1-(4-hydroxyphenyl)-3-(pyrrolidin-1-yl)propan-1-one | 92041-16-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-hydroxyphenyl)-3-(pyrrolidin-1-yl)propan-1-one
• 英文别名: 1-(4-hydoxyphenyl)-3-(pyrrolidin-1-yl)propan-1-one；4-<3-Pyrrolidino-propionyl>-phenol；4-(3-Pyrrolidino-propionyl)-phenol；1-(4-Hydroxyphenyl)-3-pyrrolidin-1-ylpropan-1-one
• CAS: 92041-16-2
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: JGVBSANSHPJAHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxyphenyl)-3-(pyrrolidin-1-yl)propan-1-one 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 甲醇 、 乙醇 、 苯 为溶剂， 反应 7.5h， 生成 2-(1H-benzo[d]imidazol-2-yl)-1-(1-p-hydroxyphenyl-3-(pyrrolidin-1yl)propyl)hydrazine
  参考文献：
  名称：

  Bishnoi, Abha; Singh, Suruchi; Tiwari, Anil K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 3, p. 325 - 331

  摘要：

  DOI：
• 作为产物：
  描述：

  四氢吡咯 、 聚合甲醛 、 对羟基苯乙酮 生成 1-(4-hydroxyphenyl)-3-(pyrrolidin-1-yl)propan-1-one
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Tacrine Based Acetylcholinesterase Inhibitors

  摘要：

  我们设计、合成并检测了一系列基于他克林的胆碱酯酶抑制剂的生物活性。其中，5 种化合物对乙酰胆碱酯酶的抑制作用在微摩尔范围内，而且大多数化合物对乙酰胆碱酯酶的选择性远远优于参考化合物他克林。

  DOI：

  10.2174/157018010791163532

文献信息

• Design, synthesis, and biological evaluation of acetophenone derivatives as dual binding acetylcholinesterase inhibitors
  作者：Shen, Yanhong、Li, Baoli、Xu, Hu、Zhang, Guoqiang

  DOI：10.1691/ph.2013.2839

  日期：——

  As part of a project aimed at developing new agents for potential application in Alzheimer's disease, a new series of acetophenone derivatives which possess alkylamine side chains were designed, synthesized and assayed as acetylcholinesterase (AChE) inhibitors that could simultaneously bind to the peripheral and catalytic sites of the enzyme. The compounds were synthesized, and the inhibitory activities toward AChE and butyrylcholinesterase (BuChE) in vitro were determined using a modified Ellman method. Of the compounds tested, 6 derivatives were found to inhibit AChE in the micromolar range. The best compound, 2e, had an IC50 of 0.13 μM. A detailed molecular modeling study was performed to explore the interaction of 2e with AChE.

  作为一个旨在开发阿尔茨海默病潜在应用新药的项目，设计、合成并评估了一系列具有烷基胺侧链的乙酰苯酮衍生物，作为能同时结合酶的外周位点和催化位点的乙酰胆碱酯酶（AChE）抑制剂。这些化合物被合成，并使用改良的埃尔曼法确定其对AChE和丁酰胆碱酯酶（BuChE）的抑制活性。在测试的化合物中，发现有6种衍生物在微摩尔范围内抑制了AChE。最佳化合物2e的IC50为0.13 μM。进行了详细的分子建模研究，以探讨2e与AChE的相互作用。
• Design, Synthesis and Evaluation of Tacrine Based Acetylcholinesterase Inhibitors
  作者：Yanhong Shen、Youzhu Yu、Huichao Lv、Liping Feng、Guoqiang Zhang

  DOI：10.2174/157018010791163532

  日期：2010.6.1

  A series of tacrine based cholinesterase inhibitors was designed, synthesized and assayed for their biological activity. Among them, five compounds inhibited acetylcholinesterase in micromolar range and most of the compounds demonstrated much better selectivity for AChE than reference compound tacrine.

  我们设计、合成并检测了一系列基于他克林的胆碱酯酶抑制剂的生物活性。其中，5 种化合物对乙酰胆碱酯酶的抑制作用在微摩尔范围内，而且大多数化合物对乙酰胆碱酯酶的选择性远远优于参考化合物他克林。
• 2-Phenoxy-indan-1-one derivatives as acetylcholinesterase inhibitors: A study on the importance of modifications at the side chain on the activity
  作者：Yanhong Shen、Rong Sheng、Jing Zhang、Qiaojun He、Bo Yang、Yongzhou Hu

  DOI：10.1016/j.bmc.2008.07.014

  日期：2008.8

  As a part of our project aimed at developing new agents of potential application in AD, a new series of 2-phenoxy-indan-1-one derivatives which possess alkylamine side chain were designed, synthesized and evaluated for their inhibitory activity against AChE and BuChE. Most of the compounds were found to inhibit AChE in the nanomolar range. The optimum inhibitor 3g exhibited 34-fold increase in AChE inhibition than donepezil and displayed neuroprotective effect against H2O2-induced cell death. (C) 2008 Elsevier Ltd. All rights reserved.
• [EN] METHOD OF TREATING LUPUS WITH CERAMIDE DERIVATIVES<br/>[FR] MÉTHODE DE TRAITEMENT D'UN LUPUS AVEC DES DÉRIVÉS DE CÉRAMIDE
  申请人：GENZYME CORP

  公开号：WO2009117150A2

  公开（公告）日：2009-09-24

  A method of treating lupus in a subject comprises administering to the subject an effective amount of a compound represented by Structural Formula (1): or a pharmaceutically acceptable salt thereof.
• Evaluation of Cytotoxic Properties of N,N'-bis[(1-aryl-3-heteroaryl)propylidene]-hydrazine dihydrochlorides
  作者：K. Kucukoglu、H. I. Gul、H. Sakagami

  DOI：10.1007/s11094-020-02274-z

  日期：2020.11

  N,N'-bis[(1-aryl-3-heteroaryl)propylidene]hydrazine dihydrochlorides, P1, P4 – P8, and R1 – R7, were assayed against human oral squamous cell carcinoma (HSC-2, HSC-3, HSC-4), human promyelocytic leukemia cell line (HL-60), and human normal oral cells (HGF, HPC, and HPLF) as non-tumor cells to evaluate their cytotoxic properties. Peplomycin was used as a reference compound. It was found that P- and R-series hydrazone compounds exhibited cytotoxicity in a range of 11 ± 0.68 – 300 ± 1.0 ± M. Compound P1 which is a non-substituted hydrazone containing piperidine ring and compound R2 which is a 4-methyl hydrazone derivative containing pyrrolidine ring showed the most potent cytotoxic activity. These hydrazone compounds may serve as promising candidates for further studies.

  N,N'-双[(1-芳基-3-杂芳基)丙烯二亚胺]二盐酸盐（P1，P4-P8，R1-R7）对人类口腔鳞状细胞癌（HSC-2，HSC-3，HSC-4）、人类前髓细胞白血病细胞系（HL-60）以及人类正常口腔细胞（HGF、HPC和HPLF）进行评估，以评价其细胞毒性特性。佩普洛霉素被用作参考化合物。结果发现，P系列和R系列的肼酮化合物在11 ± 0.68 – 300 ± 1.0 ± M范围内表现出细胞毒性。化合物P1是一种含有哌啶环的非取代肼酮，化合物R2是一种含有吡咯烷环的4-甲基肼酮衍生物，显示出最强的细胞毒活性。这些肼酮化合物可能成为进一步研究的有前景的候选者。