2-heptylthiobenzothiazole | 15647-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-heptylthiobenzothiazole
• 英文别名: 2-heptylsulfanyl-benzothiazole；2-Heptylmercapto-benzothiazol；Benzothiazole, 2-(heptylthio)-；2-heptylsulfanyl-1,3-benzothiazole
• CAS: 15647-75-3
• 化学式: C₁₄H₁₉NS₂
• 分子量: 265.444
• InChiKey: YAPCOOZZOPRYLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-heptylthiobenzothiazole 在 sodium tungstate (VI) dihydrate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.58h， 生成 allyl 2-(benzo[d]thiazol-2-ylsulfonyl)octanoate
  参考文献：
  名称：

  Practical synthesis of β-oxo benzo[d]thiazolyl sulfones: Scope and limitations

  摘要：

  本文中，我们讨论了基于烷基苯并[d]噻唑基（BT）砜与各种亲电试剂（例如R-CO-X、RO-CO-X、RS-CO-X、Ts-X等）的重新结合，合成功能化BT砜的新方法。通过计算和竞争实验，评估了这种偶联反应的所有重要方面，包括相关和不良的副反应。本文还确立了该方法的范围和局限性。

  DOI：

  10.1039/c1ob06510f
• 作为产物：
  描述：

  2-甲硫基苯并噻唑 、 1-碘己烷 在 lithium diisopropyl amide 作用下， 生成 2-heptylthiobenzothiazole
  参考文献：
  名称：

  Katritzky, Alan R.; Aurrecoechea, Jose M.; Vazques de Miguel, Luis M., Journal of the Chemical Society. Perkin transactions I, 1987, p. 769 - 774

  摘要：

  DOI：

文献信息

• Synthesis of enol ethers from lactones using modified Julia olefination reagents: application to the preparation of tri- and tetrasubstituted exoglycals
  作者：Benjamin Bourdon、Matthieu Corbet、Patrice Fontaine、Peter G. Goekjian、David Gueyrard

  DOI：10.1016/j.tetlet.2007.11.206

  日期：2008.1

  A new route to substituted exoglycals from the corresponding lactones is described. The enol ethers synthesis via a modified Julia olefination of sugar-derived lactones is extended to substituted benzothiazolyl sulfones to furnish tri- and tetrasubstituted exoglycals.

  描述了从相应的内酯取代取代的外糖的新途径。通过对糖衍生的内酯进行改进的朱莉亚烯化反应，将烯醇醚合成扩展到取代的苯并噻唑基砜，以提供三取代和四取代的外糖。
• Practical Synthesis of β-Acyl and β-Alkoxycarbonyl Heterocyclic Sulfones
  作者：Jiří Pospíšil、Hitoshi Sato

  DOI：10.1021/jo102326p

  日期：2011.4.1

  A short and efficient synthesis for beta-acyl and beta-alkoxycarbonyl heterocyclic sulfones containing benzothiazol (BT) and phenyltetrazol (PT) heterocydic core is presented here. The method seems to be general and provides the desired C-nudeophiles in very good to excellent yields from readily available starting materials.
• Identification of Novel ROS Inducers: Quinone Derivatives Tethered to Long Hydrocarbon Chains
  作者：Yeonsun Hong、Sandip Sengupta、Wooyoung Hur、Taebo Sim

  DOI：10.1021/jm501846y

  日期：2015.5.14

  We performed the first synthesis of the 17-carbon chain-tethered quinone moiety 22 (SAN5201) of irisferin A, a natural product exhibiting anticancer activity, and its derivatives. We found that 22 is a potent ROS inducer and cytotoxic agent. Compound 25 (SAN7401), the hydroquinone form of 22, induced a significant release of intracellular ROS and apoptosis (EC50 = 1.3-2.6 mu M) in cancer cell lines, including A549 and HCT-116. Compared with the activity of a well-known ROS inducer, piperlongumine, 22 and 25 showed stronger cytotoxicity and higher selectivity over noncancerous cells. Another hydroquinone tethering 12-carbon chain, 26 (SAN4601), generated reduced levels of ROS but showed more potent cytotoxicity (EC50 = 0.8-1.6 mu M) in cancer cells, although it lacked selectivity over noncancerous cells, implying that the naturally occurring 17-carbon chain is also crucial for ROS production and a selective anticancer effect. Both 25 and 26 displayed strong, equipotent activities against vemurafenib-resistant SK-Mel2 melanoma cells and p53-deficient H1299 lung cancer cells as well, demonstrating their broad therapeutic potential as anticancer agents.
• KATRITZKY A. R.; AURRECOECHEA J. M.; VAZQUEZ DE MIGUEL L. M., J. CHEM. SOC. PERKIN TRANS.,(1987) N 4, 769-774
  作者：KATRITZKY A. R.、 AURRECOECHEA J. M.、 VAZQUEZ DE MIGUEL L. M.

  DOI：——

  日期：——