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CAS 106486-76-4

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Azinomycin B

Description:
Azinomycin B is a naturally occurring antibiotic that belongs to the class of compounds known as azinomycin antibiotics. It is produced by certain strains of the bacterium Streptomyces. This compound is characterized by its complex molecular structure, which includes a unique bicyclic core and various functional groups that contribute to its biological activity. Azinomycin B exhibits potent antibacterial properties, particularly against Gram-positive bacteria, and has been studied for its potential use in cancer therapy due to its ability to inhibit DNA synthesis. The compound's mechanism of action involves interference with nucleic acid metabolism, making it a subject of interest in medicinal chemistry. Additionally, Azinomycin B has shown promise in research related to its cytotoxic effects on tumor cells. Its stability, solubility, and reactivity are influenced by its structural features, which are critical for its biological efficacy. As with many antibiotics, the development of resistance is a concern, prompting ongoing research into its pharmacological properties and potential therapeutic applications.
Formula:C31H33N3O11
InChI:InChI=1/C31H33N3O11/c1-14-7-6-8-18-19(14)9-17(42-5)10-20(18)30(41)45-27(31(4)13-43-31)29(40)33-23(28(39)32-21(12-35)15(2)36)24-26(44-16(3)37)25(38)22-11-34(22)24/h6-10,12,22,25-27,35,38H,11,13H2,1-5H3,(H,32,39)(H,33,40)/b21-12+,24-23+
InChI key:InChIKey=QIKVYJOCQXXRSJ-PKDLRSQSSA-N
SMILES:C(\NC([C@@H](OC(=O)C=1C2=C(C=C(OC)C1)C(C)=CC=C2)[C@]3(C)CO3)=O)(/C(N/C(/C(C)=O)=C\O)=O)=C\4/N5[C@@](C5)([C@@H](O)[C@@H]4OC(C)=O)[H]
Synonyms:
  • BRN 5696947
  • Carzinophillin A
  • 1-Naphthalenecarboxylic acid, 3-methoxy-5-methyl-, 2-((1-(3-(acetyloxy)-4-hydroxy-1-azabicyclo(3.1.0)hex-2-ylidene)-2-((1-(hydroxymethylene)-2-oxopropyl)amino)-2-oxoethyl)amino)-1-(2-methyloxiranyl)-2-oxoethyl ester
  • Carzinophilin A
  • 1-Naphthalenecarboxylic acid, 3-methoxy-5-methyl-, (1S)-2-[[(1E)-1-[(3R,4R,5S)-3-(acetyloxy)-4-hydroxy-1-azabicyclo[3.1.0]hex-2-ylidene]-2-[[(1Z)-1-(hydroxymethylene)-2-oxopropyl]amino]-2-oxoethyl]amino]-1-[(2S)-2-methyloxiranyl]-2-oxoethyl ester
  • 2-{[(1E)-1-[3-(acetyloxy)-4-hydroxy-1-azabicyclo[3.1.0]hex-2-ylidene]-2-{[(1E)-1-(hydroxymethylidene)-2-oxopropyl]amino}-2-oxoethyl]amino}-1-(2-methyloxiran-2-yl)-2-oxoethyl 3-methoxy-5-methylnaphthalene-1-carboxylate
  • (1S)-2-{[(1E)-1-[(3R,4R,5S)-3-(acetyloxy)-4-hydroxy-1-azabicyclo[3.1.0]hex-2-ylidene]-2-{[(1Z)-1-hydroxy-3-oxobut-1-en-2-yl]amino}-2-oxoethyl]amino}-1-[(2S)-2-methyloxiran-2-yl]-2-oxoethyl 3-methoxy-5-methylnaphthalene-1-carboxylate
  • Azinomycin B
  • 1-Naphthalenecarboxylic acid, 3-methoxy-5-methyl-, (1S)-2-(((1E)-1-((3R,4R,5S)-3-(acetyloxy)-4-hydroxy-1-azabicyclo(3.1.0)hex-2-ylidene)-2-(((1Z)-1-(hydroxymethylene)-2-oxopropyl)amino)-2-oxoethyl)amino)-1-((2S)-2-methyloxiranyl)-2-oxoethyl ester
  • azinomycin B
  • See more synonyms
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