Abstract
An easy and efficient method for the synthesis of novel deoxycholic acid bis-1,3,4-thiadiazol-carbamate derivatives under microwave irradiation has been developed. Twelve new methyl 3α,12α-bis-[(5-aryl-1,3,4-thiadiazol-2-yl) carbamoyloxy]-cholan-24-oates were obtained in better yield (78–91%) and shorter time (15–22 min). Their structures were identified by 1H NMR, IR, MS spectra and elemental analyses.
References
1.
Kadi A.A.
,
El-Brollosy N.R.
,
Al-Deeb O.A.
,
Habib E.E.
,
Ibrahim T.M.
, and
El-Emam A.A.
, Eur. J. Med. Chem. , 2007 , 42 , 235 .
2.
Foroumadi A.
,
Soltani F.
,
Moshafi M.H.
, and
Ashraf-Askari R.
, Il Farmaco , 2003 , 58 , 1023 .
3.
Foroumadi A.
,
Daneshtalab M.
, and
Shafiee A.
, Arzneim. Forsch. Drug Res. , 1999 , 49 , 1035 .
4.
Lee J.
,
Lee S.H.
,
Seo H.J.
,
Son E.J.
,
Lee S.H.
,
Jung M.E.
,
Lee M.W.
,
Han H.K.
,
Kim J.
,
Kang J.
, and
Lee J.
, Bioorg. Med. Chem. , 2010 , 18 , 2178 .
5.
Shirote P.J.
, and
Bhatia M.S.
, Chin. J. Chem. , 2010 , 28 , 1429 .
6.
Amir M.
, and
Shikha K.
, Eur. J. Med. Chem. , 2004 , 39 , 535 .
7.
Yusuf M.
,
Khan R.A.
, and
Ahmed B.
, Bioorg. Med. Chem. , 2008 , 16 , 8029 .
8.
Song B.A.
,
Chen C.J.
,
Yang S.
,
Jin L.H.
,
Xue W.
,
Zhang S.M.
,
Zou Z.H.
,
Hu D.Y.
, and
Liu G.
, Acta Chim. Sinica , 2005 , 63 , 1720 (in Chinese).
9.
Jatav V.
,
Mishra P.
,
Kashaw S.
, and
Stables J.P.
, Eur. J. Med. Chem. , 2008 , 43 , 1945 .
10.
Song X.J.
,
Wang Z.Y.
,
Wang Y.G.
,
Zhang Z.W.
, and
Chen C.B.
, Chin. J. Appl. Chem. , 2005 , 22 , 334 (in Chinese).
11.
Matysiak J.
,
Nasulewicz A.
,
Pełczynska M.
,
Switalska M.
,
Jaroszewicz I.
, and
Opolski A.
, Eur. J. Med. Chem. , 2006 , 41 , 475 .
12.
Vorstrup S.
,
Henriksen L.
, and
Paulson O.B.
, J. Clin. Invest. , 1984 , 74 , 1634 .
13.
Yang J.
,
Zhao Z.G.
,
Shi Z.C.
,
Li X.R.
, and
Peng Y.L.
, Chin. J. Synth. Chem. , 2011 , 19 , 504 (in Chinese).
14.
Loncle C.
,
Brunel J.M.
,
Vidal N.
,
Dherbomez M.
, and
Letourneux Y.
, Eur. J. Med. Chem. , 2004 , 39 , 1067 .
15.
Aher N.G.
,
Pore V.S.
,
Mishra N.N.
,
Shukla P.K.
, and
Gonnade R.G.
, Bioorg. Med. Chem. Lett. , 2009 , 19 , 5411 .
16.
Bulbul M.
,
Saracoglu N.
,
Kufrevioglu O.I.
, and
Ciftci M.
, Bioorg. Med. Chem. , 2002 , 10 , 2561 .
17.
Samstein R.M.
,
Perica K.
,
Balderrama F.
,
Look M.
, and
Fahmy T.M.
, Biomaterials , 2008 , 29 , 703 .
18.
Enhsen A.
,
Kramer W.
, and
Wess G.
, Drug Discovery Today , 1998 , 3 , 409 .
19.
Li C.
,
Peters A.S.
,
Meredith E.L.
,
Allman G.W.
, and
Savage P.B.
, J. Am. Chem. Soc. , 1998 , 120 , 2961 .
20.
Shi Z.C.
,
Zhao Z.G.
,
Liu X.L.
, and
Wu L.L.
, J. Chem. Res. , 2011 , 35 , 198 .
21.
Appukkuttan P.
,
Mehta V.P.
, and
Van der Eycken E.V.
, Chem. Soc. Rev. , 2010 , 39 , 1467 .
22.
Polshettiwar V.
, and
Varma R.S.
, Acc. Chem. Res. , 2008 , 41 , 629 .
23.
Zhao Z.G.
,
Liu X.L.
,
Chen Y.
, and
Shi Z.C.
, J. Chem. Res. , 2010 , 34 , 481 .
24.
Liu X.L.
,
Zhao Z.G.
, and
Zeng B.T.
, Chin. J. Org. Chem. , 2007 , 27 , 994 (in Chinese).
25.
Wan R.
,
Wang P.
,
Han F.
,
Wang Y.
, and
Zhang J.Q.
, Synth. Commun. , 2011 , 41 , 864 .
26.
An Y.
,
Wei W.
,
Mu P.P.
,
Jia J.Y.
,
Lu J.Z.
, and
Chen X.
, Chin. J. Org. Chem. , 2010 , 30 , 1726 (in Chinese).
27.
Mullick P.
,
Khan S.A.
,
Verma S.
, and
Alam O.
, Bull. Korean Chem. Soc. , 2010 , 31 , 2345 .
28.
Tang Z.L.
,
Zhang C.Y.
,
Liu H.W.
,
Chang S.H.
,
Pei W.C.
, and
Feng Y.
, Fine Chem. Intermediates , 2010 , 40 , 19 (in Chinese).
29.
Liu Y.T.
,
Zhou Y.
, and
Yin D.W.
, Speciality Petrochemicals , 2011 , 28 , 61 (in Chinese).
30.
Jatav V.
,
Mishra P.
,
Kashaw S.
, and
Stables J.P.
, Eur. J. Med. Chem. , 2008 , 43 , 135 .
31.
Li S.H.
,
Li G.
,
Huang H.M.
,
Xiong F.
,
Liu C.M.
, and
Tu G.G.
, Arch. Pharm. Res. , 2008 , 31 , 1231 .
