465-22-5

Usage

Uses

Used in Pharmaceutical Industry:
Scillarenin is used as a cardiotonic agent for its ability to strengthen the contractions of the heart and increase heart rate. This makes it a potential treatment for heart failure and other cardiovascular conditions where the heart's pumping action is weakened.
Used in Drug Development:
Scillarenin is used in the development of new drugs and therapies for cardiovascular diseases. Its cardiotonic properties are being studied for their potential to improve heart function and treat conditions such as congestive heart failure, arrhythmias, and cardiomyopathies.
Used in Research:
Scillarenin is used as a research tool to study the mechanisms of heart function and the effects of various compounds on cardiac performance. This helps scientists to better understand the underlying causes of heart diseases and develop more effective treatments.

InChI:InChI=1/C24H32O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,13-14,17-20,25,27H,4-5,7-12H2,1-2H3/t17-,18?,19-,20+,22-,23+,24-/m0/s1

Upstream product

• 41059-91-0 helleborogenone 
• 466-06-8 proscillaridin A 

Downstream Products

• 545-51-7 14β-hydroxybufa-3,5,20,22-tetraenolide 
• 545-28-8 14-hydroxy-3-oxo-bufa-4,20,22-trienolide 
• 1060725-90-7 5-Isobutoxycarbonyloxy-5-oxo-pentanoic acid (3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 99223-92-4 3-Tyraminyl-3-deoxyscillarenin 

Relevant academic research and scientific papers

GLYCOSIDE COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF

The present invention provides glycoside compounds, methods of preparing such compounds, pharmaceutical compositions comprising such compounds, and a method for the treatment of hyperproliferative diseases using the same.

Modulators of Hypoxia Inducible Factor-1 and Related Uses

The invention features compounds of formulas I or II: and pharmaceutically acceptable salts and prodrugs thereof, as well methods for modulating the effects of local and systemic hypoxic events using the compounds.

MODULATORS OF HYPOXIA INDUCIBLE FACTOR-1 AND RELATED USES

The invention features compounds of formula (I): and pharmaceutically acceptable salts and prodrugs thereof, as well methods for modulating the effects of local and systemic hypoxic events using the compounds.

Studies on cardiac ingredients of plants. XI. synthesis of new bufotoxin homologues utilizing scillarenin (the genuine aglycone of proscillaridin), and their biological activities

New bufotoxin homologues (3) with various lengths of alkyl chain including longer ones thana suberoyl group at C-3 of the steroid nucleus were prepared from proscillaridin (1) via its genuine aglycone, scillarenin (2), in excellent yield. In the course of preparation, we established conditions for efficient enzymatic glycolysis of 1 to give 2 quantitatively. The pharmacological activities of the resulting bufotoxin homologues (3) were evaluated by measurement of the effect on smooth muscle using the mesenteric artery from spontaneously hypertensive rats, inhibitory: effect on Na+, K+-adenosine triphosphatase (ATPase) prepared from dog kidney, and positive inotropic effect (PIE) on isolated guinea-pig papillary muscle preparations; The bufotoxin homologues (3) showed only slight contraction of vascular muscle followed by a small-relaxation,in addition to the high Na+, K+-ATPase inhibitory activity and PIE comparable to those of clinically used ouabain, digoxin, and digitoxin. Those bufotoxin homologues (3) may be useful as cardiac agents with a minimal vascular contractile effect.

Crystal Structures of 14-Hydroxy-3-oxo-14β-bufa-1,4,20,22-tetraenolide and 3β,14-Hydroxy-14β-bufa-4,20,22-trienolide

14-Hydroxy-3-oxo-14β-bufa-1,4,20,22-tetraenolide (I) is the base of a suberic acid ester prepared by extraction of the subterranean parts of Helleborus atrirubens W.K. and other Helleborus species.The partial saturation of its Δ1,4-3-one ring A resulted in 3β,14-dihydroxy-14β-bufa-4,20,22-trienolide (II) .The crystal data for I: monoclinic system, P21, a = 8.319(1), b = 15.387(2), c = 7.744(1) Angstroem, β = 96.11(1) deg, Z = 2.The crystal data for II = orthorhombic, P212121, a = 10.387(2), b = 12.075(4), c = 16.431(6) Angstroem, Z = 4.Both structures were solved by direct methods and refined to the final R values of 0.053 for I and 0.070 for II using 2133 and 1735 diffractometer observations, respectively.Apart from the planar ring A in I and its 1α,2β half chair form in II the other parts of the steroid back bone are the same as the cardenolide prototype molecule digitoxigenin.The similarities and differences between the structures of II and bufalin are also discussed.

Synthesis of 4,5-Methylenebufadienolides

Stereospecific cis-addition of methylene to the 4,5-double bond of the 3,14-dihydroxybufatrienolides 1 and 3 gives 2 and 4.Synthesis of the isomeric bufadienolides 6 and 8 with trans configuration of the 3-hydroxy group and the 4,5-methylene group is achieved starting from 2 or 4 respectively by oxidation with chromic trioxide followed by stereoselective reduction with lithium tri-tert-butoxohydridoaluminate.Reaction of the proscillaridin derivatives 10 and 11 according to Simmons-Smith affords 12 and 13, which are converted into 4β,5β-methyleneproscillaridin (14) by acid hydrolysis.