3-[(4-Methoxyphenyl)methylidene]-1-methylpyrrolidine-2,5-dione | 754194-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-[(4-Methoxyphenyl)methylidene]-1-methylpyrrolidine-2,5-dione
• CAS: 754194-01-9
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: GADANLPQUZIQIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  肌氨酸 、 1-苄基-1H-吲哚-2,3-二酮 、 3-[(4-Methoxyphenyl)methylidene]-1-methylpyrrolidine-2,5-dione 以 甲醇 为溶剂， 反应 3.5h， 以76%的产率得到
  参考文献：
  名称：

  Synthesis, antibacterial activity evaluation and QSAR studies of novel dispiropyrrolidines

  摘要：

  A series of novel dispiropyrrolidines have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide generated from sarcosine and isatin with the dipolarophile 3-benzylidene-1-methylpyrrolidine-2,5-dione. Their antibacterial activity was evaluated against Bacillus subtilis NCIM 2718, Staphylococcus aureus NCIM5021, Salmonella typhi NCIM2501, Pseudomonas aeruginosa NCIM 5029 and Proteus vulgaris NCIM2813 by two fold dilution method. Compound 6e exhibits reasonably good activity and compound 6c exhibits poor activity against all the organisms. The QSAR's were developed for all antibacterial activities. The models had either one or two descriptors (r(2) = 0.81-0.97, r(2)adj = 0.75-0.96, q(2) = 0.57-0.92, F-ratio = 12.73-162.76). Topology, shape, charge distribution and hydrophobic nature of the molecules had pronounced effect on their antibacterial activity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.035
• 作为产物：
  描述：

  N-甲基马来酰亚胺 、 4-甲氧基苯甲醛 在 三苯基膦 作用下， 反应 0.75h， 以72%的产率得到3-[(4-Methoxyphenyl)methylidene]-1-methylpyrrolidine-2,5-dione
  参考文献：
  名称：

  Synthesis, antibacterial activity evaluation and QSAR studies of novel dispiropyrrolidines

  摘要：

  A series of novel dispiropyrrolidines have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide generated from sarcosine and isatin with the dipolarophile 3-benzylidene-1-methylpyrrolidine-2,5-dione. Their antibacterial activity was evaluated against Bacillus subtilis NCIM 2718, Staphylococcus aureus NCIM5021, Salmonella typhi NCIM2501, Pseudomonas aeruginosa NCIM 5029 and Proteus vulgaris NCIM2813 by two fold dilution method. Compound 6e exhibits reasonably good activity and compound 6c exhibits poor activity against all the organisms. The QSAR's were developed for all antibacterial activities. The models had either one or two descriptors (r(2) = 0.81-0.97, r(2)adj = 0.75-0.96, q(2) = 0.57-0.92, F-ratio = 12.73-162.76). Topology, shape, charge distribution and hydrophobic nature of the molecules had pronounced effect on their antibacterial activity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.035

文献信息

• NOVEL BENZYLIDENE AZOLIDINE DERIVATIVE OR SALT THEREOF
  申请人：ROHTO Pharmaceutical Co., Ltd.

  公开号：US20150065728A1

  公开（公告）日：2015-03-05

  A novel compound which has excellent ultraviolet-absorbing function (especially UVA absorbing function) and excellent hydrophilicity. A benzylidene azolidine derivative represented by structural formula (I) or a salt thereof. In structural formula (I), n represents an integer of 1-5; A 1 represents O, S or N-A 4 ; and each of A 2 , A 3 and A 4 independently represents a hydrogen atom, an alkyl group which may be substituted by a hydroxyl group and has 1-8 carbon atoms, or the like (provided that at least one of A 2 , A 3 and A 4 contains one or more hydroxyl groups). In this connection, when n is an integer of 2-5, the plurality of A 3 O— moieties may be the same as or different.

  一种新型化合物，具有优异的紫外吸收功能（特别是UVA吸收功能）和优异的亲水性。该化合物为结构式（I）所表示的苯甲酰亚氮杂环衍生物或其盐。在结构式（I）中，n表示1-5的整数；A1表示O、S或N-A4；每个A2、A3和A4独立地表示氢原子、烷基（其可以被羟基取代，并具有1-8个碳原子）或类似物（前提是A2、A3和A4中至少有一个含有一个或多个羟基）。在此情况下，当n为2-5的整数时，多个A3O-基团可以相同或不同。
• Multifunctional Derivatives of Spiropyrrolidine Tethered Indeno-Quinoxaline Heterocyclic Hybrids as Potent Antimicrobial, Antioxidant and Antidiabetic Agents: Design, Synthesis, In Vitro and In Silico Approaches
  作者：Nouha Bouali、Manel Ben Hammouda、Iqrar Ahmad、Siwar Ghannay、Amira Thouri、Amal Dbeibia、Harun Patel、Walid Sabri Hamadou、Karim Hosni、Mejdi Snoussi、Mohd Adnan、Md Imtaiyaz Hassan、Emira Noumi、Kaïss Aouadi、Adel Kadri

  DOI：10.3390/molecules27217248

  日期：——

  To combat emerging antimicrobial-resistant microbes, there is an urgent need to develop new antimicrobials with better therapeutic profiles. For this, a series of 13 new spiropyrrolidine derivatives were designed, synthesized, characterized and evaluated for their in vitro antimicrobial, antioxidant and antidiabetic potential. Antimicrobial results revealed that the designed compounds displayed good activity against clinical isolated strains, with 5d being the most potent (MIC 3.95 mM against Staphylococcus aureus ATCC 25923) compared to tetracycline (MIC 576.01 mM). The antioxidant activity was assessed by trapping DPPH, ABTS and FRAP assays. The results suggest remarkable antioxidant potential of all synthesized compounds, particularly 5c, exhibiting the strongest activity with IC50 of 3.26 ± 0.32 mM (DPPH), 7.03 ± 0.07 mM (ABTS) and 3.69 ± 0.72 mM (FRAP). Tested for their α-amylase inhibitory effect, the examined analogues display a variable degree of α-amylase activity with IC50 ranging between 0.55 ± 0.38 mM and 2.19 ± 0.23 mM compared to acarbose (IC50 1.19 ± 0.02 mM), with the most active compounds being 5d, followed by 5c and 5j, affording IC50 of 0.55 ± 0.38 mM, 0.92 ± 0.10 mM, and 0.95 ± 0.14 mM, respectively. Preliminary structure–activity relationships revealed the importance of such substituents in enhancing the activity. Furthermore, the ADME screening test was applied to optimize the physicochemical properties and determine their drug-like characteristics. Binding interactions and stability between ligands and active residues of the investigated enzymes were confirmed through molecular docking and dynamic simulation study. These findings provided guidance for further developing leading new spiropyrrolidine scaffolds with improved dual antimicrobial and antidiabetic activities.

  为了对付新出现的抗菌微生物，迫切需要开发出治疗效果更好的新型抗菌药物。为此，研究人员设计、合成、表征并评估了一系列 13 种新的螺吡咯烷衍生物的体外抗菌、抗氧化和抗糖尿病潜力。抗菌结果显示，所设计的化合物对临床分离菌株具有良好的活性，与四环素（MIC 576.01 mM）相比，5d 的活性最强（对金黄色葡萄球菌 ATCC 25923 的 MIC 为 3.95 mM）。抗氧化活性通过 DPPH、ABTS 和 FRAP 试验进行评估。结果表明，所有合成化合物都具有显著的抗氧化潜力，尤其是 5c 的活性最强，其 IC50 分别为 3.26 ± 0.32 mM（DPPH）、7.03 ± 0.07 mM（ABTS）和 3.69 ± 0.72 mM（FRAP）。与阿卡波糖（IC50 1.19 ± 0.02 mM）相比，这些类似物的 IC50 介于 0.55 ± 0.38 mM 和 2.19 ± 0.23 mM 之间，其中活性最高的化合物是 5d，其次是 5c 和 5j，IC50 分别为 0.55 ± 0.38 mM、0.92 ± 0.10 mM 和 0.95 ± 0.14 mM。初步的结构-活性关系显示了这些取代基在提高活性方面的重要性。此外，还应用 ADME 筛选测试优化了这些化合物的理化性质，并确定了它们的类药物特性。通过分子对接和动态模拟研究，证实了配体与所研究酶的活性残基之间的结合相互作用和稳定性。这些发现为进一步开发具有更好的抗菌和抗糖尿病双重活性的新型螺吡咯烷支架提供了指导。
• US9422246B2
  申请人：——

  公开号：US9422246B2

  公开（公告）日：2016-08-23