1-(4-nitrophenyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one | 848393-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(4-nitrophenyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one
• 英文别名: 1-(4-nitrophenyl)-1,3-dihydrobenzimidazol-2-one；1-(4-Nitro-phenyl)-1,3-dihydro-benzimidazol-2-on；3-(4-nitrophenyl)-1H-benzimidazol-2-one
• CAS: 848393-58-8
• 化学式: C₁₃H₉N₃O₃
• 分子量: 255.233
• InChiKey: UJQKLEKMBVPQPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-nitrophenyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one 在 钯 吡啶 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 1-(3-carbamimidoylphenyl)-N-[4-(2-oxo-2,7a-dihydro-1H-1,3-benzodiazol-1-yl)phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  SAR and factor IXa crystal structure of a dual inhibitor of factors IXa and Xa

  摘要：

  Modifications to the P4 moiety and pyrazole C3 substituent of factor Xa inhibitor SN-429 provided several new compounds, which are 5-10nM inhibitors of factor IXa. An X-ray crystal structure of one example complexed to factor IXa shows that these compounds adopt a similar binding mode to that previously observed with pyrazole inhibitors in the factor Xa active site both with regard to how the inhibitor binds and the position of Tyr99.

  DOI：

  10.1016/j.bmcl.2004.08.034
• 作为产物：
  描述：

  N-(2-amino-phenyl)-N'-(4-nitro-benzenesulfonyl)-urea 在 sodium hydroxide 作用下， 生成 1-(4-nitrophenyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one
  参考文献：
  名称：

  The Interrelationship Among Muscle Mass, Strength, and the Ability to Perform Physical Tasks of Daily Living in Younger and Older Women

  摘要：

  The purpose of this study was to objectively compare the difficulty and determine the contribution of strength and muscle mass to the performance of physical tasks of daily living in a group of younger and older women. A cross-sectional design was used. Volunteer participants were from the community of Birmingham, AL; there were 21 older (aged 60-75 years) and 20 younger (23-34 years) healthy women in the study. Subjects were matched for height and weight. Their testing included total and regional body composition evaluation by use of dual-energy x-ray absorptiometry, isometric strength tests of elbow flexors and knee extensors, and integrated electromyography (IEMG) evaluation while the subjects were standing from and sitting into a chair, and while they were carrying a small load (weight relative to strength). A two-way analysis of variance and a two-way analysis of covariance with repeated measures, Pearson product correlation, and first-order partial correlations were used to analyze the data. A significant inverse correlation was observed between age and isometric strength of both the knee extensors and elbow flexors. Adjusting for upper leg lean tissue did not change the significant inverse correlation between age and knee extensor strength. However, after an adjustment for arm lean tissue, there was no significant correlation between elbow flexor strength and age. Older women experienced significantly greater difficulty in standing than younger women as measured by quadriceps normalized IEMG (i.e., IEMG during task/IEMG during maximum isometric strength test). This difference persisted even after the covariate upper leg lean tissue was added to the model. No significant difference was observed between younger and older women for difficulty (biceps normalized IEMG) during the carry task after the covariate arm lean tissue was added to the model. The older women in this study had less strength in the knee extensors and experienced greater difficulty standing from a chair than the younger women, even after the covariate, upper leg lean tissue was added to the model. This suggests that other factors, in addition to loss of lean tissue, contribute to the age-related decline of muscular strength and the ability to perform tasks with the legs. In contrast, although elbow flexor strength declined, this appeared to be largely due to decreased arm lean tissue mass.

  DOI：

  10.1093/gerona/56.10.b443

文献信息

• Chan-Lam cross-coupling reaction based on the Cu 2 S/TMEDA system
  作者：Kateřina Janíková、Lukáš Jedinák、Tereza Volná、Petr Cankař

  DOI：10.1016/j.tet.2017.12.042

  日期：2018.2

  several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding

  基于Chan-Lam交叉偶联反应，开发了一种基于使用稳定铜（I）源的现成Cu 2 S / TMEDA系统的催化剂。用1 H-苯并[ d ]咪唑-2（3 H）-1，1 H-苯并[ d ]咪唑和1 H-咪唑以及缺电子，富电子和在室温下，在大气氧的存在下，对空间需求量高的硼酸，以中等至极好的收率得到交叉偶联的产物。另外，1 H-苯并[ d]的偶联反应]咪唑与几种频哪醇或新戊二醇硼酸酯表明该催化剂的进一步潜力。反应条件容许羟基和溴官能团。该催化体系还能够由伯脂族胺合成单-N-取代的苯胺。但是，仲胺和芳族胺的两种模型化合物哌啶和苯胺不会反应。两个空间要求的产品与受限Ç N键的旋转，通过将合成的Ñ 1的-arylation ħ -苯并[ d ]咪唑-2（3 H ^） -酮与ö-甲苯磺酸，能够确认由Chan-Lam交叉偶联反应制得的阻转异构体。此外，已经报道了一锅Chan-Lam和Suzuki-Miyaura反应的例子。
• Identification and Development of Novel Inhibitors of <i>Toxoplasma gondii</i> Enoyl Reductase
  作者：Suresh K. Tipparaju、Stephen P. Muench、Ernest J. Mui、Sergey N. Ruzheinikov、Jeffrey Z. Lu、Samuel L. Hutson、Michael J. Kirisits、Sean T. Prigge、Craig W. Roberts、Fiona L. Henriquez、Alan P. Kozikowski、David W. Rice、Rima L. McLeod

  DOI：10.1021/jm9017724

  日期：2010.9.9

  Toxoplasmosis causes significant morbidity and mortality, and yet available medicines are limited by toxicities and hypersensitivity. Because improved medicines are needed urgently, rational approaches were used to identify novel lead compounds effective against Toxoplasma gondii enoyl reductase (TgENR), a type II fatty acid synthase enzyme essential in parasites but not present in animals. Fifty-three compounds, including three classes that inhibit ENRs, were tested. Six compounds have antiparasite MIC(90)s <= 6 mu M without toxicity to host cells, three compounds have IC(90)s < 45 nM against recombinant TgENR, and two protect mice. To further understand the mode of inhibition, the cocrystal structure of one of the most promising candidate compounds in complex with TgENR has been determined to 2.7 angstrom. The crystal structure reveals that the aliphatic side chain of compound 19 occupies, as predicted, space made available by replacement of a bulky hydrophobic residue in homologous bacterial ENRs by Ala in TgENR. This provides a paradigm, conceptual foundation, reagents, and lead compounds for future rational development and discovery of improved inhibitors of T. gondii.