diosgenyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-D-glucopyranoside | 1028758-85-1

• 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
• 英文名称: diosgenyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-amino-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1028758-85-1
• 化学式: C₃₉H₅₉NO₁₀
• 分子量: 701.898
• InChiKey: GRZJFXUNODBESU-RQPIFAOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  50
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  diosgenyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-D-glucopyranoside 、 Thioctic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以158 mg的产率得到diosgenyl 3,4,6-tri-O-acetyl-2-{5-[(R/S)-1,2-dithiolan-3-yl]-pentanamido}-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and cytotoxic activity of diosgenyl saponin analogues

  摘要：

  Diosgenyl saponins are steroidal glycosides that are often found as major components in many traditional oriental medicines. Recently, a number of naturally occurring diosgenyl saponins have been shown to exert cytotoxic activity against several strains of human cancer cells. Use of these saponin compounds for cancer treatment is hampered due to the lack of understanding of their action mechanism as well as limited access to such structurally complicated molecules. In the present paper, we have prepared a group of diosgenyl saponin analogues which contain a beta-D-2-amino-2-deoxy-glucopyranose residue having different substituents at the amino group. Moderate cytotoxic activity is found for most analogues against neuroblastoma (SK-N-SH) cells, breast cancer (MCF-7) cells, and cervical cancer (HeLa) cells. The analogue 13 that contains an alpha-lipoic acid residue exhibits the highest potency against all three cancer cell lines with IC50 ranging from 4.8 mu M in SK-N-SH cells to 7.3 mu M in HeLa cells. Preliminary mechanistic investigation with one saponin analogue (10) shows that the compound induces cell cycle arrest at G(1) phase in SK-N-SH cells, but the same compound induces cell cycle arrest at G(2) phase in MCF-7 cells. This result suggests that the cytotoxic activity of these saponin analogues may involve different action mechanisms in cell lines derived from different cancer sites. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.022
• 作为产物：
  描述：

  diosgenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxy-carbonylamino)-β-D-glucopyranoside 在 溶剂黄146 、 锌 作用下， 反应 16.0h， 生成 diosgenyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and cytotoxic activity of diosgenyl saponin analogues

  摘要：

  Diosgenyl saponins are steroidal glycosides that are often found as major components in many traditional oriental medicines. Recently, a number of naturally occurring diosgenyl saponins have been shown to exert cytotoxic activity against several strains of human cancer cells. Use of these saponin compounds for cancer treatment is hampered due to the lack of understanding of their action mechanism as well as limited access to such structurally complicated molecules. In the present paper, we have prepared a group of diosgenyl saponin analogues which contain a beta-D-2-amino-2-deoxy-glucopyranose residue having different substituents at the amino group. Moderate cytotoxic activity is found for most analogues against neuroblastoma (SK-N-SH) cells, breast cancer (MCF-7) cells, and cervical cancer (HeLa) cells. The analogue 13 that contains an alpha-lipoic acid residue exhibits the highest potency against all three cancer cell lines with IC50 ranging from 4.8 mu M in SK-N-SH cells to 7.3 mu M in HeLa cells. Preliminary mechanistic investigation with one saponin analogue (10) shows that the compound induces cell cycle arrest at G(1) phase in SK-N-SH cells, but the same compound induces cell cycle arrest at G(2) phase in MCF-7 cells. This result suggests that the cytotoxic activity of these saponin analogues may involve different action mechanisms in cell lines derived from different cancer sites. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.022

文献信息

• Structural analogues of diosgenyl saponins: Synthesis and anticancer activity
  作者：Matthew J. Kaskiw、Mary Lynn Tassotto、Mac Mok、Stacey L. Tokar、Roxanne Pycko、John Th’ng、Zi-Hua Jiang

  DOI：10.1016/j.bmc.2009.09.046

  日期：2009.11

  Saponins display various biological activities including anti-tumor activity. Recently intensive research has been focused on developing saponins for tumor therapies. The diosgenyl saponin dioscin is one of the most common steroidal saponins and exhibits potent anticancer activity in several human cancer cells through apoptosis-inducing pathways. In this paper, we describe the synthesis of several diosgenyl saponin analogues containing either a 2-amino-2-deoxy-beta-D-glucopyranosyl residue or an alpha-L-rhamnopyranosyl-(1 -> 4)-2-amino-2-deoxy-beta-D-glucopyranosyl residue with different acyl substituents on the amino group. The cytotoxic activity of these compounds was evaluated in MCF-7 breast cancer cells and HeLa cervical cancer cells. Structure-activity relationship studies show that the disaccharide saponin analogues are in general less active than their corresponding monosaccharide analogues. The incorporation of an aromatic nitro functionality into these saponin analogues does not exhibit significant effect on their cytotoxic activity. (C) 2009 Elsevier Ltd. All rights reserved.
• 2,3,4,6-tetra-<i>O</i>-Acetyl-D-Gluconic Acid: Crystal Structure and Application in the Synthesis of <i>N</i>-(D-gluconyl) Derivatives of D-Glucosamine
  作者：Monika Norkowska、Henryk Myszka、Magdalena Cyman、Daria Grzywacz、Damian Trzybiński、Artur Sikorski、Beata Liberek

  DOI：10.1080/07328303.2013.872790

  日期：2014.1.2