p-Ethylbenzamidine hydrochloride | 29147-96-4

• 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: p-Ethylbenzamidine hydrochloride
• 英文别名: 4-Ethyl-benzamidin-hydrochlorid；p-ethylbenzamidinium chloride；4-Ethylbenzene-1-carboximidamide hydrochloride；4-ethylbenzenecarboximidamide;hydrochloride
• CAS: 29147-96-4
• 化学式: C₉H₁₂N₂*ClH
• mdl: MFCD19381940
• 分子量: 184.669
• InChiKey: KVZPICRJHAAEDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  49.9
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  p-Ethylbenzamidine hydrochloride 、 5-氰基-2-氟苯甲醛 在 potassium peroxomonocarbonate 、 4 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以69%的产率得到6-Cyano-2-(4-ethylphenyl)quinazoline
  参考文献：
  名称：

  A New Quinazoline Synthesis

  摘要：

  氰基和硝基活化的邻氟苯甲醛与脒类在回流的乙腈中，在K2CO3和4A型粉末分子筛的存在下，进行缩合反应，以良好的收率得到了多种喹唑啉衍生物。

  DOI：

  10.1055/s-1999-2998
• 作为产物：
  描述：

  4-乙基苯甲腈 在 盐酸 、 氨 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 59.0h， 生成 p-Ethylbenzamidine hydrochloride
  参考文献：
  名称：

  Understanding Binding Affinity:  A Combined Isothermal Titration Calorimetry/Molecular Dynamics Study of the Binding of a Series of Hydrophobically Modified Benzamidinium Chloride Inhibitors to Trypsin

  摘要：

  The binding of a series of p-alkylbenzamidinium chloride inhibitors to the serine proteinase trypsin over a range of temperatures has been studied using isothermal titration (micro)calorimetry and molecular dynamics simulation techniques. The inhibitors have small structural variations at the para position of the benzamidinium ion. They show small differences in relative binding affinity but large compensating differences in enthalpy and entropy. Binding affinity decreases with increased branching at the first carbon but increases with increasing the length of a linear alkyl substituent, suggesting that steric hindrance and hydrophobic interactions play dominant roles in binding. Structural analysis showed that the backbone of the enzyme was unaffected by the change of the para substituent. In addition, binding does not correlate strongly with octanol/water partition data. To further characterize this system, the change in the heat capacity on binding, the change in solvent-accessible surface area on binding, the effect of inhibitor binding on the hydration of the active site, the pK(a) of His57, and interactions within the catalytic triad have been investigated. Although the changes in inhibitor structure are small, it is demonstrated that simple concepts such as steric hindrance, hydrophobicity, and buried surface area are insufficient to explain the binding data. Other factors, such as access to the binding site and the cost of dehydration of the active site, are of equal or greater importance.

  DOI：

  10.1021/ja034676g

文献信息

• Pyrazolopyrimidines: Potent Inhibitors Targeting the Capsid of Rhino- and Enteroviruses
  作者：Vadim A. Makarov、Heike Braun、Martina Richter、Olga B. Riabova、Johannes Kirchmair、Elena S. Kazakova、Nora Seidel、Peter Wutzler、Michaela Schmidtke

  DOI：10.1002/cmdc.201500304

  日期：2015.10

  characterization of pyrazolopyrimidines, a well‐tolerated and potent class of novel EV inhibitors. The compounds inhibit the replication of a broad spectrum of EV in vitro with IC50 values between 0.04 and 0.64 μM for viruses resistant to pleconaril, a known capsid‐binding inhibitor, without affecting cytochrome P450 enzyme activity. Using virological and genetics methods, the viral capsid was identified

  当前尚无可用于治疗由肠病毒（EV）引起的急性和慢性疾病的药物，例如普通感冒，脑膜炎，脑炎，肺炎和心肌炎，伴或不伴连续性扩张性心肌病。在这里，我们报告吡唑并嘧啶的发现和表征，吡唑并嘧啶是一类耐受性强且有效的新型EV抑制剂。化合物抑制EV的体外广谱与IC的复制50值之间的0.04和0.64μ中号适用于对pleconaril（一种已知的衣壳结合抑制剂）有抗性的病毒，而不会影响细胞色素P450酶的活性。使用病毒学和遗传学方法，病毒衣壳被确定为最有希望的，口服生物利用的化合物3-（4-三氟甲基苯基）氨基-6-苯基吡唑并[3,4- d ]嘧啶-4-胺（OBR-5 ）的靶标-340）。柯萨奇病毒B3引起的小鼠慢性心肌炎的预防性和治疗性应用都得到了证明。小鼠体内良好的药代动力学，毒理学和药效学特征使OBR-5340成为高度有前途的候选药物，并且正在进行非临床监管计划。
• Interaction of 2-aryl-4-cyano-1,3-oxazole-5-sulfonyl chlorides with amidines
  作者：A. N. Kornienko、S. G. Pil’o、V. M. Prokopenko、E. B. Rusanov、V. S. Brovarets

  DOI：10.1134/s1070363213070165

  日期：2013.7

  Reaction of 4-cyano-1,3-oxazole-5-sulfonyl chlorides with amidines results in new 7-amino-1,3-oxazolo[5,4-d]pyrimidines. Their structure was confirmed by spectral methods and X-ray diffraction analysis.
• Biering, A.; Demus, D.; Lichter, L., Molecular Crystals and Liquid Crystals (1969-1991), 1980, vol. 62, p. 1 - 24
  作者：Biering, A.、Demus, D.、Lichter, L.、Sackmann, H.、Wiegeleben, A.、et al.

  DOI：——

  日期：——
• Synthesis of methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates and their reactions with amines and amidines
  作者：A. N. Kornienko、S. G. Pil’o、V. M. Prokopenko、V. S. Brovarets

  DOI：10.1134/s1070363214080210

  日期：2014.8

  Previously unknown methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates have been synthesized. Their reactions with amines and amidines have yielded the corresponding sulfonamides and 6H, 7H-[1,3]oxazolo[5,4-d] pyrimidin-7-ones.
• Kraus, G.; Zaschke, H., Journal fur praktische Chemie (Leipzig 1954), 1981, vol. 323, # 2, p. 199 - 206
  作者：Kraus, G.、Zaschke, H.

  DOI：——

  日期：——