acido α-(6-metossi-2-naftil)propionilossiacetico | 97699-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: acido α-(6-metossi-2-naftil)propionilossiacetico
• 英文别名: 2-(6-methoxy-naphthalen-2-yl)-propionic acid carboxymethyl ester；2-((2S)-2-(6-Methoxy(2-naphthyl))propanoyloxy)acetic Acid；2-[2-(6-Methoxynaphthalen-2-yl)propanoyloxy]acetic acid
• CAS: 97699-68-8
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: AFKOPSOLFOZNHU-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  480.5±30.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  acido α-(6-metossi-2-naftil)propionilossiacetico 在 silver nitrate 、 三乙胺 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 24.0h， 生成 2-(6-methoxy-naphthalen-2-yl)-propionic acid 3-nitrooxy-propoxy carbonyl methyl ester
  参考文献：
  名称：

  Controlled Release of Nitric Oxide And Drugs From Functionalized Macromers And Oligomers

  摘要：

  本发明提供了一氧化氮(NO)和可选的药物释放的大分子和寡聚物，其中药物分子和一氧化氮释放部分通过可吸收的大分子或可水解降解的寡聚物链连接，并且大分子或寡聚物由来自诸如乙醇酸、乳酸、己内酰胺和对二恶烷等安全且生物相容的分子的重复单元组成。此外，本发明还涉及从一氧化氮和/或药物分子释放的大分子或寡聚物控制释放一氧化氮(NO)。此外，本发明还涉及包含本发明的一氧化氮和药物释放大分子和寡聚物的医疗器械、医疗器械涂层和治疗方法。

  公开号：

  US20120035259A1
• 作为产物：
  描述：

  2-(6-甲氧基-2-萘基)丙酸 在 氯化亚砜 、 TEA 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 21.0h， 生成 acido α-(6-metossi-2-naftil)propionilossiacetico
  参考文献：
  名称：

  Low-molecular-weight proteins as carriers for renal drug targeting. Preparation of drug-protein conjugates and drug-spacer derivatives and their catabolism in renal cortex homogenates and lysosomal lysates

  摘要：

  Low molecular weight proteins (LMWPs) are known to be reabsorbed and catabolized primarily by the proximal tubular cells of the kidneys. As such, LMWPs might serve as drug carriers that release drugs site-specifically in the kidney. We tested this concept in vitro by coupling different drugs to the LMWP lysozyme both directly (amide bond) and via different spacers: oligopeptides (amide bond), (poly-)alpha-hydroxy acids (ester bond), and a pH sensitive cis-aconityl spacer (amide bond). The capability of the kidney to release the parent drug from such drug-spacer derivatives and drug-LMWP conjugates by enzymatic or chemical hydrolysis of the bond was tested by incubation experiments in renal cortex homogenates and lysosomal lysates. Directly coupled conjugates of terminal carboxyl group containing drugs and lysozyme were catabolized to single amino acids, but did not result in release of the parent drug. The amide bond between the drug and the final amino acid (lysine) appeared to be stable in the incubation milieu. Different oligopeptide spacers coupled to the drugs showed similar results: the oligopeptide itself was cleaved but the amide bond between the drug and different single amino acids remained untouched. Only amide bonds of derivatives of carboxylic drugs with peptide structures themselves were cleaved. Some of the directly coupled conjugates of terminal amino drugs and oligopeptides showed clear release of the parent drug whereas others were stable. Terminal amino drugs were rapidly released from an acid-sensitive cis-aconityl spacer. Terminal carboxyl group containing drugs were enzymatically released from their glycolic and lactic ester spacers at different rates. These kinds of drugs were also released as parent drug from LMWP conjugates with ester spacers like L-lactic acid. Increasing spacer length by intercalating a tetra(L-lactic acid) molecule between the drug and the protein further increased the extent and rate of drug release, indicating increased accessability of the bond to the enzymes. Terminal amino group containing drugs were rapidly generated as parent drug from LMWP conjugates using an acid-sensitive spacer. In addition the conjugates were found to be adequately stable in plasma, considering their rapid clearance from the bloodstream. It is concluded that LMWPs may indeed be of use as carriers for specific renal delivery of drugs, since renal cortex homogenates and lysosomal lysates are able to catabolize the protein and generate the parent drug from drug-LMWP conjugates bearing suitable spacers. The option of enzymatic release is limited by the narrow specificity of the lysosomal enzymes. This has profound implications for the synthesis of suitable conjugates, since the nature of the drug itself, the type of bond, and also spacer length largely determine whether release of the parent drug will occur. Tailor-made spacers containing the correct mode of attachment and the right spacer length are required for this option. Chemical hydrolysis, using acid-sensitive linkers, is suggested as a viable alternative approach.

  DOI：

  10.1021/jm00085a012

文献信息

• ABSORBABLE BRANCHED POLYESTERS AND POLYURETHANES
  申请人：Bezwada Biomedical, LLC

  公开号：US20140142199A1

  公开（公告）日：2014-05-22

  The present invention relates to the discovery of a new class of hydrolysable isocyanates, hydrolysable branched polyols and branched absorbable polyesters and polyurethanes prepared therefrom. The resultant absorbable polymers are useful for drug delivery, stents, highly porous foam, reticulated foam, tissue engineering, tissue adhesives, adhesion prevention, bone wax formulations, medical device coatings, surface modifying agents and other implantable medical devices. In addition, these absorbable polymers can have a controlled hydrolytic degradation profile.

  本发明涉及一种新型可水解异氰酸酯、可水解支链多元醇及其制备的支链可吸收聚酯和聚氨酯的发现。由此得到的可吸收聚合物可用于药物输送、支架、高孔隙率泡沫、网状泡沫、组织工程、组织粘合剂、防止粘连、骨蜡制剂、医疗设备涂层、表面改性剂以及其他可植入医疗设备。此外，这些可吸收聚合物可以具有受控的水解降解特性。
• High molecular weight prodrug derivatives of antiinflammatory drugs
  申请人：Larsen, Claus Selch

  公开号：EP0331471B1

  公开（公告）日：1992-12-16
• Calvi; Picciola; Carenini, Farmaco, Edizione Scientifica, 1985, vol. 40, # 5, p. 334 - 346
  作者：Calvi、Picciola、Carenini、Gentili

  DOI：——

  日期：——
• CALVI, E.;PICCIOLA, G.;CARENINI, G.;GENTILI, P., FARMACO. ED. SCI., 1985, 40, N 5, 335-346
  作者：CALVI, E.、PICCIOLA, G.、CARENINI, G.、GENTILI, P.

  DOI：——

  日期：——
• CONTROLLED RELEASE OF NITRIC OXIDE AND DRUGS FROM FUNCTIONALIZED MACROMERS AND OLIGOMERS
  申请人：Bezwada Biomedical, LLC

  公开号：EP2398761A2

  公开（公告）日：2011-12-28