Synthesis and evaluation of a series of C5'-substituted duocarmycin SA analogs.
The synthesis and evaluation of a key series of analogs of duocarmycin SA, bearing a single substituent at the C5' position of the DNA binding subunit, are described.
Robertson
William M
WM
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Kastrinsky
David B
DB
Hwang
Inkyu
I
Boger
Dale L
DL
D000477:Alkylating Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D000818:Animals; D045744:Cell Line, Tumor; D004247:DNA / Q000737:chemistry; D000080890:Duocarmycins; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D051379:Mice; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D013329:Structure-Activity Relationship
D000477:Alkylating Agents; D000080890:Duocarmycins; D007211:Indoles; D011758:Pyrroles; C066098:duocarmycin SA; D004247:DNA
Bioorg Med Chem Lett. 1999 Nov 1;9(21):3087-92
10560730
J Mol Biol. 1997 Sep 19;272(2):237-52
9299351
Bioorg Med Chem. 2003 Aug 15;11(17):3815-38
12901927
J Am Chem Soc. 2008 Dec 10;130(49):16521-3
19554689
J Med Chem. 2009 Oct 8;52(19):5771-80
19639994
Nat Chem Biol. 2006 Feb;2(2):79-82
16415862
Bioorg Med Chem. 1996 Jun;4(6):859-67
8818235
J Org Chem. 1996 Mar 8;61(5):1710-1729
11667041
Tetrahedron. 2009 Aug 15;65(33):6591-6599
20161204
Acc Chem Res. 2004 Jan;37(1):61-9
14730995
J Am Chem Soc. 2003 Sep 10;125(36):10971-6
12952479
Bioorg Med Chem Lett. 2009 Dec 15;19(24):6962-5
19879753
J Org Chem. 2000 Jun 30;65(13):4088-100
10866626
J Org Chem. 2003 Nov 14;68(23):8984-90
14604371
J Am Chem Soc. 2004 Jan 14;126(1):80-1
14709069
J Org Chem. 2001 Oct 5;66(20):6654-61
11578217
J Am Chem Soc. 2006 Dec 13;128(49):15683-96
17147378
J Org Chem. 1999 Jul 9;64(14):5241-5244
34237882
J Org Chem. 2001 Jul 27;66(15):5163-73
11463270
Proc Natl Acad Sci U S A. 1995 Apr 25;92(9):3642-9
7731958
J Am Chem Soc. 2007 Sep 5;129(35):10858-69
17691783
J Mol Biol. 2000 Jul 28;300(5):1195-204
10903864
Chem Rev. 1997 May 8;97(3):787-828
11848889
J Org Chem. 1999 Oct 29;64(22):8350-8362
11674758
J Med Chem. 1994 Jan 21;37(2):232-9
8295210
J Antibiot (Tokyo). 1988 Dec;41(12):1915-7
3209484
Bioorg Med Chem Lett. 2002 Feb 11;12(3):303-6
11814783
J Am Chem Soc. 2004 Jul 14;126(27):8396-8
15237994
J Org Chem. 2001 Apr 6;66(7):2207-16
11281757
Bioorg Med Chem. 2004 Nov 15;12(22):5845-56
15498660
Org Lett. 2003 Jul 10;5(14):2577-9
12841785
J Am Chem Soc. 2001 Sep 26;123(38):9299-306
11562212
Bioorg Med Chem. 1997 Feb;5(2):263-76
9061191
Bioorg Med Chem Lett. 2010 Mar 15;20(6):1854-7
20171886
Biochemistry. 1988 May 17;27(10):3886-92
3408734
J Antibiot (Tokyo). 1981 Sep;34(9):1119-25
7328053
J Org Chem. 1999 Jul 23;64(15):5666-5669
11674637
J Antibiot (Tokyo). 1990 Aug;43(8):1037-8
2211354
J Org Chem. 2000 Jun 30;65(13):4101-11
10866627
Chem Biol. 2004 Dec;11(12):1607-17
15610844
J Med Chem. 1988 Mar;31(3):590-603
3346875
J Org Chem. 1997 May 2;62(9):2676-2677
11671622
Tetrahedron. 1991;47(14-15):2661-82
30260354
Bioorg Med Chem. 1994 Feb;2(2):115-35
7922122
J Am Chem Soc. 2009 Jan 28;131(3):1187-94
19154178
Chem Rev. 2002 Jul;102(7):2477-95
12105933
J Am Chem Soc. 2007 Nov 14;129(45):14092-9
17948994
Chem Biol Interact. 1990;73(1):29-52
2406033
Chembiochem. 2003 Nov 7;4(11):1188-93
14613110
Bioorg Med Chem Lett. 2001 Aug 6;11(15):2021-4
11454471
Proc Natl Acad Sci U S A. 1991 Feb 15;88(4):1431-5
1847523
J Antibiot (Tokyo). 2003 Feb;56(2):107-13
12715869
Nat Prod Rep. 2008 Apr;25(2):220-6
18389136