Literature DB >> 17935987

Anti-AIDS agents 73: structure-activity relationship study and asymmetric synthesis of 3-O-monomethylsuccinyl-betulinic acid derivatives.

Keduo Qian1, Kyoko Nakagawa-Goto, Donglei Yu, Susan L Morris-Natschke, Theodore J Nitz, Nicole Kilgore, Graham P Allaway, Kuo-Hsiung Lee.   

Abstract

3-O-3'(or 2')-Methylsuccinyl-betulinic acid (MSB) derivatives were separated by using recycle HPLC. The structures of four isomers were assigned by NMR and asymmetric synthesis. 3-O-3'S-Methylsuccinyl-betulinic acid (3'S-MSB, 4) exhibited potent anti-HIV activity with an EC(50) value of 0.0087microM and a TI value of 6.3x10(3), which is comparable to the data for bevirimat (DSB, PA-457), a current clinical trials drug that was also derived from betulinic acid. The anti-HIV potency of 4 was slightly better than that of AZT.

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Year:  2007        PMID： 17935987      PMCID： PMC2140232          DOI： 10.1016/j.bmcl.2007.09.081

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  15 in total

1.  The impact of initial highly active antiretroviral therapy on future treatment sequences in HIV infection.

Authors:  Marina B Klein; Patrick Willemot; Tanya Murphy; Richard G Lalonde
Journal:  AIDS       Date:  2004-09-24       Impact factor: 4.177

2.  Anti-AIDS agents 69. Moronic acid and other triterpene derivatives as novel potent anti-HIV agents.

Authors:  Donglei Yu; Yojiro Sakurai; Chin-Ho Chen; Fang-Rong Chang; Li Huang; Yoshiki Kashiwada; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2006-09-07       Impact factor: 7.446

3.  Drug interactions in patients infected with human immunodeficiency virus.

Authors:  S C Piscitelli; C Flexner; J R Minor; M A Polis; H Masur
Journal:  Clin Infect Dis       Date:  1996-10       Impact factor: 9.079

4.  Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents.

Authors:  Y Kashiwada; F Hashimoto; L M Cosentino; C H Chen; P E Garrett; K H Lee
Journal:  J Med Chem       Date:  1996-03-01       Impact factor: 7.446

5.  Rapid turnover of T lymphocytes in SIV-infected rhesus macaques.

Authors:  H Mohri; S Bonhoeffer; S Monard; A S Perelson; D D Ho
Journal:  Science       Date:  1998-02-20       Impact factor: 47.728

6.  Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids.

Authors:  T Fujioka; Y Kashiwada; R E Kilkuskie; L M Cosentino; L M Ballas; J B Jiang; W P Janzen; I S Chen; K H Lee
Journal:  J Nat Prod       Date:  1994-02       Impact factor: 4.050

7.  Anti-AIDS agents--XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives.

Authors:  F Hashimoto; Y Kashiwada; L M Cosentino; C H Chen; P E Garrett; K H Lee
Journal:  Bioorg Med Chem       Date:  1997-12       Impact factor: 3.641

8.  Declining morbidity and mortality among patients with advanced human immunodeficiency virus infection. HIV Outpatient Study Investigators.

Authors:  F J Palella; K M Delaney; A C Moorman; M O Loveless; J Fuhrer; G A Satten; D J Aschman; S D Holmberg
Journal:  N Engl J Med       Date:  1998-03-26       Impact factor: 91.245

Review 9.  Goals and milestones during treatment of HIV-1 infection with antiretroviral therapy: a pathogenesis-based perspective.

Authors:  Michael Louie; Martin Markowitz
Journal:  Antiviral Res       Date:  2002-07       Impact factor: 5.970

10.  An improved colorimetric assay for cell proliferation and viability utilizing the tetrazolium salt XTT.

Authors:  N W Roehm; G H Rodgers; S M Hatfield; A L Glasebrook
Journal:  J Immunol Methods       Date:  1991-09-13       Impact factor: 2.303
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  9 in total

Review 1.  Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.

Authors:  Kuo-Hsiung Lee
Journal:  J Nat Prod       Date:  2010-03-26       Impact factor: 4.050

Review 2.  Structure and Anti-HIV Activity of Betulinic Acid Analogues.

Authors:  Qiu-Xia Huang; Hong-Fei Chen; Xing-Rui Luo; Yin-Xiang Zhang; Xu Yao; Xing Zheng
Journal:  Curr Med Sci       Date:  2018-06-22

Review 3.  Plant-derived triterpenoids and analogues as antitumor and anti-HIV agents.

Authors:  Reen-Yen Kuo; Keduo Qian; Susan L Morris-Natschke; Kuo-Hsiung Lee
Journal:  Nat Prod Rep       Date:  2009-08-13       Impact factor: 13.423

4.  Anti-AIDS agents. 78. Design, synthesis, metabolic stability assessment, and antiviral evaluation of novel betulinic acid derivatives as potent anti-human immunodeficiency virus (HIV) agents.

Authors:  Keduo Qian; Donglei Yu; Chin-Ho Chen; Li Huang; Susan L Morris-Natschke; Theodore J Nitz; Karl Salzwedel; Mary Reddick; Graham P Allaway; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2009-05-28       Impact factor: 7.446

5.  Anti-AIDS agents 81. Design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors.

Authors:  Keduo Qian; Reen-Yun Kuo; Chin-Ho Chen; Li Huang; Susan L Morris-Natschke; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2010-04-22       Impact factor: 7.446

6.  Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents.

Authors:  Kyoko Nakagawa-Goto; Koji Yamada; Masahiko Taniguchi; Harukuni Tokuda; Kuo-Hsiung Lee
Journal:  Bioorg Med Chem Lett       Date:  2009-05-18       Impact factor: 2.823

7.  Hypericum lanceolatum (Hypericaceae) as a potential source of new anti-malarial agents: a bioassay-guided fractionation of the stem bark.

Authors:  Denis Zofou; Théodora K Kowa; Hippolyte K Wabo; Moses N Ngemenya; Pierre Tane; Vincent P K Titanji
Journal:  Malar J       Date:  2011-06-17       Impact factor: 2.979

8.  Betulinic Acid from Zizyphus Joazeiro Bark Using Focused Microwave-Assisted Extraction and Response Surface Methodology.

Authors:  Fernanda Carolina Sousa Fonseca; Letícia Caribé Batista Reis; Jener David Gonçalves Dos Santos; Carla Rodrigues Cardoso Branco; Sergio Luis da Costa Ferreira; Jorge Mauricio David; Alexsandro Branco
Journal:  Pharmacogn Mag       Date:  2017-04-18       Impact factor: 1.085

9.  Bioactive oleanane, lupane and ursane triterpene acid derivatives.

Authors:  Maria de L e Silva; Juceni P David; Lidércia C R C Silva; Rauldenis A F Santos; Jorge M David; Luciano S Lima; Pedro S Reis; Renato Fontana
Journal:  Molecules       Date:  2012-10-17       Impact factor: 4.411
  9 in total

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