N-(1H-苯并咪唑-2-基)-4-硝基苯磺酰胺 | 193696-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(1H-苯并咪唑-2-基)-4-硝基苯磺酰胺
• 中文别名: N-1H-苯并咪唑-2-基-4-硝基苯磺酰胺
• 英文名称: 4-nitro-benzenesulfonic acid-(1H-benzimidazol-2-ylamide)
• 英文别名: 4-Nitro-benzolsulfonsaeure-(1H-benzimidazol-2-ylamid)；N-(1H-benzimidazol-2-yl)-4-nitrobenzenesulfonamide
• CAS: 193696-66-1
• 化学式: C₁₃H₁₀N₄O₄S
• 分子量: 318.313
• InChiKey: IWICJKDNRXWNKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(1H-苯并咪唑-2-基)-4-硝基苯磺酰胺 在 palladium 10% on activated carbon 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 50.0 ℃ 、5.0 MPa 条件下， 生成 4-amino-N-(1,3-dihydrobenzoimidazol-2-ylidene)benzenesulfonamide
  参考文献：
  名称：

  4-（（2-羟基-3-甲氧基苄基）氨基）苯磺酰胺衍生物作为 12-脂氧化酶的强效和选择性抑制剂的合成和构效关系研究

  摘要：

  人类脂肪氧化酶 (LOX) 是一类含铁酶，可催化多不饱和脂肪酸氧化以提供相应的生物活性羟基二十碳四烯酸 (HETE) 代谢物。这些类二十烷酸信号分子参与了许多生理反应，例如血小板聚集、炎症和细胞增殖。我们小组对血小板型 12-( S )-LOX (12-LOX)产生了特别的兴趣，因为它在皮肤病、糖尿病、血小板止血、血栓形成和癌症中发挥了重要作用。在此，我们报告了基于 4-（（2-羟基-3-甲氧基苄基）氨基）苯磺酰胺的支架的鉴定和药物化学优化。顶级化合物，以35和36为例, 显示对 12-LOX 的 nM 效力，对相关脂肪氧化酶和环氧化酶具有出色的选择性，并具有良好的 ADME 特性。此外，这两种化合物均抑制 PAR-4 诱导的人血小板聚集和钙动员，并减少 β 细胞中的 12-HETE。

  DOI：

  10.1021/jm4016476
• 作为产物：
  描述：

  o-phenylenediamine dihydrochloride 在 phosphorus pentoxide 、 甲苯 作用下， 生成 N-(1H-苯并咪唑-2-基)-4-硝基苯磺酰胺
  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

• Metal-Free β-Amino Alcohol Synthesis: A Two-step Smiles Rearrangement
  作者：Di Yang、Cai-Xia Xie、Xiao-Tian Wu、Luo-Ran Fei、Lei Feng、Chen Ma

  DOI：10.1021/acs.joc.0c01543

  日期：2020.12.4

  A novel method for the synthesis of β-amino alcohols has been demonstrated under mild reaction conditions with a broad scope via a two-step Smiles rearrangement. What is more, theoretical calculations have been performed to confirm the rationality of the mechanism. The method has been proved to be notably effective for N-arylated amino alcohols, which are difficult to synthesize by traditional methods

  通过两步Smiles重排，在温和的反应条件下，已证明了在宽泛范围内合成β-氨基醇的新方法。此外，已经进行了理论计算以确认该机制的合理性。已经证明该方法对于N-芳基化的氨基醇特别有效，N-芳基化的氨基醇难以通过传统方法合成。
• Benvenuti; Severi; Sacchetti, Il Farmaco, 1997, vol. 52, # 4, p. 231 - 235
  作者：Benvenuti、Severi、Sacchetti、Melegari、Vampa、Zani、Mazza、Antolini

  DOI：——

  日期：——
• Synthesis and Structure–Activity Relationship Studies of 4-((2-Hydroxy-3-methoxybenzyl)amino)benzenesulfonamide Derivatives as Potent and Selective Inhibitors of 12-Lipoxygenase
  作者：Diane K. Luci、J. Brian Jameson、Adam Yasgar、Giovanni Diaz、Netra Joshi、Auric Kantz、Kate Markham、Steve Perry、Norine Kuhn、Jennifer Yeung、Edward H. Kerns、Lena Schultz、Michael Holinstat、Jerry L. Nadler、David A. Taylor-Fishwick、Ajit Jadhav、Anton Simeonov、Theodore R. Holman、David J. Maloney

  DOI：10.1021/jm4016476

  日期：2014.1.23

  demonstrated role in skin diseases, diabetes, platelet hemostasis, thrombosis, and cancer. Herein, we report the identification and medicinal chemistry optimization of a 4-((2-hydroxy-3-methoxybenzyl)amino)benzenesulfonamide-based scaffold. Top compounds, exemplified by 35 and 36, display nM potency against 12-LOX, excellent selectivity over related lipoxygenases and cyclooxygenases, and possess favorable

  人类脂肪氧化酶 (LOX) 是一类含铁酶，可催化多不饱和脂肪酸氧化以提供相应的生物活性羟基二十碳四烯酸 (HETE) 代谢物。这些类二十烷酸信号分子参与了许多生理反应，例如血小板聚集、炎症和细胞增殖。我们小组对血小板型 12-( S )-LOX (12-LOX)产生了特别的兴趣，因为它在皮肤病、糖尿病、血小板止血、血栓形成和癌症中发挥了重要作用。在此，我们报告了基于 4-（（2-羟基-3-甲氧基苄基）氨基）苯磺酰胺的支架的鉴定和药物化学优化。顶级化合物，以35和36为例, 显示对 12-LOX 的 nM 效力，对相关脂肪氧化酶和环氧化酶具有出色的选择性，并具有良好的 ADME 特性。此外，这两种化合物均抑制 PAR-4 诱导的人血小板聚集和钙动员，并减少 β 细胞中的 12-HETE。
• The Interrelationship Among Muscle Mass, Strength, and the Ability to Perform Physical Tasks of Daily Living in Younger and Older Women
  作者：K. A. Landers、G. R. Hunter、C. J. Wetzstein、M. M. Bamman、R. L. Weinsier

  DOI：10.1093/gerona/56.10.b443

  日期：2001.10.1

  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.