(S)-octyl (2-oxotetrahydrofuran-3-yl)carbamodithioate | 1446270-42-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-octyl (2-oxotetrahydrofuran-3-yl)carbamodithioate
• 英文别名: octyl N-[(3S)-2-oxooxolan-3-yl]carbamodithioate
• CAS: 1446270-42-3
• 化学式: C₁₃H₂₃NO₂S₂
• 分子量: 289.463
• InChiKey: QMXPVCXCHNTKSS-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二硫化碳 、 1-氯辛烷 、 (S)-α-氨基-γ-丁内酯 盐酸盐 在 sodium phosphate dodecahydrate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以76%的产率得到(S)-octyl (2-oxotetrahydrofuran-3-yl)carbamodithioate
  参考文献：
  名称：

  新型AHL类似物的设计，合成和抗菌评估

  摘要：

  设计，合成了两个系列的新型AHL类似物，并在体外细胞膜条件下评估了其抗菌活性。类似物4a – c和4g – m表现出对革兰氏阳性细菌有效的活性。尤其是类似物4l对枯草芽孢杆菌具有最强的抑制作用，MIC 50值为1.443μg/ ml。令我们惊讶的是，类似物6a – c和6g对MIC 50的革兰氏阴性菌抑制作用较弱值范围从17.589到67.840μg/ ml。这是有关含二硫酯键的AHL类似物的合成和体外抗菌评估的第一份报告。

  DOI：

  10.1016/j.bmcl.2013.05.035

文献信息

• Discovery of novel AHLs as potent antiproliferative agents
  作者：Jing-Li Ren、Xu-Yao Zhang、Bin Yu、Xi-Xin Wang、Kun-Peng Shao、Xiao-Ge Zhu、Hong-Min Liu

  DOI：10.1016/j.ejmech.2015.02.026

  日期：2015.3

  Three series of novel AHL analogs were synthesized and evaluated for their in vitro cytotoxic activity against four human cancer cell lines. The SARs investigation indicated that AHLs with a terminal phenyl group, especially those with the chalcone scaffold had remarkably enhanced cytotoxicity than those with the hydrophobic side chains. Besides, some of these compounds were much more potent than 5-Fu and natural OdDHL. Through the detailed SARs discussions, we found that compounds 10a-k and 14 with the 4-amino chalcone scaffold showed excellent inhibition against all the tested cancer cell lines and were much more potent than 5-Fu and AHLs. Such scaffold may act as a template for further lead optimization. Compound 10i with a 3, 4, 5-trimethoxy group was the most potent one against all the tested cancer cell lines. Flow cytometry analysis indicated that analog lie induced the cellular apoptosis and cell cycle arrest of MCF-7 cells at G2/M phase in a concentration-and time-dependent manner. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Design, synthesis and antibacterial evaluation of novel AHL analogues
  作者：Jing-Li Ren、En Zhang、Xian-Wei Ye、Meng-Meng Wang、Bin Yu、Wen-Hua Wang、Ya-Zhuo Guo、Hong-Min Liu

  DOI：10.1016/j.bmcl.2013.05.035

  日期：2013.7

  Two series of novel AHL analogues were designed, synthesized and evaluated for antibacterial activity under cell membrane conditions in vitro. Analogues 4a–c and 4g–m presented potent activity against Gram-positive bacteria. Especially the analogue 4l exerted the most potent inhibition against Bacillus subtilis with MIC50 value of 1.443 μg/ml. To our surprise, analogues 6a–c and 6g showed weak inhibition

  设计，合成了两个系列的新型AHL类似物，并在体外细胞膜条件下评估了其抗菌活性。类似物4a – c和4g – m表现出对革兰氏阳性细菌有效的活性。尤其是类似物4l对枯草芽孢杆菌具有最强的抑制作用，MIC 50值为1.443μg/ ml。令我们惊讶的是，类似物6a – c和6g对MIC 50的革兰氏阴性菌抑制作用较弱值范围从17.589到67.840μg/ ml。这是有关含二硫酯键的AHL类似物的合成和体外抗菌评估的第一份报告。