Abstract
Ten novel methyl 3α-(4-nitrobenzoylhydrazides)-12α-(L-amino acid carbamates)-cholan-24-oate chiral molecular tweezers based on deoxycholic acid have been easily constructed using microwave irradiation. Their structures were characterised by IR, 1H NMR, MS spectra and elemental analysis and their molecular recognition properties were investigated by UV-Vis spectral titration. The preliminary study indicated that these target compounds possess good selectivity for D/L amino acid methyl esters.
References
1.
Skibinski M.
,
Gomez R.
,
Lork E.
, and
Azov V.A.
, Tetrahedron , 2009 , 65 , 10348 .
2.
Graton J.
,
Legouin B.
,
Besseau F.
,
Uriac P.
,
Questel J-Y.L.
,
Weghe P.
, and
Jacquemin D.
, J. Phys. Chem. , 2012 , 116 , 23067 .
3.
Or1owska M.
,
Mroczkiewicz M.
,
Guzowa K.
,
Ostaszewski R.
, and
K1onkowski A.M.
, Tetrahedron , 2010 , 66 , 2486 .
4.
Nakagaki T.
,
Shin-ichiro K.
,
Harano A.
, and
Shinmyozu T.
, Tetrahedron , 2010 , 66 , 976 .
5.
Li Z.Y.
,
Zhang C.
,
Ren Y.L.
,
Yin J.
, and
Liu S.H.
, Org. Lett. , 2011 , 13 , 6222 .
6.
McDonald K.P.
,
Ramabhadran R.O.
,
Lee S.
,
Raghavachari K.
, and
Flood A.H.
, Org. Lett. , 2011 , 13 , 6260 .
7.
Ghosh K.
,
Sarkar A.R.
,
Samadder A.
, and
Khuda-Bukhsh A.R.
, Org. Lett. , 2012 , 14 , 4314 .
8.
Leblond J.
,
Gao H.
,
Petitjean A.
, and
Leroux J-C.
, J. Am. Chem. Soc. , 2010 , 132 , 8544 .
9.
Schazmann B.
,
Alhashimy N.
, and
Diamond D.
, J. Am. Chem. Soc. , 2006 , 128 , 8607 .
10.
Devedec F.L.
,
Fuentealba D.
,
Strandman S.
,
Bohne C.
, and
Zhu X.X.
, Langmuir , 2012 , 28 , 13431 .
11.
Chhatra R.K.
,
Kumar A.
, and
Pandey P.S.
, J. Org. Chem. , 2011 , 76 , 9086 .
12.
Vargas P.S.
,
Rosa F.A.
,
Buriol L.
,
Rotta M.
,
Moreira D.N.
,
Frizzo C.P.
,
Bonacorso H.G.
,
Zanatta N.
, and
Martins M.A.P.
, Tetrahedron Lett. , 2012 , 53 , 3131 .
13.
Collados J.F.
,
Toledano E.
,
Guijarro D.
, and
Yus M.
, J. Org. Chem. , 2012 , 77 , 5744 .
14.
Li X.R.
,
Zhao Z.G.
,
Cheng Y.Y.
, and
Li H.
, J. Chem. Res. , 2011 , 35 , 234 .
15.
Bisceglia J.
,
Díaz J.E.
,
Torres R.A.
, and
Orelli L.R.
, Tetrahedron Lett. , 2011 , 52 , 5238 .
16.
Hu J.
,
Yu P.
,
Zhou T.Y.
, and
Xu Y.H.
, J. Chem. Res. , 2011 , 35 , 672 .
17.
Mei Z.Y.
,
Liu P.
,
Li Z.H.
,
Liang F.G.
, and
Jun G.L.
, J. Chem. Res. , 2012 , 36 , 536 .
18.
Pingali S.R.K.
, and
Jursic B.S.
, Tetrahedron Lett. , 2011 , 52 , 4371 .
19.
Xu H.
,
Tian H.
,
Zheng L.Y.
,
Liu Q.W.
,
Wang L.
, and
Zhang S.Q.
, Tetrahedron Lett. , 2011 , 52 , 2873 .
20.
Liu X.L.
,
Zhao Z.G.
, and
Zeng B.T.
, Chin. J. Org. Chem. , 2007 , 27 , 994 (in Chinese).