Benzyl 5-oxo-2-(phenylmethoxycarbonylamino)-5-[2-(2-phenylmethoxyphenyl)hydrazinyl]pentanoate

• 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: Benzyl 5-oxo-2-(phenylmethoxycarbonylamino)-5-[2-(2-phenylmethoxyphenyl)hydrazinyl]pentanoate
• 英文别名: benzyl 5-oxo-2-(phenylmethoxycarbonylamino)-5-[2-(2-phenylmethoxyphenyl)hydrazinyl]pentanoate
• 化学式: C₃₃H₃₃N₃O₆
• 分子量: 567.642
• InChiKey: ZGTFRFXBWYXDCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzyl 5-oxo-2-(phenylmethoxycarbonylamino)-5-[2-(2-phenylmethoxyphenyl)hydrazinyl]pentanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 ramalin
  参考文献：
  名称：

  METHOD FOR SYNTHESIZING RAMALIN BY USING A GLUTAMIC ACID DERIVATIVE AND HYDROXY ANILINE OR HYDROXY ANILINE HAVING PROTECTED HYDROXY GROUP

  摘要：

  公开号：

  EP2816028B1
• 作为产物：
  描述：

  N-carbobenzyloxy-L-glutamic acid alphabenzyl ester 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 Benzyl 5-oxo-2-(phenylmethoxycarbonylamino)-5-[2-(2-phenylmethoxyphenyl)hydrazinyl]pentanoate
  参考文献：
  名称：

  METHOD FOR SYNTHESIZING RAMALIN BY USING A GLUTAMIC ACID DERIVATIVE AND HYDROXY ANILINE OR HYDROXY ANILINE HAVING PROTECTED HYDROXY GROUP

  摘要：

  公开号：

  EP2816028B1

文献信息

• Ramalin inhibits differentiation of 3T3-L1 preadipocytes and suppresses adiposity and body weight in a high-fat diet-fed C57BL/6J mice
  作者：Seo-Young Kim、Yeon Jeong Jang、Bongkyun Park、Joung-Han Yim、Hong-Kum Lee、Dong-Kwon Rhee、Suhkneung Pyo

  DOI：10.1016/j.cbi.2016.07.034

  日期：2016.9

  Obesity is a serious global health problem. Natural substances that could be effective remedies for treatment of obesity, and which are relatively safe, are desired. The aim of this study was to examine the anti-obesity effect and the mechanism of ramalin in 3T3-L1 preadipocytes and high fat diet (HFD)-induced obese mice. In this study, 3T3-L1 cells were treated with various concentrations of ramalin (1,5, and 10 mu g/ml). Ramalin reduced the accumulation of intracellular lipid droplets in 3T3-L1 cells. In addition, ramalin inhibited 3T3-L1 adipocyte differentiation by blocking adipogenic gene expression including CCAAT enhancer binding proteins (C/EBPs), peroxisome proliferator-activated receptors gamma (PPAR gamma), adipocyte fatty acid-binding protein (aP2), and leptin. The suppression of adipogenesis by ramalin was mediated through the inhibition of MAPK pathways. Ramalin also reduced the secretion of INF-alpha and IL-6 in 3T3-L1 adipocytes. Oral administration of ramalin (50 and 100 mg/kg) to HFD-fed mice reduced body weight gain and abdominal fat accumulation without changes in food intake. Ramalin also attenuated organ weight and basal serum level by inhibiting liver X receptors (LXRs), sterol regulatory element-binding protein-1c (SREBP-1c), and lipoprotein lipase (LPL) mRNA expression in HFD-fed mice. Taken together, these results indicate that ramalin inhibits adipogenesis in 3T3-L1 preadipocytes and prevents HFD-induced obesity. The present study also provides insight into the mechanisms underlying the anti-obesity activity of ramalin and suggests that ramalin has the potential to prevent obesity. (C) 2016 Elsevier Ireland Ltd. All rights reserved.
• METHOD FOR SYNTHESIZING RAMALIN AND RAMALIN PRECURSOR BY USING GLUTAMIC ACID DERIVATIVE AND HYDROXY ANILINE OR HYDROXY ANILINE HAVING PROTECTED HYDROXY GROUP
  申请人：Yim Joung Han

  公开号：US20150038733A1

  公开（公告）日：2015-02-05

  Disclosed is a method of the synthesis of ramalin. It comprises reacting a glutamic acid derivative, which is prepared using alkylchloroformate, with a hydrazine salt compound, which is prepared from hydroxy aniline, whether protected or not. The synthesis method allows ramalin, excellent in antioxidant and anti-inflammatory activity, to be simply synthesized at stable yield even without use of a highly toxic solvent such as DMF. In addition, the method is cost competitive, and provides ramalin at high efficiency, thus enabling the mass production of ramalin.
• METHOD FOR SYNTHESIZING RAMALIN BY USING A GLUTAMIC ACID DERIVATIVE AND HYDROXY ANILINE OR HYDROXY ANILINE HAVING PROTECTED HYDROXY GROUP
  申请人：Korea Institute of Ocean Science and Technology

  公开号：EP2816028B1

  公开（公告）日：2019-11-27