(Z)-5-(4-fluorobenzylidene)imidazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (Z)-5-(4-fluorobenzylidene)imidazolidine-2,4-dione
• 英文别名: 5-[1-(4-Fluoro-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione；(5Z)-5-[(4-fluorophenyl)methylidene]imidazolidine-2,4-dione
• 化学式: C₁₀H₇FN₂O₂
• 分子量: 206.176
• InChiKey: NIIDHJDIIPZAEZ-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-5-(4-fluorobenzylidene)imidazolidine-2,4-dione 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 (R,R)-f-spiroPhos 、 氢气 作用下， 以 二氯甲烷 为溶剂， 30.0 ℃ 、2.03 MPa 条件下， 反应 6.0h， 以94%的产率得到(-)-5-(4-fluorobenzyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  通过不对称氢化反应选择性合成手性取代的 2,4-二酮咪唑烷和 2,5-二酮哌嗪

  摘要：

  已经开发了在温和条件下由 Rh/ f -spiroPhos 络合物催化的 5-亚烷基-2,4-二酮咪唑烷（乙内酰脲）和 3-亚烷基-2,5-酮哌嗪的对映选择性氢化，这提供了一种高效的方法。手性乙内酰脲和 2,5-酮哌嗪衍生物的对映选择性合成，对映选择性高达 99.9% ee。

  DOI：

  10.1021/acs.orglett.1c01894
• 作为产物：
  描述：

  海因 、 对氟苯甲醛 在 碳酸氢钠 作用下， 反应 0.5h， 以51%的产率得到(Z)-5-(4-fluorobenzylidene)imidazolidine-2,4-dione
  参考文献：
  名称：

  硫酸和氧代咪唑啉衍生物：合成，抗氧化活性和光介导的抗菌活性。

  摘要：

  具有不同环外取代基的咪唑啉衍生物可以简单地从常见的起始原料制备。该程序以环保的方式进行。这些衍生物的抗氧化活性通过不同的实验测定方法进行了探索，例如ABTS。+和DPPH。清除测定以及降低功率测定。根据结果​​讨论结构差异。含硫类似物显示出比其含氧同类物更高的抗氧化活性。在微生物学研究中观察到了相同的趋势，其中分析了相同的咪唑啉化合物对金黄色葡萄球菌和大肠杆菌菌株的光介导活性。暴露于UV-A（400-320 nm）光后，几乎所有硫酸化的咪唑啉均观察到光增强活性。

  DOI：

  10.1002/cmdc.202000048

文献信息

• Sulfated and Oxygenated Imidazoline Derivatives: Synthesis, Antioxidant Activity and Light‐Mediated Antibacterial Activity
  作者：Martín S. Faillace、Ana P. Silva、Antonio L. Alves Borges Leal、Luciana Muratori da Costa、Humberto M. Barreto、Walter J. Peláez

  DOI：10.1002/cmdc.202000048

  日期：2020.5.19

  analogs showed higher antioxidant activity than their oxygenated counterparts. The same tendency was observed in microbiological studies, in which the same imidazoline compounds were assayed for light-mediated activity against of Staphylococcus aureus and Escherichia coli strains. A light-enhanced activity was observed for almost all the sulfated imidazolines after exposure to UV-A (400-320 nm) light

  具有不同环外取代基的咪唑啉衍生物可以简单地从常见的起始原料制备。该程序以环保的方式进行。这些衍生物的抗氧化活性通过不同的实验测定方法进行了探索，例如ABTS。+和DPPH。清除测定以及降低功率测定。根据结果​​讨论结构差异。含硫类似物显示出比其含氧同类物更高的抗氧化活性。在微生物学研究中观察到了相同的趋势，其中分析了相同的咪唑啉化合物对金黄色葡萄球菌和大肠杆菌菌株的光介导活性。暴露于UV-A（400-320 nm）光后，几乎所有硫酸化的咪唑啉均观察到光增强活性。
• Synthesis of Tetracyclic Spirooxindolepyrrolidine-Engrafted Hydantoin Scaffolds: Crystallographic Analysis, Molecular Docking Studies and Evaluation of Their Antimicrobial, Anti-Inflammatory and Analgesic Activities
  作者：Amani Toumi、Faiza I.A. Abdella、Sarra Boudriga、Tahani Y. A. Alanazi、Asma K. Alshamari、Ahlam Abdulrahman Alrashdi、Amal Dbeibia、Khaled Hamden、Ismail Daoud、Michael Knorr、Jan-Lukas Kirchhoff、Carsten Strohmann

  DOI：10.3390/molecules28217443

  日期：——

  µg/mL). Compound 4e bearing a p-chlorophenyl group on the pyrrolidine ring exhibited the greatest antifungal potential toward Candida albicans and Candida krusei (MIC values of 23.43 µg/mL and 46.87 µg/mL, respectively) as compared to Amphotericin B (MIC = 31.25 and 62.50 µg/mL, respectively). The target compounds were also tested in vitro against the lipoxygenase-5 (LOX-5) enzyme. Compounds 4i and

  在持续寻找具有多谱治疗应用的新型潜在候选药物的过程中，通过靛红衍生物、2-苯基甘氨酸和多种亚芳基-咪唑烷-2,4-二酮（乙内酰脲）之间的区域选择性三组分反应，设计并合成了一系列新型螺吲哚。 。通过 X 射线衍射研究和 NMR 光谱法确定了建议的立体化学。筛选所得四环杂环化合物的体外和体内抗炎和镇痛活性及其体外抗菌效力。体外抗菌筛选表明，几种衍生物对不同目标微生物表现出显着的生长抑制作用。与参比药物四环素 (MIC = 500 µg/mL) 相比，所有测试化合物均表现出优异的抗藤黄微球菌菌株活性 (93.75 µg/mL ≤ MIC ≤ 375 µg/mL)。与两性霉素 B（MIC = 31.25 和 62.50）相比，吡咯烷环上带有对氯苯基的化合物 4e 对白色念珠菌和克柔念珠菌表现出最大的抗真菌潜力（MIC 值分别为 23.43 µg/mL 和 46.87 µg/mL）分别为 µg/mL）。目标化合物还针对脂氧合酶
• Enzyme variants
  申请人：Technische Universität Graz

  公开号：EP2574667A1

  公开（公告）日：2013-04-03

  The present invention relates to a variant of an alpha-keto acid dependent enzyme catalyzing the oxidative decarboxylation of an alpha-keto acid having an amino acid sequence varying from that of a precursor alpha-keto acid dependent enzyme catalyzing the oxidative decarboxylation of an alpha-keto acid, said precursor enzyme comprising - a motif (A) X1X2X3X4(X)nFGX5X6NX7X8X9X10X11, wherein X1 is serine, X2 is an amino acid residue selected from the group consisting of threonine, lysine, isoleucine, arginine and glutamine, X3 is valine or alanine and X4 is an amino acid residue selected from the group consisting of valine, methionine and isoleucine, X5 and X6 are independently any amino acid residue, X7 is isoleucine or phenylalanine, X8 is an amino acid residue selected from the group consisting of lysine, glutamine, arginine and threonine, X9 is an amino acid residue selected from the group consisting of alanine, serine and glycine, X10 is leucine or isoleucine, X11 is tyrosine or phenylalanine, X is any amino acid residue, and n is an integer between 100 and 150, and - a metal ion binding motif (B) H(X12)mH(X13)oE, wherein X12 and X13 are independently any amino acid residue, m and o are independently an integer between 70 and 90, wherein amino acid residue X1 and/or amino acid residue X3 within motif (A) of the variant is an amino acid residue having a molecular volume of more than 150 Å3 and/or amino acid residue X11 within motif (A) of the variant has an amino acid residue having a molecular volume of less than 120 Å3.

  本发明涉及一种催化α-酮酸氧化脱羧的α-酮酸依赖性酶的变体，其氨基酸序列与催化α-酮酸氧化脱羧的前体α-酮酸依赖性酶的氨基酸序列不同，所述前体酶包括 - 图案 (A) X1X2X3X4(X)nFGX5X6NX7X8X9X10X11 其中 X1 是丝氨酸，X2 是选自苏氨酸、赖氨酸、异亮氨酸、精氨酸和谷氨酰胺组成的组的氨基酸残基，X3 是缬氨酸或丙氨酸，X4 是选自缬氨酸、蛋氨酸和异亮氨酸组成的组的氨基酸残基，X5 和 X6 独立地是任何氨基酸残基、X7 是异亮氨酸或苯丙氨酸，X8 是选自由赖氨酸、谷氨酰胺、精氨酸和苏氨酸组成的组的氨基酸残基，X9 是选自由丙氨酸、丝氨酸和甘氨酸组成的组的氨基酸残基，X10 是亮氨酸或异亮氨酸，X11 是酪氨酸或苯丙氨酸，X 是任何氨基酸残基，n 是 100 到 150 之间的整数，以及 - 金属离子结合基团 (B)H(X12)mH(X13)oE，其中 X12 和 X13 独立地是任何氨基酸残基，m 和 o 独立地是介于 70 和 90 之间的整数、 其中变体图案（A）中的氨基酸残基 X1 和/或氨基酸残基 X3 是分子体积大于 150 Å3 的氨基酸残基，和/或变体图案（A）中的氨基酸残基 X11 是分子体积小于 120 Å3 的氨基酸残基。
• Anticonvulsant Activity of Phenylmethylenehydantoins:  A Structure−Activity Relationship Study
  作者：Jeyanthi Chinnappa Thenmozhiyal、Peter Tsun-Hon Wong、Wai-Keung Chui

  DOI：10.1021/jm030450c

  日期：2004.3.1

  Phenylmethylenehydantoins (PMHs) and their des-phenyl analogues were synthesized and evaluated for anticonvulsant activity using the maximal electroshock seizure (MES) assay. The phenyl rings of PMHs were substituted with a wide spectrum of groups, and the selection of substituents was guided by Craig's plot. Phenylmethylenehydantoins substituted with alkyl (2, 3, 5, 6, 12, 14), halogeno (35, 38, 41), trifluoromethyl (11), and alkoxyl (23) groups at the phenyl ring were found to exhibit good anticonvulsant activity with EDMES(2.5) ranging from 28 to 90 mg/kg. Substitution of polar groups such as -NO2, -CN, and -OH was found to be less active or inactive on PMHs. Replacement of the phenyl ring with heteroaromatic rings reduced or caused the loss of anticonvulsant activity. The study identified two PMHs, 14 (EDMES(2.5) = 28 +/- 2 mg/kg) and 12 (EDMES(2.5) = 39 4 mg/kg), to be the most active candidates of the series, which are comparable to phenytoin (55, EDMES(2.5) = 30 +/- 2 mg/kg) in their protection against seizure. Multivariate analysis performed on the whole series of 54 PMHs further supported the finding that the alkylated phenylmethylenehydantoins are the best acting compounds. The SAR model derived on the basis of 12 of the most active phenylmethylenehydantoins demonstrated good predicting ability (root-mean-square error of prediction (RMSEP) = 0.134; RMSEE = 0.057) and identified LUMO energy and the log P as critical parameters for their anticonvulsant activity.
• Inhibition of the NorA efflux pump of S. aureus by (Z)-5-(4-Fluorobenzylidene)-Imidazolidines
  作者：Martín S. Faillace、Antonio L. Alves Borges Leal、Felipe Araújo de Oliveira Alcântara、Josie H.L. Ferreira、José P. de Siqueira-Júnior、Carlos E. Sampaio Nogueira、Humberto M. Barreto、Walter J. Peláez

  DOI：10.1016/j.bmcl.2020.127670

  日期：2021.1