灰白糖芥甙 | 630-64-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 灰白糖芥甙
• 中文别名: 黄草次甙；七里香甙甲
• 英文名称: Alleoside A
• 英文别名: helveticoside；erysimin；3β-(β-D-ribo-2,6-dideoxy-hexopyranosyloxy)-5,14-dihydroxy-19-oxo-5β,14β-card-20(22)-enolide；3β-(β-D-ribo-2,6-Didesoxy-hexopyranosyloxy)-5,14-dihydroxy-19-oxo-5β,14β-card-20(22)-enolid；(3S,5S,8R,9S,10S,13R,14S,17R)-3-[(2R,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• CAS: 630-64-8
• 化学式: C₂₉H₄₂O₉
• 分子量: 534.647
• InChiKey: QBILRDAMJUPXCX-AGAUEGNUSA-N

物化性质

• 熔点：
  170°C (dec.)
• 沸点：
  532.44°C (rough estimate)
• 密度：
  1.36±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  9

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  T+
• 危险类别码：
  R26/27/28
• 危险品运输编号：
  UN 3249
• RTECS号：
  FH4919830
• 包装等级：
  III
• 危险类别：
  6.1(b)
• WGK Germany：
  3

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Cyclopentanohelveticosid	38561-79-4	C34H48O9	600.75

反应信息

• 作为反应物：
  描述：

  灰白糖芥甙 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 以3.7 g的产率得到erysimin-19-carboxylic acid
  参考文献：
  名称：

  Imidazolylcardenolides

  摘要：

  新型化合物毒毛旋花子苷-19-羰基咪唑（1）、毛旋花子苷-19-羰基咪唑（2）、洋地黄苷-19-羰基咪唑（3）以及17α-毒毛旋花子苷-19-羰基咪唑（4）是通过反应洋地黄苷羧酸和N,N′-羰基二咪唑合成的。这是首次证明该反应可以采用角型羧酸进行。同时，还描述了毛旋花子苷-19-羧酸、洋地黄苷-19-羧酸以及17α-毒毛旋花子苷-19-羧酸的制备方法及此前未知的性质。

  DOI：

  10.1007/s10600-008-9097-9
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 enzyme-substance from erysimum diffusum 作用下， 生成 灰白糖芥甙
  参考文献：
  名称：

  Maslennikowa et al., Doklady Akademii Nauk SSSR, 1959, vol. 124, p. 822,823

  摘要：

  DOI：

文献信息

• ACYL-HYDRAZONE AND OXADIAZOLE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AND USES THEREOF
  申请人：Universidade Federal de Santa Catarina

  公开号：US20150191445A1

  公开（公告）日：2015-07-09

  The present invention relates to acyl-hydrazone compounds, in particular 3,4,5-trimethoxyphenyl-hydrazide derivatives, as well as the oxadiazole analogs thereof and other similar compounds, and to the pharmaceutical use of the same for the treatment of various diseases associated with cell proliferation, such as leukemias, including acute lymphoblastic leukemia (ALL), tumours and inflammation. Acyl-hydrazones have been obtained having activity similar to that of the compound used as a standard in experiments (colchicine). The greater selectivity of the compounds according to the invention is an important feature, associated with fewer side effects than the pharmaceuticals used at present in clinical treatments. The synthetised acyl-hydrazones, more particularly the compounds 02 and 07, exhibited important antileukemic activity, which suggests 02 and 07 as candidates to pharmaceutical prototypes, or to pharmaceuticals for the treatment of leukemias, in particular acute lymphoblastic leukemia (ALL), tumours and other proliferative diseases, such as inflammation. The action mechanism of the most active compounds was determined by using DNA microarrays and subsequent tests indicated by the chip, besides selectivity studies in healthy human lymphocytes.

  本发明涉及酰基腙化合物，特别是3,4,5-三甲氧基苯基腙衍生物，以及其噁二唑类似物和其他类似化合物，以及它们在治疗与细胞增殖相关的各种疾病，如白血病（包括急性淋巴细胞白血病（ALL））、肿瘤和炎症方面的药用。已获得具有与实验中使用的化合物（秋水仙碱）相似活性的酰基腙。根据本发明的化合物具有更大的选择性，与目前在临床治疗中使用的药物相比，副作用更少是一个重要特征。合成的酰基腙，尤其是化合物02和07，表现出重要的抗白血病活性，这表明02和07可能成为药物原型的候选，或用于治疗白血病，特别是急性淋巴细胞白血病（ALL）、肿瘤和其他增殖性疾病，如炎症的药物。最活性化合物的作用机制是通过使用DNA微阵列确定的，并且通过芯片指示的后续测试，以及对健康人类淋巴细胞的选择性研究。
• COMPOSITIONS AND METHODS FOR ENHANCING CELLULAR UPTAKE AND INTRACELLULAR DELIVERY OF LIPID PARTICLES
  申请人：Lin Paulo J.C.

  公开号：US20120264810A1

  公开（公告）日：2012-10-18

  Compositions, methods and compounds useful for enhancing the uptake of a lipid particle b\ a cell are described In particular embodiments, the methods of the invention include contacting a cell with a lipid particle and a compound that binds a Na+/K+ ATPase to enhance uptake of the lipid particle b\ the cell Related compositions useful in practicing methods include lipid particles comprising a conjugated compound that enhances uptake of the lipid particles b\ the cell The methods and compositions are useful in delivering a therapeutic agent to a cell, e g for the treatment of a disease or disorder in a subject

  描述了用于增强细胞对脂质粒的摄取的组成物、方法和化合物。在特定的实施例中，发明的方法包括将细胞与脂质粒和一种与Na+/K+ ATPase结合的化合物接触，以增强细胞对脂质粒的摄取。在实践方法中使用的相关组成物包括包含一种共轭化合物的脂质粒，该共轭化合物增强细胞对脂质粒的摄取。这些方法和组成物可用于将治疗剂递送到细胞中，例如用于治疗主体中的疾病或失调。
• Aldimines of Cardenolides and Cardenolide-Glycosides
  作者：I. F. Makarevich、Yu. I. Gubin、R. Megges

  DOI：10.1007/s10600-005-0142-7

  日期：2005.5

  New aldimines were synthesized from the cardenolide strophantidin and cardenolide-glycosides erysimin and cymarin and included morpholine, nitrile, pyridine, furan, hydroxy- and methoxyphenyl, piperidine, and other derivatives. An effective modified method for synthesizing aldimines was proposed. 52 new compounds were synthesized. Their structures were confirmed by IR and PMR spectra and elemental analysis.

  新的烯胺由毛地黄毒苷和毛地黄毒糖苷、毛地黄苷以及诸如吗啉、腈、吡啶、呋喃、羟基和甲氧基苯基、哌啶以及其他衍生物合成。提出了一种有效的合成烯胺改性方法。合成了52种新化合物。它们结构由红外和质子磁共振谱和元素分析确证。
• Cardenolide alkylideneglycosides
  作者：S. V. Kovalev、I. F. Makarevich

  DOI：10.1007/s10600-007-0040-2

  日期：2007.1

  Alkylidene derivatives of cardiac glycosides were synthesized for increased lipophilicity. The synthesis was based on reaction of aldehydes and ketones with the natural glycosides erysimin, digoxin, and digoxigenin-bis-digitoxoside. A total of 19 biologically active compounds was prepared.

  基于醛和酮与天然糖苷毛地黄毒苷、地高辛和地高辛双毛地黄毒糖苷的反应，合成了增加亲脂性的甾体配基衍生物。总共制备了 19 种具有生物活性的化合物。
• New azomethine cardenolide glycosides
  作者：S. V. Kovalev

  DOI：10.1007/s10600-006-0178-3

  日期：2006.7

  New azomethines (aldimines) were synthesized from cardiac glycosides erysimin and cymarin. The structures of the new compounds were confirmed by PMR spectra and elemental analysis.

  新的偶氮甲碱（醛亚胺）是由强心苷益心素和水仙苷合成的。通过核磁共振谱和元素分析确认了新化合物的结构。