1444555-12-7

Basic information

• Product Name: (3S,8R,10R,12R,14R,17S)-17-((S)-2-hydroxy-5-((3-phenylpropyl)amino)pentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol
• Synonyms: (3S,8R,10R,12R,14R,17S)-17-((S)-2-hydroxy-5-((3-phenylpropyl)amino)pentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol
• CAS NO: 1444555-12-7
• Molecular Weight: 553.869
• Mol File: 1444555-12-7.mol

Chemical Properties

• CAS DataBase Reference: (3S,8R,10R,12R,14R,17S)-17-((S)-2-hydroxy-5-((3-phenylpropyl)amino)pentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,8R,10R,12R,14R,17S)-17-((S)-2-hydroxy-5-((3-phenylpropyl)amino)pentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol(1444555-12-7)
• EPA Substance Registry System: (3S,8R,10R,12R,14R,17S)-17-((S)-2-hydroxy-5-((3-phenylpropyl)amino)pentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol(1444555-12-7)

Safety Data

• Hazardous Substances Data: 1444555-12-7(Hazardous Substances Data)

Upstream product

• 2038-57-5 3-Phenylpropan-1-amine 
• 6892-79-1 protopanaxadiol 

Relevant articles and documents

Discovery, synthesis, and structure-activity relationships of 20(S)-protopanaxadiol (PPD) derivatives as a novel class of AMPKα2β 1γ1 activators

Adenosine 5′-monophosphate-activated protein kinase (AMPK) has been demonstrated as a promising drug target due to its regulatory function in glucose and lipid metabolism. 20(S)-protopanoxadiol (PPD) was firstly identified from high throughput screening as a small molecule activator of AMPK subtype α2β1γ1. In order to enhance its potency on AMPK, a series of PPD derivatives were synthesized and evaluated. Structure-activity relationship study showed that the amine derivatives at the 24-position (groups I-VI) can improve the potency (EC50: 0.7-2.3 μM) and efficacy (fold: 2.5-3.8). Among them, compounds 12 and 13 exhibited the best potency (EC 50: 1.2 and 0.7 μM) and efficacy (fold: 3.7 and 3.8). Further study suggested the mechanism of AMPK activation may functioned at the allosteric position, resulting the inhibition of the lipid synthesis in HepG2 cell model.

20(S)-Protopanaxadiol (PPD) analogues chemosensitize multidrug-resistant cancer cells to clinical anticancer drugs

Novel 20(S)-protopanoxadiol (PPD) analogues were designed, synthesized, and evaluated for the chemosensitizing activity against a multidrug resistant (MDR) cell line (KBvcr) overexpressing P-glycoprotein (P-gp). Structure-activity relationship analysis showed that aromatic substituted aliphatic amine at the 24-positions (groups V) effectively and significantly sensitized P-gp overexpressing multidrug resistant (MDR) cells to anticancer drugs, such as docetaxel (DOC), vincristine (VCR), and adriamycin (ADM). PPD derivatives 12 and 18 showed 1.3-2.6 times more effective reversal ability than verapamil (VER) for DOC and VCR. Importantly, no cytotoxicity was observed by the active PPD analogues (5 μM) against both non-MDR and MDR cells, suggesting that PPD analogues serve as novel lead compounds toward a potent and safe resistance modulator. Moreover, a preliminary mechanism study demonstrated that the chemosensitizing activity of PPD analogues results from inhibition of P-glycoprotein (P-gp) overexpressed in MDR cancer cells.