Abstract
An efficient and novel method for the synthesis of a series of 11-aryl-10,12-dihydrodiindino[1,2-b‘,2′,1′-e]pyridine via one-pot multi-component reactions of aldehydes, indan-1-one and ammonium acetate has been delineated. All prepared compounds were structurally elucidated by IR, UV-Vis, 1H and 13C NMR and X-ray diffraction techniques. The molecules adopted monoclinic crystal system with P21/c space group and almost similar unit cell dimensions. The X-ray molecular geometries of the studied compounds were in excellent agreement with those computed by B3LYP/6-311++G(d,p) level of theory. The energies of the frontier orbitals calculated by B3LYP/6-311++G(d,p) level of theory enabled monitoring the reactivity and stability of the title molecules. The non-linear optical properties (NLO) and pNA were also computed and discussed. Compounds have shown broad spectrum cytotoxic activity against some human tumour cell lines; two of them rendering the most profound effect.
References
1.
Martinez I.
,
Zarate X.
,
Schott E.
,
Morales-Verdejo C.
,
Castillo F.
,
Manríquez M. J.
, and
Chávez I.
, Chem. Phys. Letters , 2015 , 636 , 31 .
2.
Lee C.-W.
,
Jang J.-G.
, and
Gong M.-S.
, Dyes Pigments , 2013 , 98 , 471 .
3.
Kim S.K.
,
Yang B.
,
Ma Y.
,
Lee J. H.
, and
Park J. W.
, J. Mater. Chem. , 2008 , 18 , 3376 .
4.
Kim Y.H.
,
Shin D. C.
,
Kim S. H.
,
Ko C. H.
,
Yu H. S.
,
Chae Y. S.
, and
Kwon S. K.
, Adv. Mater. , 2001 , 13 , 1690 .
5.
Jiang H.-J.
,
Sun J.
,
Yuan K.
, and
Zhang Q.-W.
, Synthetic Met. , 2014 , 197 , 217 .
6.
Ci Z.
,
Yu X.
,
Wang C.
,
Ma T.
, and
Bao M.
, Dyes Pigments , 2014 , 104 , 8 .
7.
Tang J.
,
Chen Y.
,
Cong L.
,
Lin B.
, and
Sun Y.
, Tetrahedron , 2014 , 70 , 3847 .
8.
Hulme C.
, and
Gore V.
, Curr. Med. Chem. , 2003 , 10 , 51 .
9.
Orru R.V. A.
, and
de Greef M.
, Synthesis , 2003 , 10 , 1471 .
10.
Domling A.
, and
Ugi I.
, Angew. Chem. Int. Ed. , 2000 , 39 , 3168 .
11.
Nair V.
,
Rajesh C.
,
Vinod A. U.
,
Bindu S.
,
Sreekanth A. R.
,
Mathen J. S.
, and
Balagopal L.
, Acc. Chem. Res. , 2003 , 36 , 899 .
12.
Zhu J.
, Eur. J. Org. Chem. , 2003 , 7 , 1133 .
13.
Domling A.
, Curr. Opin. Chem. Biol. , 2002 , 6 , 306 .
14.
Faidallah H.M.
,
Khan K. A.
, and
Asiri A. M.
, J. Chem. Sci. , 2012 , 124 , 625 .
15.
Faidallah H.M.
,
Al-Shaikh K. M. A.
,
Sobahi T. R.
,
Khan K. A.
, and
Asiri A. M.
, Molecules , 2013 , 18 , 15704 .
16.
Faidallah H.M.
,
Rostom S. A. F.
,
Asiri A. M.
,
Khan K. A.
,
Radwan M. F.
, and
Asfour H. Z.
, J. Enz. Inhib. Med. Chem. , 2013 , 28 , 123 .
17.
Faidallah H.M.
,
Khan K. A.
,
Rostom S. A. F.
, and
Asiri A. M.
, J. Enz. Inhib. Med. Chem. , 2013 , 28 , 495 .
18.
Taib L.A.
,
Faidallah H. M.
,
Sahin Z. S.
,
Asiri A. M.
,
Sahin O.
, and
Arshad M. N.
, J. Mol. Struct. , 2014 , 1076 , 272 .
19.
Faidallah H.M.
,
Saqer A. A.
,
Alamry K. A.
,
Khan K. A.
, and
Asiri A. M.
, J. Enz. Inhib. Med. Chem. , 2014 , 29 , 367 .
20.
Faidallah H.M.
, and
Rostom S. A. F.
, Eur. J. Med. Chem. , 2013 , 63 , 133 .
21.
Ishihara T.
,
Kakuta H.
,
Moritani H.
,
Ugawa T.
,
Sakamoto S.
,
Tsukamoto S. I.
, and
Yanagisawa I.
, Bioorg. Med. Chem. , 2003 , 11 , 2403 .
22.
Skalova L.
,
Nobilis M.
,
Szotakova B.
,
Kondrova E.
,
Savlik M.
,
Wosol V.
,
Pichard G. L.
, and
Maser E.
, Biochem. Pharm. , 2002 , 64 , 297 .
23.
Bryant H.U.
, and
Cullinan G. J.
, Chem. Abstr. , 1998 , 129 , 302558 .
24.
Harvey R.G.
, Polycyclic aromatic hydrocarbons , Wiley-VCH , New York, USA , 1997 .
25.
Clar E.
, Polycyclic hydrocarbons ; Academic Press , New York, USA , 1964 .
26.
Zhang F.J.
,
Cortez C.
, and
Harvey R. G.
, J. Org. Chem. , 2000 , 65 , 3952 .
27.
Harvey R.G.
, Chemistry and carcinogenicity. Polycyclic aromatic hydrocarbons ; Cambridge University Press , Cambridge, UK , 1991 .
28.
Becker F.F.
, and
Banik B. K.
, Bioorg. Med. Chem. Lett. , 1998 , 8 , 2877 .
29.
Palmer B.D.
,
Rewcastle G. W.
,
Atwell G. J.
,
Baguley B. C.
, and
Denny W. A.
, J. Med. Chem. , 1998 , 31 , 707 .
30.
Katritzky A.R.
,
Abdel-Fattah A. A. A.
,
Tymoshenko D. O.
, and
Essawy S. A.
, Synthesis. , 1999 , 2114 .
31.
Rong L.
,
Han H.
,
Jiang H.
, and
Tu S.
, J. Heterocyclic Chem. , 2009 , 46 , 465 .
32.
Al-Mutairi T.M.
,
Al-Hazimi H. M.
, and
El-Baih F. E. M.
, J. Saudi Chem. Soc. , 2009 , 13 , 199 .
33.
Mosmann T.
, J. Immunol. Methods , 1983 , 65 , 55 .
34.
Denizot F.
, and
Lang R.
, J. Immunol. Methods , 1986 , 22 , 271 .
35.
Watts J.D.
, and
Huang M.-L.
, J. Phys. Chem. A , 2009 , 113 , 1886 .
36.
Garza A.J.
,
Osman O. I.
,
Wazzan N. A.
,
Khan S. B.
,
Gustavo G. E.
, and
Asiri A. M.
, Comp. Theoret. Chem. , 2013 , 1022 , 82 .
37.
Merrick J.P.
,
Moran D.
, and
Radom L.
, J. Phys. Chem. A , 2007 , 111 , 11683 .
38.
Dabbagh H.A.
,
Teimouri A.
,
Chermahini A. N.
, and
Shahraki M.
, Spectrochim. Acta A , 2008 , 69 , 449 .
39.
Fleming I.
, Frontier orbitals and organic chemical reactions , Wiley , London, UK , 1976 .
40.
Kavitha E.
,
Sandaraganesan N.
, and
Sebastian S.
, Indian J. Pure Appl. Phys. , 2010 , 48 , 20 .
41.
Kim K.H.
,
Han Y. K.
, and
Jung J.
, Theor. Chem. Acc. , 2005 , 113 , 233 .
42.
Aihara J.
, J. Phys. Chem. A , 1999 , 103 , 7487 .
43.
Frisch M.J.
,
Trucks G. W.
,
Schlegel H. B.
,
Scuseria G. E.
,
Robb M. A.
,
Cheeseman J. R.
Gaussian 09, Revision B.01. Gaussian, Inc. , Wallingford CT , 2009 .
44.
Pearson R.G.
, J. Chem. Sci. , 2005 , 117 , 369 .
45.
Chattaraj P.K.
, and
Maiti B.
, J. Am. Chem. Soc. , 2003 , 125 , 2705 .
46.
Parr P.G.
, and
Pearson R. G.
, J. Am. Chem. Soc. , 1983 , 105 , 7512 .
47.
Charles A.M.
, J. Chem. Sci. , 2011 , 123 , 727 .
48.
Reis H.
, J. Chem. Phys. , 2006 , 125 , 014506 .
49.
Kaatz P.
,
Donley E. A.
, and
Shelton D. P.
, J. Chem. Phys. , 1997 , 108 , 849 .
50.
Sim F.
,
Chin S.
,
Dupuis M.
, and
Rice J. E.
, J. Phys. Chem. , 1993 , 97 , 1158 .
51.
Silverstein R.M.
,
Bassler G. C.
, and
Morrill T. C.
, Spectrometric identification of organic compounds. John Willey , Chistester, UK , 1991 .
52.Agilent , CrysAlis PRO. Agilent Technologies , Yarnton, England , 2012 .
53.
Sheldrick G.M.
, Acta Cryst. A , 2008 , 64 , 112 .
54.
Barbour L.J.
, J. Supramol. Chem. , 2001 , 1 , 189 .
55.
Spek A.L.
, PLATON-a multipurpose crystallographic tool. Utrecht University , Utrecht , 2005 .
56.
Farrugia L.J.
, J. Appl. Cryst. , 2012 , 45 , 849 .
57.
Farrugia L.J.
, J. Apply. Cryst. , 1999 , 32 , 837 .
58.
Frisch A.
,
Dennington R. D.
II
,
Keith T. A.
,
Milliam J.
,
Nielsen A. B.
,
Holder A. J.
, and
Hiscocks J.
, GaussView Reference, Version 5.0. Gaussian Inc. , Pittsburgh , 2007 .
59.
Wolinski J.K.
,
Hincon J. F.
, and
Pulay P.
, J. Am. Chem. Soc. , 1990 , 112 , 8251 .