3-azidopropyl 4-cyano-4-thiobenzoylsulfanylpentanoate | 927816-04-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-azidopropyl 4-cyano-4-thiobenzoylsulfanylpentanoate
• 英文别名: 3-azidopropyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate；3-Azidopropyl 4-cyano-4-thiobenzoylsulfanyl-pentanoate；3-azidopropyl 4-(benzenecarbonothioylsulfanyl)-4-cyanopentanoate
• CAS: 927816-04-4
• 化学式: C₁₆H₁₈N₄O₂S₂
• 分子量: 362.477
• InChiKey: QZQHNJMNVVRJRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-azidopropyl 4-cyano-4-thiobenzoylsulfanylpentanoate 、 1-ethynyl cobaltocenium hexafluorophosphate 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 以34%的产率得到
  参考文献：
  名称：

  阳离子Cobaltocenium Mechanophore的机械化学

  摘要：

  最近对茂金属机械团机械化学的研究揭示了这些热和化学稳定的有机金属化合物的力响应性。在这项工作中，我们报告了对主链二茂钴聚合物的机械化学的实验和计算研究的结合。阳离子二茂铁的酯衍生物虽然与中性二茂铁等电子，但在其二茂铁类似物所适应的非机械控制实验条件下是不稳定的。用供电子的 C-烷基取代吸电子的 C-酯键赋予必要的稳定性，并使二茂钴的机械化学得以评估。尽管它们的键解离能很高，在声力学激活下，Cococenium 机械载体是主链断裂的选择性位点。计算 CoGEF 计算表明，CoGEF 的反离子的存在通过促进与初始滑动相结合的解离剥离机制发挥着至关重要的作用。

  DOI：

  10.1021/jacs.1c05233
• 作为产物：
  描述：

  3-叠氮基丙醇 、 4-氰基-4-(硫代苯甲酰)戊酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到3-azidopropyl 4-cyano-4-thiobenzoylsulfanylpentanoate
  参考文献：
  名称：

  Versatile grafting approaches to star-shaped POSS-containing hybrid polymers using RAFT polymerization and click chemistry

  摘要：

  含炔基的多面体低聚倍半硅氧烷（POSS）核被用于利用“接枝到”或“从接枝”策略结合可逆链转移和点击化学制备含POSS的聚合物杂化材料。

  DOI：

  10.1039/c1cc13412d

文献信息

• Versatile grafting approaches to star-shaped POSS-containing hybrid polymers using RAFT polymerization and click chemistry
  作者：Yun-Sheng Ye、Wei-Chung Shen、Chi-Yung Tseng、John Rick、Yao-Jheng Huang、Feng-Chih Chang、Bing-Joe Hwang

  DOI：10.1039/c1cc13412d

  日期：——

  An alkyne-bearing polyhedral oligomeric silsesquioxane (POSS) core was used to prepare POSS-containing polymer hybrids using ‘grafting to’ or ‘grafting from’ strategies in combination with reversible chain transfer and click chemistry.

  含炔基的多面体低聚倍半硅氧烷（POSS）核被用于利用“接枝到”或“从接枝”策略结合可逆链转移和点击化学制备含POSS的聚合物杂化材料。
• Polymeric drug delivery conjugates and methods of making and using thereof
  申请人：Pan Huaizhong

  公开号：US09289510B2

  公开（公告）日：2016-03-22

  Described herein are biodegradable drug delivery conjugates for effectively delivering bioactive agents to a subject. The drug delivery conjugates comprise a water-soluble high molecular weight linear biodegradable polymer backbone comprising a plurality of linear water-soluble polymeric segments connected to one another by a first (main-chain) cleavable linker, wherein a bioactive agent is covalently bonded to at least one water-soluble polymeric segment, at least one cleavable linker, or a combination thereof. The conjugates possess numerous advantages over prior art delivery conjugates. Also described herein are methods for making and using the conjugates.

  本文描述了一种可降解的药物传递共轭物，用于有效地将生物活性剂传递给受试者。药物传递共轭物包括水溶性高分子量线性可降解聚合物骨架，该骨架包括通过第一（主链）可切割连接子连接在一起的多个线性水溶性聚合物段，其中生物活性剂与至少一个水溶性聚合物段、至少一个可切割连接子或二者的组合共价结合。这些共轭物相对于先前技术的传递共轭物具有许多优点。本文还描述了制备和使用这些共轭物的方法。
• RAFT and click chemistry: A versatile approach to well-defined block copolymers
  作者：Damien Quémener、Thomas P. Davis、Christopher Barner-Kowollik、Martina H. Stenzel

  DOI：10.1039/b611224b

  日期：——

  The combination of reversible chain transfer chemistry with highly orthogonal [2 + 3] cycloadditions (‘click chemistry’) allows for the synthesis of well-defined block copolymers of monomers with extremely disparate reactivities.

  可逆链转移化学与高度正交的[2 + 3]环加成反应（“点击化学”）的结合，使得合成具有极其不同反应性的单体的明确区分的嵌段共聚合物成为可能。
• Reactive Oxygen Species (ROS)-Responsive Polymersomes with Site-Specific Chemotherapeutic Delivery into Tumors via Spacer Design Chemistry
  作者：Eliézer Jäger、Vladimir Sincari、Lindomar J. C. Albuquerque、Alessandro Jäger、Jana Humajova、Jan Kucka、Jan Pankrac、Petr Paral、Tomas Heizer、Olga Janouskova、Rafał Konefał、Ewa Pavlova、Ondrej Sedlacek、Fernando C. Giacomelli、Pavla Pouckova、Ludek Sefc、Petr Stepanek、Martin Hruby

  DOI：10.1021/acs.biomac.9b01748

  日期：2020.4.13

  The lack of cellular and tissue specificities in conventional chemotherapies along with the generation of a complex tumor microenvironment (TME) limits the dosage of active agents that reaches tumor sites, thereby resulting in ineffective responses and side effects. Therefore, the development of selective TME-responsive nanomedicines is of due relevance toward successful chemotherapies, albeit challenging. In this framework, we have synthesized novel, ready-to-use ROS-responsive amphiphilic block copolymers (BCs) with two different spacer chemistry designs to connect a hydrophobic boronic ester-based ROS sensor to the polymer backbone. Hydrodynamic flow focusing nanoprecipitation microfluidics (MF) was used in the preparation of well-defined ROS-responsive PSs; these were further characterized by a combination of techniques [1H NMR, dynamic light scattering (DLS), static light scattering (SLS), transmission electron microscopy (TEM), and cryogenic TEM (cryo-TEM)]. The reaction with hydrogen peroxide releases an amphiphilic phenol or a hydrophilic carboxylic acid, which affects polymersome (PS) stability and cargo release. Therefore, the importance of the spacer chemistry in BC deprotection and PS stability and cargo release is herein highlighted. We have also evaluated the impact of spacer chemistry on the PS-specific release of the chemotherapeutic drug doxorubicin (DOX) into tumors in vitro and in vivo. We demonstrate that by spacer chemistry design one can enhance the efficacy of DOX treatments (decrease in tumor growth and prolonged animal survival) in mice bearing EL4 T cell lymphoma. Side effects (weight loss and cardiotoxicity) were also reduced compared to free DOX administration, highlighting the potential of the well-defined ROS-responsive PSs as TME-selective nanomedicines. The PSs could also find applications in other environments with high ROS levels, such as chronic inflammations, aging, diabetes, cardiovascular diseases, and obesity.

  常规化疗中缺乏细胞和组织特异性，加上复杂的肿瘤微环境（TME）的形成，限制了有效药物到达肿瘤部位的剂量，从而导致疗效不佳和副作用。因此，开发选择性TME响应的纳米药物对成功的化疗具有重要意义，尽管这具有挑战性。在此背景下，我们合成了新型的即用型ROS响应性两亲区块共聚物（BCs），采用两种不同的间隔化学设计，将疏水性硼酸酯基ROS传感器连接到聚合物主链上。通过水动力聚焦纳米沉淀微流体（MF）技术制备了定义良好的ROS响应性聚合体（PSs）；随后使用多种技术对其进行了表征[1H NMR、动态光散射（DLS）、静态光散射（SLS）、透射电子显微镜（TEM）和冷冻透射电子显微镜（cryo-TEM）]。与过氧化氢反应释放出两亲性酚或亲水性羧酸，影响聚合体（PS）的稳定性和载荷释放。因此，间隔化学在BC去保护、PS稳定性和载荷释放中的重要性在此得到了强调。我们还评估了间隔化学对PS特异性释放化疗药物多柔比星（DOX）至肿瘤的影响，包括体外和体内实验。我们证明，通过间隔化学设计可以增强DOX治疗的效果（肿瘤生长减缓和动物存活时间延长），在携带EL4 T细胞淋巴瘤的小鼠中。与游离DOX给药相比，副作用（体重减轻和心脏毒性）也有所减少，突显了定义良好的ROS响应性PS作为TME选择性纳米药物的潜力。PS还可以在其他高ROS水平的环境中应用，如慢性炎症、衰老、糖尿病、心血管疾病和肥胖等。
• POLYMERIC DRUG DELIVERY CONJUGATES AND METHODS OF MAKING AND USING THEREOF
  申请人：Kopecková Pavla

  公开号：US20130156722A1

  公开（公告）日：2013-06-20

  Described herein are biodegradable drug delivery conjugates for effectively delivering bioactive agents to a subject. The drug delivery conjugates comprise a water-soluble high molecular weight linear biodegradable polymer backbone comprising a plurality of linear water-soluble polymeric segments connected to one another by a first (main-chain) cleavable linker, wherein a bioactive agent is covalently bonded to at least one water-soluble polymeric segment, at least one cleavable linker, or a combination thereof. The conjugates possess numerous advantages over prior art delivery conjugates. Also described herein are methods for making and using the conjugates.

  本文描述了一种可生物降解的药物传递共轭物，用于有效地将生物活性物质传递给受试者。药物传递共轭物包括水溶性高分子量线性可生物降解聚合物骨架，该骨架包括通过第一（主链）可断裂连接剂相互连接的多个线性水溶性聚合物段，其中生物活性物质与至少一个水溶性聚合物段，至少一个可断裂连接剂或其组合共价键合。与先前的传递共轭物相比，这些共轭物具有许多优点。本文还描述了制备和使用这些共轭物的方法。