ramalin | 1225997-63-6

• 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
• 英文名称: ramalin
• 英文别名: Pygmeine；(2S)-2-amino-5-[2-(2-hydroxyphenyl)hydrazinyl]-5-oxopentanoic acid
• CAS: 1225997-63-6
• 化学式: C₁₁H₁₅N₃O₄
• 分子量: 253.258
• InChiKey: CRSVHQICRXRCEP-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  125
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-Troc-L-glutamic acid 在 水 、 1-羟基苯并三唑 、 对甲苯磺酸 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 16.12h， 生成 ramalin
  参考文献：
  名称：

  METHOD FOR PREPARING RAMALIN

  摘要：

  公开号：

  EP2594552B1

文献信息

• Design, synthesis and biological evaluation of glutamic acid derivatives as anti-oxidant and anti-inflammatory agents
  作者：Suvarna H. Pagire、Eunhye Lee、Haushabhau S. Pagire、Eun Jung Bae、Soo Jung Ryu、Dahye Lee、Min Hee Kim、Geum Ran Kim、Kyu-Seok Hwang、Sukyung Ahn、Jin Hee Maeng、Jin Sook Song、Myung Ae Bae、Don Hang Lee、Jin Hee Ahn

  DOI：10.1016/j.bmcl.2017.11.012

  日期：2018.2

  A series of glutamic acid derivatives was synthesized and evaluated for their antioxidant activity and stability. We found several potent and stable glutamic acid derivatives. Among them, compound 12b exhibited good in vitro activity, chemical stability and cytotoxicity. A prototype compound 12b showed an anti-inflammatory effect in LPS-stimulated RAW 264.7 cell lines and in a zebrafish model.

  合成了一系列谷氨酸衍生物，并评估了其抗氧化活性和稳定性。我们发现了几种有效且稳定的谷氨酸衍生物。其中，化合物12b显示出良好的体外活性，化学稳定性和细胞毒性。原型化合物12b在LPS刺激的RAW 264.7细胞系和斑马鱼模型中显示出抗炎作用。
• Potential of Ramalin and Its Derivatives for the Treatment of Alzheimer’s Disease
  作者：Tai Kyoung Kim、Ju-Mi Hong、Kyung Hee Kim、Se Jong Han、Il-Chan Kim、Hyuncheol Oh、Joung Han Yim

  DOI：10.3390/molecules26216445

  日期：——

  The pathogenesis of Alzheimer’s disease (AD) is still unclear, and presently there is no cure for the disease that can be used for its treatment or to stop its progression. Here, we investigated the therapeutic potential of ramalin (isolated from the Antarctic lichen, Ramalina terebrata), which exhibits various physiological activities, in AD. Specifically, derivatives were synthesized based on the structure of ramalin, which has a strong antioxidant effect, BACE-1 inhibition activity, and anti-inflammatory effects. Therefore, ramalin and its derivatives exhibit activity against multiple targets associated with AD and can serve as potential therapeutic agents for the disease.

  阿尔茨海默病（AD）的发病机制仍不清楚，目前还没有可用于治疗或阻止其进展的治疗方法。在这里，我们研究了南极地衣Ramalina terebrata中分离出的ramalin的治疗潜力，该物质展示了各种生理活性。具体来说，基于ramalin的结构合成了衍生物，具有强抗氧化作用、BACE-1抑制活性和抗炎作用。因此，ramalin及其衍生物对于与AD相关的多个靶点具有活性，可以作为潜在的治疗药物用于治疗该疾病。
• A novel aryl-hydrazide from the marine lichen Lichina pygmaea: Isolation, synthesis of derivatives, and cytotoxicity assays
  作者：Catherine Roullier、Marylène Chollet-Krugler、Pierre van de Weghe、Françoise Lohézic-Le Devehat、Joël Boustie

  DOI：10.1016/j.bmcl.2010.06.013

  日期：2010.8

  A new aryl-hydrazide L-glutamic acid derivative, pygmeine (3), was isolated from a methanolic extract of Lichina pygmaea, a marine lichen. Synthetic derivatives obtained via a two-step coupling of L-glutamic acid with phenylhydrazine moieties were useful to elucidate the structure of 3 and to carry out biological assays. Thus, the cytotoxicity of the ortho-, meta-, and para-hydroxyl isomers along with their respective benzyl intermediates, and a natural methoxylated analog, were evaluated on murine and human melanoma cells (B16, A375). The para-hydroxyl isomer 6 was found to be the most active (IC50 = 1.6 mu M) on B16 cells. (C) 2010 Elsevier Ltd. All rights reserved.
• [EN] METHOD FOR PREPARING RAMALIN<br/>[FR] PROCÉDÉ DE PRÉPARATION DE LA RAMALINE
  申请人：KOREA OCEAN RES AND DEV INSITUTE

  公开号：WO2012008785A2

  公开（公告）日：2012-01-19

  본 발명은 라말린의 합성방법에 관한 것으로, 더욱 상세하게는, 2-하이드라지닐-페놀(2-Hydrazinylphenol)과, 1번탄소의 카복실기 및 2번탄소의 아미노기가 보호된 L-글루탐산을 반응시키는 것을 특징으로 하는, 라말린의 합성방법 및 상기 라말린의 분해 방지방법에 관한 것이다. 본 발명에 따르면, 항산화 및 항염증 효과가 뛰어난 라말린을 안정적인 수율로 합성할 수 있어, 라말린의 대량생산이 가능하다. 또한, 라말린을 장기간 안정적으로 유지할 수 있어 라말린을 산업상 이용하기 용이하다.
• METHOD FOR PREPARING RAMALIN
  申请人：Korea Ocean Research and Development Institute

  公开号：EP2594552B1

  公开（公告）日：2017-01-11