3-({1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}-imino)-1,3-dihydro-2H-indol-2-one

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3-({1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}-imino)-1,3-dihydro-2H-indol-2-one
• 英文别名: 3-[1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2-oxopyrimidin-4-yl]imino-1H-indol-2-one
• 化学式: C₁₆H₁₄N₄O₄S
• 分子量: 358.378
• InChiKey: CMZMQXRHSRTYBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-({1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}-imino)-1,3-dihydro-2H-indol-2-one 、 聚合甲醛 、 诺氟沙星 以 乙醇 为溶剂， 以80%的产率得到1-Ethyl-6-fluoro-7-(4-{3-[(Z)-1-(2-hydroxymethyl-[1,3]oxathiolan-5-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylimino]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis, anti-HIV and antitubercular activities of lamivudine prodrugs

  摘要：

  The synthesis of a novel series of lamivudine prodrugs involving N-4-substitution with isatin derivatives is described. The in-vitro antiretroviral activities indicated that compound 3b was found to be equipotent to lamivudine with EC50 of 0.0742 +/- 0.04 mu M. Lamivudine prodrugs bearing fluoroquinoles antibacterial showed 92-100% inhibition against Mycobacterium tuberculosis strain H(37)Rv at 6.25 pg ml(-1). At pH 7.4, 37 degrees C, the hydrolytic t(1/2) ranged between 120 and 240 min. (c) 2005 Published by Elsevier SAS.

  DOI：

  10.1016/j.ejmech.2005.07.006
• 作为产物：
  描述：

  靛红 、 lamivudine 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以84%的产率得到3-({1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}-imino)-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  Synthesis, anti-HIV and antitubercular activities of lamivudine prodrugs

  摘要：

  The synthesis of a novel series of lamivudine prodrugs involving N-4-substitution with isatin derivatives is described. The in-vitro antiretroviral activities indicated that compound 3b was found to be equipotent to lamivudine with EC50 of 0.0742 +/- 0.04 mu M. Lamivudine prodrugs bearing fluoroquinoles antibacterial showed 92-100% inhibition against Mycobacterium tuberculosis strain H(37)Rv at 6.25 pg ml(-1). At pH 7.4, 37 degrees C, the hydrolytic t(1/2) ranged between 120 and 240 min. (c) 2005 Published by Elsevier SAS.

  DOI：

  10.1016/j.ejmech.2005.07.006

文献信息

• Synthesis, anti-HIV and antitubercular activities of lamivudine prodrugs
  作者：Dharmarajan Sriram、Perumal Yogeeswari、Gayatri Gopal

  DOI：10.1016/j.ejmech.2005.07.006

  日期：2005.12

  The synthesis of a novel series of lamivudine prodrugs involving N-4-substitution with isatin derivatives is described. The in-vitro antiretroviral activities indicated that compound 3b was found to be equipotent to lamivudine with EC50 of 0.0742 +/- 0.04 mu M. Lamivudine prodrugs bearing fluoroquinoles antibacterial showed 92-100% inhibition against Mycobacterium tuberculosis strain H(37)Rv at 6.25 pg ml(-1). At pH 7.4, 37 degrees C, the hydrolytic t(1/2) ranged between 120 and 240 min. (c) 2005 Published by Elsevier SAS.