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 …

Design, synthesis, and evaluation of linker-duocarmycin payloads: toward selection of HER2-targeting antibody–drug conjugate SYD985

RC Elgersma, RGE Coumans, T Huijbregts… - Molecular …, 2015 - ACS Publications
Antibody–drug conjugates (ADCs) that are currently on the market or in clinical trials are
predominantly based on two drug classes: auristatins and maytansinoids. Both are tubulin …

The difference a single atom can make: synthesis and design at the chemistry–biology interface

DL Boger - The Journal of organic chemistry, 2017 - ACS Publications
A Perspective of work in our laboratory on the examination of biologically active compounds,
especially natural products, is presented. In the context of individual programs and along …

Asymmetric Synthesis of Triazole Antifungal Agents Enabled by an Upgraded Strategy for the Key Epoxide Intermediate

Y Tang, Z Li, M Zeng, R Li, H Song… - The Journal of …, 2024 - ACS Publications
A streamlined and efficient approach to the key epoxide intermediate for the asymmetric
synthesis of triazole antifungal agents is presented. This synthesis highlights a P (NMe2) 3 …

A unique class of duocarmycin and CC-1065 analogues subject to reductive activation

W Jin, JD Trzupek, TJ Rayl, MA Broward… - Journal of the …, 2007 - ACS Publications
N-Acyl O-amino phenol derivatives of CBI-TMI and CBI-indole2 are reported as prototypical
members of a new class of reductively activated prodrugs of the duocarmycin and CC-1065 …

A novel, unusually efficacious duocarmycin carbamate prodrug that releases no residual byproduct

AL Wolfe, KK Duncan, NK Parelkar… - Journal of Medicinal …, 2012 - ACS Publications
A unique heterocyclic carbamate prodrug of seco-CBI-indole2 that releases no residual
byproduct is reported as a new member of a class of hydrolyzable prodrugs of the …

Design, Synthesis, and Evaluation of Duocarmycin O-Amino Phenol Prodrugs Subject to Tunable Reductive Activation

JP Lajiness, WM Robertson, I Dunwiddie… - Journal of medicinal …, 2010 - ACS Publications
A series of N-acyl O-amino derivatives of seco-CBI-indole2 are reported and examined as
prototypical members of a unique class of reductively activated (cleaved) prodrugs of the …

Asymmetric Synthesis of 1,2,9,9a-Tetrahydrocyclopropa[c]benzo[e]indol-4-one (CBI)

JP Lajiness, DL Boger - The Journal of organic chemistry, 2011 - ACS Publications
A short, asymmetric synthesis of the 1, 2, 9, 9a-tetrahydrocyclopropa [c] benzo [e] indol-4-
one (CBI) analogue of the CC-1065 and duocarmycin DNA alkylation subunits is described …

Effective Asymmetric Synthesis of 1,2,9,9a-Tetrahydrocyclopropa[c]benzo[e]indol-4-one (CBI)

DB Kastrinsky, DL Boger - The Journal of Organic Chemistry, 2004 - ACS Publications
A short, asymmetric synthesis of the 1, 2, 9, 9a-tetrahydrocyclopropa [c] benzo [e] indol-4-
one (CBI) analogue of the CC-1065 and duocarmycin alkylation subunits is detailed that …

Applications of free radicals in organic synthesis

DL Boger - Israel journal of chemistry, 1997 - Wiley Online Library
A summary of studies on the generation of acyl radicals and their subsequent use in
intermolecular, intramolecular, macrocyclization, and tandem alkene addition reactions is …