Fundamental relationships between structure, reactivity, and biological activity for the duocarmycins and CC-1065

KS MacMillan, DL Boger - Journal of medicinal chemistry, 2009 - ACS Publications
The duocarmycins (1 and 2) 1 belong to a small family of natural products (Figure 1) that
also include yatakemycin (3) 2 and CC-1065 (4). 3 Their exceptionally potent cytotoxic …

Duocarmycins-natures prodrugs?

M Searcey - Current pharmaceutical design, 2002 - ingentaconnect.com
The duocarmycins and (+)-CC-1065 are amongst the most potent antitumour antibiotics
discovered to date and yet have not progressed into the clinic. The natural products are …

Duocarmycin SA shortened, simplified, and extended agents: a systematic examination of the role of the DNA binding subunit

DL Boger, DL Hertzog, B Bollinger… - Journal of the …, 1997 - ACS Publications
The examination of shortened, simplified, and extended analogs of duocarmycin SA is
described and constitutes a detailed study of the role of linked DNA binding subunit. In …

Synthesis and Evaluation of a Series of C3-Substituted CBI Analogues of CC-1065 and the Duocarmycins

DL Boger, SR Brunette… - The Journal of Organic …, 2001 - ACS Publications
The synthesis and evaluation of a series of C3-substituted 1, 2, 9, 9a-tetrahydrocyclopropa
[c] benz [e] indol-4-one (CBI) analogues of the CC-1065 and duocarmycin alkylation …

Establishment of substituent effects in the DNA binding subunit of CBI analogues of the duocarmycins and CC-1065

JP Parrish, DB Kastrinsky, F Stauffer… - Bioorganic & medicinal …, 2003 - Elsevier
An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring
substituent effects within the first indole DNA binding subunit is detailed. In general …

Synthesis and Evaluation of CC-1065 and Duocarmycin Analogs Incorporating the 1,2,3,4,11,11a-Hexahydrocyclopropa[c]naphtho[2,1-b]azepin-6-one (CNA) …

DL Boger, P Turnbull - The Journal of Organic Chemistry, 1997 - ACS Publications
The synthesis of 1, 2, 3, 4, 11, 11a-hexahydrocyclopropa [c] naphtho [2, 1− b] azepin-6-one
(CNA), a seven-membered C-ring analog of the alkylation subunits of CC-1065 and the …

Synthesis and evaluation of a carbocyclic analogue of the CC-1065 and duocarmycin alkylation subunits: role of the vinylogous amide and implications on DNA …

DL Boger, P Turnbull - The Journal of Organic Chemistry, 1998 - ACS Publications
The synthesis and chemical properties of 1, 2, 9, 9a-tetrahydro-1 H-cyclopropa [c] benz [e]
inden-4-one (CBIn, 10), a carbocyclic C-ring analogue of the alkylation subunits of CC-1065 …

Synthesis and antitumor activity of duocarmycin derivatives: modification of segment-A of A-ring pyrrole compounds

N Amishiro, A Okamoto, C Murakata… - Journal of medicinal …, 1999 - ACS Publications
A series of 3-substituted A-ring pyrrole compounds of duocarmycin were synthesized and
evaluated for in vitro anticellular activity against HeLa S3 cells and in vivo antitumor activity …

Critical role of the linking amide in CC-1065 and the duocarmycins: implications on the source of DNA alkylation catalysis

DL Boger, A Santillán, M Searcey… - Journal of the American …, 1998 - ACS Publications
The preparation and evaluation of both enantiomers of 5 are described and it constitutes an
analogue of CBI-TMI (4), the duocarmycins, and CC-1065 in which the amide linking the …

Synthesis and antitumor activity of duocarmycin derivatives: A-ring pyrrole compounds bearing β-(5′, 6′, 7′-trimethoxy-2′-indolyl) acryloyl group

N Amishiro, S Nagamura, E Kobayashi… - Bioorganic & medicinal …, 2000 - Elsevier
A series of A-ring pyrrole derivatives of duocarmycin bearing β-(5′, 6′, 7′-trimethoxy-2′-
indolyl) acryloyl group were synthesized, and evaluated for in vitro anticellular activity …