(E)-2,5-dioxopyrrolidin-1-yl 3-(4-methoxyphenyl)acrylate

• 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
• 英文名称: (E)-2,5-dioxopyrrolidin-1-yl 3-(4-methoxyphenyl)acrylate
• 英文别名: (2,5-dioxopyrrolidin-1-yl) (E)-3-(4-methoxyphenyl)prop-2-enoate
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: LFQSOFCYBLZLOY-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-2,5-dioxopyrrolidin-1-yl 3-(4-methoxyphenyl)acrylate 在 碳酸氢钠 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 51.0h， 生成 N-(4-methoxycinnamoyl)glycine sodium salt
  参考文献：
  名称：

  신남산으로부터 제조한 미백 기능성 유도체

  摘要：

  本发明涉及从新南山制备的美白功能衍生物，更详细地说，涉及化学式1中的N-丙酰氨基酸衍生物和化学式2中的N-丙酰二肽衍生物。根据本发明，N-丙酰氨基酸衍生物和N-丙酰二肽通过抑制酪氨酸酶酶活性具有美白功效，并可用于美白功能化妆品。[化学式1] [化学式2] 在上述化学式1和2中，R表示H，C-C的烷基，卤素基，甲氧基，乙氧基，羟基，氨基，芳香族或杂环芳香族基。R和R表示H，C-C的烷基，-CHCHCOOH，-CHCHCHCOOH，芳香族或杂环芳香族基。

  公开号：

  KR20170010496A
• 作为产物：
  描述：

  (e)-p-甲氧基肉桂酸甲酯 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 (E)-2,5-dioxopyrrolidin-1-yl 3-(4-methoxyphenyl)acrylate
  参考文献：
  名称：

  Very Short and Efficient Syntheses of the Spermine Alkaloid Kukoamine A and Analogs Using Isolable Succinimidyl Cinnamates

  摘要：

  摘要 用多种可分离的琥珀酰亚胺基肉桂酸酯对精胺和亚精胺的初级氨基功能进行直接选择性酰化，然后进行催化氢化反应，可获得高产率的精胺生物碱 Kukoamine A 和适合结构-活性关系研究的类似物。通过芳香醛与酰化物 Ph3P=CRCO2Me 的 Wittig 反应，然后在 N,N′-二环己基碳二亚胺存在下用 N-hydroxysuccinimide 进行皂化和活化，很容易获得合适的琥珀酰亚胺肉桂酸盐。

  DOI：

  10.1246/cl.2005.264

文献信息

• Development of potent and selective CCK-A receptor agonists from Boc-CCK-4: tetrapeptides containing Lys(N.epsilon.)-amide residues
  作者：Kazumi Shiosaki、Chun Wel Lin、Hana Kopecka、Richard A. Craig、Bruce R. Bianchi、Thomas R. Miller、David G. Witte、Michael Stashko、Alex M. Nadzan

  DOI：10.1021/jm00089a010

  日期：1992.5

  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.
• Substrate Specificity of Chalcone Synthase:  Enzymatic Formation of Unnatural Polyketides from Synthetic Cinnamoyl-CoA Analogues
  作者：Ikuro Abe、Hiroyuki Morita、Ayumi Nomura、Hiroshi Noguchi

  DOI：10.1021/ja0027113

  日期：2000.11.1
• Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship
  作者：Antonio Maciel Fregnan、Guilherme Andrade Brancaglion、Alexandre Francisco Cerqueira Galvão、Cinara Oliveira D’Sousa Costa、Diogo Rodrigo Magalhães Moreira、Milena Botelho Pereira Soares、Daniel Pereira Bezerra、Naiara Chaves Silva、Stella Maria de Souza Morais、Josidel Conceição Oliver、Amanda Latercia Tranches Dias、Luiz Felipe Leomil Coelho、Diogo Teixeira Carvalho、Danielle Ferreira Dias、Thiago Belarmino de Souza

  DOI：10.1007/s00044-016-1774-9

  日期：2017.3

  In this work it is described the synthesis, characterization and antimicrobial and toxicity evaluation of a series of analogs of piplartine, a piperamide found in Piper sp. The compounds structures were confirmed by infrared spectroscopy, H-1, C-13 nuclear magnetic resonance, high resolution mass spectroscopy and were evaluated against strains of Candida spp., Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Derivative 24 was almost four-fold more potent (IC50: 48.83 mu M) and five-fold less toxic (SI > 3) than piplartine (IC50: 189.2 mu M; SI: 0.21) against Candida krusei, as well as two-fold more potent than fluconazole (IC50: 104.48 mu M). This compound was also active against Candida tropicalis at 97.67 mu M. Benzoyl derivative 17 was three-fold more potent (IC50: 85.2 mu M) and more than five-fold less toxic (CC50: 231.71 mu M) than piplartine (IC50: 315.33 mu M and CC50: 41.14 mu M) against Staphylococcus aureus. Given these findings, we have found analogs of piplartine which can be assumed as prototypes for the optimization and the development of new antimicrobial (compounds 24 and 17) agents.
• [EN] DERIVATIVES OF TETRAPEPTIDES AS CCK AGONISTS
  申请人：ABBOTT LABORATORIES

  公开号：WO1990006937A1

  公开（公告）日：1990-06-28

  (EN) Tetrapeptide analogs are disclosed which possess CCK agonist activity.(FR) Les analogues de tétrapeptides décrits possèdent une activité similaire à la cholécystokinine (CCK).
• 신남산으로부터 제조한 미백 기능성 유도체
  申请人：N. CosmeCeu Co. 주식회사 앤코스메슈(120140132229) Corp. No ▼ 214911-0039290BRN ▼403-81-70441

  公开号：KR20170010496A

  公开（公告）日：2017-02-01

  본 발명은 신남산으로부터 제조한 미백 기능성 유도체에 관한 것으로, 더욱 상세하게는 아래 화학식 1의 N-신나모일아미노산 유도체와 화학식 2의 N-신나모일디펩티드 유도체에 관한 것이다. 본 발명에 따른 N-신나모일아미노산 유도체 및 N-신나모일디펩티드는 티로시나제 효소 활성을 저해함으로써 미백 효능을 보유하고 있으며, 미백 기능성 화장품의 용도로 제공될 수 있다. [화학식 1] [화학식 2] 상기 화학식 1 및 2에서 R은 H, C-C의 알킬, 할로겐기, 메톡시, 에톡시, 히드록시, 아미노, 방향족 또는 헤테로 방향족기를 나타낸다. R 및 R는 H, C-C의 알킬, -CHCHCOOH, -CHCHCHCOOH, 방향족 또는 헤테로 방향족기를 나타낸다.

  本发明涉及从新南山制备的美白功能衍生物，更详细地说，涉及化学式1中的N-丙酰氨基酸衍生物和化学式2中的N-丙酰二肽衍生物。根据本发明，N-丙酰氨基酸衍生物和N-丙酰二肽通过抑制酪氨酸酶酶活性具有美白功效，并可用于美白功能化妆品。[化学式1] [化学式2] 在上述化学式1和2中，R表示H，C-C的烷基，卤素基，甲氧基，乙氧基，羟基，氨基，芳香族或杂环芳香族基。R和R表示H，C-C的烷基，-CHCHCOOH，-CHCHCHCOOH，芳香族或杂环芳香族基。