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Synthesis and anti-HIV-1 activity of S-dihydro(alkyloxy)benzyloxypyrimidine derivatives

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Abstract

Several 2-heteroaryl-, 2-heteroarylcarbonylmethyl-, 2-arylcarbonylmethyl, and 2-arylethyl derivatives of S-dihydro(alkyloxy)benzyloxypyrimidines have been synthesized and the anti-HIV activities of these compounds were tested in C8166 cell and against RT enzyme. It was found that some of these compounds showed good activity against HIV-1 (EC 50 = 0.014–0.8 μM) with low toxicity (CC 50 value of 222–564 μM) and high selectivity (SI value of 278–37743). The structure-activity relationships (SAR) of these compounds have also been discussed.

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Authors and Affiliations

  1. Key Laboratory of Medicinal Chemistry for Natural Resource Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, People’s Republic of China

    Zhi-Kun Rao, Cong Li, Sui-Shuan Zhang, Mei He, Ling-Cheng Ou & Yan-Ping He

  2. Laboratory of Molecular Immunopharmacology, Key Laboratory of Animal Models and Human Disease Mechanisms, Chinese Academy of Sciences, Kunming Institute of Zoology, Kunming, People’s Republic of China

    Jing Long & Yong-Tang Zheng

Authors
  1. Zhi-Kun Rao
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  2. Jing Long
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  3. Cong Li
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  4. Sui-Shuan Zhang
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  5. Mei He
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  6. Ling-Cheng Ou
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  7. Yong-Tang Zheng
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  8. Yan-Ping He
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Corresponding authors

Correspondence to Yong-Tang Zheng or Yan-Ping He.

Additional information

First two authors contributed equally to this work

Correspondence: Yan-Ping He, Key Laboratory of Medicinal Chemistry for Natural Resource Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People’s Republic of China; Yong-Tang Zheng, Laboratory of Molecular Immunopharmacology, Key Laboratory of Animal Models and Human Disease Mechanisms, Chinese Academy of Sciences, Kunming Institute of Zoology, Kunming, Yunnan 650223, People’s Republic of China.

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Rao, ZK., Long, J., Li, C. et al. Synthesis and anti-HIV-1 activity of S-dihydro(alkyloxy)benzyloxypyrimidine derivatives. Monatsh Chem 139, 967–974 (2008). https://doi.org/10.1007/s00706-007-0834-8

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  • DOI: https://doi.org/10.1007/s00706-007-0834-8

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