Abstract
The synthesis and characterisation of a new type of chalcone bearing a –N=N– bond is reported using an environmentally benign approach. The synthesis consists of two steps. (E)-4-((5-acetyl-2-hydroxyphenyl)diazenyl)benzenesulfonamide was synthesised by an easy structural modification of sulfanilamide. The key step then involved the solvent-free Claisen–Schmidt condensation of benzaldehydes to form the chalcones. The structures of all compounds were confirmed by FTIR, NMR and MS spectroscopy.
References
1.
Nowakowska Z.A.
, Eur. J. Med. Chem. , 2007 , 42 , 125 .
2.
Shenvi S.
,
Kumar K.
,
Hatti K.S.
,
Rijesh K.
,
Diwakar L.
, and
Reddy G.C.
, Eur. J. Med. Chem. , 2013 , 62 , 435 .
3.
Modzelewska A.
,
Pettit C.
,
Achanta G.
,
Davidson N.E.
,
Huang P.
, and
Khana S.R.
, Bioorg. Med. Chem. , 2006 , 14 , 3491 .
4.
Hsieh C.T.
,
Hsieh T.J.
,
El-Shazly M.
,
Chuang D.W.
,
Tsai Y.H.
,
Yen C.T.
,
Wu S.F.
,
Wu Y.C.
, and
Chang F.R.
, Bioorg. Med. Chem. Lett. , 2012 , 12 , 3912 .
5.
Furman C.
,
Lebeau J.
,
Fruchart J.C.
,
Bernier J.L.
,
Duriez P.
,
Cotelle N.
, and
Teissier E.
, J. Biochem. Mol. Toxicol. , 2001 , 15 , 270 .
6.
Yaylı N.
,
Ucuncu O.
,
Yasar A.
,
Kucuk M.
,
Yaylı N.
,
Akyuz E.
, and
Karaoglu S.A.
, Turk. J. Chem. , 2006 , 30 , 505 .
7.
Kazuhiro S.
,
Yoh-ichi M.
,
Kana M.
,
Chiaki K.
, and
Takanao M.
, Tetrahedron , 2011 , 67 , 5346 .
8.
Lopez S.N.
,
Castelli M.V.
,
Zacchino S.A.
,
Dominguez J.N.
,
Lobo G.
,
Jaime C.C.
,
Cortes J.C.G.
,
Ribas J.C.
,
Devia C.
,
Ana M.R.
, and
Ricardo D.E.
, Bioorg. Med. Chem. , 2001 , 9 , 1999 .
9.
Cheenpracha S.
,
Karalai C.
,
Ponglimanont C.
,
Subhadhirasakul S.
, and
Tewtrakul S.
, Bioorg. Med. Chem. , 2006 , 14 , 1710 .
10.
Sarojini B.K.
,
Narayana B.
,
Ashalatha B.V.
,
Indira J.
, and
Lobo K.G.
, J. Cryst. Growth , 2006 , 295 , 54 .
11.
Delavaux-Nicot B.
,
Maynadie J.
,
Lavabre D.
, and
Fery-Forgues S.
, J. Organomet. Chem , 2007 , 692 , 874 .
12.
Shettigar S.
,
Umesh G.
,
Chandrasekharan K.
,
Sarojini B.K.
, and
Narayana B.
, Opt. Mater. , 2008 , 30 , 1297 .
13.
Lu Z.
,
Zhang F.
,
Lei X.
,
Yang L.
,
Xu S.
, and
Duan X.
, Chem. Eng. Sci. , 2008 , 63 , 4055 .
14.
Zhao R.
,
Tan C.
,
Xie Y.
,
Gao C.
,
Liu H.
, and
Jiang Y.
, Tetrahedron Lett. , 2011 , 52 , 3805 .
15.
Hunger K.J.
, Wiley industrial dyes chemistry properties applications. Wiley-VCH , Weinheim , 2003 .
16.
Denizli A.
, and
Piskin E.
, J. Biochem. Biophys. Methods , 2001 , 49 , 391 .
17.
Sandborn W.J.
, and
Hanauer S.B.
, Aliment Pharmacol Ther. , 2003 , 17 , 29 .
18.
Qiu F.
,
Cao Y.
,
Xu H.
,
Jiang Y.
, and
Zhou Liu Y.
J. Dyes Pigm. , 2007 , 75 , 454 .
19.
Kanis D.
,
Ratner M.
, and
Marks T.
, Chem. Rev. , 1994 , 94 , 195 .
20.
Browing C.H.
,
Cohen J.B.
,
Ellingworth S.
, and
Gulbransen R.J.J.
, Storage , 1926 , 100 , 293 .
21.
Ginni S.
,
Karnawat R.
,
Sharma I.K.
, and
Verma P.S.
, Int. J. Appl. Biol. Pharm. Tech. , 2011 , 2 , 332 .
22.
Song Y.M.
,
Ha Y.M.
,
Jin-Ah K.
,
Chung K.W.
,
Uehara Y.
,
Lee K.J.
,
Chun P.
,
Byun Y.
,
Chung H.Y.
, and
Moona H.R.
, Bioorg. Med. Chem. Lett. , 2012 , 22 , 7451 .
23.
Wainwright M.
, and
Kristiansen J.E.
, Dyes Pigm. , 2011 , 88 , 231 .
24.
Feely M.G.
, and
O'Dell J.R.
, Curr. Opin. Rheumatol. , 2010 , 22 , 316 .
25.
Arslan T.
,
Turkoglu E.A.
,
Senturk M.
, and
Supuran C.T.
, Bioorg. Med. Chem. Lett. , 2016 , 26 , 5867 .
26.
Shetonde O.M.
,
Mammo W.
,
Bezabih M.
,
Andrae-Marobela K.
, and
Abegaz B.M.
, Bioorg. Med. Chem. , 2010 , 18 , 2464 .
27.
Kumar P.
,
Kumar S.
,
Husain K.
, and
Kumar A.
, Chin. Chem. Lett. , 2011 , 22 , 37 .
28.
Moon M.E.
,
Choi Y.
,
Lee Y.M.
,
Vajpayee V.
,
Trusova M.
,
Filimonov V.D.
, and
Chi K.W.
, Tetrahedron Lett. , 2010 , 51 , 6769 .
29.
Arslan T.
,
Celik G.
,
Celik H.
,
Senturk M.
,
Yaylı N.
, and
Ekinci D.
, Arch. Pharm. Chem. Life Sci. , 2016 , 349 , 741 .
