tigogenin 3β-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside) | 885453-92-9

• 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: tigogenin 3β-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside)
• 英文别名: 3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]tigogenin；tigogenine 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside)；[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 885453-92-9
• 化学式: C₆₁H₇₀O₁₂
• 分子量: 995.22
• InChiKey: NPABHEINAKWFNV-XXXJLPAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.08
• 重原子数：
  73.0
• 可旋转键数：
  11.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  tigogenin 3β-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside) 在 sodium methylate 、 吡啶 、 叔丁基二苯基氯硅烷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 以67%的产率得到tigogen-3-yl 2,3,4-tri-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  糖醛酸的自由基脱羧氟化合成逆糖基氟化物和稀有糖基氟化物

  摘要：

  描述了一种有效的合成逆向糖基氟化物的方法，该方法依赖于在温和的反应条件下，银促进结构上多样的戊呋喃和六吡喃葡萄糖醛酸的脱羧氟化作用。该反应的潜在应用通过通过C1-C5转换策略将容易获得的d-糖醛酸衍生物转化为不常见的d - 1-糖苷氟来进一步证明。反应机理是通过5-证实外切-三角函数烯丙基α-的自由基环化d -C葡吡喃糖醛酸通过脱羧氟化触发。

  DOI：

  10.1021/acs.orglett.0c03514
• 作为产物：
  描述：

  薯蓣皂素 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 tigogenin 3β-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside)
  参考文献：
  名称：

  Synthesis of the Cytotoxic Gitogenin 3β-O-[2-O-(α-l-Rhamnopyranosyl)-β-d-galactopyranoside] and its Congeners

  摘要：

  (25R)-5a-螺甾-2a,3b-二醇 (gitogenin) 3β-O-[2-O-(α-l-鼠李吡喃糖基)-β-d-半乳吡喃糖苷] (1)，一种从长茎黄精（百合科）地下部分分离得到的细胞毒性螺甾皂苷，被简明地合成出来。在此过程中，其类似物2-4也被制备出来。所有四个化合物在抑制癌细胞生长方面与薯蓣皂苷具有相当的效力。

  DOI：

  10.1055/s-2006-926316

文献信息

• Antifungal activity of 2α,3β-functionalized steroids stereoselectively increases with the addition of oligosaccharides
  作者：Amy Cammarata、Sunil Kumar Upadhyay、Branko S. Jursic、Donna M. Neumann

  DOI：10.1016/j.bmcl.2011.10.015

  日期：2011.12

  Invasive fungal infections pose a significant problem to the immune-compromised. Moreover, increased resistance to common antifungals requires development of novel compounds that can be used to treat invasive fungal infections. Naturally occurring steroidal glycosides have been shown to possess a range of functional antimicrobial properties, but synthetic methodology for their development hinders thorough exploration of this class of molecules and the structural components required for broad spectrum antifungal activity. In this report, we outline a novel approach to the synthesis of glycoside-linked functionalized 2 alpha,3 beta-cholestane and spirostane molecules and present data from in vitro screenings of the antifungal activities against human fungal pathogens and as well as mammalian cell toxicity of these derivatives. (C) 2011 Elsevier Ltd. All rights reserved.
• Effect of C-ring modifications on the cytotoxicity of spirostan saponins and related glycosides
  作者：Karell Pérez-Labrada、Ignacio Brouard、Sara Estévez、María Teresa Marrero、Francisco Estévez、Daniel G. Rivera

  DOI：10.1016/j.bmc.2012.05.018

  日期：2012.7

  Twelve C-ring modified spirostanyl glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). With the aim of assessing the influence of the hydrophobic character, the conformational flexibility and the stereochemistry of the C-ring functionalities on the cytotoxic activity, a variety of spirostanic aglycones incorporating methylene, methoxyl, alpha,beta-unsaturated ketone and lactone groups were subjected to a linear glycosylation strategy leading to glycosides derived from the 3,6-dipivaloylated beta-D-glucoside and the beta-chacotrioside moieties. The 3,6-dipivaloylated spirostanyl beta-D-glucosides showed moderate to good cytotoxic activity against HL-60, but no significant cytotoxicity against benign blood cells. However, the cytotoxicity of spirostanyl beta-chacotriosides was highly dependent on the nature of the C-ring functional groups of the steroidal aglycones. Actually, the chacotrioside-based saponins either with no functionality or bearing a hydrophobic methylene group at C-12 were the most cytotoxic ones against both HL-60 and benign blood cells. On the other hand, the incorporation of very polar functionalities and the opening of the ring C with the consequent loss of rigidity led to a significant drop in the cytotoxicity against HL-60. These results confirm that spirostanyl beta-chacotriosides including very lipophilic aglycones are the most cytotoxic ones among their congeners. (C) 2012 Elsevier Ltd. All rights reserved.
• HASHIMOTO, SHUN-ICHI;HONDA, TAKESHI;IKEGAMI, SHIRO, HETEROCYCLES, 30,(1990) N, C. 775-778
  作者：HASHIMOTO, SHUN-ICHI、HONDA, TAKESHI、IKEGAMI, SHIRO

  DOI：——

  日期：——