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123027-56-5 | 2,4(1H,3H)-Pyrimidinedione, 1-[(2-hydroxyethoxy)methyl]-5-methyl-6-(phenylthio)-
CAS No: 123027-56-5 Catalog No: AG000JYQ MDL No:
Product Description
Catalog Number:
AG000JYQ
Chemical Name:
2,4(1H,3H)-Pyrimidinedione, 1-[(2-hydroxyethoxy)methyl]-5-methyl-6-(phenylthio)-
CAS Number:
123027-56-5
Molecular Formula:
C14H16N2O4S
Molecular Weight:
308.3528
IUPAC Name:
1-(2-hydroxyethoxymethyl)-5-methyl-6-phenylsulfanylpyrimidine-2,4-dione
InChI:
InChI=1S/C14H16N2O4S/c1-10-12(18)15-14(19)16(9-20-8-7-17)13(10)21-11-5-3-2-4-6-11/h2-6,17H,7-9H2,1H3,(H,15,18,19)
InChI Key:
HDMHBHNRWDNNCD-UHFFFAOYSA-N
SMILES:
OCCOCn1c(Sc2ccccc2)c(C)c(=O)[nH]c1=O
Properties
Complexity:
433
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
308.083g/mol
Formal Charge:
0
Heavy Atom Count:
21
Hydrogen Bond Acceptor Count:
5
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
308.352g/mol
Monoisotopic Mass:
308.083g/mol
Rotatable Bond Count:
6
Topological Polar Surface Area:
104A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.1
Literature
| Title | Journal |
|---|---|
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| 4D-QSAR study of HEPT derivatives by electron conformational-genetic algorithm method. | SAR and QSAR in environmental research 20120701 |
| Docking, molecular dynamics and quantitative structure-activity relationship studies for HEPTs and DABOs as HIV-1 reverse transcriptase inhibitors. | Journal of molecular modeling 20120501 |
| Comparative QSAR analysis of cyclo-oxygenase2 inhibiting drugs. | Bioinformation 20120101 |
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| Application of ant colony optimization in development of models for prediction of anti-HIV-1 activity of HEPT derivatives. | Journal of computational chemistry 20100901 |
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| Non-nucleoside HIV-1 reverse transcriptase inhibitors, Part 7. Synthesis, antiviral activity, and 3D-QSAR investigations of novel 6-(1-naphthoyl) HEPT analogues. | Chemical & pharmaceutical bulletin 20060901 |
| A novel simple QSAR model for the prediction of anti-HIV activity using multiple linear regression analysis. | Molecular diversity 20060801 |
| Novel tight binding PETT, HEPT and DABO-based non-nucleoside inhibitors of HIV-1 reverse transcriptase. | Journal of enzyme inhibition and medicinal chemistry 20060801 |
| Quantitative structure-activity relationship studies on HEPTs by supervised stochastic resonance. | Bioorganic & medicinal chemistry letters 20060601 |
| Non-nucleoside HIV reverse transcriptase inhibitors, Part 6[1]: synthesis and anti-HIV activity of novel 2-[(arylcarbonylmethyl)thio]-6-arylthio DABO analogues. | Archiv der Pharmazie 20051001 |
| Nonnucleoside HIV-1 reverse-transcriptase inhibitors, part 5. Synthesis and anti-HIV-1 activity of novel 6-naphthylthio HEPT analogues. | Chemical & pharmaceutical bulletin 20050801 |
| 'In silico' design of potential anti-HIV actives using fragment descriptors. | Combinatorial chemistry & high throughput screening 20050801 |
| Topochemical model for prediction of anti-HIV activity of HEPT analogs. | Bioorganic & medicinal chemistry letters 20050117 |
| Nonnucleoside HIV-1 reverse transcriptase inhibitors; part 3. Synthesis and antiviral activity of 5-alkyl-2-[(aryl and alkyloxyl-carbonylmethyl)thio]-6-(1-naphthylmethyl) pyrimidin-4(3H)-ones. | Bioorganic chemistry 20041201 |
| 5-Alkyl-2-[(aryl and alkyloxylcarbonylmethyl)thio]-6-(1-naphthylmethyl) pyrimidin-4(3H)-ones as an unique HIV reverse transcriptase inhibitors of S-DABO series. | Bioorganic & medicinal chemistry letters 20040621 |
| QSAR study on some anti-HIV HEPT analogues using physicochemical and topological parameters. | Bioorganic & medicinal chemistry 20040315 |
| Computer-aided design, synthesis, and anti-HIV-1 activity in vitro of 2-alkylamino-6-[1-(2,6-difluorophenyl)alkyl]-3,4-dihydro-5-alkylpyrimidin-4(3H)-ones as novel potent non-nucleoside reverse transcriptase inhibitors, also active against the Y181C variant. | Journal of medicinal chemistry 20040212 |
| Development of neural network QSPR models for Hansch substituent constants. 2. Applications in QSAR studies of HIV-1 reverse transcriptase and dihydrofolate reductase inhibitors. | Journal of chemical information and computer sciences 20040101 |
| Artificial neural networks: non-linear QSAR studies of HEPT derivatives as HIV-1 reverse transcriptase inhibitors. | Molecular diversity 20040101 |
| Non-nucleoside reverse transcriptase inhibitors (NNRTIs): past, present, and future. | Chemistry & biodiversity 20040101 |
| Evolutionary optimization, backpropagation, and data preparation issues in QSAR modeling of HIV inhibition by HEPT derivatives. | Bio Systems 20031101 |
| Hologram quantitative structure-activity relationships investigations of non-nucleoside reverse transcriptase inhibitors. | Current medicinal chemistry 20030901 |
| Nonnucleoside HIV-1 reverse transcriptase inhibitors: Part I. Synthesis and structure-activity relationship of 1-alkoxymethyl-5-alkyl-6-naphthylmethyl uracils as HEPT analogues. | Chemical & pharmaceutical bulletin 20030701 |
| Neural networks: Accurate nonlinear QSAR model for HEPT derivatives. | Journal of chemical information and computer sciences 20030101 |
| Comparative QSAR based on neural networks for the anti-HIV activity of HEPT derivatives. | Current pharmaceutical design 20030101 |
| Anti-HIV activity of HEPT, TIBO, and cyclic urea derivatives: structure-property studies, focused combinatorial library generation, and hits selection using substructural molecular fragments method. | Journal of chemical information and computer sciences 20030101 |
| QSAR: then and now. | Current topics in medicinal chemistry 20021201 |
| QSAR for anti-HIV activity of HEPT derivatives. | SAR and QSAR in environmental research 20021001 |
| Prediction of activity for nonnucleoside inhibitors with HIV-1 reverse transcriptase based on Monte Carlo simulations. | Journal of medicinal chemistry 20020704 |
| HEPT derivatives as non-nucleoside inhibitors of HIV-1 reverse transcriptase: QSAR studies agree with the crystal structures. | Journal of computer-aided molecular design 20020401 |
| Structure-cytotoxicity relationships for a series of HEPT derivatives. | Journal of molecular modeling 20020101 |
| Predicting anti-HIV activity: computational approach using a novel topological descriptor. | Journal of computer-aided molecular design 20010701 |
| Estimation of binding affinities for HEPT and nevirapine analogues with HIV-1 reverse transcriptase via Monte Carlo simulations. | Journal of medicinal chemistry 20010118 |
| 3D-quantitative structure-activity relationships of HEPT derivatives as HIV-1 reverse transcriptase inhibitors, based on Ab initio calculations. | Journal of chemical information and computer sciences 20010101 |
| Effect of nucleoside analogs and non-nucleoside inhibitors of HIV-1 reverse transcriptase on cell-free virions. | Archives of virology 19990101 |
| Synthesis and anti-HIV-1 activity of novel 2,3-dihydro-7H-thiazolo[3,2-a]pyrimidin-7-ones. | Journal of medicinal chemistry 19980115 |
| Synthesis and anti-HIV-1 activity of a series of 1-alkoxy-5-alkyl-6-(arylthio)uracils. | Journal of medicinal chemistry 19970718 |
| Inhibition of replication of HIV in primary monocyte/macrophages by different antiviral drugs and comparative efficacy in lymphocytes. | Journal of leukocyte biology 19970701 |
| Synthesis and anti-HIV activity of novel N-1 side chain-modified analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). | Journal of medicinal chemistry 19970606 |
| Antiviral activity and mechanism of action of calanolide A against the human immunodeficiency virus type-1. | The Journal of pharmacology and experimental therapeutics 19961101 |
| Synthesis and potent anti-HIV-1 activity of novel 6-benzyluracil analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine. | Journal of medicinal chemistry 19960607 |
| Assessment of a cytoprotection assay for the discovery and evaluation of anti-human immunodeficiency virus compounds utilizing a genetically-impaired virus. | Journal of virological methods 19960426 |
| Complexes of HIV-1 reverse transcriptase with inhibitors of the HEPT series reveal conformational changes relevant to the design of potent non-nucleoside inhibitors. | Journal of medicinal chemistry 19960412 |
| Biological and biochemical anti-human immunodeficiency virus activity of UC 38, a new non-nucleoside reverse transcriptase inhibitor. | The Journal of pharmacology and experimental therapeutics 19960101 |
| A new series of pyridinone derivatives as potent non-nucleoside human immunodeficiency virus type 1 specific reverse transcriptase inhibitors. | Journal of medicinal chemistry 19951110 |
| Synthesis and antiviral activity of 6-benzyl analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as potent and selective anti-HIV-1 agents. | Journal of medicinal chemistry 19950721 |
| Resistance to 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives is generated by mutations at multiple sites in the HIV-1 reverse transcriptase. | Virology 19950620 |
| Design and synthesis of novel inhibitors of HIV-1 reverse transcriptase. | Journal of medicinal chemistry 19950609 |
| Synthesis and anti-HIV activity of [AZT]-[TSAO-T] and [AZT]-[HEPT] dimers as potential multifunctional inhibitors of HIV-1 reverse transcriptase. | Journal of medicinal chemistry 19950512 |
| Differential activities of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives against different human immunodeficiency virus type 1 mutant strains. | Antimicrobial agents and chemotherapy 19950401 |
| Resistance of human immunodeficiency virus type 1 to acyclic 6-phenylselenenyl- and 6-phenylthiopyrimidines. | Antimicrobial agents and chemotherapy 19941001 |
| HIV resistance to reverse transcriptase inhibitors. | Biochemical pharmacology 19940120 |
| Knocking-out concentrations of HIV-1-specific inhibitors completely suppress HIV-1 infection and prevent the emergence of drug-resistant virus. | Virology 19931001 |
| Human immunodeficiency virus type 1 drug-resistance patterns with different 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives. | Molecular pharmacology 19931001 |
| Effect of human serum on the in vitro anti-HIV-1 activity of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) derivatives as related to their lipophilicity and serum protein binding. | Biochemical pharmacology 19930622 |
| Analysis of nonnucleoside drug-resistant variants of human immunodeficiency virus type 1 reverse transcriptase. | Journal of virology 19930401 |
| A single conservative amino acid substitution in the reverse transcriptase of human immunodeficiency virus-1 confers resistance to (+)-(5S)-4,5,6,7-tetrahydro-5-methyl-6-(3-methyl-2-butenyl)imidazo[4,5, 1- jk][1,4]benzodiazepin-2(1H)-thione (TIBO R82150). | Molecular pharmacology 19930101 |
| Synthesis and antiviral activity of deoxy analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as potent and selective anti-HIV-1 agents. | Journal of medicinal chemistry 19921211 |
| 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. | Journal of medicinal chemistry 19920724 |
| Kinetics of inhibition of endogenous human immunodeficiency virus type 1 reverse transcription by 2',3'-dideoxynucleoside 5'-triphosphate, tetrahydroimidazo-[4,5,1-jk][1,4]-benzodiazepin-2(1H)-thion e, and 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives. | The Journal of biological chemistry 19920615 |
| Common features in the interaction of tetrahydroimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-one and -thione and 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives with the human immunodeficiency virus type 1 reverse transcriptase. | Molecular pharmacology 19920501 |
| HIV-1 reverse transcriptase inhibition by a dipyridodiazepinone derivative: BI-RG-587. | Biochemical pharmacology 19920317 |
| In vitro selection and molecular characterization of human immunodeficiency virus-1 resistant to non-nucleoside inhibitors of reverse transcriptase. | Molecular pharmacology 19920301 |
| Structure-activity relationships of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine analogues: effect of substitutions at the C-6 phenyl ring and at the C-5 position on anti-HIV-1 activity. | Journal of medicinal chemistry 19920124 |
| Specific HIV-1 reverse transcriptase inhibitors. | Journal of enzyme inhibition 19920101 |
| Activity of acyclic 6-(phenylselenenyl)pyrimidine nucleosides against human immunodeficiency viruses in primary lymphocytes. | Journal of medicinal chemistry 19911101 |
| Highly potent and selective inhibition of human immunodeficiency virus type 1 by a novel series of 6-substituted acyclouridine derivatives. | Molecular pharmacology 19910601 |
| Synthesis and anti-HIV activity of 2-, 3-, and 4-substituted analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). | Journal of medicinal chemistry 19910401 |
| Specific anti-HIV-1 'acyclonucleosides' which cannot be phosphorylated: synthesis of some deoxy analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine. | Journal of medicinal chemistry 19910401 |
| Potent and selective inhibition of human immunodeficiency virus type 1 (HIV-1) by 5-ethyl-6-phenylthiouracil derivatives through their interaction with the HIV-1 reverse transcriptase. | Proceedings of the National Academy of Sciences of the United States of America 19910315 |
| A new class of HIV-1-specific 6-substituted acyclouridine derivatives: synthesis and anti-HIV-1 activity of 5- or 6-substituted analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). | Journal of medicinal chemistry 19910101 |
| Anti-human immunodeficiency virus type 1 activities and pharmacokinetics of novel 6-substituted acyclouridine derivatives. | Antimicrobial agents and chemotherapy 19901201 |
| Highly specific inhibition of human immunodeficiency virus type 1 by a novel 6-substituted acyclouridine derivative. | Biochemical and biophysical research communications 19891229 |
| A novel lead for specific anti-HIV-1 agents: 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine. | Journal of medicinal chemistry 19891201 |
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