Synthesis and Biological Evaluation of Simplified Ansellone Analogues with Lipophilic Side Chains as HIV Latency-Reversing Agents

被引：1
|
作者：
Yanagihara, Mizushi [1 ]
Kishimoto, Naoki [2 ]
Nakahara, Kanae [1 ]
Abe, Towa [2 ]
Miura, Satoshi [2 ]
Lin, Bangzhong [1 ]
Fumimoto, Megumi [1 ]
Haruta, Junichi [1 ]
Misumi, Shogo [2 ]
Arisawa, Mitsuhiro [1 ]
Murai, Kenichi [1 ]
机构：
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
[2] Kumamoto Univ, Fac Med & Pharmaceut Sci, Dept Environm & Mol Hlth Sci, Kumamoto 8620973, Japan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2023年 / 29卷 / 44期
基金：
日本学术振兴会;
关键词：
ansellone; HIV latency-reversing agents; medicinal chemistry; natural products; oxygen heterocycles; PROTEIN-KINASE-C; NATURAL-PRODUCTS; INHIBITOR; DRUGS;
D O I：
10.1002/chem.202300677
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Structurally simplified analogues of ansellone A, in which the decalin skeleton is replaced with a lipophilic chain, were prepared and their HIV latency-reversing activities biologically evaluated. In particular, two analogues bearing ether and alkenyl side chains, respectively, showed comparable activities to that of ansellone A. Each of the simplified compounds was easily synthesized using Prins cyclisation chemistry.
引用
收藏
页数：7
相关论文
共 50 条
  • [1] Total Synthesis and Biological Evaluation of the Potent HIV Latency-Reversing Agent Ansellone A and its Analogues
    Yanagihara, Mizushi
    Murai, Kenichi
    Kishimoto, Naoki
    Abe, Towa
    Misumi, Shogo
    Arisawa, Mitsuhiro
    ORGANIC LETTERS, 2021, 23 (05) : 1720 - 1725
  • [2] Synthesis and preclinical evaluation of tigilanol tiglate analogs as latency-reversing agents for the eradication of HIV
    Gentry, Zachary O.
    Mcateer, Owen D.
    Hamad, Jennifer L.
    Moran, Jose A.
    Kim, Jocelyn T.
    Marsden, Matthew D.
    Zack, Jerome A.
    Wender, Paul A.
    SCIENCE ADVANCES, 2025, 11 (04):
  • [3] Total Syntheses of Phorbol and 11 Tigliane Diterpenoids and Their Evaluation as HIV Latency-Reversing Agents
    Watanabe, Ayumu
    Nagatomo, Masanori
    Hirose, Akira
    Hikone, Yuto
    Kishimoto, Naoki
    Miura, Satoshi
    Yasutake, Tae
    Abe, Towa
    Misumi, Shogo
    Inoue, Masayuki
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (12) : 8746 - 8756
  • [4] Structure-Activity Relationship Analysis of Benzotriazine Analogues as HIV-1 Latency-Reversing Agents
    Sorensen, Eric S.
    Macedo, Amanda B.
    Resop, Rachel S.
    Howard, J. Natalie
    Nell, Racheal
    Sarabia, Indra
    Newman, Daniel
    Ren, Yanqin
    Jones, R. Brad
    Planelles, Vicente
    Spivak, Adam M.
    Bosque, Alberto
    ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2020, 64 (08)
  • [5] Determinants of the efficacy of HIV latency-reversing agents and implications for drug and treatment design
    Ke, Ruian
    Conway, Jessica M.
    Margolis, David M.
    Perelson, Alan S.
    JCI INSIGHT, 2018, 3 (20):
  • [6] Harmine enhances the activity of the HIV-1 latency-reversing agents ingenol A and SAHA
    Taylor, Jared P.
    Armitage, Lucas H.
    Aldridge, Daniel L.
    Cash, Melanie N.
    Wallet, Mark A.
    BIOLOGY OPEN, 2020, 9 (12):
  • [7] Mechanistic differences underlying HIV latency in the gut and blood contribute to differential responses to latency-reversing agents
    Telwatte, Sushama
    Kim, Peggy
    Chen, Tsui-Hua
    Milush, Jeffrey M.
    Somsouk, Ma
    Deeks, Steven G.
    Hunt, Peter W.
    Wong, Joseph K.
    Yukl, Steven A.
    AIDS, 2020, 34 (14) : 2013 - 2024
  • [8] HIV Latency-Reversing Agents Have Diverse Effects on Natural Killer Cell Function
    Garrido, Carolina
    Spivak, Adam M.
    Soriano-Sarabia, Natalia
    Checkley, Mary Ann
    Barker, Edward
    Karn, Jonathan
    Planelles, Vicente
    Margolis, David M.
    FRONTIERS IN IMMUNOLOGY, 2016, 7
  • [9] Advances in structure-activity relationships of HDAC inhibitors as HIV latency-reversing agents
    Khatun, Samima
    Amin, Sk. Abdul
    Choudhury, Debasmita
    Chowdhury, Boby
    Jha, Tarun
    Gayen, Shovanlal
    EXPERT OPINION ON DRUG DISCOVERY, 2024, 19 (03) : 353 - 368
  • [10] Isolation, Synthesis, and Structure-Activity Relationship Study on Daphnane and Tigliane Diterpenes as HIV Latency-Reversing Agents
    El-Desoky, Ahmed H. H.
    Eguchi, Keisuke
    Kishimoto, Naoki
    Asano, Toshifumi
    Kato, Hikaru
    Hitora, Yuki
    Kotani, Shunsuke
    Nakamura, Teruya
    Tsuchiya, Soken
    Kawahara, Teppei
    Watanabe, Masato
    Wada, Mikiyo
    Nakajima, Makoto
    Watanabe, Takashi
    Misumi, Shogo
    Tsukamoto, Sachiko
    JOURNAL OF MEDICINAL CHEMISTRY, 2022, 65 (04) : 3460 - 3472
12345