phthaloylasparic anhydride | 4443-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: phthaloylasparic anhydride
• 英文别名: Phthaloyl-DL-asparaginanhydrid；Phthalylasparaginsaeureanhydrid；N,N-phthaloyl-DL-aspartic acid-anhydride；N,N-Phthaloyl-DL-asparaginsaeure-anhydrid；2-phthalimido-succinic anhydride；2-(2,5-dioxooxolan-3-yl)isoindole-1,3-dione
• CAS: 4443-40-7
• 化学式: C₁₂H₇NO₅
• 分子量: 245.191
• InChiKey: WPBHZDLGZBIMLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phthaloylasparic anhydride 在 乙醇 、 氨 、 水 作用下， 生成 N²,N²-phthaloyl-DL-isoasparagine
  参考文献：
  名称：

  Preparation of Isoasparagine by the Phthaloyl Method

  摘要：

  DOI：

  10.1021/ja01103a527
• 作为产物：
  描述：

  Phthaloyl-Dl-asparaginsaeure 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 phthaloylasparic anhydride
  参考文献：
  名称：

  Synthesis of pyrrolizidine-and indolizidinedione derivatives based on N-phthalylaspartic acid

  摘要：

  A procedure was developed for the synthesis of pyrrolizidine- and indolizidinediones derivatives from the keto-stabilized sulfonium alpha- and beta-ylides of N-phthalylaspartic acid.

  DOI：

  10.1134/s1070428008070117

文献信息

• Studies on Hepatic Agents. I. Synthesis of Aminoacyl (and Hydroxyacyl) Aminoacetonitriles
  作者：SEIGO SUZUE、TUTOMU IRIKURA

  DOI：10.1248/cpb.16.1417

  日期：——

  For the purpose of elucidating the structural relationship between lathyrism and inhibition of necrosis induced by CCl4 in the liver of the rat, many compounds related to aminoacetonitrile were synthesized. N-Aminoacylaminoacetonitriles (VIII, XIV) were synthesized from phthaloylaminoacylaminoacetonitriles. VIII were converted to 2-hydroxyimino-5-oxopiperazine derivatives (XV) and 5-oxo-2-thio-piperazines (XX). Preparations of N-(N-acylaminoacyl) aminoacetonitriles were also described. Further, N-α-hydroxyacylaminoacetonitriles were prepared from chloralides of α-hydroxyacids with aminoacetonitrile. In addition, XV (R=H) was converted to 2-acetamino-5-acetoxypyrazine by treatment with acetic anhydride.

  为了阐明贻贝症与四氯化碳诱导的大鼠肝脏坏死抑制之间的结构关系，合成了许多与氨基乙腈相关的化合物。N-氨基酰氨基乙腈（VIII，XIV）是从邻苯二甲酰氨基酰氨基乙腈合成的。VIII被转化为2-羟基亚胺-5-氧杂哌嗪衍生物（XV）和5-氧-2-硫杂哌嗪（XX）。还描述了N-(N-酰氨基酰)氨基乙腈的制备。此外，N-α-羟基酰氨基乙腈是由α-羟基酸的氯化物与氨基乙腈反应制备的。此外，通过用醋酸无水物处理，XV（R=H）被转化为2-乙酰氨基-5-乙酰氧基吡唑。
• Regioselective functionalization of chiral nickelacycles derived from N-protected aspartic and glutamic anhydrides
  作者：Ana M. Castaño、Antonio M. Echavarren

  DOI：10.1016/s0040-4039(00)97733-5

  日期：1990.1

  The electrophilic cleavage of the nickelacycles resulting from oxidative addition of Ni(0) complexes to N-protected aspartic and glutamic anhydrides, followed by decarbonylation, gives rise regioselectively to derivatives of α-and β-alanine or α-and γ-aminobutyric acid, respectively.

  通过将Ni（0）络合物氧化添加到N保护的天冬氨酸和谷氨酸酐中，然后脱羰作用，镍环的亲电裂解，使α-和β-丙氨酸或α-和γ-氨基丁酸的衍生物在区域上选择性升高，分别。
• Drug Transfer into Living Cells
  申请人：Brecht Andreas

  公开号：US20110014196A1

  公开（公告）日：2011-01-20

  The invention relates to compounds comprising a plurality of enzyme substrates suitably linked and further carrying one or more cargo entities. In particular such compounds have the structure (substrate) n -linker-(cargo) m wherein “substrate” is a substrate specific for an enzyme-type protein; n is 2 or more; “linker” is a linking unit consisting of 1 to 300 atoms; “cargo” is a drug, a label detectable by a fluorescence detector, magnetic resonance imaging (MRI), positron emission tomography (PET) or scintigraphy, or a functional group which can be transformed into a drug or a detectable label; and m is 1 or more. The invention further relates to a corresponding molecular shuttles having the structure (fusion protein) n -linker-(cargo) m wherein “fusion protein” is a proteinaceous binding entity fused to an enzyme-type protein for which specific substrates exist. The proteinaceous binding entity is designed to bind to a target structure in vitro or in vivo, for example a cellular receptor.

  该发明涉及包含多个酶底物的化合物，适当连接并进一步携带一个或多个载体实体。特别是这种化合物具有结构（底物）n-连接物-（载体）m，其中“底物”是特异于酶型蛋白质的底物；n为2或更多；“连接物”是由1至300个原子组成的连接单元；“载体”是一种药物，可被荧光探测器、核磁共振成像（MRI）、正电子发射断层扫描（PET）或闪烁摄影法检测的标记，或者是可转化为药物或可检测标记的功能基团；m为1或更多。该发明还涉及具有结构（融合蛋白）n-连接物-（载体）m的相应分子穿梭体，其中“融合蛋白”是与存在特定底物的酶型蛋白质融合的蛋白质结合实体。蛋白质结合实体设计用于在体外或体内结合到目标结构，例如细胞受体。
• Synthesis and anticancer activity of asparagine analogs
  作者：Michael J. Murphy、James F. Stubbins

  DOI：10.1002/jps.2600690520

  日期：1980.5

  A series of 11 asparagines substituted on N4 was prepared and evaluated for their ability to inhibit the growth of L5178Y leukemia cell cultures. These cells require an exogenous source of L-asparagine and should be sensitive to an asparagine antimetabolite. The compounds were prepared by reaction of phthalylaspartic anhydride with a primary or secondary amine, followed by removal of the phthalyl group

  制备了一系列在N4上取代的11种天冬酰胺，并评估了它们抑制L5178Y白血病细胞培养物生长的能力。这些细胞需要L-天冬酰胺的外源来源，并且应对天冬酰胺抗代谢药物敏感。该化合物是通过邻苯二甲酸酐和伯或仲胺反应，然后用肼除去邻苯二甲酰基而制备的。一种化合物，N，N-二苄基天冬酰胺，显示出明显的活性。值得进一步研究在N4带有较大亲脂基团的天冬酰胺衍生物。
• Synthesis of Aspartic and Glutamic Hydrazides and their Chromatographic and Ionophoretic Separation. C-Terminal Groups of Whale Insulin
  作者：Kozo Narita、Yumiko Ohta

  DOI：10.1246/bcsj.32.1023

  日期：1959.10

  Aspartic α- and β-monohydrazides and aspartic α, β- and glutamic α, γ-dihydrazides were prepared and their qualitative separation has been performed by means of paper ionophoresis and chromatography. During ionophoresis in acidic medium, the dihydrazide partially decomposed into the isomers of monohydrazides liberating hydrazine. The hydrazinolysis products of whale and beef insulins were analyzed by the aid of elution chromatography on a Dowex 50 column and it was observed that the C-terminal positions were occupied by each one mole of alanine and asparagine in both cases. Furthermore, the present experiments suggested that all of the non-terminal carboxyl groups of the hormone belonged to only glutamic acid residues. Complicated reaction of the acidic amino acids or their amides with hydrazine was discussed.

  制备了天冬氨酸α-和β-单酰肼以及天冬氨酸α、β-和谷氨酸α,γ-二酰肼，并通过纸离子电泳和色谱法对其进行了定性分离。在酸性介质中的离子电渗过程中，二酰肼部分分解成一酰肼的异构体，释放出肼。在Dowex 50柱上借助洗脱色谱分析鲸胰岛素和牛胰岛素的肼解产物，观察到在两种情况下C末端位置各被一摩尔丙氨酸和天冬酰胺占据。此外，本实验表明激素的所有非末端羧基仅属于谷氨酸残基。讨论了酸性氨基酸或其酰胺与肼的复杂反应。

表征谱图