Ultrasonic promoted synthesis of novel s-triazine-Schiff base derivatives; molecular structure, spectroscopic studies and their preliminary anti-proliferative activities

Journal of Molecular Structure

Volumn 1125, Issue , 2016, Pages 121-135

  El Faham, Ayman ^a,c   Soliman, Saied M ^b,c   Ghabbour, Hazem A ^d,e   Elnakady, Yasser A ^a   Mohaya, Talal A ^f   Siddiqui, Mohammed R H ^a   Albericio, Fernando ^a,g,h  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

^c Alexandria University Faculty Of Science   (Egypt)

^d KING SAUD UNIVERSITY   (Saudi Arabia)

^e MANSOURA UNIVERSITY   (Egypt)

^f KING ABDULAZIZ CITY FOR SCIENCE AND TECHNOLOGY   (Saudi Arabia)

^g UNIVERSITY OF KWAZULU NATAL   (South Africa)

^h UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Anti proliferative activities; DFT NBO; s triazine; Schiff base; Ultrasonic; X ray crystallography

Indexed keywords

CELL CULTURE; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; IRRADIATION; MOLECULAR STRUCTURE; POLYOLS; SINGLE CRYSTALS; SPECTROSCOPIC ANALYSIS; ULTRASONICS;

ANTI-PROLIFERATIVE ACTIVITIES; ANTIPROLIFERATIVE EFFECT; S-TRIAZINES; SCHIFF-BASE; SCHIFF-BASE DERIVATIVES; SPECTROSCOPIC PROPERTY; ULTRASOUND IRRADIATION; X-RAY SINGLE-CRYSTAL DIFFRACTION;

X RAY CRYSTALLOGRAPHY;

EID: 84976541524     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2016.06.061     Document Type: Article

References (73)

1. [1] Cella, R., Stefani, H.A., Ultrasound in heterocycles chemistry. Tetrahedron 65 (2009), 2619–2641.
2. [2] Jiang, Y., Chen, X., Qu, L., Wang, J., Yuan, J., Chen, S., Li, X., An efficient ultrasound-assisted method for the synthesis of 1,4-disubstituted triazoles. Z. Naturforsch 66b (2011), 77–82.
3. [3] Singh, A.K., Shukla, S.K., Quraishi, M.A., Ultrasound mediated green synthesis of hexahydro triazines. J. Mater. Environ. Sci. 2 (2011), 403–406.
4. [4] Srinivas, K., Dubey, P.K., A simple, rapid and environmentally benign synthesis of N-alkyl/aryalkyl benzimidazoles promoted by ultrasound irradiation. Adv. Appl. Sci. Res. 5 (2014), 336–341.
5. [5] Singh, A.K., Shukla, S.K., Ahamad, I., Quraishi, M.A., Solvent free microwave assisted synthesis of 1H-Indole-2,3-dione derivatives. J. Heterocycl. Chem. 46 (2009), 571–574.
6. [6] Li, J.T., Yang, W.Z., Wang, S.X., Li, S.H., Li, T.S., Improved synthesis of chalcones under ultrasound irradiation. Ultrason. Sonochem 9 (2002), 237–239.
7. [7] Li, J.T., Chen, G.F., Yang, W.Z., Li, T.S., Ultrasound promoted synthesis of 2-aroyl-1,3,5-triaryl-4-carbethoxy-4- cyanocyclohexenols. Ultrason. Sonochem 10 (2003), 123–126.
8. [8] Ding, L., Wang, W., Zhang, A., Synthesis of 1,5-dinitroaryl-1,4-pentadien-3-ones under ultrasound irradiation. Ultrason. Sonochem, 14, 2007 563–267.
9. [9] Cravotto, G., Cintas, P., Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications. Chem. Soc. Rev. 35 (2006), 180–196.
10. [10] Li, J.T., Chen, G.F., Xu, W.Z., Li, T.S., The Michael reaction catalyzed by KF/basic alumina under ultrasound irradiation. Ultrason. Sonochem 10 (2003), 115–118.
11. [11] Babu, P.N.K., Devi, B.R., Dubey, P.K., Ultrasound assisted convenient, rapid and environmentally benign synthesis of N-alkylbenzimidazoles. Der Chem. Sin. 4 (2013), 105–111.
12. [12] Feng, H., Li, Y., Lin, S., der Eycken, E.V.V., Song, G., Nano Cu-catalyzed efficient and selective reduction of nitroarenes under combined microwave and ultrasound irradiation. Sustain. Chem. Pro 2 (2014), 1–6.
13. [13] Mady, M.F., El-Kateb, A.A., Zeid, I.F., Jørgensen, K.B., Comparative studies on conventional and ultrasound-assisted synthesis of novel homoallylic alcohol derivatives linked to sulfonyl dibenzene moiety in aqueous media. J. Chem. 2013 (2013), 1–9.
14. [14] Sączewski, F., Bułakowska, A., Bednarski, P., Synthesis and anticancer activity of novel 2,4-diamino-1,3,5-triazine derivatives. Eur. J. Med. Chem. 41 (2006), 219–225.
15. [15] Sączewski, F., Bułakowska, A., Synthesis and anticancer activity of novel alkenyl-1,3,5-triazine derivatives. Eur. J. Med. Chem. 41 (2006), 611–615.
16. [16] Patel, R., Premlata, K., Dhanji, P.R., Chikhalia, K., Synthesis and studies of novel 2-(4-cyano-3-trifluoro methyl phenyl amino) -4 -(quinoline-4-yloxy)-6-(piperazinyl/piperidinyl)-s-triazines as potential antimicrobial, anti-mycobacterial and anticancer agents. Eur. J. Med. Chem. 46 (2011), 4354–4365.
17. [17] Mohmmad, Y.W., Abdul, R.B., Amir, A., Fareeda, A., Probing the antiamoebic and cytotoxicity potency of novel tetrazole and triazine derivatives. Eur. J. Med. Chem. 48 (2012), 313–320.
18. [18] Arya, K., Dandia, A., Synthesis and cytotoxic activity of trisubstituted-1,3,5-triazines. Bioorg. Med. Chem. 17 (2007), 3298–3304.
19. [19] Pandey, V.K., Tusi, Z., Tandon, M., Synthesis of thiadiazolo-s-triazines for their antiviral activity based on QSAR studies. Indian J. Chem. 42B (2003), 2583–2588.
20. [20] Xiong, Y.-Z., J-Balzarini, F.C., De Clercq, E., Structural modulation of diaryltriazine with potent anti-HIV activity. Eur. J. Med. Chem. 43 (2008), 1230–1236.
21. [21] Srinivas, K., Srinivas, U., Bhanuprakash, K., Harakishore, K., Murthy, U.S.N., Jayathirtha, V., Synthesis and antibacterial activity of various substituted s-triazines. Eur. J. Med. Chem. 41 (2006), 1240–1246.
22. [22] Sunduru, N., Agarwal, A., Katiyar, S.B., Synthesis of 2,4,6-trisubstituted pyrimidine and triazine heterocycles as antileishmanial agents. Bioorg. Med. Chem. 14 (2006), 7706–7715.
23. [23] Geoffrey, A.M., Reddy, R., Francis, A., Belley, A., Lehoux, D., Moeck, G., Triaminotriazine DNA helicase inhibitors with antibacterial activity. Bioorg. Med. Chem. 16 (2006), 1286–1290.
24. [24] Pradip, P., Berad, B.N., Synthesis and antibacterial activity of 1,3,5-thiadiazines and their isomerism into 1,3,5-triazines. Indian J. Chem. 44B (2005), 638–639.
25. [25] Solankee, A., Patel, J., Synthesis of chalcones, pyrazolines, amino pyrimidines and pyrimidinethiones as antibacterial agents. Indian J. Chem. 43B (2004), 1580–1584.
26. [26] Gadaginamath, G.S., Kavali, R.S., Pujar, S.R., Synthesis and antibacterial activity of some new 1-n-butyl-3-acetyl-5-(2,4-diamino-1,3,5-triazin-6-yl)methoxy-2-methyl inodole derivatives. Indian J. Chem. 38B (1999), 1226–1228.
27. [27] Shelar, A.R., Adure, S.A., Shelar, M.A., Synthesis and antibacterial activity mono aryloxy-s-triazine derivatives of penicillin, cephalosporin, ampicillin and cephalexin. Indian J. Chem. 37B (1998), 358–364.
28. [28] Basedia, D.K., Shrivastava, B., Dubey, B.K., Sharma, P., Synthesis, characterization and antimicrobial activity of novel 2,5-substituted aryl-7 phenyl-1,3,4-oxadiazolo-[3,2-a]-1,3,5-triazine derivatives. Int. J. Biomed. Res. 5 (2014), 13–18.
29. [29] Khare, R.K., Srivastava, A.K., Singh, H., Synthesis and fungicidal activity of some 6-aryl-2-(B-D-glucopyranosyl)-3-oxo-2,3-dihydro-1,3,4-oxadiazolo[3,2-b]-1,2,4,6-thiatriazine-1,1-dioxides. Indian J. Chem. 44B (2005), 163–166.
30. [30] Indorkar, D., Chourasia, O.P., Limaye, S.N., Synthesis, characterization, antimicrobial, antifungal activity of some s-triazine derivatives of Isoxazoline, Pyrazoline and PC model computational studies. Res. J. Pharm. Sci. 1 (2012), 10–16.
31. [31] Parikh, K.S., Vyas, S.P., Synthesis and antimicrobial screening of some new s-Triazine based Piperazine and Piperidine derivatives. Der Chem. 3 (2012), 430–434.
32. [32] Srivastava, A.K., Raja, S.K., Puri, S.K., Chauhan, M.S., Synthesis and bioevaluation of hybrid 4-aminoquinoline triazines as a new class of antimalarial agents. Bioorg. Med. Chem. 18 (2008), 6530–6533.
33. [33] Agarwal, A., Srivastava, K., Puri, S.K., Prem, M.S., Synthesis of 2,4,6-trisubstituted triazines as antimalarial agents. Bioorg. Med. Chem. 15 (2005), 531–535.
34. [34] Srivastava, A.K., Raja, S.R., Siddiqi, M.I., Puri, S.K., Sexana, J.K., Chauhan, M.S., 4-Anilinoquinoline triazines: a novel class of hybrid antimalarial agents. Eur. J. Med. Chem. 46 (2011), 676–690.
35. [35] Gajare, A.S., Bhawsar, S.B., Shinde, D.B., Shingare, M.S., Synthesis of 2,4-diaryl amino-6-(3,5,6-trichloropyridin-2-yl)oxy triazine and its herbicidal activity. Indian J. Chem. 37B (1998), 510–513.
36. [36] Rafat, M., Fleita, D.H., Sakka, O.K., Novel Synthesis of hydrazide-hydrazone derivatives and their utilization in the synthesis of coumarin, pyridine, thiazole and thiophene derivatives with antitumor activity. Molecules 16 (2011), 16–27.
37. [37] Padmini, K., Jaya Preethi, P., Divya, M., Rohini, P., Lohita, M., Swetha, K., Kaladar, P., A Review on biological importance of hydrazones. J. Pharma Res. Rev. 2 (2013), 43–58.
38. [38] Vicini, P., Zani, F., Cozzini, P., Doytchinova, I., Hydrazones of 1,2-benzisothiazole hydrazides: synthesis, antimicrobial activity and QSAR investigations. Eur. J. Med. Chem. 37 (2002), 553–564.
39. [39] Arshad, M.N., Bibi, A., Mahmood, T., Asiri, A.M., Ayub, K., Synthesis, crystal structures and spectroscopic properties of Ttriazine-based hydrazone derivatives; a comparative experimental-theoretical study. Molecules 20 (2015), 5851–5874.
40. [40] Amir, M., Ali, I., Hassan, M.Z., Mulakayala, N., Design, synthesis, and biological evaluation of hydrazone incorporated 1,2,4-triazines as anticonvulsant agents. Arch. Pharm. 347 (2014), 958–968.
41. [41] Ji, K., Lee, C., Janesko, B.G., Simanek, E.E., Triazine-substituted and acyl hydrazones: experiment and computation reveal a stability inversion at low pH. Mol. Pharm. 12 (2015), 2924–2927.
42. [42] Chaudhari, J.A., Novel piperazinylo bisaryl hydrazino-s-triazine derivatives and their application as epoxy resin curing agents. Int. J. Polym. Mater. Polym. Biomater. 58 (2009), 401–408.
43. [43] Chaudhari, J.A., Patel, R.P., Novel s-triazine–epoxy resin curing system and their material applications. J. Chem. Biol. Phys. Sci. 2 (2012), 1234–1240.
44. [44] Bakharev, V.V., Gidaspov, A.A., Parenov, V.E., Ulyankina, I.V., Zavodskaya, A.V., Selezneva, E.V., Suponitskii, K.Y., Sheremetev, A.B., Synthesis of 4amino-6-chloro1,3,5triazin2(1H)ones. Russ. Chem. Bull. Int. Ed. 61 (2012), 99–112.
45. 2O {R = bis(2-diphenylmethylene) hydrazinyl; R’ = piperidin-1-yl}. J. Coord. Chem. 62 (2009), 1902–1913.
46. [46] Asundaria, S.T., Patel, S.A., Mehta, K.M., Patel, K.C., Synthesis, characterization and antimicrobial studies of some novel 1,3,4-thiadiazolium-2-thiolate derivatives. S. Afr. J. Chem. 63 (2010), 141–144.
47. [47] Naseer, M.M., Wang, De, Zhao, L., Huang, Z.-T., Wang, M.-X., Synthesis and functionalization of heteroatom-bridged bicyclocalixaromatics, large molecular triangular prisms with electron-rich and -deficient aromatic interiors. J. Org. Chem. 76 (2011), 1804–1813 The product 4 was obtained as white solid from CH2Cl2/hexane in yield 92%; mp 79–81 °C (Lit.[47] yield 89 %; mp 76–78 °C); 1H NMR (CDCl3) δ: 4.14 (6H, s, 2OCH3); 13C NMR (CDCl3) δ: 56.8, 171.4, 172.5). The product 6 was obtained as white solid in yield 96%; mp 87 °C (Lit. [47] yield 98 %; mp 86–87 °C); 1H NMR (CDCl3) δ: 4.12 (3H, s, OCH3).
48. [48] Mikhaylichenko, S.N., Patel, S.M., Dalili, S., Chesnyuk, A.A., Zaplishny, V.N., Synthesis and structure of new 1,3,5-triazine-pyrazole derivatives. Tetrahedron Lett. 50 (2009), 2505–2508 The product 3a obtained as a white solid in 93% yield; m.p131-132oC.
49. [49] Sari, N., Nartop, D., Karci, F., Disli, A., Novel hydrazine derivatives and their tetracoordinated metal complexes. Asian J. Chem. 20 (2008), 1975–1985.
50. [50] Inoue, Y., Kamo, Y., Togo, M., Hsu, Y.-C., Keumi, T., Kitajima, H., Synthesis of phenylazo-1,3,5-triazines by the oxidative coupling of hydrazine-1,3,5-triazines with N,N-disubstituted anilines. Chem. Lett., 1981, 1733–1736 The product 3b obtained as white solid in 95% yield; m.p. 180–181 °C; (Lit.[46] yield 74 %; m.p. 183–185 °C).
51. 2+ ions by naked eye. Res. Chem. Intermed. 41 (2015), 5059–5069 The product 5 was obtained as white solid in yield 96 %; m.p 177 °C (dec).
52. [52] Sheldrick, G.M., A short history of SHELX. Acta Crystallogr. A 64 (2008), 112–122.
53. [53] Sheldrick, G.M., SHELXTL-PC (Version 5.1). 1997, Siemens Analytical Instruments, Inc., Madison, WI.
54. [54] Frisch, M.J., Trucks, G.W., Schlegel, H.B., et al. Gaussian-03, Revision C.01. 2004, Gaussian, Inc., Wallingford, CT (supporting information).
55. [55] Dennington, R. II, Keith, T., Millam, J., Gauss View, Version 4.1. 2007, SemichemInc., Shawnee Mission, KS.
56. [56] Glendening, E.D., Reed, A.E., Carpenter, J.E., Weinhold, F., NBO Version 3.1, CI. 1998, University of Wisconsin, Madison.
57. [57] Reed, A.E., Curtiss, L.A.F., Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev. 88 (1988), 899–926.
58. [58] Frisch, M.J., Pople, J.A., Binkley, J.S., Self-consistent molecular orbital methods 25. Supplementary functions for Gaussian basis sets. J. Chem. Phys. 80 (1984), 3265–3269.
59. [59] Mosmann, T., MTT colorimetric assay for cell growth and survival. J. Immunol. Methods 65 (1983), 55–63 (supporting information).
60. [60] Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., Taylor, R., Tables of bond lengths determined by x-ray and neutron diffraction. Part. J. Chem. Soc. Perkins Trans. II (1987), 1–19.
61. [61] Otwinowski, Z., Minor, W., Processing of X-ray diffraction data collected in oscillation mode. Carter, C.W., Sweet, R., (eds.) Methods in Enzymology Macromolecular Crystallography, Part a, Vol. 276, 1997, Academic press, New York, 307–326.
62. [62] El-Faham, A., Soliman, S.M., Osman, S.M., Ghabbour, H.A., Siddiqui, M.R., Fun, H.K., Albericio, F., One pot synthesis, molecular structure and spectroscopic studies (X-ray, IR, NMR, UV–Vis) of novel 2-(4,6-dimethoxy-1,3,5-triazin-2-yl) amino acid ester derivatives. Spectrochim. Acta Part A: Mol. Biomol. Spectrosc. 159 (2016), 184–198.
63. [63] Gupta, V.P., Sharma, A., Virdi, V., Ram, V.J., Structural and spectroscopic studies on some chloropyrimidine derivatives by experimental and quantum chemical methods. Spectrochim. Acta A 64 (2006), 57–67.
64. [64] Huang, G., Zhang, X., Fan, Y., Bi, C., Yan, X., Zhang, Z., Zhang, N., Synthesis, Crystal Structure and Theoretical Calculation of a novel nickel(II) complex with dibromotyrosine and 1,10-Phenanthroline. Bull. Korean Chem. Soc. 34 (2013), 2889–2894.
65. [65] Foresman, J.B., Frisch, A.E., Exploring Chemistry with Electronic Structure Methods. second ed., 1996, Gaussian, Pittsburgh, PA.
66. [66] Chang, R., Chemistry. seventh Ed., 2001, McGraw-Hill, New York.
67. [67] Kosar, B., Albayrak, C., Spectroscopic investigations and quantum chemical computational study of (E)-4-methoxy-2-[(p-tolylimino)methyl]phenol. Spectrochim. Acta A 78 (2011), 160–167.
68. [68] Koopmans, T.A., Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms. Physica 1 (1934), 104–113.
69. [69] Parr, R.G., Weitao, Y., Density-functional Theory of Atoms and Molecules. 1989, Oxford University Press, New York.
70. [70] Parr, R.G., von Szentpàly, L., Liu, S.B., Electrophilicity index. J. Am. Chem. Soc. 121 (1999), 1922–1924.
71. [71] Singh, R.N., Kumar, A., Tiwari, R.K., Rawat, P., Gupta, V.P., A combined experimental and quantum chemical (DFT and AIM) study on molecular structure, spectroscopic properties, NBO and multiple interaction analysis in a novel ethyl 4-[2-(carbamoyl)hydrazinylidene]-3,5-dimethyl-1H-pyrrole-2-carboxylate and its dime. J. Mol. Struct. 1035 (2013), 427–440.
72. [72] Sebastian, S., Sundaraganesan, N., The spectroscopic (FT-IR, FT-IR gas phase, FT-Raman and UV) and NBO analysis of 4-Hydroxypiperidine by density functional method. Spectrochim. Acta Part A 75 (2010), 941–952.
73. [73] Joe, I.H., Kostova, I., Ravikumar, C., Amalanathan, M., Pinzaru, S.C., Theoretical and vibrational spectral investigation of sodium salt of acenocoumarol. J. Raman Spectrosc. 40 (2009), 1033–1038.