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Optimization of the indenone ring of indenoisoquinoline topoisomerase I inhibitors.
J Med Chem. 2007 Sep 06; 50(18):4388-404.JM

Abstract

Two series of indenoisoquinoline topoisomerase I inhibitors have been prepared to investigate optimal substituents on the indenone ring at the 9-position. The more exhaustive series was prepared using a nitrated isoquinoline ring that has been previously demonstrated to enhance biological activity. After preliminary biological evaluation, a more focused series of inhibitors was prepared utilizing a 2,3-dimethoxy-substituted isoquinoline ring. The results of the two series indicate the existence of superior functional groups such as methoxy, fluorine, and cyano for the indenoisoquinoline 9-position. Interestingly, these functional groups coincide with established structure-activity relationships for the 11-position of camptothecin.

Authors+Show Affiliations

Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmaceutical Sciences, Purdue Cancer Center, Purdue University, West Lafayette, Indiana 47907, USA.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, N.I.H., Intramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17676830

Citation

Morrell, Andrew, et al. "Optimization of the Indenone Ring of Indenoisoquinoline Topoisomerase I Inhibitors." Journal of Medicinal Chemistry, vol. 50, no. 18, 2007, pp. 4388-404.
Morrell A, Placzek M, Parmley S, et al. Optimization of the indenone ring of indenoisoquinoline topoisomerase I inhibitors. J Med Chem. 2007;50(18):4388-404.
Morrell, A., Placzek, M., Parmley, S., Grella, B., Antony, S., Pommier, Y., & Cushman, M. (2007). Optimization of the indenone ring of indenoisoquinoline topoisomerase I inhibitors. Journal of Medicinal Chemistry, 50(18), 4388-404.
Morrell A, et al. Optimization of the Indenone Ring of Indenoisoquinoline Topoisomerase I Inhibitors. J Med Chem. 2007 Sep 6;50(18):4388-404. PubMed PMID: 17676830.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Optimization of the indenone ring of indenoisoquinoline topoisomerase I inhibitors. AU - Morrell,Andrew, AU - Placzek,Michael, AU - Parmley,Seth, AU - Grella,Brian, AU - Antony,Smitha, AU - Pommier,Yves, AU - Cushman,Mark, Y1 - 2007/08/04/ PY - 2007/8/7/pubmed PY - 2007/11/2/medline PY - 2007/8/7/entrez SP - 4388 EP - 404 JF - Journal of medicinal chemistry JO - J Med Chem VL - 50 IS - 18 N2 - Two series of indenoisoquinoline topoisomerase I inhibitors have been prepared to investigate optimal substituents on the indenone ring at the 9-position. The more exhaustive series was prepared using a nitrated isoquinoline ring that has been previously demonstrated to enhance biological activity. After preliminary biological evaluation, a more focused series of inhibitors was prepared utilizing a 2,3-dimethoxy-substituted isoquinoline ring. The results of the two series indicate the existence of superior functional groups such as methoxy, fluorine, and cyano for the indenoisoquinoline 9-position. Interestingly, these functional groups coincide with established structure-activity relationships for the 11-position of camptothecin. SN - 0022-2623 UR - https://www.unboundmedicine.com/medline/citation/17676830/Optimization_of_the_indenone_ring_of_indenoisoquinoline_topoisomerase_I_inhibitors_ L2 - https://doi.org/10.1021/jm070307+ DB - PRIME DP - Unbound Medicine ER -