Zur Kenntnis der Triterpene. (70. Mitteilung). Über weitere Umwandlungen des β‐Amyradien‐dionols

Růžička, L.; Jeger, O.

doi:10.1002/hlca.19420250628

Cited by 10 publications

(4 citation statements)

References 3 publications

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“…Methyl 3 β-Acetoxy-18 βH-olean-12-en-30-oate (4): [ 43 ] A solution of conc. hydrochloric acid (50 mL) was added dropwise at 10°C to a stirred suspension of 3 (9.1 g, 17.3 mmol) and zinc powder (18.2 g, 280 mmol) in dioxane (300 mL) over 2 h. The reaction mixture was stirred for a further 3 h at 5–10°C, concentrated in a vacuum, diluted with water (1 L), and filtered.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Pro‐Apoptotic Activity of Novel Glycyrrhetinic Acid Derivatives

et al. 2011

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Triterpenoids are used for medicinal purposes in many countries. Some, such as oleanolic and glycyrrhetinic acids, are known to be anti-inflammatory and anticarcinogenic. However, the biological activities of these naturally occurring molecules against their particular targets are weak, so the synthesis of new synthetic analogues with enhanced potency is needed. By combining modifications to both the A and C rings of 18βH-glycyrrhetinic acid, the novel synthetic derivative methyl 2-cyano-3,12-dioxo-18βH-olean-9(11),1(2)-dien-30-oate was obtained. This derivative displays high antiproliferative activity in cancer cells, including a cell line with a multidrug-resistance phenotype. It causes cell death by inducing the intrinsic caspase-dependent apoptotic pathway.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Pro‐Apoptotic Activity of Novel Glycyrrhetinic Acid Derivatives

et al. 2011

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“…Studies relating to the oxidation of complex polyterpene compounds with selenium dioxide have been made by Bilharn, Kon, and Ross (22), Jones and Meakins (116), Mowrer, Green, and Spring (176), Picard and Spring (185), and Ruzicka and his collaborators (204)(205)(206)(207)(208)211). Sapogenin derivatives have been studied by Marker (143) and by Marker and Turner (147).…”

Section: Unsaturated Compoundsmentioning

confidence: 99%

Selenium Dioxide: Preparation, Properties, and Use as Oxidizing Agent.

Waitkins¹,

Clark²

1945

Chem. Rev.

106

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“…Methyl 3«-Acetoxy-2/3-hydroxy-18d-olean-12-en-30-oate (3). Continued elution of the CC-7 column described directly above with 95:5 PhH-EtOAc yielded 3 (701 mg, 35%) which was recrystallized from CH2Cl3-MeOH: mp 181-183°; nmr (CDC13) 5 3.96 (t, J = 7 Hz, 1 H), assigned to C2H, 4.95 (d, J = 7 Hz), assigned to C3H.…”

Section: Methodsmentioning

confidence: 99%