3,4-bis(4-methoxyphenyl)-1-methyl-1H-pyrrole-2,5-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,4-bis(4-methoxyphenyl)-1-methyl-1H-pyrrole-2,5-dione
• 英文别名: 3,4-bis(4-methoxyphenyl)-1-methylpyrrole-2,5-dione
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: WWDDCLVWILXBLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-bis(4-methoxyphenyl)-1-methyl-1H-pyrrole-2,5-dione 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  CN114907249

  摘要：

  公开号：
• 作为产物：
  描述：

  对甲氧基苯乙腈 在 potassium tert-butylate 、 碘 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 3,4-bis(4-methoxyphenyl)-1-methyl-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  α，β-二氰基苯乙烯的衍生物：二苯基马来酰亚胺化合物的合成，E - Z异构化，晶体结构和固态荧光的便捷前体

  摘要：

  通过改进的合成的二芳基取代的富马腈，开发了一种方便有效的方法来制备3,4-二芳基取代的马来酰亚胺。分析并改进了由苯基乙腈化合​​物合成二苯基取代的富马腈衍生物的方法。我们发现甲醇钠的化学计量和原料苯乙腈衍生物的浓度对于产品的高收率和易于纯化至关重要。特别是，通过简单的抽滤将双（4-溴苯基）富马腈，双（3-三氟甲基苯基）富马腈和双（4-甲氧基苯基）富马腈以70-90％的高收率分离出来。此外，1 H NMR提供了令人信服的证据，表明E - Z富马腈或马来腈衍生物与马来酰亚胺化合物的形成反应涉及异构化。获得了前三种三类富马腈衍生物的单晶X射线结构，揭示了非平面分子结构。我们将这些二苯基富马腈衍生物的强固态荧光归因于非平面结构，该结构抑制了分子​​聚集的紧密堆积，从而抑制了荧光猝灭。

  DOI：

  10.1021/jo049512c

文献信息

• The colourful fluorescence from readily-synthesised 3,4-diaryl-substituted maleimide fluorophores
  作者：Hsiu-Chih Yeh、Wei-Ching Wu、Chin-Ti Chen

  DOI：10.1039/b211537a

  日期：2003.1.23

  A new synthesis procedure has been developed for a series of maleimide-based fluorophores, exhibiting a large variation of emission spectra spanning the entire visible range.

  已经开发出一种新的合成程序，用于一系列基于马来酰亚胺的荧光染料，展示了涵盖整个可见光范围的发射光谱的较大变化。
• Palladium-catalyzed direct arylation of maleimides: A simple route to bisaryl-substituted maleimides
  作者：Farnaz Jafarpour、Mitra Shamsianpour、Salumeh Issazadeh、Masoumeh Dorrani、Hamideh Hazrati

  DOI：10.1016/j.tet.2017.01.069

  日期：2017.3

  Palladium-catalyzed direct arylation of maleimides via Heck as well as organoboron-mediated Heck-type reactions are developed. These methods offer an approach to a wide variety of biologically interesting 3,4-diarylmaleimide scaffolds from readily accessible starting materials. These approaches led to the feasible one-pot construction of bisaryl-substituted maleimides which have historically been problematic

  开发了钯催化的经由Heck的马来酰亚胺的直接芳基化反应以及有机硼介导的Heck型反应。这些方法提供了从容易获得的起始原料制备多种生物学上有趣的3，4-二芳基马来酰亚胺支架的方法。这些方法导致双芳基取代的马来酰亚胺的一锅法可行的构建，这在历史上一直是有问题的。
• Discovery of new effective N-alkyl-3,4-diarylmaleimides-based drugs for reversing the bacterial resistance to rhodamine 6G in Bacillus subtilis
  作者：Claudia Leticia Mendoza-Macías、Cesar Rogelio Solorio-Alvarado、Angel Josabad Alonso-Castro、Clara Alba-Betancourt、Martha Alicia Deveze-Álvarez、Felipe Padilla-Vaca、Arturo Reyes-Gualito

  DOI：10.1007/s11696-019-00992-7

  日期：2020.5

  Multidrug resistance (MDR) is a great concern worldwide. There is a great need to develop new drugs with the potential to attack target cells that show MDR phenotype. The purpose of this study was to assess the reversing effect of new N-alkyl-3,4-diarylmaleimides on Bacillus subtilis resistant to rhodamine 6G as an indicator of its activity as modulators of efflux pumps and their additional potential as new antimicrobials. The efflux pump modulator effects of N-alkyl-3-4-diarylmaleimides were tested using the minimal inhibitory concentration (MIC) method on B. subtilis wild type and B. subtilis resistant to R6G, as well as on MDR bacteria isolated from clinical samples (Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Enterococcus faecium, and Acinetobacter baumannii). In addition, their antimicrobial activity was evaluated on clinical isolates. Five N-alkyl-3,4-diarylmaleimides showed the highest reversing activity on the resistance in the Bacillus model as well as with the bacteria isolated from clinical samples. Antimicrobial activity was observed in N-alkyl-3,4-diarylmaleimides against bacteria isolated from clinical samples. The results suggest that N-alkyl-3,4-diarylmaleimides have a potential activity in reversing MDR phenotype and as antimicrobials and may be considered as a potentially molecules to improve chemotherapy on resistant cells.

  多药耐药性（MDR）是全世界都非常关注的问题。目前亟需开发出能攻击表现出 MDR 表型的靶细胞的新药。本研究的目的是评估新型 N-烷基-3,4-二芳基马来酰亚胺对对罗丹明 6G 产生耐药性的枯草芽孢杆菌的逆转作用，以此作为其作为外排泵调节剂的活性指标以及作为新型抗菌药物的其他潜力。采用最小抑菌浓度（MIC）法测试了 N-烷基-3-4-二芳基马来酰亚胺对枯草杆菌野生型、对罗丹明 6G 耐药的枯草杆菌以及从临床样本中分离的 MDR 细菌（大肠杆菌、金黄色葡萄球菌、铜绿假单胞菌、粪肠球菌和鲍曼不动杆菌）的外排泵调节作用。此外，还对它们在临床分离物上的抗菌活性进行了评估。五种 N-烷基-3,4-二芳基马来酰亚胺对芽孢杆菌模型以及从临床样本中分离出来的细菌的耐药性具有最高的逆转活性。N-烷基-3,4-二芳基马来酰亚胺对从临床样本中分离出来的细菌具有抗菌活性。结果表明，N-烷基-3,4-二芳基马来酰亚胺在逆转 MDR 表型和作为抗菌剂方面具有潜在的活性，可被视为改善对耐药细胞化疗的潜在分子。
• Dynamic Covalent Reactions and Chirality Sensing with Diphenylethene Derived Hemiaminals
  作者：Guoshan Jiang、Lifeng Wang、Hebo Ye、Hanxun Zou、Lei You

  DOI：10.1002/cplu.202300080

  日期：2023.5

  The differentiation of enantiomers is of significance in synthetic chemistry and pharmaceutical chemistry. Herein, we report a facile method for chirality sensing of monoalcohols, a challenging target due to the poor reactivity, by combining dynamic covalent chemistry with helical chirality. Four diphenylethene (DPE) derived cyclic hemiaminals were constructed, and the incorporation of a broad range of alcohols and thiols with high efficiency was achieved. The reversibility was further verified by dynamic component exchange. The helical chirality of the DPE motif was induced through chirality transfer by the central chirality of the analytes, resulting in circular dichroism responses. The chirality differentiation of seven chiral secondary alcohols including both alkyl and aryl alcohols was realized, further allowing the quantification of enantiomeric excess with high accuracy. The results described should lay a foundation for future endeavors in chemical sensing, asymmetric synthesis, and chiroptical materials.

  摘要 对映体的区分在合成化学和药物化学中具有重要意义。在此，我们报告了一种将动态共价化学与螺旋手性相结合的简便方法，用于单醇的手性传感。我们构建了四种由二苯基乙烯（DPE）衍生的环状半二胺，并高效地结合了多种醇和硫醇。通过动态成分交换进一步验证了其可逆性。分析物的中心手性通过手性转移诱导了 DPE 主题的螺旋手性，从而产生了圆二色性反应。实现了包括烷基和芳基醇在内的七种手性仲醇的手性区分，进一步实现了对映体过量的高精度定量。上述成果为今后在化学传感、不对称合成和光电材料方面的研究奠定了基础。
• Highly efficient and tunable dual-state emission from diarylmaleimide derivatives in both solution and solid states for sensing and lighting
  作者：Yuanshan Huang、Xin Zheng、Limei Huang、Qidan Ling、Zhenghuan Lin

  DOI：10.1016/j.dyepig.2023.111875

  日期：2024.3

  adjustment of emission color from blue to red, but also exhibit effective DSE performance. Their quantum yields in solution range from 58.2 % to 88.2 %, while the ones in solid exceed 80 %, with a maximum of nearly 100 % for three derivatives. In addition, DPM6 with tert-butoxycarbonylamino terminal group obtains three different crystals with yellow, orange and red emission. DPM6 crystals realize the reversible

  双态发射（DSE）材料因其在溶液和固态下的强发光而引起了广泛的关注。然而，获得可调谐DSE材料仍然是一个挑战。通过末端基团的剪裁，设计合成了一系列具有扭曲结构的二苯基马来酰亚胺衍生物DPM1-DPM7。这些化合物不仅实现了从蓝色到红色的发射颜色的大范围调节，而且还表现出有效的DSE性能。它们在溶液中的量子产率范围为58.2%至88.2%，而在固体中的量子产率超过80%，其中三种衍生物的最高值接近100%。此外，带有叔丁氧基羰基氨基端基的DPM6得到了三种不同的晶体，分别发出黄色、橙色和红色的光。DPM6晶体在溶剂蒸气的刺激下实现三种颜色的可逆转换，可用于鉴别氯仿和二氯甲烷。DSE活性DPM可用于选择性检测溶液中的Fe 3+离子，并且在固态照明领域也有重要应用，实现高达320 lm/W的超高发光效率的白光。