acetone oxime acrylate | 145355-61-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: acetone oxime acrylate
• 英文别名: (Propan-2-ylideneamino) prop-2-enoate
• CAS: 145355-61-9
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: PUKZMABSDUJDGX-UHFFFAOYSA-N

物化性质

• 沸点：
  155.8±23.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  acetone oxime acrylate 、 肌苷 以 四氢呋喃 为溶剂， 反应 15.0h， 以80%的产率得到Acrylic acid (2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  A useful and versatile procedure for the acylation of nucleosides through an enzymic reaction

  摘要：

  Lipase-mediated acylation of nucleosides with oxime esters in organic solvents has been achieved. Candida antarctica lipases (SP435 and SP435A) showed high regioselectivity toward the primary hydroxyl group of both deoxy- and ribonucleosides, whereas other lipases exhibited poor results for this goal. 2'-Deoxynucleosides, such as thymidine and 2'-deoxyadenosine, were acylated with oxime esters carrying saturated, unsaturated, aromatic, and functionalized chains, giving 5'-O-acylated compounds together with small quantities of the 3'-O-acylated regioisomer. Uridine, adenosine, and inosine, as representative ribonucleosides, were acylated exclusively at the 5'-OH by using the same methodology. Nucleosides bearing a cytosine ring were found to be unreactive with oxime esters under the same conditions. 2'-Deoxycytidine was acylated with acid anhydrides and C. antarctica lipase to give N,5'-O-diacylated compounds, whereas cytidine gave mixtures, reason for which it had to be previously chemically N-acylated and then subjected to the oxime esters and lipase, giving the same results as ribonucleosides.

  DOI：

  10.1021/jo00055a018
• 作为产物：
  描述：

  丙烯酰氯 、 丙酮肟 以 水 为溶剂， 反应 1.0h， 生成 acetone oxime acrylate
  参考文献：
  名称：

  三嵌段共聚物纳米胶束释放喜树碱和 toll 样受体 7/8 激动剂用于协调化学免疫治疗的顺序酸/还原反应

  摘要：

  免疫抑制性肿瘤免疫微环境 (TIME) 会降低免疫治疗效果。此外，肿瘤区域的低渗透效率和不可预测的药物释放限制了肿瘤治疗。开发了一种三嵌段共聚胶束 (NanoPCPT+PIMDQ)，用于携带化疗药物喜树碱 (CPT) 和 TLR7/8 激动剂 1-(4-(氨基甲基)苄基)-2-丁基-1H-咪唑[4,5-c ] quinoline-4-amine (IMDQ) 通过依次响应酸和还原刺激来实现深度肿瘤穿透和按需药物释放。NanoPCPT+PIMDQ 的协同抗肿瘤功效在体外和体内进行了评估。NanoPCPT+PIMDQ由亲水性PEG（聚乙二醇）外层、酸敏感EPEMA中间层和药物内核组成。瘤内注射后，(i) NanoPCPT+PIMDQ首先响应酸性肿瘤微环境，分解为PIMDQ和PCPT，穿透肿瘤深层；(ii) 肿瘤细胞被释放的 CPT 杀死；(iii) DCs 被 PIMDQ 激活以增加细胞毒性 T

  DOI：

  10.1186/s12951-022-01577-5

文献信息

• [EN] FORCE-RESPONSIVE POLYMERSOMES AND NANOREACTORS; PROCESSES UTILIZING THE SAME<br/>[FR] POLYMERSOMES ET NANORÉACTEURS SENSIBLES À LA FORCE; PROCÉDÉS LES UTILISANT
  申请人：ADOLPHE MERKLE INSTITUTE UNIV OF FRIBOURG

  公开号：WO2019034597A1

  公开（公告）日：2019-02-21

  The mechanically induced melting properties of DNA were employed to achieve force labile membranes is described. Nucleobase pairs were used as mechanophores. Adenine and thymine functionalized complementary amphiphilic block copolymers were self-assembled into polymersomes. The nucleobases formed hydrogen bonds which were disrupted upon force stimulation. The exposure of the disconnected nucleobases to the hydrophobic matrix of the membranes lead to a change of permeability which permitted the exchange of water-soluble molecules throughout the polymer matrix. Moreover, the encapsulation of horseradish peroxidase enabled the reaction of luminol with hydrogen peroxide to yield a luminescence producing species similar to the marine bioluminescence. Moreover, the same nano-reactors were employed to catalyze the formation of a polyacrylamide gel when force was applied. Insights into the change of permeability of supramolecular networks upon force are provided. These systems are useful for drug delivery, as nanoreactors and for the selective release of curing agents for 3D printing, or fragrances.

  DNA的机械诱导熔化特性被用来实现易受力破裂的膜。核碱基对被用作机械感受器。腺嘌呤和胸腺嘧啶功能化的互补两性分块共聚物自组装成聚合体囊。核碱基形成氢键，在受力刺激下被破坏。断开的核碱基暴露在膜的疏水基质中，导致渗透性的改变，从而允许水溶性分子在聚合物基质中交换。此外，封装辣根过氧化物酶使得辣根酰胺与过氧化氢反应产生类似海洋生物发光的发光物种。此外，当施加力时，相同的纳米反应器被用来催化聚丙烯酰胺凝胶的形成。提供了关于受力下超分子网络渗透性变化的见解。这些系统可用于药物传递、纳米反应器以及用于3D打印的固化剂或香料的选择性释放。
• Intramolecular Diels−Alder Reaction of Chiral Silatrienes: Synthesis of 4a,7,8,8a-Tetrahydro-4-silaisochroman-1-ones
  作者：Paulo J. Coelho、Luis Blanco

  DOI：10.1002/1099-0690(200009)2000:17<3039::aid-ejoc3039>3.0.co;2-x

  日期：2000.9

  Intramolecular Diels−Alder reactions of chiral 2-silahexa-3,5-dienyl α,β-unsaturated esters have been found to afford tetrahydro-4-silaisochroman-1-ones in moderate yields. The best diastereoselectivity was achieved in the reaction of silatriene 8c, in which methyl and triisopropylsilyloxymethyl groups are attached to the silicon atom, with an acrylate as the dienophile under EtAlCl2-catalyzed conditions

  已发现手性 2-silahexa-3,5-二烯基 α,β-不饱和酯的分子内 Diels-Alder 反应以中等产率提供四氢-4-silaisochroman-1-ones。最好的非对映选择性是在硅三烯 8c 的反应中实现的，其中甲基和三异丙基甲硅烷氧基甲基连接到硅原子上，丙烯酸酯作为在 EtAlCl2 催化条件下的亲二烯体。
• Macromolecular prodrugs of ribavirin combat side effects and toxicity with no loss of activity of the drug
  作者：Mille B. L. Kryger、Benjamin M. Wohl、Anton A. A. Smith、Alexander N. Zelikin

  DOI：10.1039/c3cc00315a

  日期：——

  Chemi-enzymatic synthesis of ribavirin acrylate and subsequent RAFT co-polymerization with acrylic acid afforded a formulation of a broad spectrum antiviral drug which avoids accumulation in erythrocytes, the origin of the main side effect of ribavirin. In cultured macrophages the macromolecular prodrugs exhibited decreased toxicity while maintaining the anti-inflammatory action of ribavirin.

  利巴韦林丙烯酸酯的化学酶促合成以及随后的RAFT与丙烯酸的共聚反应提供了一种广谱抗病毒药物的配方，该药物可避免在红细胞中积累，这是利巴韦林主要副作用的起源。在培养的巨噬细胞中，大分子前药显示出降低的毒性，同时保持了利巴韦林的抗炎作用。
• Narrow Therapeutic Window of Ribavirin as an Inhibitor of Nitric Oxide Synthesis is Broadened by Macromolecular Prodrugs
  作者：Benjamin M. Wohl、Anton A. A. Smith、Mille B. L. Kryger、Alexander N. Zelikin

  DOI：10.1021/bm401048s

  日期：2013.11.11

  However, this effect was characterized by a rather narrow therapeutic window with experimental values of EC50 and IC50 being 7 and 19 μM, respectively. Macromolecular prodrugs were obtained using an acrylate derivative of RBV, RAFT polymerization technique, and N-vinyl pyrrolidone as a partner monomer. The synthesized polymers were characterized with uniform molecular weights, relatively narrow polydispersities

  利巴韦林（RBV）是一种广谱抗病毒药，是抗丙型肝炎病毒（HCV）的标准药物。然而，尽管在临床上已经取得了数十年的成功，但是这种药物对抗HCV的作用机制仍然是一个争论的话题。此外，不利的药代动力学大大降低了该治疗剂的吸引力。这项跨学科研究有助于理解RBV发挥的细胞内作用，并提出了成功设计RBV的大分子前药以实现更安全的治疗。具体而言，我们证明RBV在培养的巨噬细胞中显示出明显的抗炎活性，这是由使用临床上相关浓度的该药物所产生的一氧化氮水平降低了2倍所证明的。然而，50和IC 50分别为7和19μM。大分子前药是使用RBV的丙烯酸酯衍生物，RAFT聚合技术和N-乙烯基吡咯烷酮作为伙伴单体。合成的聚合物具有均一的分子量，相对窄的多分散性和逐渐增加的RBV含量的特征。所得的聚合物治疗剂有效地将其有效载荷递送至培养的巨噬细胞，并提供了明显更宽的治疗窗口，高达> 1000μM（相对值的18倍）。综上所
• Macromolecular Prodrugs for Controlled Delivery of Ribavirin
  作者：Mille B. L. Kryger、Anton A. A. Smith、Benjamin M. Wohl、Alexander N. Zelikin

  DOI：10.1002/mabi.201300244

  日期：2014.2

  (RBV)‐containing polymers are synthesized based on poly(N‐vinylpyrrolidone) and poly(acrylic acid), two polymers with extensive characterization in biomedicine. The copolymers are shown to exhibit a minor to negligible degree of association with erythrocytes, thus effectively eliminating the origin of the main side effects of RBV. The therapeutic benefit of macromolecular RBV prodrugs is illustrated

  含利巴韦林（RBV）的聚合物是基于聚（N-乙烯基吡咯烷酮）和聚（丙烯酸）合成的，这两种聚合物在生物医学中具有广泛的特性。显示该共聚物与红细胞的结合程度较小至可忽略不计，因此有效消除了RBV主要副作用的根源。与没有相关细胞毒性的原始RBV相比，通过刺激的培养巨噬细胞抑制一氧化氮的刺激产生的大分子RBV前药具有治疗效果，这与基于RBV的治疗明显相反。细胞活力。这些结果特别有助于抗病毒聚合物疗法的发展以及RBV的递送。