4-oxopentyl 4-methylbenzoate | 95483-15-1

• 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-oxopentyl 4-methylbenzoate
• 英文别名: 4-Oxopentyl 4-methylbenzoate
• CAS: 95483-15-1
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: UBGOTPOTMKYJOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  DL-去甲肾上腺素 、 4-oxopentyl 4-methylbenzoate 在 platinum(IV) oxide 氢气 、 溶剂黄146 作用下， 反应 10.0h， 生成 4-[[2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]amino]pentyl 4-methylbenzoate
  参考文献：
  名称：

  Conjugates of Catecholamines. 6. Synthesis and β-Adrenergic Activity of N - (Hydroxyalkyl)catecholamine Derivatives

  摘要：

  A new series of catecholamines has been prepared in which the N-alkyl substituent of dl-epinephrine or dl-isoproterenol has been extended by a methylene chain terminated by a hydroxyl group or derived functionality (e.g., carbamate or ester). These functionalized catecholamines (congeners) and model compounds were prepared with the goal of eventual attachment to polymeric carrier molecules. The beta-adrenergic agonist activity of the derivatives was evaluated in vitro by measuring the intracellular accumulation of cyclic AMP in S49 mouse lymphoma cells and by the displacement of iodocyanopindolol (ICYP). A n-butylcarbamate derivative (compound 15) was the most active compound in this series with a potency 190 times greater than dl-isoproterenol in the S49 assay. The biological results indicate that minor modifications in structure in the N-alkyl substituent of the catecholamine can influence the pharmacologic activity.

  DOI：

  10.1021/jm50001a018
• 作为产物：
  描述：

  5-羟基-2-戊酮 、 对甲基苯甲酰氯 在 吡啶 作用下， 以78%的产率得到4-oxopentyl 4-methylbenzoate
  参考文献：
  名称：

  致力于合成肌苷结构单元，用于制备在核苷酸单元之间具有疏水性烷基链的寡核苷酸。

  摘要：

  本手稿中报告的研究的科学目标是合成用于制备亲脂性寡核苷酸的新型亚磷酰胺构件。在原甲酸三乙酯和 4M HCl 的 1,4-二恶烷中，肌苷 (4) 与 4-氧代戊基-4-甲基苯甲酸酯 (2c) 的反应得到缩酮 5 的非对映异构混合物。 5'-羟基得到(R)-6 + (S)-6，其可通过色谱分离。去甲苯酰化得到化合物(R)-7和(S)-7。7 的非对映异构体混合物的磷酸化导致相应的 2-氰乙基亚磷酰胺 8 的四种非对映异构体的混合物。

  DOI：

  10.3390/molecules14114326

文献信息

• Novel Nucleolipids of Pyrimidine<i>β</i>-<scp>D</scp>-Ribonucleosides: Combinatorial Synthesis, Spectroscopic Characterization, and Cytostatic/Cytotoxic Activities
  作者：Christine Knies、Katharina Hammerbacher、Gabriel A. Bonaterra、Ralf Kinscherf、Helmut Rosemeyer

  DOI：10.1002/cbdv.201500158

  日期：2016.2

  first tested on their cytotoxic effect towards PMA‐differentiated human THP‐1 macrophages. Those compounds which did not exhibit a significant inhibitory effect on the survival of the macrophages were next tested on their cytostatic/cytotoxic effect towards the human astrocytoma/oligodendroglioma GOS‐3 cells as well as against the rat malignant neuroectodermal BT4Ca cell line. Additionally, induction

  已经以组合（非平行！）方式制备了四个系列的以尿苷、5-甲基尿苷、5-氟尿苷和 6-氮杂尿苷作为 β-D-核糖核苷组分的核脂（见公式）。所有化合物均已通过元素分析、ESI 质谱以及 1H-、13C-NMR 和 UV 光谱进行表征。根据早期发现，选择了具有不同亲脂性部分的八种核脂，以及作为对照的 5-氟尿苷，首先测试了它们对 PMA 分化的人 THP-1 巨噬细胞的细胞毒性作用。接下来测试那些对巨噬细胞存活没有显着抑制作用的化合物对人星形细胞瘤/少突胶质细胞瘤 GOS-3 细胞以及大鼠恶性神经外胚层 BT4Ca 细胞系的细胞抑制/细胞毒性作用。此外，评估了细胞系凋亡的诱导。结果证明，特别是通过 2',3'-O-乙基乙酰丙酸酯残基加上相应核脂的嘧啶部分的 N(3) 处的法呢基部分对核苷的组合亲脂化导致了具有最高概率的活性化合物.
• O-2′,3′-Ketal-Nucleolipids of the Cytostatic 5-Fluorouridine: Synthesis, Lipophilicity, and Acidic Stability
  作者：Edith Malecki、Helmut Rosemeyer

  DOI：10.1002/hlca.201000121

  日期：——

  The synthesis of a series of cyclic and acyclic O‐2′,3′‐ketal derivatives of the cancerostatic 5‐fluorouridine (2a) is described. The novel compounds were characterized by 1H‐ and 13C‐NMR, and UV spectroscopy, as well as by elemental analyses. The lipophilicity values (log P, retention times in RP‐18 HPLC) of the cyclic ketals were determined and related to the ring tensions as well as the acid stability

  描述了一系列抗癌的5-氟尿苷（2a）的环状和无环O -2'，3'-缩酮衍生物的合成。新型化合物的特征在于1 H-和13 C-NMR，UV光谱以及元素分析。测定了环状缩酮的亲脂性值（log P，在RP-18 HPLC中的保留时间），并与环张力以及螺旋连接的缩酮环的酸稳定性有关。
• Nucleolipids of Canonical Purine ß‐ <scp>d</scp> ‐Ribo‐Nucleosides: Synthesis and Cytostatic/Cytotoxic Activities Toward Human and Rat Glioblastoma Cells
  作者：Christine Knies、Katharina Hammerbacher、Gabriel A. Bonaterra、Ralf Kinscherf、Helmut Rosemeyer

  DOI：10.1002/open.201500197

  日期：2016.4

  the synthesis of two series of canonical purine ß‐d‐ribonucleoside nucleolipids derived from inosine and adenosine, which have been characterized by elemental analyses, electrospray ionization mass spectrometry (ESI MS) as well as by 1H and 13C NMR, and pH‐dependent UV/Vis spectroscopy. A selection of the novel nucleolipids with different lipophilic moieties were first tested on their cytotoxic effect

  我们报告了由肌苷和腺苷衍生的两个系列经典嘌呤β- d-核糖核苷核苷酸的合成，其特征在于元素分析，电喷雾电离质谱（ESI MS）以及1 H和1313 C NMR和pH依赖的UV / Vis光谱。首先测试选择具有不同亲脂性部分的新型核苷对人巨噬细胞的细胞毒性作用。测试了对巨噬细胞活力无明显抑制作用的化合物对人星形细胞瘤/少突胶质瘤GOS-3细胞以及对大鼠恶性神经外胚层BT4Ca细胞系的细胞抑制/细胞毒性作用。为了进一步研究该衍生物对GOS-3或BT4Ca细胞的细胞毒性作用的潜在分子机制，我们评估了细胞凋亡的诱导作用，并观察了3– 4-‐羟甲基-2-甲基-6-6 [6-氧代-1-（3,7,11-三甲基-十二烷基-2,6,10-三烯基）-1,6-二氢嘌呤-9-基]-四氢呋喃[3,4 -[d] [1,3]二氧-2--2-基}丙酸酯（8 c）体外针对人和大鼠胶质母细胞瘤细胞系。
• Identification of Nucleoside Analogs as Inducers of Neuronal Differentiation in a Human Reporter Cell Line and Adult Stem Cells
  作者：Katharina Raasch、Edith Malecki、Maria Siemann、Malayko M. Martinez、Jürgen J. Heinisch、Janine Müller、Lidia Bakota、Christian Kaltschmidt、Barbara Kaltschmidt、Helmut Rosemeyer、Roland Brandt

  DOI：10.1111/cbdd.12488

  日期：2015.8

  Nucleoside analogs (NSAs) were among the first chemotherapeutic agents and could also be useful for the manipulation of cell fate. To investigate the potential of NSAs for the induction of neuronal differentiation, we developed a novel phenotypic assay based on a human neuron‐committed teratocarcinoma cell line (NT2) as a model for neuronal progenitors and constructed a NT2‐based reporter cell line that expressed eGFP under the control of a neuron‐specific promoter. We tested 38 structurally related NSAs and determined their activity to induce neuronal differentiation by immunocytochemistry of neuronal marker proteins, live cell imaging, fluorometric detection and immunoblot analysis. We identified twelve NSAs, which induced neuronal differentiation to different extents. NSAs with highest activity carried a halogen substituent at their pyrimidine nucleobase and an unmodified or 2′‐O‐methyl substituted 2‐deoxy‐β‐D‐ribofuranosyl residue as glyconic moiety. Cladribine, a purine nucleoside with similar structural features and in use to treat leukemia and multiple sclerosis, induced also differentiation of adult human neural crest‐derived stem cells. Our results suggest that NSAs could be useful for the manipulation of neuronal cell fate in cell replacement therapy or treatment of neurodegenerative disorders. The data on the structure and function relationship will help to design compounds with increased activity and low toxicity.