1526915-17-2

Basic information

• Product Name: (3S,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-3-((1-benzyl-1H-1,2,3-triazol-4-yl)(hydroxy)methyl)-5-(methoxymethoxy)-11-(((3aR,4R,6S,7S,7aR)-7-(methoxymethoxy)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-3a,8,8-trimethyltetradecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxine-12a,14b-diol
• Synonyms: (3S,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-3-((1-benzyl-1H-1,2,3-triazol-4-yl)(hydroxy)methyl)-5-(methoxymethoxy)-11-(((3aR,4R,6S,7S,7aR)-7-(methoxymethoxy)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-3a,8,8-trimethyltetradecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxine-12a,14b-diol
• CAS NO: 1526915-17-2
• Molecular Weight: 858.039
• Mol File: 1526915-17-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-3-((1-benzyl-1H-1,2,3-triazol-4-yl)(hydroxy)methyl)-5-(methoxymethoxy)-11-(((3aR,4R,6S,7S,7aR)-7-(methoxymethoxy)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-3a,8,8-trimethyltetradecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxine-12a,14b-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-3-((1-benzyl-1H-1,2,3-triazol-4-yl)(hydroxy)methyl)-5-(methoxymethoxy)-11-(((3aR,4R,6S,7S,7aR)-7-(methoxymethoxy)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-3a,8,8-trimethyltetradecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxine-12a,14b-diol(1526915-17-2)
• EPA Substance Registry System: (3S,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-3-((1-benzyl-1H-1,2,3-triazol-4-yl)(hydroxy)methyl)-5-(methoxymethoxy)-11-(((3aR,4R,6S,7S,7aR)-7-(methoxymethoxy)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-3a,8,8-trimethyltetradecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxine-12a,14b-diol(1526915-17-2)

Safety Data

• Hazardous Substances Data: 1526915-17-2(Hazardous Substances Data)

Upstream product

• 1526915-14-9 (3S,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-12a,14b-dihydroxy-5-(methoxymethoxy)-11-(((3aR,4R,6S,7S,7aR)-7-(methoxymethoxy)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-3a,8,8-trimethylhexadecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxine-3-carbaldehyde 
• 630-60-4 ouabain 
• 1526915-15-0 (3S,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-3-(1-hydroxyprop-2-yn-1-yl)-5-(methoxymethoxy)-11-(((3aR,4R,6S,7S,7aR)-7-(methoxymethoxy)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-3a,8,8-trimethyltetradecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxine-12a,14b-diol 
• 622-79-7 benzyl azide 
• 1526915-12-7 4-((3R,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-12a,14b-dihydroxy-5-(methoxymethoxy)-11-(((3aR,4R,6S,7S,7aR)-7-(methoxymethoxy)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-3a,8,8-trimethylhexadecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-3-yl)furan-2(5H)-one 
• 326805-71-4 4-((3R,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-5,12a,14b-trihydroxy-11-(((3aR,4R,6S,7S,7aR)-7-hydroxy-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-3a,8,8-trimethylhexadecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-3-yl)furan-2(5H)-one 

Downstream Products

• 1526915-19-4 (1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-17-((1-benzyl-1H-1,2,3-triazol-4-yl)(hydroxy)methyl)-10-(hydroxymethyl)-13-methyl-3-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetradecahydro-5H-cyclopenta[a]phenanthrene-1,5,11,14(2H)-tetraol 

Relevant articles and documents

Design, Synthesis, and in Vitro and in Vivo Evaluation of Ouabain Analogues as Potent and Selective Na,K-ATPase α4 Isoform Inhibitors for Male Contraception

Na,K-ATPase α4 is a testis-specific plasma membrane Na+ and K+ transporter expressed in sperm flagellum. Deletion of Na,K-ATPase α4 in male mice results in complete infertility, making it an attractive target for male contraception. Na,K-ATPase α4 is characterized by a high affinity for the cardiac glycoside ouabain. With the goal of discovering selective inhibitors of the Na,K-ATPase α4 and of sperm function, ouabain derivatives were modified at the glycone (C3) and the lactone (C17) domains. Ouabagenin analogue 25, carrying a benzyltriazole moiety at C17, is a picomolar inhibitor of Na,K-ATPase α4, with an outstanding α4 isoform selectivity profile. Moreover, compound 25 decreased sperm motility in vitro and in vivo and affected sperm membrane potential, intracellular Ca2+, pH, and hypermotility. These results proved that the new ouabagenin triazole analogue is an effective and selective inhibitor of Na,K-ATPase α4 and sperm function.