2-(benzo[d]thiazol-2-yl)-6-bromo-1H-benzo[de]isoquinoline-1,3(2H)-dione | 29363-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(benzo[d]thiazol-2-yl)-6-bromo-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 2-(1,3-Benzothiazol-2-yl)-6-bromobenzo[de]isoquinoline-1,3-dione；2-(1,3-benzothiazol-2-yl)-6-bromobenzo[de]isoquinoline-1,3-dione
• CAS: 29363-13-1
• 化学式: C₁₉H₉BrN₂O₂S
• 分子量: 409.263
• InChiKey: JLBOQAKUKYXTBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(benzo[d]thiazol-2-yl)-6-bromo-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 三乙胺 作用下， 以 乙醇 、 乙二醇甲醚 为溶剂， 生成 (Z)-6-(4-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl)piperazin-1-yl)-2-(benzo[d]thiazol -2-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  An unanticipated discovery towards novel naphthalimide corbelled aminothiazoximes as potential anti-MRSA agents and allosteric modulators for PBP2a

  摘要：

  DOI：

  10.1016/j.ejmech.2021.114050
• 作为产物：
  描述：

  5-溴苊 在 吡啶 、 potassium dichromate 、 zinc diacetate 、 溶剂黄146 作用下， 反应 4.58h， 生成 2-(benzo[d]thiazol-2-yl)-6-bromo-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  一种用于精确和选择性检测血清白蛋白和抗癌活性的新型靶标和生物标志物苯并噻唑基-萘酰亚胺探针

  摘要：

  设计和合成了基于N-苯并噻唑基-1,8-萘酰亚胺的荧光探针，用于选择性检测各种生物分析物中的人血清白蛋白 (HSA) 和牛血清白蛋白 (BSA)，并进一步研究了它们对 60 人的体外抗增殖活性癌细胞系。萘酰亚胺衍生物 2-(benzo[ d ]thiazol-2-yl)-6-(4-methoxyphenyl)-1 H -benzo [ de ]isoquinoline-1,3( 2H )-dione 的结合相互作用( 8 ) 组和 2-(苯并[ d ]噻唑-2-基)-6-(2-氟苯基)-1 H-苯并[ de ]异喹啉-1,3( 2H)-二酮具有吸电子基团 ( 12 ) 与 HSA 和 BSA 通过光谱以及分子建模技术进行了探索。在这两种衍生物中，与探针8相比，探针12与人血清白蛋白和牛血清白蛋白的结合亲和力更好，发现12对HSA的检测限为4.3 μM。此外，在苯环上具有氟的化合物12显示出

  DOI：

  10.1039/d1nj03650e

文献信息

• Synthesis of naphthalimide derivatives bearing benzothiazole and thiazole moieties: In vitro anticancer and in silico ADMET study
  作者：Pramod D. JawalePatil、Keerti Bhamidipati、Manoj G. Damale、Jaiprakash N. Sangshetti、Nagaprasad Puvvada、Rajesh S. Bhosale、Rajita D. Ingle、Rajendra P. Pawar、Sidhanath V. Bhosale、Sheshanath V. Bhosale

  DOI：10.1016/j.molstruc.2022.133173

  日期：2022.9

  we report the synthesis and characterization of 1–16 new naphthalimide derivatives. These compounds 1–16 were tested for their anticancer activity against cancerous cells B16F10, MCF7, PANC1, and CHO cell lines. Among these substances, the derivatives 2 and 6 showed moderate cytotoxicity against B16F10 cell lines in vitro. Whereas, compound 14 exhibited excellent cytotoxic activity against B16F10

  在此，我们报告了1-16种新型萘酰亚胺衍生物的合成和表征。测试了这些化合物1-16对癌细胞 B16F10、MCF7、PANC1 和 CHO 细胞系的抗癌活性。在这些物质中，衍生物2和6在体外对B16F10细胞系表现出中等的细胞毒性。而化合物14对 B16F10、MCF7 和 PANC1 细胞表现出优异的细胞毒活性。分子对接研究还表明，化合物2、6和14是有效的候选化合物，可用于药物发现过程中的先导。化合物的药代动力学和毒性特征通过对吸收、分布、代谢、消除和毒性 (ADMET) 参数的预测来访问1-16 。体外细胞系和分子对接研究结果表明，化合物2、6和14是进一步结构操作和评估新一代更有效的细胞毒剂的良好候选者。
• Three polarity-sensitive fluorescence probe possessing AIE activity and its application on lipid droplets imaging
  作者：Dongxiao Wang、Lihua Tang、Junjun Wang、Zheng Zheng、Huimei Cai、Longchun Li、Xiaoping Gan、Hongping Zhou

  DOI：10.1016/j.dyepig.2023.111082

  日期：2023.3

  fluorescence in toluene and red fluorescence in dichloromethane. Meanwhile, they all possessed AIE effect in mixed solution of DMSO/H2O, which were suitable to intracellular lipid droplets imaging. Moreover, the three probes exhibited excellent pH and kinetic stability, low biotoxicity and large Stokes shift. All these properties suggest that the three compounds can be used as potential probes for lipid droplets

  作为中性脂质储存细胞器，脂滴在细胞代谢和生长中起着重要作用。在这项研究中，我们基于萘酰亚胺衍生物开发了三种靶向具有DA型结构的脂滴的荧光探针，分别命名为TPA-NDI-1、TPA-NDI-2和TPA-NDI-3。有趣的是，这三种化合物表现出极性敏感特性，在甲苯中发出绿黄色荧光，在二氯甲烷中发出红色荧光。同时，它们在DMSO/H 2混合溶液中均具有AIE效应O，适合细胞内脂滴成像。此外，这三种探针表现出优异的pH和动力学稳定性、低生物毒性和大斯托克斯位移。所有这些特性表明这三种化合物可以用作脂滴可视化检测的潜在探针。
• Intrachain Energy Migration to Weak Charge-Transfer State in Polyfluorene End-Capped with Naphthalimide Derivative
  作者：Emanuelle R. Simas、Marcelo H. Gehlen、Melissa F. S. Pinto、Jonathas Siqueira、Lino Misoguti

  DOI：10.1021/jp108168f

  日期：2010.12.2

  Polyfluorene end-capped with N-(2-benzothiazole)-1 8-naphthalimide (PF-BNI) is a highly fluorescent material with fluorescence emission modulated by solvent polarity Its low energy excited state is assigned as a mixed configuration state between the singlet S-1 of the fluorene backbone (F) with the charge transfer (CI) of the end group BNI The triexponential fluorescence decays of PF-BNI were associated with fast energy migration to form an intrachain charge-transfer (ICCT) state polyfluorene backbone decay and ICCT deactivation Time-resolved fluorescence anisotropy exhibited biexponential relaxation with a fast component of 12-16 ps in addition to a slow one in the range 0 8-1 4 ns depending on the solvent showing that depolarization occurs from two different processes energy migration to form the ICCT state and slow rotational diffusion motion of end segments at a longer time Results from femtosecond transient absorption measurements agreed with anisotropy decay and showed a decay component of about 16 ps at 605 nm in PF BNI ascribed to the conversion of S-1 to the ICCT excited state From the ratio of asymptotic and initial amplitudes of the transient absorption measurement the efficiency of intrachain ICCT formation is estimated in 0 5 which means that on average, half of the excited state formed in a BNI-(F)(n)-BNI chain with n = 32 is converted to its low energy intrachain charge-transfer (ICCT) state
• An unanticipated discovery towards novel naphthalimide corbelled aminothiazoximes as potential anti-MRSA agents and allosteric modulators for PBP2a
  作者：Peng-Li Zhang、Lavanya Gopala、Shao-Lin Zhang、Gui-Xin Cai、Cheng-He Zhou

  DOI：10.1016/j.ejmech.2021.114050

  日期：2022.2
• A novel target and biomarker benzothiazolyl–naphthalimide probes for precise and selective detection of serum albumin and anticancer activity
  作者：Sudesh Rani、Saurabh Gupta、Vijay Luxami、Kamaldeep Paul

  DOI：10.1039/d1nj03650e

  日期：——

  N-Benzothiazolyl-1,8-naphthalimide based fluorescent probes were designed and synthesized for selective detection of human serum albumin (HSA) and bovine serum albumin (BSA) among various bioanalytes and further studied for their in vitro anti-proliferative activity against 60 human cancer cell lines. Binding interactions of naphthalimide derivative 2-(benzo[d]thiazol-2-yl)-6-(4-methoxyphenyl)-1H-

  设计和合成了基于N-苯并噻唑基-1,8-萘酰亚胺的荧光探针，用于选择性检测各种生物分析物中的人血清白蛋白 (HSA) 和牛血清白蛋白 (BSA)，并进一步研究了它们对 60 人的体外抗增殖活性癌细胞系。萘酰亚胺衍生物 2-(benzo[ d ]thiazol-2-yl)-6-(4-methoxyphenyl)-1 H -benzo [ de ]isoquinoline-1,3( 2H )-dione 的结合相互作用( 8 ) 组和 2-(苯并[ d ]噻唑-2-基)-6-(2-氟苯基)-1 H-苯并[ de ]异喹啉-1,3( 2H)-二酮具有吸电子基团 ( 12 ) 与 HSA 和 BSA 通过光谱以及分子建模技术进行了探索。在这两种衍生物中，与探针8相比，探针12与人血清白蛋白和牛血清白蛋白的结合亲和力更好，发现12对HSA的检测限为4.3 μM。此外，在苯环上具有氟的化合物12显示出