 561 (2010)

    Article  CAS  Google Scholar 

  17. M.M. Heravia, F. Nahavandi, S. Sadjadi, H.A. Oskooie, F.F. Bamoharram, Syn. Commu. 40, 498 (2010)

    Article  CAS  Google Scholar 

  18. J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)

    Article  CAS  Google Scholar 

  19. S. Kadir, A.A. Dar, K.Z. Khan, Synth. Comm. 38, 3490 (2008)

    Article  CAS  Google Scholar 

  20. R. Okenne, R.D. Thomes, Coumarins: Biology Application and Modes of Action (Wiley, Chichester, 1997)

    Google Scholar 

  21. I. Manolova, N.D. Danchev, Arch. Pharm. Pharm. Med. Chem. 332, 243 (1999)

    Article  Google Scholar 

  22. H. Madari, D. Panda, L. Wilson, R. Jacobs, Cancer. Res. 63, 1214 (2003)

    CAS  PubMed  Google Scholar 

  23. J.N. Sangshetti, N.D. Kokare, D.B. Shinde, Green Chem. Lett. and Rev. 2(4), 233 (2009)

    Article  CAS  Google Scholar 

  24. N. Hamdia, M.C. Puertab, P. Valerga, Eur. J. Med. Chem. 43, 2541 (2008)

    Article  CAS  Google Scholar 

  25. K. Tabatabaeian, H. Heidari, A. Khorshidi, M. Mamaghani, N.O. Mahmoodi, J. Serb. Chem. Soc. 77, 407 (2012)

    Article  CAS  Google Scholar 

  26. F. Shirini, M. Abedini, S.A. Kiaroudi, Phosph. Sul. Sili. Relat. Elem. 189, 1279 (2014)

    Article  CAS  Google Scholar 

  27. B. Karmakar, A. Nayak, J. Banerji, Tetrahedron Lett. 53, 4343 (2012)

    Article  CAS  Google Scholar 

  28. A.R. Kiasat, L. Hemat-Alian, Res. Chem. Intermed. 41, 873 (2015)

    Article  CAS  Google Scholar 

  29. J. Albadi, A. Mansournezhad, S. Salehnasab, Res. Chem. Intermed. 41, 5713 (2015)

    Article  CAS  Google Scholar 

  30. F. Shirini, A. Fallah-Shojaei, L. Samavi, M. Abedini, RSC Adv. 6, 48469 (2016)

    Article  CAS  Google Scholar 

  31. M. Zarei, M.A. Zolfigol, A.R. Moosavi-Zare, E. Noroozizadeh, J. Irani. Chem. Soci. 14, 2187 (2017)

    Article  CAS  Google Scholar 

  32. B. Mayank, P.K. Kaur Billing, N. Agnihotri, N. Kaur, D.O. Singh, A.C.S. Jang, Sust. Chem. Eng. 6, 3714 (2018)

    Article  CAS  Google Scholar 

  33. F. Abbasi, N. Azizi, M. Abdoli-Senejani, J. Iran. Chem. Soci. 14, 2097 (2017)

    Article  CAS  Google Scholar 

  34. C. Yang, W.Q. Su, D.Z. Xu, RSC Adv. 6, 99656 (2016)

    Article  CAS  Google Scholar 

  35. A. Zhu, M. Wang, L. Li, J. Wang, RSC Adv. 5, 73974 (2015)

    Article  CAS  Google Scholar 

  36. M. Seddighi, F. Shirini, M. Mamaghani, RSC Adv. 3, 24046 (2013)

    Article  CAS  Google Scholar 

  37. M.S. Lamba, J.K. Makrandi, J. Chem. Res. 10, 585 (2007)

    Google Scholar 

  38. S. Ghosh, P. Mondal, D. Das, K. Tuhina, S.M. Islam, J. Org. Chem. 866, 1 (2018)

    Article  CAS  Google Scholar 

  39. M.M. Heravi, M. Daraie, Res. Chem. Intermed. 42, 2979 (2015)

    Article  CAS  Google Scholar 

  40. Y. Fu, Z. Lu, K. Fang, X. He, H. Huang, Y. Hu, Bioorg. Med. Chem. Lett. 29, 1236 (2019)

    Article  CAS  PubMed  Google Scholar 

  41. M.C. Allen, W. Fuhrer, B. Tuck, R. Wade, J.M. Wood, J. Med. Chem. 32, 1652 (1989)

    Article  CAS  PubMed  Google Scholar 

  42. A. Peyman, W. Stahl, K. Wagner, D. Ruppert, K.H. Budt, Bioorg. Med. Chem. Lett. 4, 2601 (1994)

    Article  CAS  Google Scholar 

  43. F.R. Atherton, C.H. Hassal, R.W. Lambert, J. Med. Chem. 29, 29 (1986)

    Article  CAS  PubMed  Google Scholar 

  44. L. Maier, H. Spoerri, Phosph. Sul. Sili. Relat. Elem. 61, 69 (1991)

    Article  CAS  Google Scholar 

  45. J. Emsley, D. Hall, The Chemistry of Phosphorous; (Harper & Row: London, 1976), 494

  46. J.H. Meyer, P.A. Barlett, J. Am. Chem. Soc. 120(19), 4600 (1998)

    Article  CAS  Google Scholar 

  47. D.J. Miller, S.M. Hammond, D. Anderluzzi, T.D.H. Bugg, J. Chem. Soc. Perkin Trans. 1, 131 (1998)

    Article  Google Scholar 

  48. K. Manabe, S. Kobayashi, Chem. Commun. 8, 669 (2000)

    Article  Google Scholar 

  49. F. Xu, Y. Luo, M. Deng, Q. Shen, Eur. J. Org. Chem. 35(15), 4728 (2003)

    Article  CAS  Google Scholar 

  50. B.C. Ranu, A. Hajra, J. Jana, Org. Lett. 1, 1141 (1999)

    Article  CAS  Google Scholar 

  51. S. Chandrasekhar, S. Jaya Prakash, V. Jagadeshwar, C. Narsihmula, Tetrahedron Lett. 42, 5561 (2001)

    Article  CAS  Google Scholar 

  52. S. Kudrimoti, V.B. Rao, Tetrahedron Lett. 46, 1209 (2005)

    Article  CAS  Google Scholar 

  53. A. Heydari, M. Zarei, R. Alijanianzadeh, H. Tavakol, Tetrahedron Lett. 42, 3629 (2001)

    Article  CAS  Google Scholar 

  54. J.S. Yadav, B.V.S. Reddy, C. Madan, Synlett 7, 1131 (2001)

    Article  Google Scholar 

  55. J.S. Yadav, B.V.S. Reddy, S. Raj, K.B. Reddy, A.R. Prasad, Synthesis 15, 2277 (2001)

    Article  Google Scholar 

  56. B. Kaboudin, R. Nazari, Tetrahedron Lett. 42, 8211 (2001)

    Article  CAS  Google Scholar 

  57. J.S. Yadav, B.V.S. Reddy, P. Sreedhar, Green Chem. 4, 436 (2002)

    Article  CAS  Google Scholar 

  58. A. Heydari, H. Hamedi, M. Pourayoubi, Catal. Commun. 8, 1224 (2007)

    Article  CAS  Google Scholar 

  59. S.M. Vahdat, R. Baharfar, M. Tajbakhsh, A. Heydari, S.M. Baghbanian, S. Khaksar, Tetrahedron Lett. 49, 6501 (2008)

    Article  CAS  Google Scholar 

  60. M. Hosseini-Sarvari, Tetrahedron 64, 5459 (2008)

    Article  CAS  Google Scholar 

  61. P. Thirumurugan, A.N. Kumar, N.S. Priya, D. Muralidaran, P.T. Perumal, Tetrahedron Lett. 51, 5708 (2010)

    Article  CAS  Google Scholar 

  62. A.K. Bhattacharya, C.K. Rana, Tetrahedron Lett. 49, 2598 (2008)

    Article  CAS  Google Scholar 

  63. P. Anastas, J. Warner, Green Chemistry: Theory and Practice Oxford University Press, New York and references cited therein, (1998)

  64. U.R. Pratap, D.V. Jawale, R.A. Waghmare, D.L. Lingampalle, R.A. Mane, New J. Chem. 35, 49 (2011)

    Article  CAS  Google Scholar 

  65. U.R. Pratap, J.R. Mali, D.V. Jawale, R.A. Mane, Tetrahedron Lett. 50, 1352 (2009)

    Article  CAS  Google Scholar 

  66. U.R. Pratap, D.V. Jawale, M.R. Bhosle, R.A. Mane, Tetrahedron Lett. 52, 1689 (2011)

    Article  CAS  Google Scholar 

  67. U.R. Pratap, D.V. Jawale, P.D. Netankar, R.A. Mane, Tetrahedron Lett. 52, 5817 (2011)

    Article  CAS  Google Scholar 

  68. U.R. Pratap, D.V. Jawale, B.S. Londhe, R.A. Mane, J. Mol. Cat. B Enzym. 68, 94 (2011)

    Article  CAS  Google Scholar 

  69. L.D. Khillare, U.R. Pratap, M.R. Bhosle, S.T. Dhumal, M.B. Bhalerao, R.A. Mane, Res. Chem. Intermed. 43, 4327 (2017)

    Article  CAS  Google Scholar 

  70. A.S. Chavan, A.S. Kharat, M.R. Bhosle, R.A. Mane, Synth. Commun. 47(19), 1777 (2017)

    Article  CAS  Google Scholar 

  71. A.S. Chavan, A.S. Kharat, M.R. Bhosle, S.T. Dhumal, R.A. Mane, Synth. Commun. 51(13), 1963 (2021)

    CAS  Google Scholar 

  72. A.S. Chavan, A.S. Kharat, M.R. Bhosle, R.A. Mane, Heter. commun. 24(2), 103 (2018)

    Article  CAS  Google Scholar 

  73. M.T. Reetz, Curr. Opin. Chem. Biol. 6, 145 (2002)

    Article  CAS  PubMed  Google Scholar 

  74. I. Alfonso, V. Gotor, Chem. Soc. Rev. 33, 201 (2004)

    Article  CAS  PubMed  Google Scholar 

  75. V. Gotor, Bioorg. Med. Chem. 7, 2189 (1999)

    Article  CAS  PubMed  Google Scholar 

  76. A. Ghanem, Tetrahedron 63, 1721 (2007)

    Article  CAS  Google Scholar 

  77. F. Hasan, A.A. Shah, A. Hameed, Enzyme Microb. Technol. 39, 235 (2006)

    Article  CAS  Google Scholar 

  78. F.V. Gotor, R. Brieva, V. Gotor, J. Mol. Cat. B: Enzym. 40, 111 (2006)

    Article  CAS  Google Scholar 

  79. E. Santaniello, S. Casati, P. Ciuffred, Curr. Org. Chem. 10, 1095 (2006)

    Article  CAS  Google Scholar 

  80. B. Stauch, S.J. Fisher, M. Cianci, J. Lipid Res. 56, 2348 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  81. J. Uppenberg, M. Trier Hansen, S. Patkar, T.A. Jones, Structure 2(4), 293 (1994)

    Article  CAS  PubMed  Google Scholar 

  82. A. Vinu, P. Kalita, V.V. Balasubramanian, H. Oveisi, T. Selvan, A. Mano, M.A. Chari, B.V.S. Reddy, Tetrahedron Lett. 50, 7132 (2009)

    Article  CAS  Google Scholar 

  83. A.K. Bhattacharya, M. Mujahid, Syn. Commun. 43, 2583 (2013)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors are thankful to Late Professor D. B. Ingle for his invaluable discussions and guidance. The authors are also thankful to SAIF, Central Drug Research Institute (CDRI), Lucknow for spectral analysis.

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Authors and Affiliations

  1. Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431004, India

    Anusaya S. Chavan, Manisha R. Bhosle, Sambhaji T. Dhumal & Ramrao A. Mane

  2. Laboratory of Applied Microbiology, School of Life Sciences, Jawaharlal Nehru University, New Delhi, 110067, India

    Arun S. Kharat

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  1. Anusaya S. Chavan
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Correspondence to Ramrao A. Mane.

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Chavan, A.S., Kharat, A.S., Bhosle, M.R. et al. CAL-B accelerated novel synthetic protocols for 3,3’-arylidenebis-4-hydroxycoumarins and dimethyl ((substituted phenyl) (phenylamino)methyl) phosphonates. Res Chem Intermed 47, 4497–4512 (2021). https://doi.org/10.1007/s11164-021-04535-2

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