3-(4-phenylphenacyl)benzothiazolium bromide | 7469-60-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-phenylphenacyl)benzothiazolium bromide
• 英文别名: 3-[2-([1,1'-Biphenyl]-4-yl)-2-oxoethyl]-1,3-benzothiazol-3-ium bromide；2-(1,3-benzothiazol-3-ium-3-yl)-1-(4-phenylphenyl)ethanone;bromide
• CAS: 7469-60-5
• 化学式: Br*C₂₁H₁₆NOS
• 分子量: 410.334
• InChiKey: AOAZNBDEHXTMBP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-phenylphenacyl)benzothiazolium bromide 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 以74%的产率得到2-([1,1'-biphenyl]-4-carbonyl)benzo[d]thiazole-3(2H)-carbaldehyde
  参考文献：
  名称：

  的合成Ñ从甲酰基2-苯甲酰Benzothiazolines，2-取代的苯并噻唑，和对称二硫化物Ñ -Phenacylbenzothiazolium溴化物

  摘要：

  通过用有机碱和无机碱处理，N-苯甲酰基苯并噻唑鎓溴化物已发展出一种不寻常的好氧水解-级联反应。在温和的反应条件下，以中等至良好的产率获得了相应的N-甲酰基-2-苯甲酰基苯并噻唑啉和2-取代的苯并噻唑产物。另外，当酮基被酯取代时，形成对称的二硫键。反应的范围是相当宽的耐受性芳基，杂芳基和烷基。

  DOI：

  10.1021/acs.orglett.9b01990
• 作为产物：
  描述：

  苯并噻唑 、 2-溴-4-苯基乙酰苯 以 乙醇 为溶剂， 生成 3-(4-phenylphenacyl)benzothiazolium bromide
  参考文献：
  名称：

  有机催化对映和非对映选择性形式多米诺 1,3-偶极环加成/重排：手性吡咯并噻嗪-2-甲醛的合成

  摘要：

  通过苯并噻唑鎓盐和α,β-不饱和醛的正式1,3-偶极环加成/重排反应，实现了手性吡咯并[1,2- d ][1,4]噻嗪-2-甲醛的有效合成方法，利用不对称有机催化剂。该过程导致形成荧光、高度对映体富集的手性分子，具有三个连续的立体中心，其中一个是手性四元中心，具有优异的产率以及对映体和非对映体选择性。计算研究证明了对反应机理的理解。该方案的合成实用性已成功用于克级合成。荧光和计算机研究显示了本方法的应用。

  DOI：

  10.1021/acs.orglett.4c00544

文献信息

• Evaluation of two novel antioxidants with differential effects on curcumin-induced apoptosis in C2 skeletal myoblasts; involvement of JNKs
  作者：Maria Peleli、Ioanna-Katerina Aggeli、Alexios N. Matralis、Angeliki P. Kourounakis、Isidoros Beis、Catherine Gaitanaki

  DOI：10.1016/j.bmc.2014.12.046

  日期：2015.2

  Excessive levels of reactive oxygen species (ROS) result in numerous pathologies including muscle disorders. In essence, skeletal muscle performance of daily activities can be severely affected by the redox imbalances occurring after muscular injuries, surgery, atrophy due to immobilization, dystrophy or eccentric muscle contraction. Therefore, research on the potential beneficial impact of antioxidants is of outmost importance. In this context, aiming at further exploring the mechanisms of action of our newly synthesized antioxidant compounds (AK1 and AK2) in a skeletal muscle experimental setting, we initially investigated their scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) and subsequently assessed their effect on the viability of C2 skeletal myoblasts in the presence of two pro-oxidants: H2O2 and curcumin (MTT assay). Interestingly, while both compounds reversed the detrimental effect of H2O2, only AK2 was cytoprotective in curcumin-treated C2 cells. We next confirmed the immediate activation of extracellular signal-regulated kinases (ERKs) and the more delayed activation profile of c-Jun NH2-terminal kinases (JNKs) in C2 skeletal myoblasts exposed to curcumin, by Western blotting. In correlation with the aforementioned results, only AK2 blocked the curcumin-induced activation of JNKs pathway. Furthermore, JNKs were revealed to mediate curcumin-induced apoptosis in C2 cells and only AK2 to effectively suppress it (by detecting its effect on poly(ADP-ribose) polymerase fragmentation). Overall, we have shown that two similar in structure novel antioxidants confer differential effects on C2 skeletal myoblasts viability under oxidative stress conditions. This result may be attributed to these antioxidants respective diverse mode of interaction with the signaling effectors involved in the observed responses. Future studies should further evaluate the mechanism of action of these compounds in order to support their potential application in therapeutic protocols against ROS-related muscle disorders. (C) 2015 Published by Elsevier Ltd.
• Synthesis of <i>N</i>-Formyl-2-benzoyl Benzothiazolines, 2-Substituted Benzothiazoles, and Symmetrical Disulfides from <i>N</i>-Phenacylbenzothiazolium Bromides
  作者：Subas Chandra Sahoo、Subhas Chandra Pan

  DOI：10.1021/acs.orglett.9b01990

  日期：2019.8.16

  An unusual aerobic hydrolysis-cascade reaction has been developed with N-phenacylbenzothiazolium bromides by treatment with organic and inorganic base. The corresponding N-formyl-2-benzoyl benzothiazoline and 2-substituted benzothiazole products were obtained in moderate to good yields under mild reaction conditions. Also, symmetrical disulfide was formed when keto group was replaced with ester. The

  通过用有机碱和无机碱处理，N-苯甲酰基苯并噻唑鎓溴化物已发展出一种不寻常的好氧水解-级联反应。在温和的反应条件下，以中等至良好的产率获得了相应的N-甲酰基-2-苯甲酰基苯并噻唑啉和2-取代的苯并噻唑产物。另外，当酮基被酯取代时，形成对称的二硫键。反应的范围是相当宽的耐受性芳基，杂芳基和烷基。
• Organocatalyzed Enantio- and Diastereoselective Formal Domino 1,3-Dipolar Cycloaddition/Rearrangement: Synthesis of Chiral Pyrrolo-thiazine-2-carbaldehydes
  作者：Solai Pandidurai、Venkata Surya Kumar Choutipalli、Venkatesan Subramanian、Govindasamy Sekar

  DOI：10.1021/acs.orglett.4c00544

  日期：2024.4.19

  the synthesis of chiral pyrrolo[1,2-d][1,4]thiazine-2-carbaldehydes is achieved via formal 1,3-dipolar cycloaddition/rearrangement reactions of benzothiazolium salt and α,β-unsaturated aldehydes, utilizing an asymmetric organocatalyst. This process results in the formation of fluorescent, highly enantioenriched chiral molecules with three contiguous stereogenic centers, one of which is a chiral quaternary

  通过苯并噻唑鎓盐和α,β-不饱和醛的正式1,3-偶极环加成/重排反应，实现了手性吡咯并[1,2- d ][1,4]噻嗪-2-甲醛的有效合成方法，利用不对称有机催化剂。该过程导致形成荧光、高度对映体富集的手性分子，具有三个连续的立体中心，其中一个是手性四元中心，具有优异的产率以及对映体和非对映体选择性。计算研究证明了对反应机理的理解。该方案的合成实用性已成功用于克级合成。荧光和计算机研究显示了本方法的应用。