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CAS 1476-46-6

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Deacetylcephalosporin C

Description:
Deacetylcephalosporin C is a beta-lactam antibiotic that serves as a crucial intermediate in the synthesis of various cephalosporin antibiotics. It is derived from cephalosporin C through the removal of an acetyl group. This compound exhibits antibacterial properties, primarily targeting Gram-positive and some Gram-negative bacteria by inhibiting cell wall synthesis. Structurally, it contains a beta-lactam ring, which is essential for its biological activity, and a thiazolidine ring, characteristic of cephalosporins. Deacetylcephalosporin C is typically a white to off-white crystalline powder, and it is soluble in water and organic solvents, which facilitates its use in pharmaceutical formulations. Its stability can be influenced by pH and temperature, making proper storage conditions essential for maintaining its efficacy. The compound is significant in medicinal chemistry, as it serves as a precursor for the development of more advanced cephalosporin derivatives, enhancing the spectrum of activity and improving pharmacological properties.
Formula:C14H19N3O7S
InChI:InChI=1S/C14H19N3O7S/c15-7(13(21)22)2-1-3-8(19)16-9-11(20)17-10(14(23)24)6(4-18)5-25-12(9)17/h7,9,12,18H,1-5,15H2,(H,16,19)(H,21,22)(H,23,24)/t7-,9-,12-/m1/s1
InChI key:InChIKey=XWCFYHBHOFBVIV-JWKOBGCHSA-N
SMILES:C(O)(=O)C=1N2[C@@]([C@H](NC(CCC[C@H](C(O)=O)N)=O)C2=O)(SCC1CO)[H]
Synonyms:
  • (6R,7R)-7-(<span class="text-smallcaps">D</span>-5-amino-5-carboxypentanamido)-3-hydroxymethylceph-3-em-4-carboxylic acid
  • (6R,7R)-7-[[(5R)-5-Amino-5-carboxy-1-oxopentyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • (6R,7R)-7-{[(5R)-5-amino-5-carboxypentanoyl]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((5-amino-5-carboxy-1-oxopentyl)amino)-3-(hydroxymethyl)-8-oxo, (6R-(6alpha,7beta(R*)))-
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-(5-amino-5-carboxyvaleramido)-3-(hydroxymethyl)-8-oxo-
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[(5-amino-5-carboxy-1-oxopentyl)amino]-3-(hydroxymethyl)-8-oxo-, [6R-[6α,7β(R*)]]-
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(5R)-5-amino-5-carboxy-1-oxopentyl]amino]-3-(hydroxymethyl)-8-oxo-, (6R,7R)-
  • Antibiotic SF 1623C
  • Antibiotic WS 3442E
  • Desacetylcephalosporin C
  • Deacetylcephalosporin C
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