4-formyl-2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 943451-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-formyl-2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: 4-formyl-2-methoxyphenyl 2,3,6,2’,3’,4’,6’-hepta-O-acetyl-β-D-lactoside；3-methoxy-4-((2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-lactosyl)oxy)benzaldehyde；3-methoxy-4-(2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-lactosyloxy)benzaldehyde；3-methoxy-4-(2,3,4,6,2',3',6'-hepta-O-acetyl-β-D-lactosyloxy)benzaldehyde；3-methoxy-4-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyloxy]-benzaldehyde；3-Methoxy-4-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyloxy]-benzaldehyd
• CAS: 943451-01-2
• 化学式: C₃₄H₄₂O₂₀
• 分子量: 770.695
• InChiKey: UCSFBCMCOOUGDV-DWJUDJHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  54.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  247.32
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  4-formyl-2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到vaniline lactoside
  参考文献：
  名称：

  相转移催化下香草醛乳糖苷区域选择性 3'-O-硫酸化合成半乳糖凝集素抑制剂

  摘要：

  使用相转移催化反应从全-O-乙酰化乳糖基溴合成基于香草醛的乳糖苷衍生物。然后对香草醛部分的醛基进行修饰，生成一系列在芳香族残基的对位具有可变官能团的相关类似物。通过 Zemplén 酯交换反应获得的相应未保护乳糖苷，使用锡化学活化进行区域选择性 3'-O-硫酸化，然后用三氧化硫-三甲胺复合物 (Men3N-SO3) 处理。还使用 Knoevenagel 反应从香兰素醛制备其他衍生物，以提供延伸的 α,β-不饱和羧酸，然后将其还原为饱和对应物。

  DOI：

  10.3390/molecules26010115
• 作为产物：
  描述：

  Lactose 在 高氯酸 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 4-formyl-2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Glycosylated Chrysin Derivatives Via Ester Linkers

  摘要：

  一系列糖基化的黄酮衍生物已通过简单的工艺和温和的反应条件合成，产率良好。通过每个酯链接引入了六种不同的糖基。

  DOI：

  10.1007/s10600-016-1721-5

文献信息

• Synthesis of a Sugar-Based Thiosemicarbazone Series and Structure-Activity Relationship versus the Parasite Cysteine Proteases Rhodesain, Cruzain, and Schistosoma mansoni Cathepsin B1
  作者：Nayara Cristina Fonseca、Luana Faria da Cruz、Filipe da Silva Villela、Glaécia Aparecida do Nascimento Pereira、Jair Lage de Siqueira-Neto、Danielle Kellar、Brian M. Suzuki、Debalina Ray、Thiago Belarmino de Souza、Ricardo José Alves、Policarpo Ademar Sales Júnior、Alvaro José Romanha、Silvane Maria Fonseca Murta、James H. McKerrow、Conor R. Caffrey、Renata Barbosa de Oliveira、Rafaela Salgado Ferreira

  DOI：10.1128/aac.04601-14

  日期：2015.5

  The pressing need for better drugs against Chagas disease, African sleeping sickness, and schistosomiasis motivates the search for inhibitors of cruzain, rhodesain, and Schistosoma mansoni CB1 (SmCB1), the major cysteine proteases from Trypanosoma cruzi , Trypanosoma brucei , and S. mansoni , respectively. Thiosemicarbazones and heterocyclic analogues have been shown to be both antitrypanocidal and inhibitory against parasite cysteine proteases. A series of compounds was synthesized and evaluated against cruzain, rhodesain, and SmCB1 through biochemical assays to determine their potency and structure-activity relationships (SAR). This approach led to the discovery of 6 rhodesain, 4 cruzain, and 5 SmCB1 inhibitors with 50% inhibitory concentrations (IC ₅₀ s) of ≤10 μM. Among the compounds tested, the thiosemicarbazone derivative of peracetylated galactoside (compound 4i) was discovered to be a potent rhodesain inhibitor (IC ₅₀ = 1.2 ± 1.0 μM). The impact of a range of modifications was determined; removal of thiosemicarbazone or its replacement by semicarbazone resulted in virtually inactive compounds, and modifications in the sugar also diminished potency. Compounds were also evaluated in vitro against the parasites T. cruzi , T. brucei , and S. mansoni , revealing active compounds among this series.

  摘要 人们迫切需要更好的药物来防治恰加斯病、非洲昏睡病和血吸虫病，这促使人们寻找克鲁扎因、罗得西亚因和曼氏血吸虫的抑制剂。 曼氏血吸虫 CB1（SmCB1）的抑制剂。 克氏锥虫 , 布氏锥虫 和 曼氏锥虫 和曼森氏杆菌。研究表明，硫代氨基羰基化合物和杂环类似物既能杀灭锥虫，又能抑制寄生虫半胱氨酸蛋白酶。我们合成了一系列化合物，并通过生化试验评估了这些化合物对克鲁沙因、罗得沙因和 SmCB1 的抑制作用，以确定它们的效力和结构-活性关系（SAR）。通过这种方法，发现了 6 种 rhodeSAin、4 种 cruzain 和 5 种 SmCB1 抑制剂，其 50％ 抑制浓度（IC 50 s）≤10 μM。在测试的化合物中，发现过乙酰化半乳糖苷的硫代氨基羰基衍生物（化合物 4i）是一种有效的 rhodeSAin 抑制剂（IC 50 = 1.2 ± 1.0 μM）。确定了一系列修饰的影响；去除硫代氨基甲酸或用半氨基甲酸取代硫代氨基甲酸会导致化合物几乎失去活性，而糖的修饰也会降低效力。还对化合物进行了 体外 对寄生虫 T. cruzi , 布鲁氏菌 和 曼森氏杆菌 的活性化合物。
• 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 and biological evaluation of glycosylated psoralen derivatives
  作者：Chao-Yue Chen、Jian-Guo Sun、Fei-Yan Liu、Kwok-Pui Fung、Ping Wu、Zhi-Zhen Huang

  DOI：10.1016/j.tet.2012.01.090

  日期：2012.3

  A novel route for the efficient synthesis of a target psoralen moiety, 4,4'-dimethylxanthotoxol, has been developed, which need only four steps using cheap pyrogallol as a starting material. Subsequently, a range of new glycosylated psoralen derivatives were synthesized in good yields with simple procedures and mild reaction conditions. The experiment of biological activity shows that some of the glycosylated psoralen derivatives have antiproliferative activities against human cancer cell lines. A strong photoinduced antiproliferative effects were found under UVA. All of the glycosylated psoralen derivatives exhibited antioxidant activities against the oxidation of DNA induced by Cu2+/glutathione (GSH). Further experiment also demonstrates that the introduction of sugar moieties in some glycosylated psoralen derivatives can improve their antioxidant activities significantly. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and Antimicrobial Activity of Glycosylated 2-Aryl‑5‑amidinobenzimidazoles
  作者：Thiago de Souza、Josidel Oliver、Ana Paula Gomes、Cícero Flávio Aragão、Leandro Ferreira、Fernando Henrique Nogueira、Amanda Dias、Ricardo Alves

  DOI：10.21577/0103-5053.20170227

  日期：——

  A series of new glycosylated 2-aryl-5-amidinobenzimidazoles derived from four different carbohydrates (D-glucose, D-galactose, N-acetyl-D-glucosamine and lactose) were synthesized by the condensation of the appropriate 4-formy1-3-methoxyphenyl glycoside with 4-amidino- or 4-N-isopropylamidino-ortho-phenylenediamine hydrochloride. All the compounds were properly characterized by high resolution mass spectrometry. uni- and bidimensional H-1 and C-13 nuclear magnetic resonance and then were evaluated for their antibacterial and antifungal potential. Considering the antifungal potential of them, two derivatives were active against Candida parapsilosis at 96.4 mu mol L-1 and another was active against this same strain at 83.5 mu mol L-1. In addition, one benzamidine showed activity against Candida glabrata at 97 mu mol L--(1). Considering the antibacterial potential of these compounds. six of them showed better activity against three different stains: three of them with IC50 of 96.4, 97 and 83.5 mu mol L-1 against Gram-positive Micrococcus luteus, the other two with IC50 96.5 and 96.4 mu mol L-1 against Gram-positive Enterococcus faecalis and one against Gram-negative Escherichia coli at 90.5 mu mol L-1. These findings suggest this structural pattern can be employed for design of more potent agents for discovery of new antimicrobial drug candidates.
• Helferich; Griebel, Justus Liebigs Annalen der Chemie, 1940, vol. 544, p. 191,201
  作者：Helferich、Griebel

  DOI：——

  日期：——