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CAS 7057-48-9

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2′,3′-Didehydro-2′,3′-dideoxyadenosine

Description:
2′,3′-Didehydro-2′,3′-dideoxyadenosine (ddA) is a synthetic nucleoside analog of adenosine, characterized by the absence of the 2′ and 3′ hydroxyl groups on the ribose sugar, as well as a double bond between the 2′ and 3′ carbon atoms. This structural modification imparts unique properties to ddA, making it a potent inhibitor of viral replication, particularly in the context of retroviruses such as HIV. ddA is known for its role in antiviral therapies, where it functions by interfering with the reverse transcription process, ultimately preventing viral DNA synthesis. The compound is typically administered in a phosphate form to enhance its solubility and bioavailability. In terms of physical properties, ddA is a white to off-white solid, soluble in water and various organic solvents. Its mechanism of action and pharmacokinetics have been the subject of extensive research, contributing to its significance in the development of antiretroviral drugs. However, like many nucleoside analogs, it may also exhibit cytotoxic effects, necessitating careful consideration in therapeutic applications.
Formula:C10H11N5O2
InChI:InChI=1/C10H11N5O2/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(3-16)17-7/h1-2,4-7,16H,3H2,(H2,11,12,13)
InChI key:InChIKey=JFUOUIPRAAGUGF-NKWVEPMBSA-N
SMILES:NC1=C2C(N(C=N2)[C@@H]3O[C@H](CO)C=C3)=NC=N1
Synonyms:
  • 2'3'-Ddda
  • 2'3'-Didehydro-2'3'-dideoxyadenosine
  • 2′,3′-Didehydro-2′,3′-dideoxyadenosine
  • 2′,3′-Dideoxy-2′,3′-didehydroadenosine
  • Adenine, 9-(2,3-dideoxy-β-<span class="text-smallcaps">D</span>-glycero-pent-2-enofuranosyl)-
  • Adenosine, 2',3'-didehydro-2',3'-dideoxy-
  • Adenosine, 2′,3′-didehydro-2′,3′-dideoxy-
  • Nsc 108602
  • Pent-2-enofuranoside, adenine-9 2,3-dideoxy-
  • [(2S,5R)-5-(6-amino-9H-purin-9-yl)-2,5-dihydrofuran-2-yl]methanol
  • See more synonyms
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