p-(2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactosyl)benzaldehyde | 139933-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-(2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactosyl)benzaldehyde
• 英文别名: 4-(2,3,4,6,2',3',6'-hepta-O-acetyl-β-D-lactosyloxy)benzaldehyde；4-formylphenyl 2,2',3,3',4',6,6'-hepta-O-acetyl-β-D-lactoside；(+)-4-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-Dglucopyranosyloxy)benzaldehyde；4-formylphenyl-(2',3',4',6', 2, 3, 6-hepta-O-acetyl)-β-D-lactoside；Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4S,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-(4-formyl-phenoxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-(4-formylphenoxy)-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 139933-35-0
• 化学式: C₃₃H₄₀O₁₉
• 分子量: 740.669
• InChiKey: JYBUVPNEGDGTCW-LZWHNZSHSA-N

物化性质

• 沸点：
  752.2±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  52
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  p-(2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactosyl)benzaldehyde 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 二甲基亚砜 、 乙腈 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  乳糖衍生的酰hydr的表面活性和生物学性质的比较研究

  摘要：

  在这项研究中，我们报告了通过缩合反应首次制备一系列乳糖衍生的酰基hydr化合物，这些化合物的烷基侧链长度为5至10个碳，是一种新型的非离子表面活性剂。研究了表面活性，起泡性能，乳化性能，热稳定性以及细胞毒性，以建立结构-性能曲线，这表明带有中等长度侧链的酰基hydr衍生物比其类似物和其他精选市售产品具有更好的整体性能。参考。该结果可作为进一步发展例如食品和制药工业中的乳糖衍生的酰hydr作为乳化剂的基础。

  DOI：

  10.1016/j.molliq.2020.114989
• 作为产物：
  描述：

  对苯二甲醛 在 sodium tetrahydroborate 、 苄基三丁基氯化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 30.5h， 生成 p-(2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactosyl)benzaldehyde
  参考文献：
  名称：

  衍生自半胱氨酸的功能化双环四酸酯作为抗菌剂。

  摘要：

  报道了从半胱氨酸衍生的双环四甲酸酯的路线，允许在杂环骨架周围的两个不同点处随时掺入功能。这使得能够鉴定出对革兰氏阳性菌具有活性的系统，其中一些系统显示出旋转酶和 RNA 聚合酶抑制活性。特别是，被糖基侧链取代的四酸酯（选择赋予极性和水溶性）在两种情况下显示出高抗菌活性和适度的旋转酶/聚合酶活性。理化性质分析表明，抗菌活性四甲酸酯通常占据MW为300-600、clog D7.4为-2.5至4和rel.的理化空间。 PSA 为 11-22%。这项工作表明，通过操纵四甲酸酯骨架可以轻松获得具有生物活性的 3D 文库。

  DOI：

  10.1039/c9ob01076a

文献信息

• Synthesis of glycosylated cationic porphyrins as potential agents in photodynamic therapy
  作者：Khalid Driaf、Robert Granet、Pierre krausz、Mourad Kaouadji、Bernard Verneuil、François Thomasson、Albert José Chulia、Marenglen Spiro、Jean-Claude Biais、Gérard Bolbach

  DOI：10.1139/v96-172

  日期：1996.8.1

  Trisalkylpyridinium porphyrins substituted by one glycosyl (glucosyl, maltosyl, and lactosyl) moiety have been prepared in acceptable yields. These glycosylated cationic porphyrins have been synthesized from pyrrole condensed with 4-pyridinecarboxaldehyde, and suitable ortho- or para peracetylglycosyloxybenzaldehyde derivatives in refluxing propionic acid –Ac₂O followed by action of alkyliodide in DMF. Deprotection of the glycosylated moieties led to a new class of representative glycosylated porphyrins. Key words: porphyrins, cationic, glycosylated; phototherapy, cancer.

  一种糖基（葡萄糖基、麦芽糖基和乳糖基）取代的三烷基吡啶卟啉已经在可接受的产率下制备。这些糖基化阳离子卟啉是从吡咯与4-吡啶甲醛、适当的邻位或对位过乙酰基糖基羟基苯甲醛衍生物在丙酸-乙酸酐回流中反应，然后在DMF中作用烷基碘化物合成的。去保护糖基后得到了一类新的代表性糖基化卟啉。关键词：卟啉、阳离子、糖基化；光疗法、癌症。
• Study on glycosylated prodrugs of toxoflavins for antibody-directed enzyme tumor therapy
  作者：Shusheng Wang、Dan Liu、Xu Zhang、Shengyu Li、Yongxu Sun、Jia Li、Yifa Zhou、Liping Zhang

  DOI：10.1016/j.carres.2007.03.006

  日期：2007.7

  Eight novel toxoflavin glycosides, which are potential prodrugs in antibody directed enzyme prodrug therapy (ADEPT), were synthesized. The structures of all toxoflavin glycosides were characterized by C-13 NMR spectroscopy, elemental analysis, and MS. Their enzymatic hydrolysis activities were tested against P-glucosidase (EC.3.2.1.21). (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of O-glycosyl α-aryl nitrones
  作者：Ying Fu、Huai Yuan Zhang、Yan Hua Liu、Xue Feng Li、Dan Feng Huang、Yu Lai Hu

  DOI：10.1016/j.cclet.2010.04.006

  日期：2010.9

  alpha-Aryl nitrone are one of the most useful kinds of nitrones and have been extensively explored in recent years. However, the sugar moieties have not been introduced into these molecules before. We presented here an efficient synthesis of alpha-aryl nitrone O-glycosides via condensation of N-substituted hydroxylamine and aryl aldehydes glycosides in benzene. (C) 2010 Ying Fu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Synthesis and biological evaluation of helicid analogues as novel acetylcholinesterase inhibitors
  作者：Huan Wen、Chonglan Lin、Ling Que、Hui Ge、Lin Ma、Rihui Cao、Yiqian Wan、Wenlie Peng、Zihou Wang、Huacan Song

  DOI：10.1016/j.ejmech.2007.03.018

  日期：2008.1

  A series of helicid analogues were prepared and evaluated in vitro for the cholinesterase (AChE and BuChE) inhibitory activities via UV spectroscopy. The results indicated that compounds 5, 6d and 8 exhibited potent AChE inhibitory activities with IC50 values of 0.45 +/- 0.02 mu M 0.49 +/- 0.02 mu M, and 0.20 +/- 0.01 mu M, respectively. High selectivity for AChE over BuChE was also observed. Kinetic study showed that the mechanism of AChE inhibition of compounds 5, 6d and 8 was all mixed-type. (C) 2007 Elsevier Masson SAS. All rights reserved.
• Discovery of 4-functionalized phenyl-O-β-d-glycosides as a new class of mushroom tyrosinase inhibitors
  作者：Wei Yi、Rihui Cao、Huan Wen、Qin Yan、Binhua Zhou、Lin Ma、Huacan Song

  DOI：10.1016/j.bmcl.2009.09.018

  日期：2009.11

  A series of 4-functionalized phenyl-O-beta-D-glycosides were designed, synthesized and evaluated as a new class of mushroom tyrosinase inhibitors. The results demonstrated that compounds 6a-13a bearing a thiosemicarbazide moiety exhibited potent activities with IC50 values range from 0.31 to 52.8 mu M. Particularly, compound 9a containing acetylated glucose moiety was found to be the most active molecule with an IC50 value of 0.31 mu M. SARs analysis suggested that (1) the thiosemicarbazide moiety remarkably contributed to the increase of inhibitory effects on tyrosinase; (2) the configuration and bond type of sugar moiety also played a very important role in determining their inhibitory activities. The inhibition kinetics and inhibition mechanism study revealed that compound 9a was reversible and competitive type inhibitor, whereas compound 13a was reversible and competitive-uncompetitive mixed-II type inhibitor. (c) 2009 Published by Elsevier Ltd.