Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C24H43N3O8SSi2 |
| Molecular Weight | 589.85 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@]3(OS(=O)(=O)C=C3N)[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)NC1=O
InChI
InChIKey=YMSLYTIPSGCZRM-DSPLJNTKSA-N
InChI=1S/C24H43N3O8SSi2/c1-15-12-27(21(29)26-19(15)28)20-18(34-38(10,11)23(5,6)7)24(16(25)14-36(30,31)35-24)17(33-20)13-32-37(8,9)22(2,3)4/h12,14,17-18,20H,13,25H2,1-11H3,(H,26,28,29)/t17-,18+,20-,24-/m1/s1
| Molecular Formula | C24H43N3O8SSi2 |
| Molecular Weight | 589.85 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
TSAO-T {[1-[2′,5′-bis-O-(tert-butyldimethyl silyl)-β-D-ribofuranosyl]thymine]-3′-spiro-5′′-(4′′-amino-1′′,2′′-ox-athiole-2′′,2′′-dioxide)} is the prototype of a unique class of NNRTIs (non-nucleoside RT inhibitors) which has structures and mechanism of actions quite distinct from conventional NNRTIs. It was discovered in a collaborative effort between the Instituto de Química Médica, CSIC (Spain) and the Rega Institute for Medical Research, KU (Belgium). TSAO-T is endowed with a potent and specific activity against human immunodeficiency virus (HIV) type 1 and is targeted at the HIV-1 reverse transcriptase (RT). Inhibition of HIV-1 RT by TSAO-T was reversible and noncompetitive. TSAO-T does not act as a DNA chain terminator. It interacts with HIV-1 RT at a nonsubstrate (dNTP)-binding site.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| 3'-Spiro nucleosides, a new class of specific human immunodeficiency virus type 1 inhibitors: synthesis and antiviral activity of [2'-5'-bis-O-(tert-butyldimethylsilyl)-beta-D-xylo- and -ribofuranose]-3'-spiro-5"-[4"-amino-1",2"-oxathiole 2",2"-dioxide] (TSAO) pyrimidine nucleosides. | 1992 Jul 24 |
|
| Kinetics of inhibition of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase by the novel HIV-1-specific nucleoside analogue [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5 "- (4"-amino-1",2"-oxathiole-2",2"-dioxide)thymine (TSAO-T). | 1992 Jun 15 |
|
| [2',5'-Bis-O-(tert-butyldimethylsilyl)]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide) (TSAO) derivatives of purine and pyrimidinenucleosides as potent and selective inhibitors of human immunodeficiency virus type 1. | 1992 May |
|
| 2',5'-Bis-O-(tert-butyldimethylsilyl)-3'-spiro-5''-(4''-amino-1'',2''- oxathiole-2'',2'-dioxide)pyrimidine (TSAO) nucleoside analogues: highlyselective inhibitors of human immunodeficiency virus type 1 that are targeted at the viral reverse transcriptase. | 1992 May 15 |
|
| Human immunodeficiency virus type 1 (HIV-1) strains selected for resistance against the HIV-1-specific [2',5'-bis-O-(tert-butyldimethylsilyl)-3'-spiro- 5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)]-beta-D-pentofurano syl (TSAO) nucleoside analogues retain sensitivity to HIV-1-specific nonnucleoside inhibitors. | 1993 Aug 1 |
|
| HIV-1-specific reverse transcriptase inhibitors show differential activity against HIV-1 mutant strains containing different amino acid substitutions in the reverse transcriptase. | 1993 Jan |
|
| Human immunodeficiency virus type 1-specific [2',5'-bis-O-(tert- butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5"-(4"-amino-1",2"- oxathiole-2",2"-dioxide)-purine analogues show a resistance spectrum that is different from that of the human immunodeficiency virus type 1-specific non-nucleoside analogues. | 1993 Jan |
|
| Human immunodeficiency virus type 1 drug-resistance patterns with different 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives. | 1993 Oct |
|
| Human immunodeficiency virus 1 (HIV-1)-specific reverse transcriptase (RT) inhibitors may suppress the replication of specific drug-resistant (E138K)RT HIV-1 mutants or select for highly resistant (Y181C-->C181I)RT HIV-1 mutants. | 1994 Jul 5 |
|
| 1,2,3-Triazole-[2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D- ribofuranosyl]-3'-spiro-5"-(4"-amino-1",2"-oxathiole 2",2"-dioxide) (TSAO) analogues: synthesis and anti-HIV-1 activity. | 1994 Nov 25 |
|
| Synthesis and anti-HIV-1 activity of novel TSAO-T derivatives modified at the 2'- and 5'-positions of the sugar moiety. | 1995 Jun |
|
| Synthesis and anti-HIV activity of [AZT]-[TSAO-T] and [AZT]-[HEPT] dimers as potential multifunctional inhibitors of HIV-1 reverse transcriptase. | 1995 May 12 |
|
| Novel L-lyxo and 5'-deoxy-5'-modified TSAO-T analogs: synthesis and anti-HIV-1 activity. | 1996 Nov |
|
| Highly potent oxathiin carboxanilide derivatives with efficacy against nonnucleoside reverse transcriptase inhibitor-resistant human immunodeficiency virus isolates. | 1997 Apr |
|
| Regiospecific synthesis and anti-human immunodeficiency virus activity of novel 5-substituted N-alkylcarbamoyl and N,N-dialkylcarbamoyl 1,2,3-triazole-TSAO analogues. | 1998 Nov |
|
| Abasic analogues of TSAO-T as the first sugar derivatives that specifically inhibit HIV-1 reverse transcriptase. | 1998 Nov 5 |
|
| TSAO-T analogues bearing amino acids at position N-3 of thymine: synthesis and anti-human immunodeficiency virus activity. | 2000 Jan |
|
| Identification of a novel family of nucleosides that specifically inhibit HIV-1 reverse transcriptase. | 2001 Dec 3 |
|
| Identification of a putative binding site for [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine (TSAO) derivatives at the p51-p66 interface of HIV-1 reverse transcriptase. | 2001 Jun 7 |
|
| The N137 and P140 amino acids in the p51 and the P95 amino acid in the p66 subunit of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase are instrumental to maintain catalytic activity and to design new classes of anti-HIV-1 drugs. | 2005 Apr 25 |
|
| Novel [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]- 3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2" -dioxide) derivatives with anti-HIV-1 and anti-human-cytomegalovirus activity. | 2005 Feb 24 |
|
| First synthesis and evaluation of the inhibitory effects of aza analogues of TSAO on HIV-1 replication. | 2005 Jun 30 |
|
| Improving the antiviral efficacy and selectivity of HIV-1 reverse transcriptase inhibitor TSAO-T by the introduction of functional groups at the N-3 position. | 2005 Oct 20 |
|
| Discovery of TSAO derivatives with an unusual HIV-1 activity/resistance profile. | 2006 Aug |
|
| Structure-activity relationships of [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]- 3'-spiro-5' '-(4' '-amino-1' ',2' '-oxathiole-2' ',2' '-dioxide)thymine derivatives as inhibitors of HIV-1 reverse transcriptase dimerization. | 2006 Aug 10 |
|
| Synthesis and anti-HIV1 biological activity of novel 5''-ATSAO compounds. | 2008 Apr 15 |
Sample Use Guides
TSAO-T was highly inhibitory to HIV-1-induced cytopathicity in MT-4 cells and HIV-1-induced giant cell formation in CEM cells. Its 50% effective concentration was about 0.03 uM in both cell systems. TSAO-T was inhibitory to HIV-1 RT at an IC50 of 17 uM when poly(C) (dG) was used as the template/primer and radiola- beled dGTP as the natural substrate.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:37:48 GMT 2023
by
admin
on
Fri Dec 15 19:37:48 GMT 2023
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| Record UNII |
WF66Y930KH
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| Record Status |
Validated (UNII)
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| Record Version |
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65005
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