摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

α-tocopheramine succinate | 832082-19-6

中文名称
——
中文别名
——
英文名称
α-tocopheramine succinate
英文别名
α-tocopheryl succinamide;4-oxo-4-[[(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl]amino]butanoic acid
α-tocopheramine succinate化学式
CAS
832082-19-6
化学式
C33H55NO4
mdl
——
分子量
529.804
InChiKey
UJFHUEFTCMRMOG-NJQVLOCASA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    9.7
  • 重原子数:
    38
  • 可旋转键数:
    16
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.76
  • 拓扑面积:
    75.6
  • 氢给体数:
    2
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    参考文献:
    名称:
    A novel synthesis of tocopheryl amines and amides
    摘要:
    We report the synthesis of tocopheryl amines and amides from commercially available tocopherols. This synthesis improves the yield and diastereomeric purity of these biologically important compounds. The tocopheryl amines were prepared from the corresponding alpha- and delta-tocopherols using two distinct synthetic routes. The introduction of the C(6)-amino group can be achieved by aryl nitration/reduction or by Pd-catalyzed Substitution of an aryl triflate, depending on the structure of the starting material. We also prepared the succinamide and maleamide derivatives of each amine. Tocopheryl amides are more potent pro-apoptotic anti-cancer agents than the corresponding alpha-tocopheryl esters. These compounds act selectively within the mitochondria of cancer cells. (C) 2008 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.tetlet.2008.10.056
点击查看最新优质反应信息

文献信息

  • Tocopheramine succinate and tocopheryl succinate: Mechanism of mitochondrial inhibition and superoxide radical production
    作者:Julia Gruber、Katrin Staniek、Christopher Krewenka、Rudolf Moldzio、Anjan Patel、Stefan Böhmdorfer、Thomas Rosenau、Lars Gille
    DOI:10.1016/j.bmc.2013.12.036
    日期:2014.1
    Tocopherols (TOH) are lipophilic antioxidants which require the phenolic OH group for their redox activity. In contrast, non-redox active esters of alpha-TOH with succinate (alpha-TOS) were shown to possess proapoptotic activity in cancer cells. It was suggested that this activity is mediated via mitochondrial inhibition with subsequent O-2(center dot-) production triggering apoptosis and that the modification of the linker between the succinate and the lipophilic chroman may modulate this activity. However, the specific mechanism and the influence of the linker are not clear yet on the level of the mitochondrial respiratory chain. Therefore, this study systematically compared the effects of alpha-TOH acetate (alpha-TOA), alpha-TOS and alpha-tocopheramine succinate (alpha-TNS) in cells and submitochondrial particles (SMP). The results showed that not all cancer cell lines are highly sensitive to alpha-TOS and alpha-TNS. In HeLa cells alpha-TNS did more effectively reduce cell viability than alpha-TOS. The complex I activity of SMP was little affected by alpha-TNS and alpha-TOS while the complex II activity was much more inhibited (IC50 = 42 +/- 8 mu M alpha-TOS, 106 +/- 8 mu M alpha-TNS, respectively) than by alpha-TOA (IC50 > 1000 mu M). Also the complex III activity was inhibited by alpha-TNS (IC50 = 137 +/- 6 lM) and alpha-TOS (IC50 = 315 +/- 23 lM). Oxygen consumption of NADH-or succinate-respiring SMP, involving the whole electron transfer machinery, was dose-dependently decreased by alpha-TOS and alpha-TNS, but only marginal effects were observed in the presence of alpha-TOA. In contrast to the similar inhibition pattern of alpha-TOS and alpha-TNS, only alpha-TOS triggered O-2 center dot- 2 formation in succinate- and NADH-respiring SMP. Inhibitor studies excluded complex I as O-2(center dot-) 2 source and suggested an involvement of complex III in O-2(center dot-) 2 production. In cancer cells only alpha-TOS was reproducibly able to increase O-2(center dot-) 2 levels above the background level but neither alpha-TNS nor alpha-TOA. Furthermore, the stability of alpha-TNS in liver homogenates was significantly lower than that of alpha-TOS. In conclusion, this suggests that alpha-TNS although it has a structure similar to alpha-TOS is not acting via the same mechanism and that for alpha-TOS not only complex II but also complex III interactions are involved. (C) 2013 Elsevier Ltd. All rights reserved.
  • Liposomal Formulations of Tocopheryl Amides
    申请人:Salvatore Brian A
    公开号:US20100260830A1
    公开(公告)日:2010-10-14
    Formulations of N-chroman dicarboxylic acid derivatives and their bioisosteres in liposomal systems. Lyophilized liposomal dosage forms of N-chromans, are found to be stable, to achieve therapeutically meaningful plasma levels on administration to a mammalian host, and to demonstrate selective pro-apoptotic oncolytic properties in vivo. Advantageously, these formulations overcome the systemic toxicity that characterized their administration by other dosage forms.
  • A novel synthesis of tocopheryl amines and amides
    作者:Elahe Mahdavian、Smink Sangsura、Geoffrey Landry、John Eytina、Brian A. Salvatore
    DOI:10.1016/j.tetlet.2008.10.056
    日期:2009.1
    We report the synthesis of tocopheryl amines and amides from commercially available tocopherols. This synthesis improves the yield and diastereomeric purity of these biologically important compounds. The tocopheryl amines were prepared from the corresponding alpha- and delta-tocopherols using two distinct synthetic routes. The introduction of the C(6)-amino group can be achieved by aryl nitration/reduction or by Pd-catalyzed Substitution of an aryl triflate, depending on the structure of the starting material. We also prepared the succinamide and maleamide derivatives of each amine. Tocopheryl amides are more potent pro-apoptotic anti-cancer agents than the corresponding alpha-tocopheryl esters. These compounds act selectively within the mitochondria of cancer cells. (C) 2008 Elsevier Ltd. All rights reserved.
查看更多

同类化合物

(5β,6α,8α,10α,13α)-6-羟基-15-氧代黄-9(11),16-二烯-18-油酸 (3S,3aR,8aR)-3,8a-二羟基-5-异丙基-3,8-二甲基-2,3,3a,4,5,8a-六氢-1H-天青-6-酮 (2Z)-2-(羟甲基)丁-2-烯酸乙酯 (2S,4aR,6aR,7R,9S,10aS,10bR)-甲基9-(苯甲酰氧基)-2-(呋喃-3-基)-十二烷基-6a,10b-二甲基-4,10-dioxo-1H-苯并[f]异亚甲基-7-羧酸盐 (+)顺式,反式-脱落酸-d6 龙舌兰皂苷乙酯 龙脑香醇酮 龙脑烯醛 龙脑7-O-[Β-D-呋喃芹菜糖基-(1→6)]-Β-D-吡喃葡萄糖苷 龙牙楤木皂甙VII 龙吉甙元 齿孔醇 齐墩果醛 齐墩果酸苄酯 齐墩果酸甲酯 齐墩果酸乙酯 齐墩果酸3-O-alpha-L-吡喃鼠李糖基(1-3)-beta-D-吡喃木糖基(1-3)-alpha-L-吡喃鼠李糖基(1-2)-alpha-L-阿拉伯糖吡喃糖苷 齐墩果酸 beta-D-葡萄糖酯 齐墩果酸 beta-D-吡喃葡萄糖基酯 齐墩果酸 3-乙酸酯 齐墩果酸 3-O-beta-D-葡吡喃糖基 (1→2)-alpha-L-吡喃阿拉伯糖苷 齐墩果酸 齐墩果-12-烯-3b,6b-二醇 齐墩果-12-烯-3,24-二醇 齐墩果-12-烯-3,21,23-三醇,(3b,4b,21a)-(9CI) 齐墩果-12-烯-3,11-二酮 齐墩果-12-烯-2α,3β,28-三醇 齐墩果-12-烯-29-酸,3,22-二羟基-11-羰基-,g-内酯,(3b,20b,22b)- 齐墩果-12-烯-28-酸,3-[(6-脱氧-4-O-b-D-吡喃木糖基-a-L-吡喃鼠李糖基)氧代]-,(3b)-(9CI) 鼠特灵 鼠尾草酸醌 鼠尾草酸 鼠尾草酚酮 鼠尾草苦内脂 黑蚁素 黑蔓醇酯B 黑蔓醇酯A 黑蔓酮酯D 黑海常春藤皂苷A1 黑檀醇 黑果茜草萜 B 黑五味子酸 黏黴酮 黏帚霉酸 黄黄质 黄钟花醌 黄质醛 黄褐毛忍冬皂苷A 黄蝉花素 黄蝉花定