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Details

Stereochemistry ACHIRAL
Molecular Formula C9H12N2O5
Molecular Weight 228.202
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIOXOLANE T

SMILES

CC1=CN([C@H]2CO[C@@H](CO)O2)C(=O)NC1=O

InChI

InChIKey=BCAWWPAPHSAUQZ-RNFRBKRXSA-N
InChI=1S/C9H12N2O5/c1-5-2-11(9(14)10-8(5)13)6-4-15-7(3-12)16-6/h2,6-7,12H,3-4H2,1H3,(H,10,13,14)/t6-,7-/m1/s1

HIDE SMILES / InChI

Molecular Formula C9H12N2O5
Molecular Weight 228.202
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Asymmetric synthesis of 1,3-dioxolane-pyrimidine nucleosides and their anti-HIV activity.
1992 May 29
Molecular mechanism of dioxolane nucleosides against 3TC resistant M184V mutant HIV.
2004 Jul
Anti-HIV activity of (-)-(2R,4R)-1- (2-hydroxymethyl-1,3-dioxolan-4-yl)-thymine against drug-resistant HIV-1 mutants and studies of its molecular mechanism.
2005 Jun 16
Phosphoramidate and phosphate prodrugs of (-)-beta-D-(2R,4R)-dioxolane-thymine: synthesis, anti-HIV activity and stability studies.
2006 Apr 1
Mechanism of action of (-)-(2R,4R)-1-(2-hydroxymethyl-1,3-dioxolan-4-yl) thymine as an anti-HIV agent.
2007
5'-O-Aliphatic and amino acid ester prodrugs of (-)-beta-D-(2R,4R)-dioxolane-thymine (DOT): synthesis, anti-HIV activity, cytotoxicity and stability studies.
2009 Feb 1
Phosphoramidate prodrugs of (-)-β-D-(2R,4R)-dioxolane-thymine (DOT) as potent anti-HIV agents.
2012 May 14
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:59:29 GMT 2023
Edited
by admin
on Fri Dec 15 17:59:29 GMT 2023
Record UNII
WT6GZM4YA8
Record Status Validated (UNII)
Record Version
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Name Type Language
DIOXOLANE T
Common Name English
DIOXOLANE THYMINE NUCLEOSIDE
Common Name English
2,4(1H,3H)-PYRIMIDINEDIONE, 1-(2-(HYDROXYMETHYL)-1,3-DIOXOLAN-4-YL)-5-METHYL-, (2R-CIS)-
Systematic Name English
DOT
Common Name English
Code System Code Type Description
PUBCHEM
451593
Created by admin on Fri Dec 15 17:59:29 GMT 2023 , Edited by admin on Fri Dec 15 17:59:29 GMT 2023
PRIMARY
CAS
136982-89-3
Created by admin on Fri Dec 15 17:59:29 GMT 2023 , Edited by admin on Fri Dec 15 17:59:29 GMT 2023
PRIMARY
FDA UNII
WT6GZM4YA8
Created by admin on Fri Dec 15 17:59:29 GMT 2023 , Edited by admin on Fri Dec 15 17:59:29 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY