顺式-5-氮杂-4-氧代-辛-2-烯-二酸 | 57079-11-5

• 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
• 中文名称: 顺式-5-氮杂-4-氧代-辛-2-烯-二酸
• 英文名称: N-maleoyl-β-alanine
• 英文别名: N-Maleoyl-β-alanin；N-(3-carboxy-acryloyl)-β-alanine；cis-5-Aza-4-oxo-oct-2-en-dioic Acid；(Z)-4-(2-carboxyethylamino)-4-oxobut-2-enoic acid
• CAS: 57079-11-5
• 化学式: C₇H₉NO₅
• 分子量: 187.152
• InChiKey: JYXLDXBKFBWKOV-UPHRSURJSA-N

物化性质

• 溶解度：
  可溶于DMF、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  顺式-5-氮杂-4-氧代-辛-2-烯-二酸 在 三乙胺 、 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 4.33h， 生成 3-马来酰亚胺基丙酸羟基琥珀酰亚胺酯
  参考文献：
  名称：

  Comblike Dendrimers Containing Tn Antigen Modulate Natural Killing and Induce the Production of Tn Specific Antibodies

  摘要：

  Comblike glycodendrimers were prepared by the chemoselective ligation of cysteine-modified glycopeptides (1-7) with a 3-maleimidopropionate-modified linear synthetic carrier (8). Glycodendrimers bearing mono-, di-, or tri-Tn clusters (9-11) were tested as inhibitors using plant and mammalian lectins. In the former group, the Codium fragile lectin showed moderate discrimination among 9, 10, and 11. In the latter group, A and B isoforms of rat NKR-P1 lectin strongly discriminated between 9 and 10. 10 caused a 4-fold increase in killing of the NK resistant tumor cell lines at concentrations as low as 10(-8) M. Surprisingly, 11 interacted exclusively with the rat NKR-P1B isoform and inhibited efficiently natural killing in both rats and humans, even in the presence of the activating compounds 9 and 10. Dinitrophenol haptenization or influenza virus hemagglutinin T-cell epitope conjugation increased the immunogenicity of the parent compounds and resulted in the production of Tn specific antibodies.

  DOI：

  10.1021/jm050741g
• 作为产物：
  描述：

  马来酸酐 、 β-丙氨酸 以 水 为溶剂， 反应 4.0h， 以69%的产率得到顺式-5-氮杂-4-氧代-辛-2-烯-二酸
  参考文献：
  名称：

  核酸触发了催化药物和探针的释放：化学治疗和诊断试剂设计的新概念。

  摘要：

  最近，我们描述了一种设计高度选择性的抗病毒和抗癌化学治疗剂的新概念，该概念利用疾病特异性核酸序列来模板化前药与催化药物释放的催化剂的缔合。本文中，我们报道了错配，空间位阻和电子学对药物和探针释放速率和特异性的影响，包括两个和三个组件模型系统，以及前药接头在人血清中的稳定性。

  DOI：

  10.1016/s0968-0896(01)00245-0

文献信息

• Linker, Antibody-Drug Conjugate Including Same and Use Thereof
  申请人：Academy of Military Medical Sciences

  公开号：US20210261505A1

  公开（公告）日：2021-08-26

  Provided are a linker represented by Formula I or I′, an antibody-drug conjugate containing the same, and use of thereof, a pharmaceutical composition comprising the antibody-drug conjugate, and use of the antibody-drug conjugate for treating and/or preventing a disease.

  提供的是由公式I或I′表示的连接剂，含有相同抗体-药物偶联物及其用途，包含该抗体-药物偶联物的药物组合物以及使用该抗体-药物偶联物治疗和/或预防疾病的用途。
• Convenient Preparation of<i>N</i>‐Maleoyl Amino Acid Succinimido Esters using<i>N</i>‐Trifluoroacetoxysuccinimide
  作者：Michael J. Paterson、Ian M. Eggleston

  DOI：10.1080/00397910701750151

  日期：2008.1

  Abstract One‐pot cyclization and esterification of readily available maleamic acid derivatives using N‐trifluoroacetoxysuccinimide provide a convenient and cost‐effective route to a variety of useful N‐maleoyl amino acid N‐hydroxysuccinimido esters.

  摘要 使用 N-三氟乙酰氧基琥珀酰亚胺对容易获得的马来酰胺酸衍生物进行一锅环化和酯化，为获得各种有用的 N-马来酰氨基酸 N-羟基琥珀酰亚胺酯提供了一种方便且经济高效的途径。
• Probing Structural Effects on Replication Efficiency through Comparative Analyses of Families of Potential Self-Replicators
  作者：Eleftherios Kassianidis、Russell J. Pearson、Douglas Philp

  DOI：10.1002/chem.200600460

  日期：2006.11.24

  creation of nanoscale molecular structures and supramolecular assemblies through molecular structures can potentially be created from systems that are capable of parallel automultiplication (self-replication). In order to achieve this goal, a detailed understanding of the relationship between molecular structure and replication efficiency is necessary. Diastereoisomeric templates that are capable of specific

  潜在的强大合成设备可以通过分子结构创建纳米级分子结构和通过分子结构的超分子组装，该系统能够进行平行自动倍增（自我复制）。为了实现这个目标，有必要对分子结构和复制效率之间的关系进行详细的了解。已经合成了能够进行特异性和同时自催化的非对映异构模板。对它们的行为以及与结构相关的系统的行为进行系统的实验和理论评估，揭示了决定自我复制功能出现并确定观察该行为的结构空间的关键决定因素。
• Self-replication vs. reactive binary complexes—manipulating recognition-mediated cycloadditions by simple structural modifications
  作者：Russell J. Pearson、Eleftherios Kassianidis、Alexandra M. Z. Slawin、Douglas Philp

  DOI：10.1039/b406862a

  日期：——

  rate of reaction and the selectivity of a Diels-Alder cycloaddition between a furan and a maleimide can be enhanced by the introduction of complementary recognition sites on the reactant species. Subtle manipulation of other structural elements allows the generation of the observed rate enhancements and selectivities through either self-replication or formation of a pre-reactive binary complex.

  通过在反应物种类上引入互补识别位点，可以提高呋喃和马来酰亚胺之间的 Diels-Alder 环加成反应速率和选择性。其他结构元素的微妙操作允许通过自我复制或形成预反应二元复合物来产生观察到的速率增强和选择性。
• On the synthesis of N-maleoyl amino acids in aqueous media: cautionary tales for the unwary traveller
  作者：Michael John Paterson、Aleksandar Jovanovic

  DOI：10.3998/ark.5550190.0011.a02

  日期：——

  cost or protracted syntheses associated with N-maleoyl amino acid derivatives coupled with a considerable demand from both the life and physical sciences has spurred the search for facile, low-cost routes to these compounds. Herein, we demonstrate that a recently published method purporting to deliver N-maleoyl amino acids by cyclization of maleamic acids in water, instead results in a hydrolysis product

  与 N-马来酰氨基酸衍生物相关的高成本或长期合成，加上生命科学和物理科学的巨大需求，促使人们寻找简便、低成本的合成这些化合物的途径。在这里，我们证明了最近发表的一种方法，旨在通过马来酰胺酸在水中的环化来传递 N-马来酰氨基酸，而是产生水解产物，即相应的半马来酸盐。