4-benzylamino-3-nitrobenzonitrile | 68502-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-benzylamino-3-nitrobenzonitrile
• 英文别名: 3-Nitro-4-[(phenylmethyl)amino]benzonitrile；4-(benzylamino)-3-nitrobenzonitrile
• CAS: 68502-47-6
• 化学式: C₁₄H₁₁N₃O₂
• mdl: MFCD09862547
• 分子量: 253.26
• InChiKey: DHFWQLMHVVPUPY-UHFFFAOYSA-N

物化性质

• 沸点：
  427.5±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-benzylamino-3-nitrobenzonitrile 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以86%的产率得到3-amino-4-benzylaminobenzonitrile
  参考文献：
  名称：

  RING CLEAVAGE OF DICYANO-SUBSTITUTED BENZIMIDAZOLES BY DIBAL

  摘要：

  DOI：

  10.1515/hc.2001.7.6.529
• 作为产物：
  描述：

  4-氯-3-硝基苯甲腈 、 苄胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以53%的产率得到4-benzylamino-3-nitrobenzonitrile
  参考文献：
  名称：

  RING CLEAVAGE OF DICYANO-SUBSTITUTED BENZIMIDAZOLES BY DIBAL

  摘要：

  DOI：

  10.1515/hc.2001.7.6.529

文献信息

• Synthesis and Potent Antimicrobial Activity of Some Novel N-(Alkyl)-2-Phenyl-1H-Benzimidazole-5-Carboxamidines
  作者：Hakan Göker、Mehmet Alp、Sulhiye Yıldız

  DOI：10.3390/10111377

  日期：——

  A series of 22 novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5- carboxamidine derivatives were synthesized and evaluated for in vitro antibacterial activity against S. aureus and methicillin resistant S. aureus (MRSA), E. coli, E. faecalis and for antifungal activity against C. albicans. Compound 59 [1-(2,4-dichlorobenzyl)-N- (2-diethylaminoethyl)-1H-benzimidazole-5-carboxamidine], with a 3

  合成了一系列 22 种新型 1,2-二取代-1H-苯并咪唑-N-烷基化-5-甲脒衍生物，并评估其对金黄色葡萄球菌和耐甲氧西林金黄色葡萄球菌 (MRSA)、大肠杆菌、 E. faecalis 和针对白色念珠菌的抗真菌活性。化合物 59 [1-(2,4-二氯苄基)-N-(2-二乙氨基乙基)-1H-苯并咪唑-5-甲脒]，在 C-2 位具有 3,4-二氯苯基，显示出最大的活性（ MIC = 3.12 microg/mL 对抗某些细菌和真菌白色念珠菌）。
• Synthesis and Potent Antimicrobial Activities of Some Novel Retinoidal Monocationic Benzimidazoles
  作者：Zeynep Ates-Alagöz、Mehmet Alp、Canan Kus、Sulhiye Yildiz、Erdem Buyukbingöl、Hakan Göker

  DOI：10.1002/ardp.200500168

  日期：2006.2

  8‐tetramethyl‐5,6,7,8‐tetrahydronaphthalen‐2‐yl)‐1H‐benzimidazole‐5‐carboxamidine analogues were synthesized for their antibacterial and antifungal activities against S. aureus, Methicillin‐resistant S. aureus (MRSA), C. albicans, and C. krusei. MIC values of the targeted compounds 43‐58 are comparable to those of Fluconazole and Sultamicillin. The most potent compounds, 51 and 53, showed MIC values as 0.78 and

  合成了几种 2-(5,5,8,8-四甲基-5,6,7,8-四氢萘-2-基)-1H-苯并咪唑-5-甲脒类似物，因为它们对金黄色葡萄球菌具有抗菌和抗真菌活性，耐甲氧西林金黄色葡萄球菌 (MRSA)、白色念珠菌和克柔念珠菌。目标化合物43-58的MIC值与氟康唑和舒他西林相当。最有效的化合物 51 和 53 对金黄色葡萄球菌和白色念珠菌的 MIC 值分别为 0.78 和 1.56 μg/mL。
• Synthesis, Molecular Docking Studies and Antibacterial Activities of Novel Monocationic Indole-benzimidazole Derivatives
  作者：Zeynep Ates-Alagoz、Mehmet Murat Kisla、Hakan Goker、Sulhiye Yildiz

  DOI：10.2174/1573406416666200420080459

  日期：2021.8

  tend to violate log P limit of Lipinski, therefore some optimizations with formulation can be made. Conclusion: This study mainly includes the design, synthesis and optimization of indolebenzimidazole- amidine derivatives. Docking studies confirmed our results, since our most potent hit compound 36 created the necessary interactions between two chains of MRSA-PK. Further optimization can be considered

  背景：在过去十年中，寻找针对医院获得性 MRSA 感染的有效疗法变得相当重要。为此，正在研究抑制丙酮酸激酶 (PK) 的抗菌活性，因为该酶控制能量产生和代谢通量分布。我们的主要支架由融合在一起的苯并咪唑和吲哚环组成。这两个环都以抗菌特性和有前途的抗 MRSA 化合物（包括吲哚环）而闻名。 方法：开发、合成了几种 1-取代-2-(1H-吲哚-3-基)-N-取代-1H-苯并咪唑-5-甲脒类似物，并评估了它们对金黄色葡萄球菌 (ATCC 25923)、甲氧西林的抗菌活性使用试管稀释法对金黄色葡萄球菌 (MRSA) (ATCC 43300) 和表皮葡萄球菌 (ATCC 12228) 产生耐药性。使用称为 MRSA-丙酮酸激酶的特征蛋白进行了分子对接分析，以评估我们的化合物对耐甲氧西林金黄色葡萄球菌 (MRSA) 的活性。 结果：在所有测试化合物中，最有效的化合物 36 对金黄色葡萄球菌、耐甲氧西林金黄色葡萄球菌
• Synthesis and cytotoxic evaluation of novel N-substituted amidino-1-hydroxybenzimidazole derivatives
  作者：Mehmet Alp、Hakan Göker、Tulin Ozkan、Asuman Sunguroglu

  DOI：10.1007/s12272-013-0197-0

  日期：2014.5

  A new class of N-substituted amidino-1-hydroxybenzimidazole derivatives (15–24) were synthesized and evaluated for their in vitro cytotoxic activities against human leukemia cell lines, HL-60 and K562. The preliminary results showed that compounds 16, 20, 21 and 23 had moderate antitumor activity against HL-60 cell line. Further investigation on the mechanism of the observed cytotoxic effects demonstrated that compound 21 increased the expression of autophagic and apoptotic genes and induced apoptosis of HL-60 cells.

  我们合成了一系列新的N-取代氨基-1-羟基苯并咪唑衍生物（15-24），并评估了它们对人类白血病细胞系HL-60和K562的体外细胞毒性活性。初步结果表明，化合物16、20、21和23对HL-60细胞系具有中等程度的抗肿瘤活性。对观察到的细胞毒性效应机制的进一步研究表明，化合物21可增加自噬和凋亡基因的表达，并诱导HL-60细胞凋亡。
• Novel anti-infection agents: Small-molecule inhibitors of bacterial transcription factors
  作者：Todd E. Bowser、Victoria J. Bartlett、Mark C. Grier、Atul K. Verma、Taduesz Warchol、Stuart B. Levy、Michael N. Alekshun

  DOI：10.1016/j.bmcl.2007.07.072

  日期：2007.10

  Structure-based drug design was utilized to identify potent small-molecule inhibitors of proteins within the AraC family of bacterial transcription factors, which control virulence in medically important microbes. These agents represent a novel approach to fight infectious disease and may be less likely to promote resistance development. These compounds lack intrinsic antibacterial activity in vitro and were able to limit a bacterial infection in a mouse model of urinary tract infection. (c) 2007 Elsevier Ltd. All rights reserved.