Synthesis and Molecular Structure Analysis of 4-(bis(2-chloroethyl)amino)-3-nitro-2H-chromen-2-one by Single crystal XRD Method

Authors(4) :-Nirav Tatamiya, Jayesh S. Babariya, Yogesh T. Naliapara, D. M. Purohit

A novel 3-nitro and 4-N-mustard functionalized coumarine has been synthesized using 4-chloro, 3-nitro coumarine and Diethanol amine using Isopropyl alcohol as solvent, resultant intermediate undergoes chlorination with Thionyl chloride and DMF as solvent is described. The synthesized compound characterized by spectroscopic techniques and finally confirmed by X-ray diffraction studies. The molecule crystallizes in the monoclinic crystal class in the space group P21/c with cell parameters a = 7.473(1)Aob =   8.169 (1)Ao ,c =  13.957(2)Ao ,a =  87.942(5)Ao ,b =  86.073(5)Ao ,g =  65.040(5)Ao and Z = 4. The Coumarine ring adopts flattened conformation.

Authors and Affiliations

Nirav Tatamiya
Zydus Cadila, Ahemdabad, Gujarat, India
Jayesh S. Babariya
Shree H.N.Shukla college of science, Rajkot, Gujarat, India
Yogesh T. Naliapara
Department of Chemistry, Saurashtra University, Rajkot, Gujarat, India
D. M. Purohit
Shree M&N Virani Science College, Rajkot, Gujarat, India

3-Nitro-4-Chloro Coumarine, Hydrogen Bonds

  1. Gmelin, R.; Hoppe-Seyler’s, Z.; Physiol. Chem., 1959, 316, 164. (b) Bell, E. A.; Foster, R. G.; Nature, 1962, 194, 91.
  2. Jansen, B. C. P.; Donath, W. F.; Chem. Weekblad., 1926, 23, 201.
  3. Tanaka, F.; Takeuchi, S.; Tanaka, N.; Yonehara, H.; Umezawa, H.; Sumiki, Y. J.; Antibiot. A, 1961, 14, 161.
  4. Lin, Y.-L.; Huang, R.-L.; Chang, C.-M.; Kuo, Y.-H.; J. Nat. Prod., 1997, 60, 982; (b) Gerlinck, R. G. S.; Braekman, J. C.; Daloze, D.; Bruno, I.;  Riccio, R.; Rogeau D.; Amade, P.;  J. Nat. Prod., 1992, 55, 528.
  5. Ohtani, I.; Moore, R. E.; Runnegar, M. T. C.;  J. Am. Chem. Soc., 1992, 114, 7941; (b) Banker, R.; Teltsch, B.; Sukenik A.; Carmeli, S.; J. Nat. Prod., 2000, 63, 387.
  6. Brugnatelli, G.; Giornale di fisica chimica, et storia Naturale (Pavia) decada seconda, 1818, 1, 117; (b) Brugnatelli, G.; Ann. Chim. Phys., 1818, 8, 201.
  7. Frankland, E.; Kolbe, H.; Justus Liebigs Ann. Chem., 1848, 65, 269.
  8. Davidson, M.H.; Expert Opin Investig Drugs, 2002, 11, 125.
  9. Radi, M.; Maga, G.; Alongi, M.; Angeli, L.; Samuele, A.; Zanoli, S.; Bellucci, L.; Tafi, A.;  Casaluce, G.; Giorgi, G.; Armand-Ugon, M.; Gonz´alez-Ortega, E.; Est´e, J. A.; Baltzinger, M.; Bec, G.;  Dumas, P.; Ennifar E.; Botta, M.; J. Med. Chem., 2009, 52, 840.
  10. Koch, U.; Attenni, B.; Malancona, S.; Colarusso, S.; Conte, I.; DiFilippo, M.; Harper, S.; Pacini, B.; Giomini, C.; F.Thomas, S.; Incitti, I.; Tomei, L.; De Francesco, R.; Altamura, S.; Matassa ,V. G.; Narjes, J., Med. Chem., 2006, 49, 1693.
  11. Chu, X.-J.; DePinto, W.; Bartkovitz, D.; So, S.-S.; Vu, B. T.; Packman, K.; Lukacs, C.; Ding, Q.; Jiang, N.; Wang, K.; Goelzer, P.; Yin, X.; Smith, M. A.; Higgins, B. X.; Chen, Y.; Xiang, Q.; Moliterni, J.; Kaplan, G.; Graves, B.; Lovey, A.; Fotouhi, N.; J. Med. Chem., 2006, 49, 6549.
  12. Giblin, G. M. P.; O’Shaughnessy, C. T.; Naylor, A.; Mitchell, W. L.; Eatherton, A. J.; Slingsby, B. P.; Rawlings, D. A.; Goldsmith, P.; Brown, A. J.; Haslam, C. P.; Clayton, N. M.; Wilson, A. W.; Chessell, I. P.; Wittington, A. R.; Green, R.; J. Med. Chem., 2007, 50, 2597.
  13. Harris, P. A.; Boloor, A.; Cheung, M.; Kumar, R.; Crosby, R. M.; Davis-Ward, R. G.;. Epperly, A. H.; Hinkle, K.W.; Hunter, R. N.; Johnson, J. H.; Knick, V. B.; Laudeman, C. P. ; Luttrell, D. K.; Mook, R. A.; Nolte, R. T.; Rudolph, S. K.; Szewczyk, J. R.; Truesdale, A. T.; Veal, J. M.; Wangand,  L.; Stafford,  J.  A.; J. Med. Chem., 2008, 51, 4632.
  14. Chang, L. C. W.; Spanjersberg, R. F.; von FrijtagDrabbe, J. K.; unzel, T. K.; Mulder-Krieger.; van den Hout, G.; Beukers, M. W.; Brusseeand, J. A.; Ijzerman, P.; J. Med. Chem., 2004, 47, 6529; (b) Lanier, M. C.; Moorjani, M.; Luo, Z.; Chen, Y.; Lin, E.; Tellew, J. E.; Zhang, X.; Williams, J. P.; Gross, R. S.; Lechner, S. M.; Markison, S.; Joswig, T.; Kargo, W.; Piercey, J.; Santos, M.; Malany, S.; Zhao, M.; Petroski, R.; Crespo, M. I.; Diaz J.-L.; Saunders, J.; Wen, J.; Brien Z. O.; Jalali, K.; Madan, A.; Slee, D. H.; J. Med. Chem., 2009, 52, 709; (c)  Cosimelli, B.; Greco, G.; Ehlardo, M.; Novellino, E.; Da Settimo, F.; Taliani, S.; La Motta, C.; Bellandi, M.; Tuccinardi, T.; Martinelli, A.; Ciampi, O.; Trincavelli M. L.; Martini, C.; J. Med. Chem., 2009, 51, 1764.

Publication Details

Published in : Volume 3 | Issue 6 | September-October 2017
Date of Publication : 2017-10-31
License:  This work is licensed under a Creative Commons Attribution 4.0 International License.
Page(s) : 110-113
Manuscript Number : IJSRSET173617
Publisher : Technoscience Academy

Print ISSN : 2395-1990, Online ISSN : 2394-4099

Cite This Article :

Nirav Tatamiya, Jayesh S. Babariya, Yogesh T. Naliapara, D. M. Purohit, " Synthesis and Molecular Structure Analysis of 4-(bis(2-chloroethyl)amino)-3-nitro-2H-chromen-2-one by Single crystal XRD Method, International Journal of Scientific Research in Science, Engineering and Technology(IJSRSET), Print ISSN : 2395-1990, Online ISSN : 2394-4099, Volume 3, Issue 6, pp.110-113, September-October-2017.
Journal URL : http://ijsrset.com/IJSRSET173617

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