Abstract

Investigation, development, and application of inverse electron demand Diels-Alder reactions of heterocyclic dienes: A critical evaluation of the mode of cycloadditon, a probe for the question of concerted versus dipolar 4 + 2 cycloaddition, a determination of factors governing or influencing regioselectivity, the implementation of general and dependable synthetic procedures and the demonstration of the synthetic power of such processes for the simplification of contemporary synthetic challenges is presented in the context of a simple two-step construction of the entire carbon framework of streptonigrin and avendamycin, potent antitumor-antibiotics.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Cancer Institute (NCI)
Type
Research Project (R01)
Project #
7R01CA042056-01
Application #
3182847
Study Section
Medicinal Chemistry Study Section (MCHA)
Project Start
1985-07-01
Project End
1986-01-31
Budget Start
1985-07-01
Budget End
1986-01-31
Support Year
1
Fiscal Year
1985
Total Cost
Indirect Cost

  Institution

Name
Purdue University
Department
Type
Schools of Arts and Sciences
DUNS #
072051394
City
West Lafayette
State
IN
Country
United States
Zip Code
47907

  Publications

Morin, Matthew D; Wang, Ying; Jones, Brian T et al. (2018) Diprovocims: A New and Exceptionally Potent Class of Toll-like Receptor Agonists. J Am Chem Soc 140:14440-14454
Wang, Ying; Su, Lijing; Morin, Matthew D et al. (2018) Adjuvant effect of the novel TLR1/TLR2 agonist Diprovocim synergizes with anti-PD-L1 to eliminate melanoma in mice. Proc Natl Acad Sci U S A 115:E8698-E8706
Glinkerman, Christopher M; Boger, Dale L (2018) Synthesis, Characterization, and Rapid Cycloadditions of 5-Nitro-1,2,3-triazine. Org Lett 20:2628-2631
Radakovic, Aleksandar; Boger, Dale L (2018) High expression of class III ?-tubulin has no impact on functional cancer cell growth inhibition of a series of key vinblastine analogs. Bioorg Med Chem Lett 28:863-865
Lukesh 3rd, John C; Carney, Daniel W; Dong, Huijun et al. (2017) Vinblastine 20' Amides: Synthetic Analogues That Maintain or Improve Potency and Simultaneously Overcome Pgp-Derived Efflux and Resistance. J Med Chem 60:7591-7604
Yang, Shouliang; Sankar, Kuppusamy; Skepper, Colin K et al. (2017) Total synthesis of a key series of vinblastines modified at C4 that define the importance and surprising trends in activity. Chem Sci 8:1560-1569
Allemann, Oliver; Cross, R Matthew; Brütsch, Manuela M et al. (2017) Key analogs of a uniquely potent synthetic vinblastine that contain modifications of the C20' ethyl substituent. Bioorg Med Chem Lett 27:3055-3059
Quiñones, Ryan E; Glinkerman, Christopher M; Zhu, Kaicheng et al. (2017) Direct Synthesis of ?-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines. Org Lett 19:3568-3571
Boger, Dale L (2017) The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry-Biology Interface. J Org Chem 82:11961-11980
Carney, Daniel W; Lukesh 3rd, John C; Brody, Daniel M et al. (2016) Ultrapotent vinblastines in which added molecular complexity further disrupts the target tubulin dimer-dimer interface. Proc Natl Acad Sci U S A 113:9691-8

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