93068-72-5

Basic information

• Product Name: (6R,7R)-7-tert-Butoxycarbonylamino-5,8-dioxo-3-[(E)-2-(pyridin-3-ylsulfanyl)-vinyl]-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS NO: 93068-72-5
• Molecular Weight: 617.747
• Mol File: 93068-72-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (6R,7R)-7-tert-Butoxycarbonylamino-5,8-dioxo-3-[(E)-2-(pyridin-3-ylsulfanyl)-vinyl]-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (6R,7R)-7-tert-Butoxycarbonylamino-5,8-dioxo-3-[(E)-2-(pyridin-3-ylsulfanyl)-vinyl]-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester(93068-72-5)
• EPA Substance Registry System: (6R,7R)-7-tert-Butoxycarbonylamino-5,8-dioxo-3-[(E)-2-(pyridin-3-ylsulfanyl)-vinyl]-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester(93068-72-5)

Safety Data

• Hazardous Substances Data: 93068-72-5(Hazardous Substances Data)

Upstream product

• 16133-26-9 pyridine-3-thiol 

Downstream Products

• 93068-78-1 diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(E)-2-(3-pyridyl)thiovinyl]-3-cephem-4-carboxylate 

Relevant articles and documents

Studies on anti-MRSA parenteral cephalosporins. IV. A novel water-soluble N-phosphono type prodrug for parenteral administration

A systematic approach for improving the water-solubility of anti-MRSA (methicillin-resistant Staphylococcus aureus) cephalosporin derivatives is described. We first tried to improve the water-solubility of 7β-[2- (5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-fluoromethoxyimino-acetamido]- 3-[(E)-2-(1-methylimidazo[1,2-b]pyridazinium-6-yl)thiovinyl]- 3-cephem-4-carboxylate (1a) by substitution of the C-3′ pharmacophore. Replacement of the C-3′ pharmacophore with a 1-methyl-4-pyridinio group improved the water-solubility without decreasing the anti-MRSA activity. Furthermore, we applied the N-modified prodrug strategy to the C-7 acyl group in order to enhance the water-solubility drastically. Among the compounds prepared, the N-phosphono type prodrugs 2a (1-methylimidazo [1,2-b]pyridazinium derivative) and 2b (1-methyl-4-pyridinio derivative) showed water-solubility appropriate for a product intended for intravenous injection and in vivo anti-MRSA activity comparable to that of vancomycin.