One-pot multicomponent synthesis of diversely substituted 2-aminopyrroles. A short general synthesis of rigidins A, B, C, and D.
Privileged medicinal scaffolds based on the structures of tetra- and pentasubstituted 2-aminopyrroles were prepared via one-pot multicomponent reactions of structurally diverse aldehydes and N-(aryl-, hetaryl-, alkylsulfonamido)acetophenones with activated methylene compounds. This methodology was used in a four-step synthesis of alkaloids rigidins A, B, C, and D in overall yields of 61%, 58%, 60%, and 53%, respectively. Of these, rigidins B, C, and D were synthesized for the first time.
Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, New Mexico 87801, USA.
Liliya V
LV
Frolova
Nikolai M
NM
Evdokimov
Kathryn
K
Hayden
Indranil
I
Malik
Snezna
S
Rogelj
Alexander
A
Kornienko
Igor V
IV
Magedov
D000098:Acetophenones / Q000138:chemical synthesis* / Q000737:chemistry; D000470:Alkaloids; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D008386:Marine Biology; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
D000098:Acetophenones; D000470:Alkaloids; D001688:Biological Products; D011743:Pyrimidines; D011758:Pyrroles; C475148:rigidin B
Bioorg Med Chem Lett. 2008 Feb 15;18(4):1392-6
18221874
Bioorg Med Chem Lett. 2010 Jul 15;20(14):4156-8
20621728
J Org Chem. 2010 Mar 5;75(5):1674-83
20131775
J Med Chem. 2005 Jun 2;48(11):3840-51
15916436
Org Lett. 2009 Nov 5;11(21):5002-5
19780532
Molecules. 2009 Feb 16;14(2):798-806
19223828
Org Lett. 2010 Jan 15;12(2):312-5
20000625
Bioorg Med Chem. 2003 Feb 20;11(4):495-503
12538014
J Med Chem. 1989 Feb;32(2):402-8
2913300
Org Lett. 2010 Jan 15;12(2):372-4
20025257
Org Lett. 2009 Oct 15;11(20):4624-7
19772313
Antimicrob Agents Chemother. 2004 Dec;48(12):4665-72
15561842
Farmaco. 2002 Aug;57(8):613-7
12361227
Bioorg Med Chem. 2009 Jul 1;17(13):4406-19
19481463
Z Naturforsch C J Biosci. 2007 Jan-Feb;62(1-2):27-31
17425101
Eur J Med Chem. 2009 Mar;44(3):1288-95
18809229
Mol Divers. 2009 Nov;13(4):519-28
19381850
Org Lett. 2004 Aug 19;6(17):2857-9
15330632
Angew Chem Int Ed Engl. 2003 Aug 11;42(31):3582-603
12916029
J Nat Prod. 2007 Apr;70(4):689-710
17362037
J Immunol Methods. 1983 Dec 16;65(1-2):55-63
6606682
Eur J Med Chem. 2002 Mar;37(3):267-72
11900871
BJU Int. 2003 Dec;92(9):1031-6
14632869
Chemistry. 2007;13(35):9973-81
17854104
J Med Chem. 1995 Sep 29;38(20):4106-14
7562946
Angew Chem Int Ed Engl. 2004 Nov 26;43(46):6238-41
15558675
Angew Chem Int Ed Engl. 2008;47(29):5430-3
18561345
Org Lett. 2009 Mar 19;11(6):1369-72
19222195
J Med Chem. 2008 Aug 14;51(15):4589-600
18605720
J Org Chem. 2010 Jun 18;75(12):4261-73
20481447
Org Lett. 2009 Sep 3;11(17):3914-7
19655734
J Org Chem. 1998 Sep 4;63(18):6234-6238
11672254
Org Lett. 2010 May 21;12(10):2290-3
20411970
Org Lett. 2009 Jun 4;11(11):2269-72
19432414
J Med Chem. 1990 Aug;33(8):2162-73
2165163
Chem Rev. 2008 Jan;108(1):264-87
18095718
J Am Chem Soc. 2007 Oct 17;129(41):12366-7
17880218
Org Lett. 2009 Apr 2;11(7):1555-8
19320503
J Nat Prod. 2003 Feb;66(2):292-4
12608870
Eur J Med Chem. 2010 Jul;45(7):2994-3004
20399543
J Org Chem. 2001 Jun 15;66(12):4427-9
11397189
Chem Biol Drug Des. 2010 Mar;75(3):277-83
20659110
J Med Chem. 2005 Dec 1;48(24):7808-20
16302820