1-[2-(1H-benzimidazol-1-yl)acetyl]-3-carboxyethyl-2,6-diphenyl-4-hydroxy-Δ3-tetrahydropyridine | 1103231-27-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 1-[2-(1H-benzimidazol-1-yl)acetyl]-3-carboxyethyl-2,6-diphenyl-4-hydroxy-Δ3-tetrahydropyridine
• 英文别名: Ethyl 1-(1H-benzimidazol-1-ylacetyl)-4-hydroxy-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate；ethyl 1-[2-(benzimidazol-1-yl)acetyl]-4-hydroxy-2,6-diphenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1103231-27-1
• 化学式: C₂₉H₂₇N₃O₄
• 分子量: 481.551
• InChiKey: AYQPTUIOTFBOQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯并咪唑 、 ethyl 1-(2-bromoacetyl)-4-hydroxy-2,6-diphenyl-3,6-dihydro-2H-pyridine-5-carboxylate 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 1-[2-(1H-benzimidazol-1-yl)acetyl]-3-carboxyethyl-2,6-diphenyl-4-hydroxy-Δ3-tetrahydropyridine
  参考文献：
  名称：

  多种功能化的四氢吡啶-4-醇的合成，晶体和抗菌研究

  摘要：

  在努力扩大与哌啶-4-酮衍生物有关的抗菌活性谱，我们已经合成了两个系列的3-羧乙基-2,6-二苯基-4-羟基- Δ 3四氢吡啶衍生物轴承多样化杂环和芳族系统通过乙酰基（6 – 18）和2-丙酰基（9 – 31）接头在氮原子上连接。与乙酰基衍生物不同，丙酰基对应物的NMR光谱图显示，由于绕N-CO键的旋转受阻，室温下溶液中存在一对旋转异构体（顺式和反式）。9和24的X射线晶体研究清楚地指出，所有化合物特别是仅以一种形式存在，呈固态的稳定合成形式。筛选了每种化合物对九种人类致病性革兰氏阳性菌株（包括多种耐药菌和七种有问题的革兰氏阴性菌株）的体外抗菌活性。在本文研究的各种杂环中，咪唑取代的衍生物12和25表现出的抗菌活性接近Linezolid和Trovafloxacin药物，特别是对多种耐药性粪便肠球菌-VanA表型菌株的抗菌活性。

  DOI：

  10.1016/j.bmcl.2010.02.015

文献信息

• A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives
  作者：Gopalakrishnan Aridoss、Shanmugasundaram Amirthaganesan、Nanjundan Ashok Kumar、Jong Tae Kim、Kwon Taek Lim、Senthamaraikannan Kabilan、Yeon Tae Jeong

  DOI：10.1016/j.bmcl.2008.10.045

  日期：2008.12

  The raise in clinical significance of multidrug-resistant bacterial pathogens has directed us to synthesize 2,6-diarylpiperidin-4-one and Delta(3)-tetrahydropyridin-4-ol based benzimidazole and O-arylsulfonyl derivatives. X-ray crystal structure of tetrahydropyridinol (23) confirmed a change in conformation and orientation of substituents upon amide formation. Antibacterial activities evaluated against a wide number of bacterial pathogens (both sensitive and multidrug-resistant) revealed that 19, 27 against Staphylococcus aureus, 27 against Enterococcus faecalis, and 19, 21, 23, and 27 against Enterococcus faecium are significantly good at lowest MIC90 (16 mu g/mL). Inhibitory power noticed by 23 against Vancomycin-Linezolid-resistant E. faecalis and 27 against Vancomycin-resistant E. faecium are onefold better than the standard Linezolid and Trovafloxacin drugs, respectively. Moreover, antitubercular activity for the selected compounds against Mycobacterium tuberculosis H37Rv revealed that compounds 23, 24, and 27 expressed onefold improved potency compared to the standard Rifampicin drug. (C) 2008 Elsevier Ltd. All rights reserved.