(2,5-二氧代吡咯烷-1-基)4-氨基苯甲酸酯 | 132445-64-8

• 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: (2,5-二氧代吡咯烷-1-基)4-氨基苯甲酸酯
• 英文名称: 2,5-dioxopyrrolidin-1-yl 4-aminobenzoate
• 英文别名: N-(4-Aminobenzoyloxy)succinimide；(2,5-dioxopyrrolidin-1-yl) 4-aminobenzoate
• CAS: 132445-64-8
• 化学式: C₁₁H₁₀N₂O₄
• 分子量: 234.211
• InChiKey: YCFHABLYVYPXAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  89.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2,5-二氧代吡咯烷-1-基)4-氨基苯甲酸酯 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 (E)-2,5-dioxopyrrolidin-1-yl 4-(((cyclooct-4-en-1-yloxy)carbonyl)amino)benzoate
  参考文献：
  名称：

  Pretargeting kit, method and agents used therein

  摘要：

  描述了一种预靶向方法，以及相关的用于靶向医学成像和/或治疗的试剂盒，其中利用表现出彼此生物正交反应性的无机反应性化学基团。该发明涉及在预靶向探针和效应探针之间提供[4+2]逆电子需求（反）Diels-Alder化学反应的偶联。为此，其中一个探针包括富电子不足的四氮唑或其他适当的二烯，另一个包括一个具有一个或多个轴取代基的E-环辛烯。

  公开号：

  US09463256B2
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 对氨基苯甲酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以31%的产率得到(2,5-二氧代吡咯烷-1-基)4-氨基苯甲酸酯
  参考文献：
  名称：

  Aniline-terminated DNA catalyzes rapid DNA–hydrazone formation at physiological pH

  摘要：

  我们将苯胺有机催化的腙酮形成集成到DNA模板变体中，以特定序列的方式增加DNA-腙酮形成的速率。通过对苯胺有机催化剂的系统优化，我们能够确定一种衍生物，能够将DNA-腙酮形成的速率加速超过未催化变体的85倍以上。

  DOI：

  10.1039/c4cc00292j

文献信息

• LIGHT-ENABLED DRUG DELIVERY
  申请人：Virginia Commonwealth University

  公开号：US20140236071A1

  公开（公告）日：2014-08-21

  Conjugates are provided which comprise a membrane permeable drug linked to a moiety that is not membrane permeable. Attachment of the moiety that is not membrane permeable prevents the drug from crossing cell membranes and entering cells. However, exposure to light either i) breaks the linkage, releasing the drug and allowing it to enter cells; or ii) converts the non-membrane permeable moiety to a membrane permeable form, allowing the entire conjugate to enter the cell, where the drug is released from the conjugate by cleavage. The membrane permeable drugs are thus delivered to cells at locations of interest, e.g. cancer cells in a tumor, in a temporally and spatially controlled manner.

  提供了一种缀合物，该缀合物包括与一个不可透过细胞膜的基团相连的可透过细胞膜的药物。不可透过细胞膜的基团的附着阻止了药物穿过细胞膜并进入细胞。然而，光照要么i）断裂这种连接，释放药物并允许其进入细胞；要么ii）将不可透过细胞膜的基团转化为可透过细胞膜的形式，允许整个缀合物进入细胞，在细胞中药物通过裂解从缀合物中释放。因此，可透过细胞膜的药物以时间和空间可控的方式被递送到感兴趣的位置，例如肿瘤中的癌细胞。
• A versatile strategy for the design and synthesis of novel ADP conjugates and their evaluation as potential poly(ADP-ribose) polymerase 1 inhibitors
  作者：Yuliya V. Sherstyuk、Alexandra L. Zakharenko、Mikhail M. Kutuzov、Polina V. Chalova、Maria V. Sukhanova、Olga I. Lavrik、Vladimir N. Silnikov、Tatyana V. Abramova

  DOI：10.1007/s11030-016-9703-x

  日期：2017.2

  aromatic acid residue. A number of conjugates containing aromatic carboxylic acids were found to inhibit poly(ADP-ribose) synthesis catalyzed by poly(ADP-ribose) polymerase-1 (PARP-1). A new class of potential PARP-1 inhibitors mimicking \(\hbox NAD}^+}\), a substrate in the PARP-1 catalyzed reaction, was proposed. Graphical Abstract

  抽象的开发了一种合成\（\ hbox NAD} ^ +} \）模拟物的通用策略，该策略涉及在含有功能氨基的关键缀合物中有效的焦磷酸盐键形成，该功能键充当进一步衍生化的有用反应性锚。这些\（\ hbox NAD} ^ +} \）模拟物由通过二磷酸链共轭到带有芳族酸残基的扩展脂族连接基上的ADP组成。发现许多包含芳族羧酸的缀合物抑制由聚（ADP-核糖）聚合酶-1（PARP-1）催化的聚（ADP-核糖）合成。提出了一类新的潜在的PARP-1抑制剂，其模仿PARP-1催化反应的底物\（\ hbox NAD} ^ +} \）。 图形概要
• Broad-Specificity Immunoassays for Sulfonamide Detection:  Immunochemical Strategy for Generic Antibodies and Competitors
  作者：Milan Franek、Iva Diblikova、Ivo Cernoch、Maria Vass、Karel Hruska

  DOI：10.1021/ac0514422

  日期：2006.3.1

  Development of antibodies with broad specificity recognition for sulfonamide drugs was found to be surprisingly difficult when conventional immunochemical strategies were applied to hapten design. To improve the cross-reactivity pattern of antibodies for the family of sulfonamide drugs, a novel strategy based on the single-ring (fragment-derived) hapten moieties with different spacer substituent lengths was employed for the preparation of immunogens, coating conjugates, and enzyme competitors. The rabbit antibodies raised against a common (one-ring) p-aminobenzenesulfonamide hapten moiety (attached to a carrier protein through the N-1 position) in combination with a homologous hapten−peroxidase tracer allowed the detection of 15 sulfonamide species at the maximum residue limit level using direct ELISA. The two-ring 6-(4-aminobenzensulfonylamino)hexanoic hapten mimics, previously reported in the literature as a weak generic antigen, generated surprisingly superior immune responses in rabbits. The antibodies raised against this two-ring hapten were capable of detecting at least 19 and 17 sulfonamides in a direct ELISA system at the regulatory level with sensitivities corresponding to 20 and 50% binding inhibition, respectively. A negligible cross-reaction with N4 metabolites makes it possible to measure responses of parent sulfonamides in the presence of their metabolized forms. In skimmed milk, the highest limit of detection (LOD) for sulfacetamide defined as 20% inhibition was 65.2 μg·L-1 (IC20 value), whereas the additional 18 sulfonamides tested exhibited LODs in the range of 0.2−36.8 μg·L-1. This sensitivity allows simple multisulfonamide tests to be established for use in the laboratory or on site.

  开发具有广谱特异性识别磺胺类药物的抗体在应用传统免疫化学策略进行半抗原设计时发现异常困难。为了改善针对磺胺类药物家族的抗体交叉反应模式，采用了基于单环（片段衍生）半抗原母体与不同间隔取代长度的策略来制备免疫原、包被偶联物和酶竞争剂。针对常见（单环）对氨基苯磺酰胺半抗原母体（通过N-1位置连接载体蛋白）以及同源半抗原-过氧化物酶示踪剂，能够利用直接ELISA法检测到15种磺胺类品种在最大残留限量的水平。先前文献报道为弱泛抗原的双环6-（4-氨基苯磺酰氨基）己酸半抗原模拟物，在兔子中引发了显著更优越的免疫反应。针对此双环半抗原产生的抗体能够在一个直接ELISA体系中以对应20%和50%结合抑制的灵敏度分别检测至少19种和17种磺胺类药物。对N4代谢物几乎无交叉反应使得在存在其代谢形式的情况下能够测量母体磺胺类药物的反应。在脱脂牛奶中，以20%抑制定义的最高检测限（LOD），磺胺醋酰为65.2 μg·L-1（IC20值），而另外测试的18种磺胺类药物的LOD范围在0.2−36.8 μg·L-1。这种灵敏度允许在实验室或现场建立简单多磺胺检测。
• PRETARGETING KIT, METHOD AND AGENTS USED THEREIN
  申请人：Lub Johan

  公开号：US20130189184A1

  公开（公告）日：2013-07-25

  Described is a pretargeting method, and related kits, for targeted medical imaging and/or therapeutics, wherein use is made of abiotic reactive chemical groups that exhibit bio-orthogonal reactivity towards each other. The invention involves the use of [4+2] inverse electron demand (retro) Diels-Alder chemistry in providing the coupling between a Pre-targeting Probe and an Effector Probe. To this end one of these probes comprises an electron-deficient tetrazine or other suitable diene, and the other an E-cyclooctene which has one or more axial substituents.

  描述了一种预靶向方法及相关试剂盒，用于靶向医学成像和/或治疗，其中利用表现出生物正交反应性的无机反应性化学基团。该发明涉及使用[4+2]逆电子需求（反）Diels-Alder化学在预靶向探针和效应探针之间提供偶联。为此，其中一种探针包括富电子缺陷的四唑或其他适当的双烯，另一种是具有一个或多个轴取代基的E-环辛烯。
• Decarboxylative Amidation of Aryl/Heteroarylacetic Acids via Activated Esters through Traceless α-Functionalized Benzylic Radicals
  作者：Joydev K. Laha、Upma Gulati、Anjali Gupta

  DOI：10.1021/acs.orglett.3c00927

  日期：2023.5.19

  amide synthesis, a decarboxylative amidation of aryl/heteroarylacetic acids by reaction with NHS and tert-butyl nitrite has been reported to afford both aliphatic and (hetero)aromatic amides in satisfactory yields. Mechanistic studies revealed a previously unexplored pathway for the formation of an activated ester through the generation and subsequent reactions of traceless α-functionalized benzylic

  与传统的酰胺合成不同，据报道，芳基/杂芳基乙酸通过与 NHS 和亚硝酸叔丁酯反应进行脱羧酰胺化，以令人满意的收率提供脂肪族和（杂）芳族酰胺。机理研究揭示了一种以前未探索过的活化酯形成途径，即通过无痕α-官能化苄基自由基的产生和随后的反应，随后与胺进行单锅反应形成酰胺。Moclobemide 的克级合成表明其实际适用性。