4-羟基肉桂酸N-羟基琥珀酰亚胺酯 | 88492-43-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 4-羟基肉桂酸N-羟基琥珀酰亚胺酯
• 英文名称: p-coumaric acid N-hydroxy succinimide ester
• 英文别名: (2,5-dioxopyrrolidin-1-yl) (E)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 88492-43-7
• 化学式: C₁₃H₁₁NO₅
• 分子量: 261.234
• InChiKey: DRWSMTDEQTZDSP-FPYGCLRLSA-N

物化性质

• 沸点：
  432.4±47.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  4-羟基肉桂酸N-羟基琥珀酰亚胺酯 在 N-甲基吗啉 、 吡啶 、 pyridinium acetyl sulfate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 Boc-Trp-Lysε-(4-(sulfoxy)cinnamoyl)>-Asp-(NMe)Phe-NH2
  参考文献：
  名称：

  Development of potent and selective CCK-A receptor agonists from Boc-CCK-4: tetrapeptides containing Lys(N.epsilon.)-amide residues

  摘要：

  A series of Boc-CCK-4 derivatives represented by the general structure Boc-Trp-Lys(N(epsilon)-COR)-Asp-Phe-NH2, where R is an aromatic, heterocyclic, or aliphatic group, are potent and selective CCK-AT receptor agonists. These amide-bearing compounds complement the previously described urea-based tetrapeptides (Shiosaki et al. J. Med. Chem. 1991, 34, 2837-2842); structure-activity studies revealed parallel as well as divergent trends between these two series. A significant correlation was observed between pancreatic binding affinity and the resonance constant R of the phenyl substituent in one particular series of derivatives. Sulfation of phenolic amides appended onto the epsilon-amino group of the lysine did not affect affinity for the CCK-AT receptor in contrast to the 500-fold increase in binding potency observed upon sulfation of CCK-8, suggesting that the lysine appendage and the sulfated tyrosine in CCK-8, both key structural elements that impart high affinity for the CCK-A receptor, are interacting differently with the receptor. The amide-bearing tetrapeptides are full agonists relative to CCK-8 in stimulating pancreatic amylase release while being partial agonists in eliciting phosphoinositide (PI) hydrolysis. Both effects were blocked by selective CCK-A receptor antagonists.

  DOI：

  10.1021/jm00089a010
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 4-香豆酸 在 N,N'-二环己基碳二亚胺 作用下， 生成 4-羟基肉桂酸N-羟基琥珀酰亚胺酯
  参考文献：
  名称：

  羽扇豆和羽扇豆中喹诺利西啶生物碱及其肉桂酸酯和羟基肉桂酸酯的酶促合成

  摘要：

  摘要 描述了羽扇豆(Lupinus angustifolius) 和黄花羽扇豆(L. luteus) 幼苗和幼苗发育过程中喹尼西啶生物碱的积累规律。催化 13-羟基羽扇豆氨酸的肉桂酸 O-酯和羽扇豆碱的羟基肉桂酸 O-酯（4-香豆酰-和阿魏酰羽扇豆碱）合成的酶被表征并归类为肉桂酰辅酶 A：13-羟基羽扇豆氨酸 O-肉桂酰转移酶（EC .1.-)和羟基肉桂酰-CoA：羽扇豆碱O-羟基肉桂酰转移酶(EC 2.3. 1.-)。

  DOI：

  10.1016/0031-9422(91)84195-x

文献信息

• Derivatives of tetrapeptides as CCK agonists
  申请人：Abbott Laboratories

  公开号：US05270302A1

  公开（公告）日：1993-12-14

  Selective and potent Type-A CCK receptor agonists of formula (I): X--Y--Z--Q (I) or a pharmaceutically acceptable salt thereof, wherein, X is selected from ##STR1## Y is selected from ##STR2## Z is ##STR3## and Q is ##STR4## or pharmaceutically-acceptable salts thereof, useful in the treatment of gastrointestinal disorders (including gallbladder disorders), central nervous system disorders, insulin-related disorders and pain, as well as in appetite regulation.

  公式（I）的选择性和有效的Type-A CCK受体激动剂为：X--Y--Z--Q（I）或其药学上可接受的盐，其中，X选自##STR1##，Y选自##STR2##，Z为##STR3##，Q为##STR4##或其药学上可接受的盐，可用于治疗胃肠道疾病（包括胆囊疾病）、中枢神经系统疾病、胰岛素相关疾病和疼痛，以及食欲调节。
• The phosphohydrolysis of hydroxycinnamoyl-coenzyme a thioesters in plant extracts
  作者：Jonathan Negrel、Terence A. Smith

  DOI：10.1016/0031-9422(84)83072-1

  日期：1984.1

  Abstract In barley seedling extracts, p -coumaroyl-CoA is rapidly hydrolysed to p -coumaroyl-dephospho-CoA, p -coumaroyl-4′-phosphopantetheine and p -coumaroyl-pantetheine. p -Coumaroyl-4′-phosphopantetheine is active as a substrate of agmatine coumaroyl transferase in the formation of p -coumaroyl-agmatine, but p -coumaroyl-pantetheine is inactive. The phosphohydrolysis can be partly inhibited by inorganic

  摘要 在大麦幼苗提取物中，对香豆酰-CoA 迅速水解为对香豆酰-脱磷酸-CoA、对-香豆酰-4'-磷酸泛酰巯基乙胺和对香豆酰-泛酰巯基乙胺。对香豆酰-4'-磷酸泛酰巯基乙胺在对香豆酰-胍丁胺形成过程中作为胍丁香豆酰转移酶的底物具有活性，但对香豆酰-泛酰巯基乙胺是无活性的。磷酸化水解可被无机焦磷酸盐、氟化钠和嘌呤核苷酸部分抑制。还描述了合成羟基肉桂酸的 N-羟基琥珀酰亚胺酯的简化方法，用于合成 CoA 硫酯。
• [EN] COMPOUNDS AND METHODS FOR TREATING CANCER<br/>[FR] COMPOSÉS ET PROCÉDÉS DE TRAITEMENT DU CANCER
  申请人：SHARE GAL RES AND DEVELOPMENT LTD

  公开号：WO2019111265A1

  公开（公告）日：2019-06-13

  The present invention relates to novel compounds, compositions and methods of preparation thereof, as well as uses thereof for treating cancer of various types, including: pancreatic, liver, breast, colon, brain and lung cancer.

  本发明涉及新颖化合物、组合物及其制备方法，以及用于治疗各种类型癌症的用途，包括：胰腺癌、肝癌、乳腺癌、结肠癌、脑癌和肺癌。
• One-Step Transformation of Coenzyme A into Analogues by Transamidation
  作者：Randy Sanichar、John C. Vederas

  DOI：10.1021/acs.orglett.7b00291

  日期：2017.4.21

  Several coenzyme A (CoA) analogues are made in a single step under mild conditions via transamidation reactions catalyzed by boric acid in water. This approach offers rapid access to compounds useful for the study of a wide spectrum of enzyme catalyzed reactions, especially processes involving acyl carrier proteins (ACP) of polyketide synthases (PKS), fatty acid synthases (FAS), and nonribosomal peptide

  几种辅酶A（CoA）类似物可在温和条件下通过硼酸在水中催化的氨基转移反应一步完成。这种方法为研究广泛的酶催化反应特别是涉及聚酮化合物合酶（PKS），脂肪酸合酶（FAS）和非核糖体肽合成酶（NRPS）的酰基载体蛋白（ACP）的过程提供了快速途径。提出的CoA类似物很容易通过针对特定应用的先有反应进行详细阐述或扩展。
• Formation of hydroxycinnamoylamides and α-hydroxyacetovanillone in cell cultures of Solanum khasianum
  作者：Ute Mühlenbeck、Albertus Kortenbusch、Wolfgang Barz

  DOI：10.1016/0031-9422(96)00173-2

  日期：1996.8

  Abstract In elicitor-treated photomixotrophic Solanum khasianum cell cultures, nine phenolic compounds accumulated in the cell culture medium. They were isolated and structurally identified as the cis - and trans -isomers of N - p -coumaroyloctopamine, N -feruloyloctopamine, N - p -coumaroyltyramine and N -feruloyltyramine as well as α-hydroxyacetovanillone. The cis -isomers of the hydroxycinnamoyl moieties

  摘要 在经过诱导剂处理的光混合营养型 Solanum khasianum 细胞培养物中，细胞培养基中积累了九种酚类化合物。它们被分离出来并在结构上被鉴定为 N-p-香豆酰氯多巴胺、N-阿魏酰氯多巴胺、N-p-香豆酰酪胺和 N-阿魏酰苯胺以及 α-羟基乙酰香草酮的顺式和反式异构体。羟基肉桂酰基部分的顺式异构体仅在培养物光照期间形成。根据化合物的不同，羟基肉桂酰胺在激发后 6 到 24 小时之间显示出最大值。化合物的减少很可能是过氧化物酶介导的反应。