Abstract
The direct amidation of esters with 4-amino-2,2,6,6-tetramethylpiperidine was achieved
by computer-controlled microwave irradiation in toluene. The microwave protocol allowed
the new amides to be prepared in three hours rather than the three days required by
traditional thermal methods.
Key words
microwave-assisted synthesis - HIV - amidation - CCR5 - gp120
References
<A NAME="RM06205SS-1">1 </A>
Hunter E.
Viral Entry and Receptor, In Retroviruses
Coffin JM.
Hughes SH.
Varmus HE.
Cold Spring Harbor Laboratory Press;
N.Y.:
1997.
p.71-119
<A NAME="RM06205SS-2">2 </A>
Sattentau QJ.
Moore JP.
J. Exp. Med.
1991,
174:
407
<A NAME="RM06205SS-3">3 </A>
Sattentau QJ.
Moore JP.
Vignaux F.
Traincard F.
Poignard P.
J. Virol.
1993,
67:
7383
<A NAME="RM06205SS-4">4 </A>
Moore JP.
Sweet RW.
Perspect. Drug Discov. Des.
1993,
1:
235
<A NAME="RM06205SS-5">5 </A>
Berger EA.
AIDS
1997,
11 (Suppl A):
S3
<A NAME="RM06205SS-6">6 </A>
Berger EA.
Adv. Exp. Med. Biol.
1998,
452:
151
<A NAME="RM06205SS-7">7 </A>
Dragic T.
Litwin V.
Allaway GP.
Martin SR.
Huang Y.
Nagashima KA.
Cayanan C.
Maddon PJ.
Koup RA.
Moore JP.
Paxton WA.
Nature (London)
1996,
381:
667
<A NAME="RM06205SS-8">8 </A>
Moore JP.
Science (Washington, D.C.)
1997,
276:
51
<A NAME="RM06205SS-9">9 </A>
Sullivan N.
Sun Y.
Sattentau Q.
Thali M.
Wu D.
Denisova G.
Gershoni J.
Robinson J.
Moore J.
Sodroski J.
J. Virol.
1998,
72:
4694
<A NAME="RM06205SS-10">10 </A>
Chang D.-K.
Cheng S.-F.
Trivedi VD.
J. Biol. Chem.
1999,
274:
5299
<A NAME="RM06205SS-11">11 </A>
Freed EO.
Myers DJ.
Risser R.
Proc. Natl. Acad. Sci. U.S.A.
1990,
87:
4650
<A NAME="RM06205SS-12">12 </A>
Melikyan GB.
Markosyan RM.
Hemmati H.
Delmedico MK.
Lambert DM.
Cohen FS.
J. Cell Biol.
2000,
151:
413
<A NAME="RM06205SS-13">13 </A>
Capon DJ.
Ward RH.
Annu. Rev. Biochem.
1991,
9:
649
<A NAME="RM06205SS-14">14 </A>
Kwong PD.
Wyatt R.
Robinson J.
Sweet RW.
Sodroski J.
Hendrickson WA.
Nature (London)
1998,
393:
648
<A NAME="RM06205SS-15">15 </A>
Wyatt R.
Kwong PD.
Desjardins E.
Sweet RW.
Robinson J.
Hendrickson WA.
Sodroski JG.
Nature (London)
1998,
393:
705
<A NAME="RM06205SS-16">16 </A>
Carter WA.
Brodsky I.
Pellegrino MG.
Henriques HF.
Parenti DM.
Schulof RS.
Robinson WE.
Volsky DJ.
Paxton H.
Kariko K.
Suhadolnik RJ.
Strayer DR.
Lewin M.
Einck L.
Simon GL.
Scheib RG.
Montefiori DC.
Mitchell WM.
Paul D.
Meyer WA.
Reichenbach N.
Gillespie DH.
Lancet
1987,
1286
<A NAME="RM06205SS-17">17 </A>
Wu L.
Gerard NP.
Wyatt R.
Choe H.
Parolin C.
Ruffing N.
Borsetti A.
Cardoso AA.
Desjardin E.
Newman W.
Gerard C.
Sodroski J.
Nature (London)
1996,
384:
179
<A NAME="RM06205SS-18">18 </A>
Kwong PD.
Wyatt R.
Majeed S.
Robinson J.
Sweet RW.
Sodroski J.
Hendrickson WA.
Structure
2000,
8:
1329
<A NAME="RM06205SS-19">19 </A>
Chen B.
Vogan EM.
Gong H.
Skehel JJ.
Wiley DC.
Harrison SC.
Nature (London)
2005,
433:
834
<A NAME="RM06205SS-20">20 </A>
Chen B.
Vogan EM.
Gong H.
Skehel JJ.
Wiley DC.
Harrison SC.
Structure (Cambridge, MA, U.S.)
2005,
13:
197
<A NAME="RM06205SS-21">21 </A>
Lin PF.
Blair W.
Wang T.
Spicer T.
Guo Q.
Zhou N.
Gong YF.
Wang HG.
Rose R.
Yamanaka G.
Robinson B.
Li CB.
Fridell R.
Deminie C.
Demers G.
Yang Z.
Zadjura L.
Meanwell N.
Colonno R.
Proc. Natl. Acad. Sci. U.S.A.
2003,
100:
11013
<A NAME="RM06205SS-22">22 </A>
Wang T.
Zhang Z.
Wallace OB.
Deshpande M.
Fang H.
Yang Z.
Zadjura LM.
Tweedie DL.
Huang S.
Zhao F.
Ranadive S.
Robinson BS.
Gong YF.
Ricarrdi K.
Spicer TP.
Deminie C.
Rose R.
Wang HG.
Blair WS.
Shi PY.
Lin PF.
Colonno RJ.
Meanwell NA.
J. Med. Chem.
2003,
46:
4236
<A NAME="RM06205SS-23">23 </A>
Zhao Q.
Ma L.
Jiang S.
Lu H.
Liu S.
He Y.
Strick N.
Neamati N.
Debnath AK.
Virology
2005,
339:
213
<A NAME="RM06205SS-24">24 </A>
Waltman AW.
Grubbs RH.
Organometallics
2004,
23:
3105
<A NAME="RM06205SS-25">25 </A>
Molteni V.
Ellis DA.
Curr. Org. Synth.
2005,
2:
333
<A NAME="RM06205SS-26">26 </A>
Strauss CR.
Chem. Aust.
2005,
72:
9
<A NAME="RM06205SS-27">27 </A>
de la Hoz A.
Diaz-Ortiz A.
Moreno A.
Chem. Soc. Rev.
2005,
34:
164
<A NAME="RM06205SS-28">28 </A>
Kappe CO.
Angew. Chem. Int. Ed.
2004,
43:
6250
<A NAME="RM06205SS-29">29 </A>
Ersmark K.
Larhed M.
Wannberg J.
Curr. Opin. Drug Discov. Dev.
2004,
7:
417
<A NAME="RM06205SS-30">30 </A>
De La Hoz A.
Diaz-Ortiz A.
Moreno A.
Curr. Org. Chem.
2004,
8:
903
<A NAME="RM06205SS-31">31 </A>
Loupy A.
C. R. Chim.
2004,
7:
103
<A NAME="RM06205SS-32">32 </A>
Nuechter M.
Ondruschka B.
Bonrath W.
Gum A.
Green Chem.
2004,
6:
128
<A NAME="RM06205SS-33">33 </A>
Srivastava KP.
Chemistry
2003,
1:
215
<A NAME="RM06205SS-34">34 </A>
Alexandre F.-R.
Domon L.
Frere S.
Testard A.
Thiery V.
Besson T.
Mol. Diversity
2003,
7:
273
<A NAME="RM06205SS-35">35 </A>
Hajek M. In Microwaves in Organic Synthesis
Loupy A.
Wiley-VCH;
Weinheim:
2002.
p.345
<A NAME="RM06205SS-36">36 </A>
Roberts BA.
Strauss CR.
Acc. Chem. Res.
2005,
38:
653
<A NAME="RM06205SS-37">37 </A>
Crystallographic data (excluding structure factors) for compound 2 have been deposited with the Cambridge Crystallographic Data Centre as supplementary
publication number CCDC 286628. Copies of the data can be obtained, free of charge,
on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax:+44 (1223)336033
or e-mail: deposit@ccdc.cam.ac.uk].
