2-[(E)-2-(3,4-dimethoxyphenyl)ethen-1-yl]benzothiazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(E)-2-(3,4-dimethoxyphenyl)ethen-1-yl]benzothiazole
• 英文别名: 2-[(E)-2-(3,4-dimethoxyphenyl)-1-ethenyl]-1,3-benzothiazole；(E)-2-(3,4-dimethoxystyryl)benzo[d]thiazole；2-[(E)-2-(3,4-dimethoxyphenyl)vinyl]-1,3-benzothiazole；2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-benzothiazole；(E)-2-(3,4-dimethoxystyryl)benzothiazole；2-(3,4-dimethoxystyryl)benzothiazole；Benzothiazole, 2-[(1E)-2-(3,4-dimethoxyphenyl)ethenyl]-
• 化学式: C₁₇H₁₅NO₂S
• 分子量: 297.378
• InChiKey: CQLOJCHQXFGESP-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(E)-2-(3,4-dimethoxyphenyl)ethen-1-yl]benzothiazole 以 乙腈 为溶剂， 生成 2-(3,4-dimethoxystyryl)benzothiazole
  参考文献：
  名称：

  新型邻苯乙烯基取代氮杂环的合成及其光谱和光化学性质

  摘要：

  摘要已经设计并合成了以前未知的双苯乙烯基衍生物，其中两个邻苯乙烯基取代的氮杂环通过聚亚甲基间隔基连接在一起。光谱和光化学研究证实了合成化合物的高光化学活性。

  DOI：

  10.1134/s1070428020040090
• 作为产物：
  描述：

  2-甲基苯并噻唑 、 3,4-二甲氧基苯甲醛 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以87 %的产率得到2-[(E)-2-(3,4-dimethoxyphenyl)ethen-1-yl]benzothiazole
  参考文献：
  名称：

  2-共轭苯并噻唑多酚杂化物体外抑制 α-突触核蛋白聚集和预制纤维解聚

  摘要：

  α-Syn 的错误折叠和聚集在连接帕金森病 (PD) 的多种病理通路中发挥着关键作用。通过使用合适的抑制剂抑制其聚集或分解现有聚集体来保持 α-Syn 蛋白质稳态和功能，这是一种有前途的 PD 预防和治疗策略。在这项研究中，设计并合成了一系列苯并噻唑-多酚杂化物。三种鉴定出的化合物在体外对 α-Syn 聚集表现出显着的抑制活性，IC 值在低微摩尔范围内。这些抑制剂在整个聚集过程中表现出持续的抑制作用，稳定了 α-Syn 蛋白质稳态构象。此外，这些化合物可能通过与纤维内的特定结构域结合，有效地分解预制的 α-Syn 低聚物和纤维，诱导原纤维不稳定、塌陷，并最终产生较小尺寸的聚集体和单体。这些发现为了解多酚杂化物与 2-共轭苯并噻唑靶向 α-Syn 聚集在 PD 治疗中的治疗潜力提供了有价值的见解。

  DOI：

  10.1016/j.bmcl.2024.129752

文献信息

• Facile Synthesis of Novel 2-Styrylbenzothiazoles Containing Crown Ether Moieties
  作者：Olga A. Fedorova、Elena N. Andryukhina、Sergey P. Gromov

  DOI：10.1055/s-2003-37348

  日期：——

  Novel 2-styrylbenzothiazoles containing crown ether moieties with different combinations of O, S, and N atoms were prepared by condensation of 2-methylbenzothiazole with formyl derivatives of benzocrown ethers in the presence of alkali metal alkoxides or by Wittig reaction. The role of complex formation in these syntheses is discussed.

  通过 2-甲基苯并噻唑与苯并冠醚的甲酰基衍生物在碱金属醇盐的存在下缩合或通过 Wittig 反应制备新型 2-苯乙烯基苯并噻唑，其含有具有不同 O、S 和 N 原子组合的冠醚部分。讨论了复合物形成在这些合成中的作用。
• Styryl dyes. Synthesis and study of the solid-state [2+2] autophotocycloaddition by NMR spectroscopy and X-ray diffraction
  作者：A. I. Vedernikov、L. G. Kuz’mina、S. K. Sazonov、N. A. Lobova、P. S. Loginov、A. V. Churakov、Yu. A. Strelenko、J. A. K. Howard、M. V. Alfimov、S. P. Gromov

  DOI：10.1007/s11172-007-0289-4

  日期：2007.9

  benzene fragment of styryl dyes extend the range of the mutual orientations of the molecules in the dimeric pairs, resulting in the formation of two or even four isomeric cyclobutanes in the PCA reactions. The structures of some dyes were established by X-ray diffraction. In the overwhelming majority of the structures, one of two packing modes, either syn-head-to-tail or syn-head-to-head, with extensive

  合成了吡啶和苯并噻唑系列的新型苯乙烯基染料，目的是研究固态 [2+2] 自光环加成 (PCA) 反应。1H NMR 光谱表明，对于大多数研究中的化合物，染料多晶薄膜的可见光照射提供了环丁烷衍生物。光反应速率取决于染料的结构，对于杂环部分含有短 N 取代基并在可见光区具有强吸收的化合物，光反应速率更高。在苯环中带有电子释放取代基的染料在 syn-head-to-tail 二聚体对中经历立体有择的 PCA，得到环丁烷衍生物的唯一 rctt 异构体。苯乙烯基染料苯片段中的吸电子和大取代基扩大了二聚体对中分子的相互取向范围，导致在 PCA 反应中形成两个甚至四个异构环丁烷。一些染料的结构是通过 X 射线衍射确定的。在绝大多数结构中，观察到具有广泛堆叠相互作用的两种包装模式之一，syn-head-to-tail 或 syn-head-to-head。在苯环中含有庞大的 N+(Et)Me2 取代基的双
• Design of crystal packings of styryl heterocycles and regularities of [2+2] photocycloaddition in their single crystals 8. Topochemical [2+2] autophotocycloaddition and back reaction in styryl dye of the benzothiazole series
  作者：L. G. Kuz’mina、A. I. Vedernikov、E. Kh. Lermontova、J. A. K. Howard、M. V. Alfimov、S. P. Gromov

  DOI：10.1007/s11172-013-0249-0

  日期：2013.8

  New styryl dye of the 2-benzothiazole series was synthesized. The new dye contains two methoxy groups in the benzene ring and tosylate counterion. The [2+2] photocycloaddition (PCA) of the dye was studied in the polycrystalline film and in single crystal. Two modifications of the dye cocrystallizate with hydroquinone differed in the ratio of components were obtained, and their ability to enter PCA was studied. According to the X-ray diffraction data, molecular cations of the dye form stack packings either of syn-“head-to-tail” type or relatively isolated stacking dimers. In all cases, the ethylene bonds of the adjacent cations are brought together and antiparallel, favoring PCA to form the centrosymmetric rctt-isomer of 1,2,3,4-tetrasubstituted cyclobutane. In two cases, the PCA reaction proceeded as the “single crystal-to-single crystal” transformation. Hydrogen bonds in crystals including hydroquinone molecules strengthen the crystal packing retarding the PCA. The back photoreaction (retro-PCA) was detected: it occurs without single crystal decomposition and results in the accumulation of the initial styryl dye in crystal consisting of the cyclobutane derivative. This is the first example of such a transformation in single crystals.

  合成了 2-苯并噻唑系列的新型苯乙烯基染料。新染料的苯环上含有两个甲氧基和甲苯磺酸盐反离子。研究了该染料在多晶膜和单晶中的 [2+2] 光环加成（PCA）。得到了染料与对苯二酚的两种不同成分比例的共晶化合物，并研究了它们进入 PCA 的能力。根据 X 射线衍射数据，该染料的分子阳离子形成了 "头对尾 "型或相对孤立的堆叠二聚体。在所有情况下，相邻阳离子的乙烯键都聚集在一起并反平行，有利于 PCA 形成 1,2,3,4 四取代环丁烷的中心对称 rctt 异构体。在两种情况下，PCA 反应以 "单晶-单晶 "转化的方式进行。包括对苯二酚分子在内的晶体中的氢键加强了晶体的堆积，从而延缓了 PCA 的发生。检测到了逆光反应（retro-PCA）：它发生时没有单晶体分解，并导致最初的苯乙烯基染料在环丁烷衍生物组成的晶体中积累。这是第一个在单晶体中发生这种转变的实例。
• ——
  作者：O. A. Fedorova、E. N. Andryukhina、A. V. Lindeman、S. S. Basok、T. Yu. Bogaschenko、S. P. Gromov

  DOI：10.1023/a:1015416029124

  日期：——

  Methods for the synthesis of unknown 2-styrylbenzothiazoles containing crown ether moieties with different combinations of O, S, and N-heteroatoms based on the Wittig reaction or condensation of 2-methylbenzothiazole with crown-ether benzaldehydes in the presence of strong bases or acids are proposed. The condensation in the presence of bases is accompanied by complex formation with participation of the crown ether moiety of the benzaldehyde. The complex formation has a pronounced influence on the yield of the target product and the pattern of condensation of 2-methylbenzothiazole with crown-ether benzaldehydes.
• Cytotoxic anionic tribromo platinum(II) complexes containing benzothiazole and benzoxazole donors: synthesis, characterization, and structure-activity correlation
  作者：César M. Lozano、Osvaldo Cox、Mariel M. Muir、Johara D. Morales、Jorge L. Rodríguez-Cabán、Pablo E. Vivas-Mejía、Fernando A. Gonzalez

  DOI：10.1016/s0020-1693(97)05952-5

  日期：1998.4

  A series of platinum(II) complexes of the type [NEt4][PtLBr3] where L is a 2-styrylbenzothiazole or 2-styrylbenzoxazole was prepared. The complexes were characterized by their melting points, elemental analyses, W-Vis and far-infrared spectra, and H-1 and Pt-195 NMR spectroscopy. The NMR data are consistent with coordination of the benzoheterazole ligands to the Pt ion through the nitrogen atom. The ligands and the complexes were assayed for cytotoxicity against U937 human histiocytic lymphoma cells. It was observed that the ligands displayed very poor cytotoxicity, while the Pt(II) complexes demonstrated marked cytotoxicities and a structure-activity correlation was established. Pt(ll) complexes containing S as the heteroatom in the benzoheterazole ring were generally more active than their O-containing counterpart. The position and type of substituents in the styryl moiety were also important for biological activity. Our data indicate that adjacent methoxy functionalities were present in the most potent drugs tested. Further development of active Pt(II) complexes with improved solubilities is warranted. (C) 1998 Elsevier Science S.A.