diosgenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxy-carbonylamino)-β-D-glucopyranoside | 1028758-82-8

• 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
• 英文名称: diosgenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxy-carbonylamino)-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-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]oxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 1028758-82-8
• 化学式: C₄₂H₆₀Cl₃NO₁₂
• 分子量: 877.297
• InChiKey: IDNUKYDQOFEKLF-JWYAFDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  58
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  diosgenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxy-carbonylamino)-β-D-glucopyranoside 在 sodium methylate 、 硝酸胍 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 以90%的产率得到diosgenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  Structural analogues of diosgenyl saponins: Synthesis and anticancer activity

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.09.046
• 作为产物：
  描述：

  1,3,4,6-四-O-乙酰基-2-氨基-2-脱氧-Β-D-葡萄糖盐酸盐 在 吡啶 、 1,1-二氯甲醚 、 silver trifluoromethanesulfonate 、 zinc(II) chloride 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 21.34h， 生成 diosgenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxy-carbonylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  Differently N-protected 3,4,6-tri-O-acetyl-2-amino-2-deoxy-d-glucopyranosyl chlorides and their application in the synthesis of diosgenyl 2-amino-2-deoxy-β-d-glucopyranoside

  摘要：

  Four differently N-protected 3,4,6-tri-O-acetyl-2-amino-2-deoxy-D-glucopyranosyl chlorides were synthesized and used as glycosyl donors in reactions with diosgenin. The following amine group protections were tested: trifluoroacetyl (TFA), 2,2,2-trichloroethoxycarbonyl (Troc), phthaloyl (Phth), and tetrachlorophthaloyl (TCP). Products of glycosylation were deprotected to yield diosgenyl 2-amino-2-deoxy-beta-D-glucopyranoside. The efficiency of the procedures is discussed. Additionally, a single-crystal X-ray diffraction analysis for 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranosyl chloride is reported. Orientations of the pyranose substituents as well as the planarity of the acetoxy and phthalimide groups in the crystal lattice are discussed. Structural evidence is presented for a mesomeric effect in both groups. The preference of the cis over trans orientation of the acetoxy group is confirmed in the crystal lattice. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.11.020

文献信息

• <i>N</i>-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity
  作者：Agata Walczewska、Daria Grzywacz、Dorota Bednarczyk、Małgorzata Dawgul、Andrzej Nowacki、Wojciech Kamysz、Beata Liberek、Henryk Myszka

  DOI：10.3762/bjoc.11.97

  日期：——

  Diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside is a synthetic saponin exhibiting attractive pharmacological properties. Different pathways tested by us to obtain this glycoside are summarized here. Moreover, the synthesis of N-alkyl and N,N-dialkyl derivatives of the glucopyranoside is presented. Evaluation of antibacterial and antifungal activities of these derivatives indicates that they have no inhibitory activity against Gram-negative bacteria, whereas many of the tested N-alkyl saponins were found to inhibit the growth of Gram-positive bacteria and human pathogenic fungi.

  Diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside是一种具有吸引人的药理特性的合成皂苷。我们测试了不同的途径来获得这种糖苷，这里总结了这些途径。此外，还介绍了合成葡萄糖吡喃糖苷的N-烷基和N,N-二烷基衍生物。对这些衍生物的抗菌和抗真菌活性评估表明，它们对革兰氏阴性菌没有抑制活性，而许多经过测试的N-烷基皂苷被发现抑制了革兰氏阳性菌和人类病原真菌的生长。
• Synthesis and cytotoxic activity of diosgenyl saponin analogues
  作者：Matthew J. Kaskiw、Mary Lynn Tassotto、John Th’ng、Zi-Hua Jiang

  DOI：10.1016/j.bmc.2007.12.022

  日期：2008.3.15

  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.
• 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