191216-18-9

Basic information

• Product Name: (+/-)-2-hydroxymethyl-8-phenyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione
• Synonyms: (+/-)-2-hydroxymethyl-8-phenyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione
• CAS NO: 191216-18-9
• Molecular Weight: 259.265
• Mol File: 191216-18-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (+/-)-2-hydroxymethyl-8-phenyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-2-hydroxymethyl-8-phenyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione(191216-18-9)
• EPA Substance Registry System: (+/-)-2-hydroxymethyl-8-phenyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione(191216-18-9)

Safety Data

• Hazardous Substances Data: 191216-18-9(Hazardous Substances Data)

Upstream product

• 15988-11-1 4-Phenylurazole 
• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 4949-20-6 (E)-2,4-pentadien-1-ol 

Downstream Products

• 193540-72-6 (±)-1-azafagomine 
• 193540-72-6 5-epi-1-azafagomine 
• 193540-63-5 (+/-)-2-acetoxymethyl-8-phenyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione 
• 193540-64-6 (+/-)-8-phenyl-2-(2,2,2-trimethylacetoxy)methyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione 

Relevant articles and documents

1-Azafagomine: A hydroxyhexahydropyridazine that potently inhibits enzymatic glycoside cleavage

(3,4-trans-4,5-trans)-4,5-dihydroxy-3-hydroxymethylhexahydropyridazine (16) was synthesized in four steps from 2,4-pentadienol (22) and 4-phenyltriazolin-3,5-dione (18) in an overall yield of 32%. In the first step a Diels Alder reaction between 18 and 22 gave (±)-2-hydroxymethyl-8-phenyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione (23c) in 88% yield. Epoxidation of 23c with trifluoromethyl(methyl)dioxirane, generated in situ, gave the trans epoxide 24c in 62% yield. Hydrolysis of the epoxide with perchloric acid gave stereoselectively (2,3-trans-3,4-trans)-3,4-dihydroxy-2-hydroxymethyl-8-phenyl-1,6,8-triazabicy clo[4.3.0]-nonane-7,9-dione (26) in 73% yield. In the fourth and final step, hydrazinolysis of 26 gave 16 in 84% yield. Pyridazine 16 was found to be a potent inhibitor of χ-and β-glucosidase, isomaltase and glycogen phosphorylase, while galactosidases and χ-mannosidase were not inhibited. The inhibition of β-glucosidase is independent of pH, and was found to be due to unprotonated 16.