메뉴 건너뛰기




Volumn 40, Issue 26, 1997, Pages 4257-4264

A 3D QSAR study of a series of HEPT analogues: The influence of conformational mobility on HIV-1 reverse transcriptase inhibition

Author keywords

[No Author keywords available]

Indexed keywords

1 [(2 HYDROXYETHOXY)METHYL] 6 (PHENYLTHIO)THYMINE; CHLORPHENOTANE; DIDANOSINE; EMIVIRINE; LAMIVUDINE; NEVIRAPINE; PYRIDONE DERIVATIVE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; TNK 651; UNCLASSIFIED DRUG; ZIDOVUDINE;

EID: 0031449527     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970110p     Document Type: Article
Times cited : (71)

References (24)
  • 1
    • 0027447133 scopus 로고
    • HIV-1 specifie RT inhibitors: Highly selective inhibitors of human immunodeficiency virus type 1 that are specifically targeted at the viral reverse transcriptase
    • De Clercq, E. HIV-1 specifie RT inhibitors: Highly selective inhibitors of human immunodeficiency virus type 1 that are specifically targeted at the viral reverse transcriptase. Med. Res. Rev. 1993, 13, 229-258.
    • (1993) Med. Res. Rev. , vol.13 , pp. 229-258
    • De Clercq, E.1
  • 2
    • 0000804347 scopus 로고
    • Competitive inhibitors of human immunodeficiency virus reverse transcriptase
    • Schinazi, R. F. Competitive inhibitors of human immunodeficiency virus reverse transcriptase. Perspect. Drug Disc. Des. 1993, 1, 151-180.
    • (1993) Perspect. Drug Disc. Des. , vol.1 , pp. 151-180
    • Schinazi, R.F.1
  • 3
    • 34250073329 scopus 로고
    • Nonnucleoside inhibitors of HIV-1 reverse transcriptase
    • Young, S. D. Nonnucleoside inhibitors of HIV-1 reverse transcriptase. Perspect. Drug Disc. Des. 1993, 1, 181-192.
    • (1993) Perspect. Drug Disc. Des. , vol.1 , pp. 181-192
    • Young, S.D.1
  • 4
    • 0028120730 scopus 로고
    • HIV resistance to reverse transcriptase inhibitors
    • De Clercq, E. HIV resistance to reverse transcriptase inhibitors. Biochem. Pharmacol. 1994, 47, 155-169.
    • (1994) Biochem. Pharmacol. , vol.47 , pp. 155-169
    • De Clercq, E.1
  • 5
    • 0027991415 scopus 로고
    • Combination Therapy: More Effective Control of HIV Type 1?
    • Jonson, V. A. Combination Therapy: More Effective Control of HIV Type 1? AIDS Res. Human Retrovir. 1994, 10, 907-912.
    • (1994) AIDS Res. Human Retrovir , vol.10 , pp. 907-912
    • Jonson, V.A.1
  • 7
    • 0027381149 scopus 로고
    • Human Immunodeficiency Virus Type 1 Drug-Resistance Patterns with Different l-[(2-Hydroxyethoxy)methyl]-6-phenylthiothymine Derivatives
    • Balzarini, J.; Karlsson, A.; De Clercq, E. Human Immunodeficiency Virus Type 1 Drug-Resistance Patterns with Different l-[(2-Hydroxyethoxy)methyl]-6-phenylthio)thymine Derivatives Mol. Pharmacol. 1993, 44, 694-701.
    • (1993) Mol. Pharmacol. , vol.44 , pp. 694-701
    • Balzarini, J.1    Karlsson, A.2    De Clercq, E.3
  • 8
    • 0028925773 scopus 로고
    • Mechanism of Inhibition of HIV-1 Reverse Transcriptase by Nonnucleoside Inhibitors
    • Spence, R. A.; Kati, W. M.; Anderson, K. S.; Johnson, K. A. Mechanism of Inhibition of HIV-1 Reverse Transcriptase by Nonnucleoside Inhibitors. Science 1995, 267, 988-993.
    • (1995) Science , vol.267 , pp. 988-993
    • Spence, R.A.1    Kati, W.M.2    Anderson, K.S.3    Johnson, K.A.4
  • 9
    • 6844222892 scopus 로고
    • Chapter 1. Introduction
    • van de Waterbeemd, H., Ed; VCH: Weinheim
    • van de Waterbeemd, H. Chapter 1. Introduction. In Chemometric Methods in Drug Design; van de Waterbeemd, H., Ed; VCH: Weinheim, 1995; pp 1-14.
    • (1995) Chemometric Methods in Drug Design , pp. 1-14
    • Van de Waterbeemd, H.1
  • 10
    • 0029096567 scopus 로고
    • 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
    • Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Inouye, N.; Baba, M.; Shigeta, Sh.; Walker, R. T.; De Clercq, E.; Miyasaka, T. 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. J. Med. Chem. 1995, 38, 2860-2865.
    • (1995) J. Med. Chem. , vol.38 , pp. 2860-2865
    • Tanaka, H.1    Takashima, H.2    Ubasawa, M.3    Sekiya, K.4    Inouye, N.5    Baba, M.6    Shigeta, Sh.7    Walker, R.T.8    De Clercq, E.9    Miyasaka, T.10
  • 11
    • 0029976422 scopus 로고    scopus 로고
    • Complexes of HIV-1 Reverse Transcriptase with Inhibitors of the HEPT Series Reveal Conformational Changes Relevant to the Design of Potent Nonnucleoside Inhibitors
    • Hopkins, A. L.; Ren, J.; Esnouf, R. M.; Willcox, B. E.; Jones, E. Y.; Ross, C.; Miyasaka, T.; Walker, R. T.; Tanaka, H.; Stammers, D. K.; Stuart, D. I. Complexes of HIV-1 Reverse Transcriptase with Inhibitors of the HEPT Series Reveal Conformational Changes Relevant to the Design of Potent Nonnucleoside Inhibitors. J. Med. Chem. 1996, 39, 1589-1600.
    • (1996) J. Med. Chem. , vol.39 , pp. 1589-1600
    • Hopkins, A.L.1    Ren, J.2    Esnouf, R.M.3    Willcox, B.E.4    Jones, E.Y.5    Ross, C.6    Miyasaka, T.7    Walker, R.T.8    Tanaka, H.9    Stammers, D.K.10    Stuart, D.I.11
  • 12
    • 0030994577 scopus 로고    scopus 로고
    • Synthesis and Anti-HIV Activity of Novel N-l Side Chain Modified Analogs of 1-[(2-Hydroethoxy)methyll-6-phenylthiothymine (HEPT)
    • Pontikis, H.; Benhida, R.; Aubertin, A,-M.; Grierson, D. S.; Monneret, C. Synthesis and Anti-HIV Activity of Novel N-l Side Chain Modified Analogs of 1-[(2-Hydroethoxy)methyll-6-phenylthio)thymine (HEPT). J. Med. Chem. 1997, 40, 1845-1854.
    • (1997) J. Med. Chem. , vol.40 , pp. 1845-1854
    • Pontikis, H.1    Benhida, R.2    Aubertin, A.-M.3    Grierson, D.S.4    Monneret, C.5
  • 13
    • 0027094782 scopus 로고
    • Synthesis and antiviral activity of Deoxy Analogs of 1-[2-Hydroxyethoxymethyl]-6-(phenylthio)thymine (HEPT) as Potent and Selective Anti-HIV-1 Agents
    • Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Nitta, I.; Baba, M.; Shigeta, Sh.; Walker, R. T.; De Clercq, E.; Miyasaka, T. Synthesis and antiviral activity of Deoxy Analogs of 1-[2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as Potent and Selective Anti-HIV-1 Agents. J. Med. Chem. 1992, 35, 4713-4719.
    • (1992) J. Med. Chem. , vol.35 , pp. 4713-4719
    • Tanaka, H.1    Takashima, H.2    Ubasawa, M.3    Sekiya, K.4    Nitta, I.5    Baba, M.6    Shigeta, Sh.7    Walker, R.T.8    De Clercq, E.9    Miyasaka, T.10
  • 14
    • 0026071537 scopus 로고
    • A New Class of HIV-1 Specific 6-Substituted Acyclouridine Derivatives: Syn thesis and Anti-HIV-1 Activity of 5- Or 6-Substituted Analogic of 1-[2-Hydroxyethoxymethyl]-6-(phenylthio)thymine (HEPT)
    • Tanaka, H.; Baba, M.; Hayakawa, H.; Sakamaki, T.; Miyasaka, T.; Ubasawa, M.; Takashima, H.; Sekiya, K.; Nitta, I.; Shigeta, Sh.; Walker, R. T.; Balzarini, J.; De Clercq, E. A New Class of HIV-1 Specific 6-Substituted Acyclouridine Derivatives: Syn thesis and Anti-HIV-1 Activity of 5- or 6-Substituted Analogic of 1-[2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). J. Med. Chem. 1991, 34, 349-357.
    • (1991) J. Med. Chem. , vol.34 , pp. 349-357
    • Tanaka, H.1    Baba, M.2    Hayakawa, H.3    Sakamaki, T.4    Miyasaka, T.5    Ubasawa, M.6    Takashima, H.7    Sekiya, K.8    Nitta, I.9    Shigeta, Sh.10    Walker, R.T.11    Balzarini, J.12    De Clercq, E.13
  • 15
    • 0026543676 scopus 로고
    • Structure-Activity Relationships of 1-[2-Hydroxyethoxymethyl]-6-(phenylthio)thymine Analogues: Effect of Substitutions at the C-6 Phenyl Ring and at the C-5 Position on AntiHIV-1 Activity
    • Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Nitta, I.; Baba, M.; Shigeta, Sh.; Walker, R. T.; De Clercq, E.; Miyasaka, T. 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 AntiHIV-1 Activity. J. Med. Chem. 1992, 35, 337-345.
    • (1992) J. Med. Chem. , vol.35 , pp. 337-345
    • Tanaka, H.1    Takashima, H.2    Ubasawa, M.3    Sekiya, K.4    Nitta, I.5    Baba, M.6    Shigeta, Sh.7    Walker, R.T.8    De Clercq, E.9    Miyasaka, T.10
  • 16
    • 84988115618 scopus 로고
    • Validation of the general purpose Tripos 5.2 force field
    • Clare, M.; Cramer, R. D. III; Opdenbosch, N. V. Validation of the general purpose Tripos 5.2 force field. J. Comput. Chem. 1989, 10, 982-1012.
    • (1989) J. Comput. Chem. , vol.10 , pp. 982-1012
    • Clare, M.1    Cramer III, R.D.2    Opdenbosch, N.V.3
  • 19
    • 0018709674 scopus 로고
    • Chance Factors in Studies of Quantitative Structure-Activity Relationships
    • Topliss, J. G.; Edwards, R. P. Chance Factors in Studies of Quantitative Structure-Activity Relationships. J. Med. Chem. 1979, 22, 1238-1244.
    • (1979) J. Med. Chem. , vol.22 , pp. 1238-1244
    • Topliss, J.G.1    Edwards, R.P.2
  • 21
    • 84987100711 scopus 로고
    • Crossvalidation, Bootstrapping, and Partial Least Squares Compared with Multiple Regression in Conventional QSAR Studies
    • Cramer, R. D.; Bunce, J. D.; Patterson, D. E.; Frank, I. E. Crossvalidation, Bootstrapping, and Partial Least Squares Compared with Multiple Regression in Conventional QSAR Studies Quantum Struct.-Act. Relat. 1988, 7, 18-25.
    • (1988) Quantum Struct.-Act. Relat , vol.7 , pp. 18-25
    • Cramer, R.D.1    Bunce, J.D.2    Patterson, D.E.3    Frank, I.E.4
  • 22
    • 0002100415 scopus 로고
    • How to Choose the Proper Statisticafe Method
    • Section 5.2.6 Conclusions. van de Waterbeemd, H., Ed; VCH: Weinheim
    • Clementi, S.; Wold, S. How to Choose the Proper Statisticafe Method. Section 5.2.6 Conclusions. In Chemometric Methods in Drug Design; van de Waterbeemd, H., Ed; VCH: Weinheim, 1995; pp 319-338.
    • (1995) Chemometric Methods in Drug Design , pp. 319-338
    • Clementi, S.1    Wold, S.2
  • 23
    • 0041076424 scopus 로고
    • Chapter 3. Experimental Design
    • van de Waterbeemd, H., Ed; VCH: Weinheim
    • Austel, V. Chapter 3. Experimental Design. In Chemometric Methods in Drug Design; van de Waterbeemd, H., Ed; VCH: Weinheim, 1995; pp 49-62.
    • (1995) Chemometric Methods in Drug Design , pp. 49-62
    • Austel, V.1
  • 24
    • 0023751431 scopus 로고
    • Comparative Molecular Field Analysis (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins
    • Cramer, R. D. III; Patterson, D. E.; Bunce, J. D. Comparative Molecular Field Analysis (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins. J. Am.Chem. Soc. 1988, 110, 5959-5967.
    • (1988) J. Am.Chem. Soc. , vol.110 , pp. 5959-5967
    • Cramer III, R.D.1    Patterson, D.E.2    Bunce, J.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.