diosgenyl 2-deoxy-2-amino-β-D-glucospyranoside hydrochloride

• 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-amino-β-D-glucospyranoside hydrochloride
• 英文别名: diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside hydrochloride；(2R,3S,4R,5R,6R)-5-amino-2-(hydroxymethyl)-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]oxyoxane-3,4-diol;hydrochloride
• 化学式: C₃₃H₅₃NO₇*ClH
• 分子量: 612.247
• InChiKey: CIQDULSGKRIAEC-MVWUUXCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  124
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  薯蓣皂素 在 silver trifluoromethanesulfonate 、 乙二胺 作用下， 以 二氯甲烷 为溶剂， 生成 diosgenyl 2-deoxy-2-amino-β-D-glucospyranoside hydrochloride
  参考文献：
  名称：

  The synthesis of diosgenyl 2-amino-2-deoxy-β-d-glucopyranoside hydrochloride

  摘要：

  The N-trifluoroacetyl- and N-tetrachlorophthaloyl-protected bromide of D-glucosamine has been used for the first time as a glycosyl donor for the glycosylation of diosgenin [(25R)-spirost-5-en-3 beta-ol]. Both 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trifluoroacetamido-beta-D-glucopyranoside and 1,3,4,6-tetra-O-acetyl-2-deoxy-2-tetrachlorophthalimido-alpha,beta-D-glucopyranoside were transformed into the appropriate glycosyl bromides. These reacted with diosgenin under mild conditions, using silver triflate as a promoter, and gave the corresponding protected diosgenyl glycosides. Each was deprotected to give diosgenyl 2-amino-2-deoxy-beta-D-glucopyranoside hydrochloride. The structures of the new glycosides were established by H-1 NMR spectroscopy. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00199-3

文献信息

• Synthesis and selective anticancer activity of steroidal glycoconjugates
  作者：María A. Fernández-Herrera、Hugo López-Muñoz、José M.V. Hernández-Vázquez、Luis Sánchez-Sánchez、María L. Escobar-Sánchez、B. Mario Pinto、Jesús Sandoval-Ramírez

  DOI：10.1016/j.ejmech.2012.06.027

  日期：2012.8

  The synthesis of glucosamine derivatives of the steroidal sapogenins diosgenin and hecogenin using the N-phthaloyl protected trichloroacetimidate of d-glucosamine as donor and TMSOTf as promoter is reported. The corresponding glycoconjugates were transformed into their acetamido derivatives and the hydrochloride salt (from diosgenin) and tested against HeLa, CaSki, and ViBo cervicouterine cancer cells

  的葡糖胺衍生物的合成的甾体皂苷元薯蓣皂苷元和使用核柯配基Ñ -phthaloyl保护的三氯乙酰d葡糖胺作为供体和将TMSOTf作为启动子的报道。将相应的糖缀合物转化为其乙酰氨基衍生物和盐酸盐（来自薯os皂素），并针对HeLa，CaSki和ViBo宫颈外膜癌细胞进行测试。这些化合物对肿瘤细胞和人淋巴细胞显示出低细胞毒性值，表明主要的细胞死亡过程可能不是坏死。重要的是，这些化合物对肿瘤细胞的抗增殖活性并不影响外周血淋巴细胞的增殖潜能。
• Synthesis and induction of apoptosis in B cell chronic leukemia by diosgenyl 2-amino-2-deoxy-β-d-glucopyranoside hydrochloride and its derivatives
  作者：Henryk Myszka、Dorota Bednarczyk、Maria Najder、Wiesław Kaca

  DOI：10.1016/s0008-6215(02)00407-x

  日期：2003.1

  2-Acetamido-2-deoxy-D-glucose hydrochloride (D-glucosamine hydrochloride) has been used for the preparation of 1,3.4.6-tetra- O-acetyl-2-deoxy-2-trifluoroacetqamido-beta- (4) and 2-tetrachlorophthalimido-alpha, beta-D-glucopyranose (6) which have been transformed into the appropriate bromides and the chloride. Both bromo and chloro sugars were used as a glycosyl donors for the glycosylation of diosgenin [(25R)-spirost-5-en-3beta-ol]. These condensations were conducted under mild conditions, using silver triflate as a promoter, and gave diosgenyl glycosides 9 and 12. Each of them was converted into diosgenyl 2-amino-2-deoxy-beta-D-glucopyranoside hydrochloride (11) and N-acylamido derivatives. The structures of all new glycosides were established by H-1 and C-13 NMR spectroscopy. These diosgenyl glycosides are the first saponins containing the D-glucosamine residue that have been synthesized. These compounds show promising antitumor activities, The synthetic saponins increase the number of apoptotic B cells, in combination with cladribine (2-CdA). that are isolated from chronic lymphotic leukemia (B-CLL) patients. (C) 2002 Published by Elsevier Science Lid.