메뉴 건너뛰기




Volumn 41, Issue 23, 1998, Pages 4648-4657

Anti-AIDS agents. 34. Synthesis and structure-activity relationships of betulin derivatives as anti-HIV agents

Author keywords

[No Author keywords available]

Indexed keywords

3,28 DI O (3',3' DIMETHYLGLUTARYL)BETULIN; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; BETULIC ACID; BETULIN DERIVATIVE; ENFUVIRTIDE; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG; ZIDOVUDINE;

EID: 0032487840     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980391g     Document Type: Article
Times cited : (151)

References (31)
  • 1
    • 0032544137 scopus 로고    scopus 로고
    • Anti-AIDS Agents. 33. Synthesis and Anti-HIV Activity of Monomethyl Substituted 3′,4′-Di-O-(-)-Camphanoyl-(+)-cis-Khellactone (DCK) Analogues
    • Xie, L.; Takeuchi, Y.; Cosentino, L. M.; Lee, K, H. Anti-AIDS Agents. 33. Synthesis and Anti-HIV Activity of Monomethyl Substituted 3′,4′-Di-O-(-)-Camphanoyl-(+)-cis-Khellactone (DCK) Analogues. Bioorg. Med. Chem. Lett. 1998, 8, 2151-2156.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 2151-2156
    • Xie, L.1    Takeuchi, Y.2    Cosentino, L.M.3    Lee, K.H.4
  • 2
    • 0028952146 scopus 로고
    • HIV Population Dynamics in vivo: Implications for Genetic Variation, Pathogenesis, and Therapy
    • Coffin, J. M. HIV Population Dynamics in vivo: Implications for Genetic Variation, Pathogenesis, and Therapy. Science 1995, 267, 483-489.
    • (1995) Science , vol.267 , pp. 483-489
    • Coffin, J.M.1
  • 7
    • 0028218592 scopus 로고
    • Pentacyclic Triterpenes Derived from Maprounea africana are Potent Inhibitors of HIV-1 Reverse Transcriptase
    • Pengsuparp, T.; Cai, L.; Fong, H. H. S.; Kinghorn, A. D.; Pezzuto, J. M.; Wani, M.; Wall, M. E. Pentacyclic Triterpenes Derived from Maprounea africana are Potent Inhibitors of HIV-1 Reverse Transcriptase. J. Nat. Prod. 1994, 57, 415-418.
    • (1994) J. Nat. Prod. , vol.57 , pp. 415-418
    • Pengsuparp, T.1    Cai, L.2    Fong, H.H.S.3    Kinghorn, A.D.4    Pezzuto, J.M.5    Wani, M.6    Wall, M.E.7
  • 8
    • 0029839826 scopus 로고    scopus 로고
    • Anti-HIV Triterpene Acids from Geum japonicum
    • Xu, H. X.; Zeng, F. Q.; Wan, M.; Sim, K. Y. Anti-HIV Triterpene Acids from Geum japonicum. J. Nat. Prod. 1996, 59, 643-645.
    • (1996) J. Nat. Prod. , vol.59 , pp. 643-645
    • Xu, H.X.1    Zeng, F.Q.2    Wan, M.3    Sim, K.Y.4
  • 9
    • 0023120973 scopus 로고
    • Inhibitory Effect of Glycyrrhizin on the in vitro Infectivity and Cytopathic Activity of the Human Immunodeficiency Virus
    • Ito, M.; Nakashima, H.; Baba, M.; Pauwels, R.; DeClercq, E.; Shigeta, A.; Yamamoto, N. Inhibitory Effect of Glycyrrhizin on the in vitro Infectivity and Cytopathic Activity of the Human Immunodeficiency Virus. Antiviral Res. 1987, 7, 127-137.
    • (1987) Antiviral Res. , vol.7 , pp. 127-137
    • Ito, M.1    Nakashima, H.2    Baba, M.3    Pauwels, R.4    Declercq, E.5    Shigeta, A.6    Yamamoto, N.7
  • 10
    • 0023183914 scopus 로고
    • A New Anti-human Immunodeficiency Virus Substance, Glycyrrhizin Sulfate; Endowment of Glycyrrhizin with Reverse Transcriptase Inhibitory Activity by Chemical Modification
    • Nakashima, H.; Matsui, T.; Yoshida, O.; Isowa, Y.; Kido, Y.; Motoki, Y.; Ito, M.; Shigeta, S.; Mori, T.; Yamamoto, N. A New Anti-human Immunodeficiency Virus Substance, Glycyrrhizin Sulfate; Endowment of Glycyrrhizin with Reverse Transcriptase Inhibitory Activity by Chemical Modification. Jpn J. Cancer Res. 1987, 78, 767-771.
    • (1987) Jpn J. Cancer Res. , vol.78 , pp. 767-771
    • Nakashima, H.1    Matsui, T.2    Yoshida, O.3    Isowa, Y.4    Kido, Y.5    Motoki, Y.6    Ito, M.7    Shigeta, S.8    Mori, T.9    Yamamoto, N.10
  • 14
    • 0028176540 scopus 로고
    • Anti-AIDS Agents, 11. Betulinic Acid and Platanic Acid as Anti-HIV Principles from Syzygium claviflorum, and the Anti-HIV Activity of Structurally Related Triterpenoids
    • Fujioka, T.; Kashiwada, Y.; Kilkuskie, R. E.; Cosentino, L. M.; Ballas, L. M.; Jiang, J. B.; Janzen, W. P.; Chen, I. S.; Lee, K. H. Anti-AIDS Agents, 11. Betulinic Acid and Platanic Acid as Anti-HIV Principles from Syzygium claviflorum, and the Anti-HIV Activity of Structurally Related Triterpenoids. J. Nat. Prod. 1994, 57, 243-247.
    • (1994) J. Nat. Prod. , vol.57 , pp. 243-247
    • Fujioka, T.1    Kashiwada, Y.2    Kilkuskie, R.E.3    Cosentino, L.M.4    Ballas, L.M.5    Jiang, J.B.6    Janzen, W.P.7    Chen, I.S.8    Lee, K.H.9
  • 16
    • 0031467377 scopus 로고    scopus 로고
    • Anti-AIDS Agents, 26. Synthesis and Anti-HIV Activity of Betulinic Acid and Dihydrobetulinic Acid Derivatives
    • Hashimoto, F.; Kashiwada, Y.; Cosentino, L. M.; Chen, C. H.; Garrett, P. E.; Lee, K. H. Anti-AIDS Agents, 26. Synthesis and Anti-HIV Activity of Betulinic Acid and Dihydrobetulinic Acid Derivatives. Bioorg. Med. Chem. 1997, 5, 2133-2143.
    • (1997) Bioorg. Med. Chem. , vol.5 , pp. 2133-2143
    • Hashimoto, F.1    Kashiwada, Y.2    Cosentino, L.M.3    Chen, C.H.4    Garrett, P.E.5    Lee, K.H.6
  • 19
    • 84920311036 scopus 로고    scopus 로고
    • note
    • According to the Aldrich catalog 1997-1998, 500 mg of betulin and betulinic acid costs $15.54 and $108.05 USD, respectively. Betulin is 7 times cheaper than that of betulinic acid.
  • 20
    • 0030062263 scopus 로고    scopus 로고
    • Selective Inhibition of Cyclic AMP-dependent Protein Kinase by Amphiphilic Triterpenoids and Related Compounds
    • Wang, B. H.; Polya, G. M. Selective Inhibition of Cyclic AMP-dependent Protein Kinase by Amphiphilic Triterpenoids and Related Compounds. Phytochemistry 1996, 41, 55-63.
    • (1996) Phytochemistry , vol.41 , pp. 55-63
    • Wang, B.H.1    Polya, G.M.2
  • 21
    • 0028836953 scopus 로고
    • Investigations on the Steroidal Anti-inflammatory Activity of Triterpenoids from Diospyros leucomelas
    • Recio, M. C.; Giner, R. M.; Manez, S.; Gueho, J.; Julien, H. R.; Hostemann, K.; Rios, J. L. Investigations on the Steroidal Anti-inflammatory Activity of Triterpenoids from Diospyros leucomelas. Planta Med. 1995, 61, 9-12.
    • (1995) Planta Med. , vol.61 , pp. 9-12
    • Recio, M.C.1    Giner, R.M.2    Manez, S.3    Gueho, J.4    Julien, H.R.5    Hostemann, K.6    Rios, J.L.7
  • 22
    • 0032546509 scopus 로고    scopus 로고
    • Anti-AIDS Agents. 32. Synthesis and Anti-HIV Activity of Betulin Derivatives
    • Sun, I. C.; Shen, J. K.; Wang, H. K.; Cosentino, L. M.; Lee, K. H. Anti-AIDS Agents. 32. Synthesis and Anti-HIV Activity of Betulin Derivatives. Bioorg. Med. Chem. Lett. 1998, 8, 1267-1272.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1267-1272
    • Sun, I.C.1    Shen, J.K.2    Wang, H.K.3    Cosentino, L.M.4    Lee, K.H.5
  • 24
    • 49549138922 scopus 로고
    • Pyridinium chlorochrornate. An Efficient Reagent for Oxidation of Primary and Secondary Alcohols to Carbonyl Compounds
    • Corey, E. J.; Suggs, J. W. Pyridinium chlorochrornate. An Efficient Reagent for Oxidation of Primary and Secondary Alcohols to Carbonyl Compounds. Tetra. Lett. 1975, 31, 2647-2650.
    • (1975) Tetra. Lett. , vol.31 , pp. 2647-2650
    • Corey, E.J.1    Suggs, J.W.2
  • 25
    • 0029794699 scopus 로고    scopus 로고
    • Synthesis of (2R)-1-(4-Chloro-2-pyridyl)-2-(2-pyridyl)ethylamine : A Selective Oxime Reduction and Crystallization-induced Asymmetric Transformation
    • Negi, S.; Matsukura, M.; Mizuno, M.; Miyake, K.; Minami, N. Synthesis of (2R)-1-(4-Chloro-2-pyridyl)-2-(2-pyridyl)ethylamine : A Selective Oxime Reduction and Crystallization-induced Asymmetric Transformation. Synthesis 1996, 991-996.
    • (1996) Synthesis , pp. 991-996
    • Negi, S.1    Matsukura, M.2    Mizuno, M.3    Miyake, K.4    Minami, N.5
  • 26
    • 0000014676 scopus 로고
    • A Mild Single-step Reduction of Oximes to Amines
    • Leeds, J. P.; Kirst, H. A. A Mild Single-step Reduction of Oximes to Amines. Synth. Commun. 1988, 18, 777-782.
    • (1988) Synth. Commun. , vol.18 , pp. 777-782
    • Leeds, J.P.1    Kirst, H.A.2
  • 27
    • 0028863269 scopus 로고
    • 15β-Hydroxysteroids (part IV). Steroids of the Human Perinatal Period: The Synthesis of 3α, 15β, 17α-Trihydroxy-5α-pregnan-20-one and Its A/B-ring Conflgurational Isomers
    • Reeder, A. Y.; Joannou, G. E. 15β-Hydroxysteroids (part IV). Steroids of the Human Perinatal Period: the Synthesis of 3α, 15β, 17α-Trihydroxy-5α-pregnan-20-one and Its A/B-ring Conflgurational Isomers. Steroids 1995, 60, 796-801.
    • (1995) Steroids , vol.60 , pp. 796-801
    • Reeder, A.Y.1    Joannou, G.E.2
  • 28
    • 0002914673 scopus 로고
    • Steroids. IX. Facile Inversion of Unhindered Sterol Configuration
    • Bose, A. K.; Lal, B.; Huffman III, R. A.; Manhas, M. S. Steroids. IX. Facile Inversion of Unhindered Sterol Configuration. Tetrahedron Lett. 1973, 18, 1619-1622.
    • (1973) Tetrahedron Lett. , vol.18 , pp. 1619-1622
    • Bose, A.K.1    Lal, B.2    Huffman III, R.A.3    Manhas, M.S.4
  • 29
    • 0027959493 scopus 로고
    • Peptides Corresponding to a Predictive α-Helical Domain of Human Immunodeficiency Virus Type 1 gp41 Are Potent Inhibitors of Virus Infection
    • Wild, C. T.; Shugars, D. C.; Greenwell, T. K.; McDanal, C. B.; Matthews, T. J. Peptides Corresponding to a Predictive α-Helical Domain of Human Immunodeficiency Virus Type 1 gp41 Are Potent Inhibitors of Virus Infection. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 9770-9774.
    • (1994) Proc. Natl. Acad. Sci. U.S.A. , vol.91 , pp. 9770-9774
    • Wild, C.T.1    Shugars, D.C.2    Greenwell, T.K.3    McDanal, C.B.4    Matthews, T.J.5
  • 30
    • 0345016834 scopus 로고
    • Interaction between the Human T-cell Lymphotropic Viurs Type III Envelope Glycoprotein gp120 and the Surface Antigen CD4: Role of Carbohydrate in Binding and Cell Fusion
    • Mathews, T. J.; Weinhold, K. J.; Lyerly, H. K.; Langlois, A. J.; Wigzell, H.; Bolognesi, D. P. Interaction Between the Human T-cell Lymphotropic Viurs Type III Envelope Glycoprotein gp120 and the Surface Antigen CD4: Role of Carbohydrate in Binding and Cell Fusion. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 5424-5428.
    • (1987) Proc. Natl. Acad. Sci. U.S.A. , vol.84 , pp. 5424-5428
    • Mathews, T.J.1    Weinhold, K.J.2    Lyerly, H.K.3    Langlois, A.J.4    Wigzell, H.5    Bolognesi, D.P.6
  • 31
    • 0026562720 scopus 로고
    • Detection of Replication Competent and Pseudotyped Human Immunodeficiency Virus with a Sensitive Cell Line on the Basis of Activation of an Integrated β-Galactosidase Gene
    • Kimpton, J.; Emerman, M. Detection of Replication Competent and Pseudotyped Human Immunodeficiency Virus with a Sensitive Cell Line on the Basis of Activation of an Integrated β-Galactosidase Gene. J. Viol. 1992, 66, 2232-2239.
    • (1992) J. Viol. , vol.66 , pp. 2232-2239
    • Kimpton, J.1    Emerman, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.