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

Abstract

[formula: see text] A new benzo[c]phenanthridine alkaloid, 7-hydroxynitidine, was synthesized by a novel synthetic procedure. The cytotoxic activity of this compound against HeLa S3 cells was strong, but not greater than those of its mother compounds, nitidine and NK109. We also synthesized other 9-oxygenated benzo[c]phenanthridine alkaloids, 7-methoxynitidine, 9-demethylnitidine, nitidine, and fagaronine, and tested their cytotoxic activities. These results suggest that the 7-hydroxy group enhances antitumor activity and an 8- or 9-hydroxy group weakens this activity.

Knowledge Graph

Similar Paper

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
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
Plant Antitumor Agents, 27. Isolation, Structure, and Structure Activity Relationships of Alkaloids from Fagara macrophylla
Journal of Natural Products 1987.0
Total synthesis of phenanthroindolizidine alkaloids (±)-antofine, (±)-deoxypergularinine, and their dehydro congeners and evaluation of their cytotoxic activity
Bioorganic & Medicinal Chemistry 2008.0
Asymmetric synthesis of phenanthroindolizidine alkaloids with hydroxyl group at the C14 position and evaluation of their antitumor activities
Bioorganic & Medicinal Chemistry Letters 2011.0
Synthesis of phenanthroindolizidine alkaloids and evaluation of their antitumor activities and toxicities
Bioorganic & Medicinal Chemistry Letters 2011.0
One-Pot Synthesis of Benzo[c]phenanthridine Alkaloids from 7-Azabenzonorbornadienes and Aryl Nitrones
Organic Letters 2023.0
Antiproliferative activity of O4-benzo[c]phenanthridine alkaloids against HCT-116 and HL-60 tumor cells
Bioorganic & Medicinal Chemistry Letters 2015.0
Synthesis and antiproliferative activity of substituted benzopyranoisoindoles: A new class of cytotoxic compounds
Bioorganic & Medicinal Chemistry Letters 2006.0