Synthesis of bufalin

Pettit, George R.; Houghton, L. E.; Knight, John; Brüschweiler, Fred

doi:10.1039/c29700000093

Cited by 12 publications

(5 citation statements)

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“…IR 1737, 1705 cm -1 . 1 H NMR: δ 2.58 (t, 1H, J ) 16 Hz, 4-H ax ), 0.88 (s, 3H, CH 3 [18]). Elemental Analysis: C 18 H 26 O 2 (MW 274), Calcd C (78.8%), H (9.48%), Found C (78.64%), H (9.21%).…”

Section: Methodsmentioning

confidence: 99%

“…MS: m/z (M +‚ ) 320. 1 H NMR: δ 3.62 (m, 1H, CHOH), 3.81 (m, 4H, OCH 2 CH 2 O), 0.87 (s, 3H, CH 3 [18]).…”

Section: Methodsmentioning

confidence: 99%

“…[14][15][16][17] The transformation of digoxin to a bufadienolide compound was also reported. 18 In the early 1970s, it was established that the main prerequisites for a biologically active cardenolide are the C/D cis ring junction, the 17β-butenolide moiety, and the 3β,14β-dihydroxy groups. The A/B ring junction can be either cis or trans without a dramatic change in activity.…”

Section: Introductionmentioning

confidence: 99%

“…Since 1969, several attempts to synthesize bufadienolides have been made. − The transformation of digoxin to a bufadienolide compound was also reported . In the early 1970s, it was established that the main prerequisites for a biologically active cardenolide are the C/D cis ring junction, the 17β-butenolide moiety, and the 3β,14β-dihydroxy groups.…”

Section: Introductionmentioning

confidence: 99%

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4-(3‘α15‘β-Dihydroxy-5‘β-estran-17‘β-yl)furan-2-methyl Alcohol: An Anti-Digoxin Agent with a Novel Mechanism of Action

et al. 2005

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The synthesis and some pharmacological properties of 4-(3'alpha-15'beta-dihydroxy-5beta-estran-17'beta-yl)furan-2-methyl alcohol (16) have been described. The compound was synthesized by reacting a synthetic 3alpha- benzyloxy-5beta-estr-15-en-17-one with the ethylene acetal of 4-bromo-2-furancarboxyaldehyde, followed by hydrolysis of the ethylene acetal and reduction of the aldehyde. Despite its resemblance to the structure of cardiac steroids (CS), 16 does not bind to the CS receptor on Na(+),K(+)-ATPase and does not increase the force of contraction of heart muscle. However, 16 inhibited the digoxin-induced increase in the force of contraction and arrhythmias in guinea pig papillary muscle and human atrial appendages. The steroid also inhibited digoxin-induced alteration in endocytosed membrane traffic, indicating a novel mechanism of action.

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Section: Methodsmentioning

confidence: 99%

“…MS: m/z (M +‚ ) 320. 1 H NMR: δ 3.62 (m, 1H, CHOH), 3.81 (m, 4H, OCH 2 CH 2 O), 0.87 (s, 3H, CH 3 [18]).…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

4-(3‘α15‘β-Dihydroxy-5‘β-estran-17‘β-yl)furan-2-methyl Alcohol: An Anti-Digoxin Agent with a Novel Mechanism of Action

et al. 2005

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“…BF has a narrow therapeutic window, extremely low water solubility, unsatisfactory bioavailability and severe adverse effects, including high cardiac toxicity, which limits its clinical applications (47,48). Since the purification and total synthesis of BF, various methods have been used to improve its activity and expand its therapeutic potential in different biological systems by modifying its structure (49,50). More importantly, efforts should be directed towards identifying additional BF derivatives that exert stronger anticancer effects and have a lower toxicity level compared with the natural compound to promote the development of novel anticancer agents from cardiac steroids, including BF.…”

Section: Promising Bf Derivatives May Have Even Greater Anticancer Activitymentioning

confidence: 99%

A research update on the anticancer effects of bufalin and its derivatives (Review)

et al. 2019

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Bufalin (BF) is a cardiotonic steroid that has recently been found to have substantial anticancer activity; however, more efforts should be directed toward clarifying the detailed molecular mechanisms underlying this activity. BF could exert its anticancer effect by inducing apoptosis in various human cancer cells and thus triggering autophagic cancer cell death. The anti-inflammatory activities of BF are potentially important for its anticancer functions. Notably, some promising synthetic BF derivatives, including poly (ethylene glycol)-based polymeric prodrug of BF and BF211, have shown potent anticancer activity. Additionally, clinical trials regarding the use of BF-related agents in patients have supported the positive effect of BF as an anticancer treatment. Currently, large-scale randomized, double-blind, placebo or positive drug parallel controlled studies are required to confirm the anticancer potential of BF in various cancer types in the clinical setting. The present review will evaluate the potential mechanisms mediated by BF in intracellular signaling events in cancer cells and various promising BF derivatives that may have greater anticancer activity, thereby clarifying BF-mediated anticancer effects. The experimental and clinical results reviewed strongly emphasize the importance of this topic in future investigations. Contents

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