单苄基癸二酰氯 | 67852-87-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 单苄基癸二酰氯
• 英文名称: monobenzyl sebacoyl chloride
• CAS: 67852-87-3
• 化学式: C₁₇H₂₃ClO₃
• 分子量: 310.821
• InChiKey: DSHUZDBIOUGBBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  21.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  单苄基癸二酰氯 在 4-二甲氨基吡啶 、 甲酸铵 、 三乙胺 、 1,2-双(二苯基膦)乙烷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 monobenzyl sebacate
  参考文献：
  名称：

  芳基甲基酯作为羧酸，碳酸和氨基甲酸的保护基：通过均相钯催化的氢解脱保护

  摘要：

  通过甲酸根离子进行钯催化的氢解反应，可以还原羧酸的4-喹啉甲基（4-QUI）酯以及碳酸和氨基甲酸的1-萘甲基（1-NAP）酯。反应条件与苄基酯和烯烃双键的存在相容。

  DOI：

  10.1016/s0040-4039(99)01457-4
• 作为产物：
  描述：

  monobenzyl sebacate 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 单苄基癸二酰氯
  参考文献：
  名称：

  用于无定形固体分散体的纤维素ω-羧基酯的合成和结构性能评估。

  摘要：

  非晶态固体分散体（ASD）的使用是一种有效且日益广泛使用的方法，用于增强药物和水溶性差的候选药物的溶解度。药物在聚合物基质中的成功分子分散需要新的聚合物，这些聚合物必须满足所有ASD要求，包括药物释放以及防止药物在储存或从溶液中重结晶。我们在本文中描述了用于ASD的一系列新的纤维素ω-羧基链烷酸酯系列纤维素的设计和合成，方法是使纤维素与长链二元酸反应，该二元酸在一端被单保护为苄基酯，而在另一端被单活化为酰氯。这些纤维素ω-羧基酯的玻璃化转变温度（Tg）超过环境温度至少50°C，从而提供足够的ΔT来防止药物迁移和结晶。用这种方法制备的乙酸纤维素辛二酸酯和癸二酸酯是难溶性抗HIV药物利托那韦的非凡的溶液晶体生长抑制剂。这些新的纤维素ω-羧基酯具有作为ASD聚合物的强大潜力，可以增强药物的溶解度和生物利用度。

  DOI：

  10.1016/j.carbpol.2012.11.049

文献信息

• Synthesis and Biological Evaluation of Oleanolic Acid Derivatives As Inhibitors of Protein Tyrosine Phosphatase 1B
  作者：Shan Qian、Haijiao Li、Yin Chen、Weiyu Zhang、Shengyong Yang、Yong Wu

  DOI：10.1021/np100064m

  日期：2010.11.29

  Protein tyrosine phosphatase 1B (PTP1B) is a negative regulator in the process of insulin signaling and a promising drug target for diabetes and obesity. Derivatives of oleanolic acid were synthesized and evaluated as PTP1B inhibitors. Several derivatives exhibited moderate to good inhibitory activities against PTP1B, with 25f displaying the most promising inhibition (IC50 = 3.12 μM). Structure−activity

  蛋白酪氨酸磷酸酶1B（PTP1B）是胰岛素信号传导过程中的负调节剂，是糖尿病和肥胖症的有希望的药物靶标。合成齐墩果酸的衍生物并评价为PTP1B抑制剂。几种衍生物对PTP1B表现出中等至良好的抑制活性，其中25f表现出最有希望的抑制作用（IC 50 = 3.12μM）。这些衍生物的结构活性关系分析表明，A环和12-烯部分的完整性在保留PTP1B酶抑制活性中很重要。此外，亲水和酸性基团以及齐墩烯与酸部分之间的距离与PTP1B抑制活性有关。25f的可能绑定模式 通过分子对接模拟进行了探索。
• Making Protein Degradation Visible: Discovery of Theranostic PROTACs for Detecting and Degrading NAMPT
  作者：Junfei Cheng、Shipeng He、Jun Xu、Min Huang、Guoqiang Dong、Chunquan Sheng

  DOI：10.1021/acs.jmedchem.2c01243

  日期：2022.12.8

  Proteolysis-targeting chimera (PROTAC) is emerging as a promising technology in targeted protein degradation and drug discovery. However, there is still a lack of effective chemical tools to real-time detect and track the protein degradation. Herein, the first fluorescent and theranostic PROTACs were designed for imaging the degradation of nicotinamide phosphoribosyltransferase (NAMPT) in living cells

  蛋白水解靶向嵌合体 (PROTAC) 正在成为靶向蛋白质降解和药物发现领域的一项有前景的技术。然而，仍然缺乏有效的化学工具来实时检测和跟踪蛋白质降解。在此，第一个荧光和治疗诊断 PROTAC 被设计用于对活细胞中烟酰胺磷酸核糖转移酶 (NAMPT) 的降解进行成像。化合物B4被证明是一种环境敏感的荧光 PROTAC，可有效降解 NAMPT (DC 50 = 8.4 nM)，并实现 A2780 细胞中降解的可视化。作为一种治疗诊断剂，PROTAC B4可显着减少烟酰胺腺嘌呤二核苷酸 (NAD + )，并在体外和体内发挥有效的抗肿瘤活性。总的来说，这项概念验证研究为蛋白质降解过程的实时可视化和提高 PROTAC 的诊断和治疗效果提供了一种新策略。
• Synthesis and Preliminary In vitro Investigation of Bivalent Ligands Containing Homo- and Heterodimeric Pharmacophores at μ, δ, and κ Opioid Receptors
  作者：Xuemei Peng、Brian I. Knapp、Jean M. Bidlack、John L. Neumeyer

  DOI：10.1021/jm050577x

  日期：2006.1.1

  A series of homo- and heterodimeric ligands containing kappa agonist and mu agonist/antagonist pharmacophores joined by a linker chain of varying lengths was synthesized and evaluated in vitro by their binding affinity at mu, delta, and kappa opioid receptors. The functional activities of these compounds were measured in the [S-35]- GTP gamma S binding assay. The data suggest that the stereochemistry of the pharmacophores, the N-substituents of the pharmacophore, ester linkages, and the spacer length were crucial factors for optimum interactions of such ligands at opioid receptor binding sites. These novel ligands as well as their pharmacological properties will serve as the basis for our continuing investigation of such bivalent ligands as probes of the opioid receptor oligomerization phenomena and for in vivo studies as analgesics.
• Synthesis and binding affinity of novel mono- and bivalent morphinan ligands for κ, μ, and δ opioid receptors
  作者：Bin Zhang、Tangzhi Zhang、Anna W. Sromek、Thomas Scrimale、Jean M. Bidlack、John L. Neumeyer

  DOI：10.1016/j.bmc.2011.03.052

  日期：2011.5

  A novel series of homo-and heterodimeric ligands containing kappa/mu agonist and mu agonist/antagonist pharmacophores joined by a 10-carbon ester linker chain were synthesized and evaluated for their in vitro binding affinity at kappa, mu, and delta opioid receptors, and their functional activities were determined at kappa and mu receptors in [S-35] GTP gamma S functional assays. Most of these compounds had high binding affinity at mu and kappa receptors (K-i values less than 1 nM). Compound 15b, which contains butorphan (1) at one end of linking chain and butorphanol (5) at the other end, was the most potent ligand in this series with binding affinity K-i values of 0.089 nM at the mu receptor and 0.073 nM at the kappa receptor. All of the morphinan-derived ligands were found to be partial kappa and mu agonists; ATPM-derived ligands 12 and 11 were found to be full kappa agonists and partial mu agonists. (C) 2011 Elsevier Ltd. All rights reserved.