title: Betulin Phosphonates; Synthesis, Structure, and Cytotoxic Activity.
abstract: Betulin derivatives are a widely studied group of compounds of natural origin due to their wide spectrum of biological activities. This paper describes new betulin derivatives, containing a phosphonate group. The allyl-vinyl isomerization and synthesis of acetylenic derivatives have been reported. Structural identification of products as E and Z isomers has been carried out using ¹H-, (13)C-, (31)P-NMR, and crystallographic analysis. The crystal structure in the orthorhombic space group and analysis of crystal packing contacts for 29-diethoxyphosphoryl-28-cyclopropylpropynoyloxy-lup-20E(29)-en-3β-ol 8a are reported. All new compounds were tested in vitro for their antiproliferative activity against human T47D (breast cancer), SNB-19 (glioblastoma), and C32 (melanoma) cell lines.
authors: Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, Poland. echrobak@sum.edu.pl.
authors: Elwira
authors: E
authors: Chrobak
authors: Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, Poland. ebebenek@sum.edu.pl.
authors: Ewa
authors: E
authors: Bębenek
authors: Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, Poland. mkadela@sum.edu.pl.
authors: Monika
authors: M
authors: Kadela-Tomanek
authors: Department of Cell Biology, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 8 Jedności Str., 41-200 Sosnowiec, Poland. mlatocha@sum.edu.pl.
authors: Małgorzata
authors: M
authors: Latocha
authors: Laboratoire Cristallographie Résonance Magnétique et Modélisations, Faculté des Sciences et Technologies, CNRS, Université de Lorraine, BP 70239, 54506 Vandoeuvre-les-Nancy, France. christian.jelsch@univ-lorraine.fr.
authors: Christian
authors: C
authors: Jelsch
authors: Laboratoire Cristallographie Résonance Magnétique et Modélisations, Faculté des Sciences et Technologies, CNRS, Université de Lorraine, BP 70239, 54506 Vandoeuvre-les-Nancy, France. emmanuel.wenger@univ-lorraine.fr.
authors: Emmanuel
authors: E
authors: Wenger
authors: Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, Poland. boryczka@sum.edu.pl.
authors: Stanisław
authors: S
authors: Boryczka
mesh_terms: D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D003603:Cytotoxins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000094062:Betulinic Acid
chemical_list: D003603:Cytotoxins; D063065:Organophosphonates; D014315:Triterpenes; C002503:betulin; D000094062:Betulinic Acid
keywords: E isomer; Z isomer; antiproliferative activity; betulin; crystallographic analysis; phosphonate