对羟基苯乙酸N-氧琥珀酰亚胺酯 | 73158-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 对羟基苯乙酸N-氧琥珀酰亚胺酯
• 英文名称: 4-hydroxyphenylacetic acid N-hydroxysuccinimide ester
• 英文别名: 4-hydroxyphenylacetic acid succinimidyl ester；p-hydroxyphenylacetic acid N-oxysuccinimide ester；(2,5-dioxopyrrolidin-1-yl) 2-(4-hydroxyphenyl)acetate
• CAS: 73158-83-5
• 化学式: C₁₂H₁₁NO₅
• 分子量: 249.223
• InChiKey: FCTPLKXSQRUSPT-UHFFFAOYSA-N

物化性质

• 沸点：
  437.1±47.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对羟基苯乙酸N-氧琥珀酰亚胺酯 在 platinum(IV) oxide 吡啶 、 3 A molecular sieve 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 48.0h， 生成 (2,5-Dioxopyrrolidin-1-yl) 2-(4-phosphonooxyphenyl)acetate
  参考文献：
  名称：

  Prodrugs of doxorubicin and melphalan and their activation by a monoclonal antibody-penicillin-G amidase conjugate

  摘要：

  The syntheses and cytotoxic activities of substituted N-phenylacetamido derivatives of doxorubicin and melphalan are described. The derivatives were designed as prodrugs which could be activated in a site-specific manner by monoclonal antibody-penicillin-G amidase (mAb-PGA) conjugates. N-(Phenylacetamido)doxorubicin (2) and N-(phenylacetyl)melphalan (6) were found to be 10- and 20-fold less cytotoxic against H2981 lung adenocarcinoma cells than doxorubicin and melphalan, respectively. When incubated with PGA, the cytotoxicity of 2 and 6 increased and became equivalent to that of the corresponding drugs from which they were made. The poor solubility characteristics of 2 in aqueous solutions provided the basis for the development of the more soluble doxorubicin derivatives, N-(4-aminophenylacetyl)doxorubicin (3) and N-(4-phosphonooxy)phenylacetyl)-doxorubicin (4). In vitro cytotoxicity assays indicated that 3 and 4 were at least 1000-fold less toxic than doxorubicin against H2981 cells. PGA and the mAb conjugate L6-PGA were able to effect the activation of 3 and 6 on H2981 cells (L6-antigen positive). Hydrolysis of the phosphate group of 4 was required prior to activation with PGA or L6-PGA. This was achieved using alkaline phosphatase, or by exposing 4 to phosphatases present in cell culture medium. The activation of 3, 4, and 6 on H2981 cells by L6-PGA occurred in an immunologically specific manner, since activation could be blocked by saturating cell surface antigens with L6 prior to treatment with L6-PGA. These results demonstrate that 3, 4, and 6 are prodrugs that can be specifically activated to release clinically approved anticancer agents by a mAb-PGA conjugate.

  DOI：

  10.1021/jm00059a018
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 对羟基苯乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 以98%的产率得到对羟基苯乙酸N-氧琥珀酰亚胺酯
  参考文献：
  名称：

  新型抗心律失常药。2,2,5,5-四甲基-3-吡咯啉-3-羧酰胺和2,2,5,5-四甲基吡咯烷-3-羧酰胺。

  摘要：

  N-（ω-氨基烷基）-2,2,5,5-四甲基-3-吡咯啉或-吡咯烷-3-羧酰胺通过反应性酸衍生物（酰氯，活化的酯，邻苯二甲酸酐，邻苯二甲酰亚胺，2-烷基-4H-3,1-苯并恶嗪-4-酮）或通过形成席夫碱和随后的硼氢化钠还原将它们烷基化。通过在涉及Favorskii重排的反应中将氨基烷基化合物与2,2,6,6-四甲基-3,5-二溴-4-哌啶酮酰化来合成其他四甲基-3-吡咯啉羧酰胺化合物。一些吡咯啉衍生物的双键的饱和提供了吡咯烷甲酰胺。每种类型的新化合物对乌头碱引起的心律失常均具有活性，其中一些具有比奎尼丁更高的活性和更好的化疗指数。从每种类型的活性新化合物中选出的一些实例显示出对哇巴因引起的心律不齐具有强活性。为了进行比较，选择了已知的药物，如利多卡因，美西律和托卡尼特。最有效的化合物被氧化为顺磁性氮氧化物，后者被还原为N-羟基衍生物。这些产品没有或仅有减少的抗心律失常作用。

  DOI：

  10.1021/jm00157a005

文献信息

• Reaction Discovery by Using a Sandwich Immunoassay
  作者：Julia Quinton、Sergii Kolodych、Manon Chaumonet、Valentina Bevilacqua、Marie-Claire Nevers、Hervé Volland、Sandra Gabillet、Pierre Thuéry、Christophe Créminon、Frédéric Taran

  DOI：10.1002/anie.201201451

  日期：2012.6.18

  Mmm, a reaction sandwich…︁ Using an immunoassay‐based technique able to monitor any kind of cross‐coupling reaction, a systematic and rapid evaluation of a large panel of random reactions was carried out. This approach led to the discovery of two new copper‐promoted reactions: a desulfurization reaction of thioureas leading to isoureas and a cyclization reaction leading to thiazole derivatives from

  嗯，反应夹心……︁使用基于免疫分析的技术能够监测任何种类的交叉偶联反应，对大量随机反应进行了系统，快速的评估。这种方法导致发现了两个新的铜促进的反应：硫脲的脱硫反应导致异脲，环化反应导致炔烃和N-羟基硫脲的噻唑衍生物。
• Cell adhesion inhibitors
  申请人：Biogen, Inc.

  公开号：US06376538B1

  公开（公告）日：2002-04-23

  The present invention relates to novel compounds that are useful for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. This invention also relates to pharmaceutical formulations comprising these compounds and methods of using them for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. The compounds and pharmaceutical compositions of this invention can be used as therapeutic or prophylactic agents. They are particularly well-suited for treatment of many inflammatory and autoimmune diseases.

  本发明涉及一种新型化合物，可用于抑制和预防细胞粘附和细胞粘附介导的病理。本发明还涉及包含这些化合物的药物配方以及使用它们用于抑制和预防细胞粘附和细胞粘附介导的病理的方法。本发明的化合物和药物组合物可用作治疗或预防剂。它们特别适用于治疗许多炎症和自身免疫性疾病。
• PCR incorporation of dUMPs modified with aromatic hydrocarbon substituents of different hydrophilicities: Synthesis of C5-modified dUTPs and PCR studies using Taq, Tth, Vent (exo-) and Deep Vent (exo-) polymerases
  作者：Olga A. Zasedateleva、Sergey A. Surzhikov、Valeriy E. Shershov、Rinat A. Miftakhov、Dmitry A. Yurasov、Viktoriya E. Kuznetsova、Alexander V. Chudinov

  DOI：10.1016/j.bioorg.2020.103829

  日期：2020.6

  been synthesized. The aromatic hydrocarbon substituents were attached to dUTPs via a CHCHCH2NHCOCH2 linker. The efficiency of the PCR incorporation of modified dUMPs using Taq, Tth, Vent (exo-) and Deep Vent (exo-) polymerases and a model DNA template containing one, two and three adjacent adenine nucleotides at three different sites within the sequence was investigated. For all the polymerases used

  已经合成了在嘧啶环的C5位被具有不同亲水性的各种芳烃取代基修饰的脱氧尿苷三磷酸衍生物（dUTP）。芳族烃取代基通过CHCHCH2NHCOCH2连接基连接到dUTP。研究了使用Taq，Tth，Vent（exo-）和Deep Vent（exo-）聚合酶以及在该序列中三个不同位点包含一个，两个和三个相邻腺嘌呤核苷酸的模型DNA模板进行PCR掺入修饰的dUMP的效率。对于所有使用的聚合酶，修饰的PCR产物的产率随着芳烃取代基亲水性的增加而显着提高。特别是对于上述聚合酶，被研究的亲水性最强的芳烃取代基（4-羟基苯基残基）改性的dUMP的掺入效率为dTMP掺入效率的60-85％。同时，被2-，4-甲氧基苯基，苯基和4-硝基苯基取代基修饰的dUMP的掺入相对效率为20％至50％，对于1-萘和4-联苯基为2-18％ ，是所研究的芳烃取代基中疏水性最高的。
• [EN] CELL ADHESION INHIBITORS<br/>[FR] INHIBITEURS DE L'ADHERENCE CELLULAIRE
  申请人：BIOGEN, INC.

  公开号：WO1996022966A1

  公开（公告）日：1996-08-01

  (EN) The present invention relates to novel compounds that are useful for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. This invention also relates to pharmaceutical formulations comprising these compounds and methods of using them for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. The compounds and pharmaceutical compositions of this invention can be used as therapeutic or prophylactic agents. They are particularly well-suited for treatment of many inflammatory and autoimmune diseases.(FR) L'invention concerne de nouveaux composés utiles pour inhiber et prévenir l'adhérence cellulaire, ainsi que les pathologies provoquées par l'adhérence cellulaire. Elle concerne également des compositions pharmaceutiques contenant ces composés, ainsi que des procédés permettant de les utiliser pour inhiber et prévenir l'adhérence cellulaire et les pathologies provoquées par l'adhérence cellulaire. On peut utiliser ces composés et ces compositions pharmaceutiques en tant qu'agents thérapeutiques et prophylactiques. Ils sont particulièrement appropriés pour le traitement de nombreuses maladies inflammatoires et auto-immunes.

  本发明涉及新型化合物，可用于抑制和预防细胞黏附和细胞黏附介导的病理过程。本发明还涉及包含这些化合物的制药配方和使用它们抑制和预防细胞黏附和细胞黏附介导的病理过程的方法。本发明的化合物和制药组合物可用作治疗或预防剂。它们特别适用于治疗许多炎症和自身免疫性疾病。
• POLYMERS FOR DELIVERING MOLECULES OF INTEREST
  申请人：Zuber Guy

  公开号：US20130096177A1

  公开（公告）日：2013-04-18

  The present invention relates to a new class of cationic polymers that self-assemble with a pH-sensitive dissolution switch, and their uses to deliver molecules of interest to a cell. The present invention also relates to compositions comprising said cationic polymers non-covalently associated with a molecule of interest, in particular with a siRNA.

  本发明涉及一种新型阳离子聚合物，它们可以自组装并带有pH敏感的溶解开关，并且它们的用途是将感兴趣的分子传递到细胞中。本发明还涉及包含所述阳离子聚合物的组合物，该组合物与感兴趣的分子非共价地结合，特别是与siRNA结合。