diosgenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside | 1202534-70-0

• 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 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
• CAS: 1202534-70-0
• 化学式: C₃₆H₅₄Cl₃NO₉
• 分子量: 751.185
• InChiKey: BIVIDAUYNLEDEZ-RNDJSGFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  49.0
• 可旋转键数：
  5.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  135.94
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  diosgenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 在 溶剂黄146 、 锌 作用下， 反应 2.0h， 生成 diosgenyl 2-amino-2-deoxy-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
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl chloride 在 甲醇 、 silver trifluoromethanesulfonate 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 40.17h， 生成 diosgenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-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

• 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.