2-(heptylsulfonyl)benzo[d]thiazole | 17271-37-3

• 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-(heptylsulfonyl)benzo[d]thiazole
• 英文别名: 2-(heptane-1-sulfonyl)-benzothiazole；2-Heptylsulfonyl-1,3-benzothiazole
• CAS: 17271-37-3
• 化学式: C₁₄H₁₉NO₂S₂
• 分子量: 297.442
• InChiKey: IVYWVXKOORBZAD-UHFFFAOYSA-N

物化性质

• 熔点：
  39-40 °C
• 沸点：
  432.2±28.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 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：
  83.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(heptylsulfonyl)benzo[d]thiazole 在 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 乙硫醇 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Identification of Novel ROS Inducers: Quinone Derivatives Tethered to Long Hydrocarbon Chains

  摘要：

  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.

  DOI：

  10.1021/jm501846y
• 作为产物：
  描述：

  2-heptylthiobenzothiazole 在 ammonium heptamolybdate 、 双氧水 作用下， 以 乙醇 为溶剂， 生成 2-(heptylsulfonyl)benzo[d]thiazole
  参考文献：
  名称：

  使用改良的Julia烯化剂从内酯合成烯醇醚：在制备三取代和四取代的外糖中的应用

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2007.11.206

文献信息

• Practical synthesis of β-oxo benzo[d]thiazolyl sulfones: Scope and limitations
  作者：Jiří Pospíšil、Raphaël Robiette、Hitoshi Sato、Kevin Debrus

  DOI：10.1039/c1ob06510f

  日期：——

  In this paper, we discuss our new synthetic approach towards functionalized benzo[d]thiazolyl (BT) sulfones, based on the reunion of alkyl BT sulfones and various electrophiles (e.g. R–CO–X, RO–CO–X, RS–CO–X, Ts–X…). All important aspects of this coupling reaction, including relevant and undesirable side reactions, are evaluated by means of calculations and competitive experiments. The scope and limitations of this method are established.

  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。
• 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.