Synthesis of derivatives of NK109, 7-OH Benzo[c]phenanthridine alkaloid, and evaluation of their cytotoxicities and reduction-resistant properties

Bioorganic & Medicinal Chemistry Letters
2000.0

Abstract

The N5-C6 double bond of NK109 (an antitumor benzo[c]phenanthridine alkaloid) is easily reduced under biological environment. To suppress the inactivation caused by reduction, we synthesized 5-, 6-, and 8-substituted NK109. 5-Substituted derivatives (4a-c) were reduced more easily than NK109. 6-Substituted ones (10a-f) inhibited biological reduction, but showed weak cytotoxic activity. 8-O-Substituted ones (13a-h), especially 8-O-hydroxyethyl NK109 (13d), suppressed biological reduction and exhibited strong cytotoxic activity.

Knowledge Graph

Similar Paper

Synthesis of derivatives of NK109, 7-OH Benzo[c]phenanthridine alkaloid, and evaluation of their cytotoxicities and reduction-resistant properties
Bioorganic & Medicinal Chemistry Letters 2000.0
Synthesis and Cytotoxic Activities of a New Benzo[c]phenanthridine Alkaloid, 7-Hydroxynitidine, and Some 9-Oxygenated Benzo[c]phenanthridine Derivatives
Organic Letters 1999.0
Synthesis and evaluation of new 6-amino- substituted benzo[c]phenanthridine derivatives
Journal of Medicinal Chemistry 1993.0
Antiproliferative activity of O4-benzo[c]phenanthridine alkaloids against HCT-116 and HL-60 tumor cells
Bioorganic & Medicinal Chemistry Letters 2015.0
Synthesis and Antileukemia Activity Evaluation of Benzophenanthridine Alkaloid Derivatives
Molecules 2022.0
Synthesis and biological evaluation of N-substituted benzo[c]phenanthrolines and benzo[c]phenanthrolinones as antiproliferative agents
European Journal of Medicinal Chemistry 2011.0
Oxoisoaporphine alkaloid derivatives: Synthesis, DNA binding affinity and cytotoxicity
European Journal of Medicinal Chemistry 2008.0
Cytotoxic Activity of Some Phenanthroindolizidine <i>N</i>-Oxide Alkaloids from <i>Cynanchum </i><i>v</i><i>incetoxicum</i>
Journal of Natural Products 2000.0
Total synthesis of phenanthroindolizidine alkaloids (±)-antofine, (±)-deoxypergularinine, and their dehydro congeners and evaluation of their cytotoxic activity
Bioorganic &amp; Medicinal Chemistry 2008.0
Synthesis of phenanthroindolizidine alkaloids and evaluation of their antitumor activities and toxicities
Bioorganic &amp; Medicinal Chemistry Letters 2011.0