(2E)-N-(1-hydroxy-2-methylpropan-2-yl)-3-phenylprop-2-enamide | 100098-70-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2E)-N-(1-hydroxy-2-methylpropan-2-yl)-3-phenylprop-2-enamide
• 英文别名: (E)-N-(2-hydroxy-1,1-dimethylethyl) cinnamamide；N-(2-hydroxymethylpropyl-2)-zimtsaeureamid；N-(2-Hydroxy-1,1-dimethylethyl)cinnamamide；(E)-N-(1-hydroxy-2-methylpropan-2-yl)-3-phenylprop-2-enamide
• CAS: 100098-70-2
• 化学式: C₁₃H₁₇NO₂
• mdl: MFCD01736652
• 分子量: 219.283
• InChiKey: HLNXBLMILSOABY-CMDGGOBGSA-N

物化性质

• 沸点：
  436.5±45.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  肉桂酸 在 氯化亚砜 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.5h， 生成 (2E)-N-(1-hydroxy-2-methylpropan-2-yl)-3-phenylprop-2-enamide
  参考文献：
  名称：

  Mehta; Musso; White, European Journal of Medicinal Chemistry, 1985, vol. 20, # 5, p. 443 - 446

  摘要：

  DOI：

文献信息

• Anti-Helicobacter pylori activities of selected N-substituted cinnamamide derivatives evaluated on reference and clinical bacterial strains
  作者：Karolina Klesiewicz、Elżbieta Karczewska、Paweł Nowak、Iwona Skiba-Kurek、Edward Sito、Katarzyna Pańczyk、Paulina Koczurkiewicz、Dorota Żelaszczyk、Elżbieta Pękala、Anna M. Waszkielewicz、Alicja Budak、Henryk Marona、Agnieszka Gunia-Krzyżak

  DOI：10.1038/s41429-018-0027-1

  日期：2018.5

  In this study, thirty-five N-substituted derivatives of cinnamic acid amide (cinnamamide) were evaluated for anti-Helicobacter pylori activity using an agar disc-diffusion method. Qualitative screening was performed on a reference H. pylori strain (ATCC 43504), resulting in the identification of the three most active compounds, 8 (R,S-(2E)-3-(4-chlorophenyl)-N-(2-hydroxypropyl)prop-2-enamide, minimal inhibitory concentration, MIC = 7.5 µg/mL), 23 ((2E)-3-(4-chlorophenyl)-N-(2-hydroxycyclohexyl)prop-2-enamide, MIC = 10 µg/mL), and 28 ((2E)-3-(4-chlorophenyl)-N-(4-oxocyclohexyl)prop-2-enamide, MIC = 10 µg/mL). These compounds were further tested on twelve well-characterized clinical strains, yielding MIC values that ranged from 10 to 1000 µg/mL. Preliminary safety assessments of the compounds were made using the MTT viability test for cytotoxicity and Ames test for mutagenicity, which showed them to be generally safe, although compounds 8 and 28 showed mutagenic activity at some of the tested concentrations. The results of this study showed the anti-H. pylori potential of cinnamamide derivatives.

  在本项研究中，使用琼脂平板扩散法对三十五种N-取代肉桂酸酰胺（肉桂酰胺）衍生物进行了抗幽门螺杆菌活性评估。通过对参考幽门螺杆菌菌株（ATCC 43504）的定性筛选，鉴定出三种最具活性的化合物，分别为8号（R,S-(2E)-3-(4-氯苯基)-N-(2-羟丙基)丙-2-烯酰胺，最小抑制浓度MIC=7.5μg/mL）、23号（(2E)-3-(4-氯苯基)-N-(2-羟环己基)丙-2-烯酰胺，MIC=10μg/mL）和28号（(2E)-3-(4-氯苯基)-N-(4-氧环己基)丙-2-烯酰胺，MIC=10μg/mL）。随后，这些化合物在十二种特征明确的临床菌株上进行了进一步测试，得到的MIC值范围从10到1000μg/mL不等。通过MTT活力度测试评估细胞毒性和Ames试验评估诱变性，对这些化合物进行了初步安全性评估，结果显示它们总体上是安全的，尽管在某些测试浓度下，8号和28号化合物表现出诱变活性。本研究结果表明，肉桂酰胺衍生物具有抗幽门螺杆菌的潜力。
• Anticonvulsant activity, crystal structures, and preliminary safety evaluation of N-trans-cinnamoyl derivatives of selected (un)modified aminoalkanols
  作者：Agnieszka Gunia-Krzyżak、Ewa Żesławska、Karolina Słoczyńska、Paulina Koczurkiewicz、Wojciech Nitek、Dorota Żelaszczyk、Natalia Szkaradek、Anna M. Waszkielewicz、Elżbieta Pękala、Henryk Marona

  DOI：10.1016/j.ejmech.2015.10.051

  日期：2016.1

  Adequate control of seizures remains an unmet need in epilepsy. In order to identify new anticonvulsant agents, a series of N-trans-cinnamoyl derivatives of selected aminoalkanols was synthetized. The compounds were obtained in the reaction of N-acylation carried out in a two-phase system. The substances were tested in animal models of seizures induced either electrically (maximal electroshock - MES; 6-Hz test) or chemically, by subcutaneous injection of pentetrazol (scPTZ). Neurotoxicity was determined by the rotarod test. Lipophilicity of the active compounds, expressed as R-M0, was determined by reversed-phase thin layer chromatography and it ranged from 1.390 to 2.219. From among the tested series of compounds, R,S-(E)-N-(1-hydroxypropan-2-yl)-3-phenylprop-2-enamide (1) and R,S-(E)-N-(2-hydroxypropyl)-3-phenylprop-2-enamide (3) exhibited the best anticonvulsant activity. Compound 1, when administered to mice by intraperitoneal (i.p.) injection, showed the ED50 values of 86.6, 60.9, and 109.6 mg/kg in the MES, 6-Hz, and scPTZ tests, respectively. For compound 3, the ED50 values were found to be 47.1 mg/kg in MES and 77.1 mg/kg in scPTZ (mice, i.p.). The distances measured in crystals of compound 1 were: 7.99 angstrom - from the phenyl ring to the hydroxyl group in the amide moiety, 5.729 angstrom - from the phenyl ring to the amide group, and 3.112 angstrom - from the amide group to the hydroxyl group in the amide moiety. The reported compounds did not exhibit mutagenic potential when assayed in the Ames test. Compounds 1 and 3 did not affect viability and morphology of human hepatocellular carcinoma cells (HepG2). (C) 2015 Elsevier Masson SAS. All rights reserved.
• Mehta; Musso; White, European Journal of Medicinal Chemistry, 1985, vol. 20, # 5, p. 443 - 446
  作者：Mehta、Musso、White

  DOI：——

  日期：——