1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)propane-2-one | 469873-50-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)propane-2-one
• 英文别名: 1'-C-(1,3,4,5-tetra-O-acetyl-β-D-glucopyranosyl)-2'-propanone；5,6,7,9-tetra-O-acetyl-4,8-anhydro-1,3-dideoxy-D-glycero-D-gulo-nonulose；1-propanonyl 2,3,4,6-tetra-O-acetyl-β-D-C-glucopyranoside；1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-propan-2-one；1-(1'-deoxy-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranos-1'-yl)propan-2-one；3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-propanone；2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-propan-2-one；per-O-acetylated β-D-glucopyranosyl-propan-2-one；[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-(2-oxopropyl)oxan-2-yl]methyl acetate
• CAS: 469873-50-5
• 化学式: C₁₇H₂₄O₁₀
• 分子量: 388.372
• InChiKey: DWRNVUXNLZJUGM-DMRKSPOLSA-N

物化性质

• 熔点：
  97-99 °C
• 沸点：
  452.4±35.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)propane-2-one 在 四氢吡咯 、 tin(II) chloride dihdyrate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (E)-4-(4-aminophenyl)-1-[1'-deoxy-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranos-1'-yl]but-3-en-2-one
  参考文献：
  名称：

  Identification of Novel Phenyl Butenonyl C-Glycosides with Ureidyl and Sulfonamidyl Moieties as Antimalarial Agents

  摘要：

  A new series of C-linked phenyl butenonyl glycosides bearing ureidyl(thioureidyl) and sulfonamidyl moieties in the phenyl rings were designed, synthesized, and evaluated for their in vitro antimalarial activities against Plasmodium falciparum 3D7 (CQ sensitive) and K1 (CQ resistant) strains. Among all the compounds screened the C-linked phenyl butenonyl glycosides bearing sulfonamidyl moiety (5a) and ureidyl moiety in the phenyl ring (7d and 8c) showed promising antimalarial activities against both 3D7 and K1 strains with IC50 values in micromolar range and low cytotoxicity offering new HITS for further exploration.

  DOI：

  10.1021/ml500211c
• 作为产物：
  描述：

  可得然胶 在 吡啶 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)propane-2-one
  参考文献：
  名称：

  Attachment of carbohydrates to methoxyaryl moieties leads to highly selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII

  摘要：

  The transmembrane isoforms of carbonic anhydrase (hCA IX and XII) have been shown to be linked to carcinogenesis and their inhibition to arrest primary tumor and metastases growth. In this paper, we present a new class of C-glycosides incorporating the methoxyaryl moiety, that was designed to selectively target and inhibit the extracellular domains of the cancer-relevant CA isozymes. The glycosides have been prepared by aldol reaction of glycosyl ketones with the appropriate aromatic aldehydes. We also present the inhibition profile of our new glycomimetics, against four isozymes of carbonic anhydrase comprising hCAs I and II (cytosolic, ubiquitous isozymes) and hCAs IX and XII (tumor associated isozymes). In this study, per-O-acetylated glycoside 4, 6 and deprotected compounds 7, 9, 10 and 12 were identified as potent and highly selective inhibitors of hCA IX and XII. These results confirm that attaching carbohydrate moieties to CA methoxyaryl pharmacophore improves and enhances its inhibitory activity. These CA inhibitors have developmental potential to selectively target cancer cells, leading to cell death.

  DOI：

  10.1016/j.bmc.2014.07.052

文献信息

• A novel class of sugar-based ether-linked-dispirooxindolo-pyrrolidines/pyrrolizidines through [3+2]-cycloaddition of azomethine ylides
  作者：Arasappan Hemamalini、Subbiah Nagarajan、Thangamuthu Mohan Das

  DOI：10.1016/j.carres.2012.01.023

  日期：2012.5

  An efficient one-pot synthesis of novel sugar based dispirooxindolo-pyrrolidines/pyrrolizidines has been accomplished by a [3+2]-cycloaddition. This method utilizes an azomethine ylide derived from isatin and sarcosine/l-proline, with an ether linked alpha-,beta-unsaturated-beta-C-glycosidic ketones as the dipolarophile. All these sugar-based heterocyclics were characterized by NMR ((1)H and (13)C)

  通过[3 + 2]-环加成反应，可以有效地一锅合成新型的基于糖的双螺毒素-吡咯烷/吡咯烷。该方法利用了衍生自靛红和肌氨酸/ 1-脯氨酸的偶氮甲碱叶立德，以及与醚连接的α-，β-不饱和β-C-糖苷酮作为双极性亲和剂。所有这些基于糖的杂环都通过NMR（（1）H和（13）C）和元素分析进行​​了表征。糖基双螺杂环化合物10的抗微生物研究显示了对不同微生物的出色活性。
• Studies on the synthesis of ether-, substituted alkyl-, or aryl-linked C-disaccharide derivatives
  作者：Subbiah Nagarajan、M. Jeganathan Shanmugam、Thangamuthu Mohan Das

  DOI：10.1016/j.carres.2011.02.009

  日期：2011.5

  A series of ether-, substituted alkyl-, or aryl-linked disaccharide derivatives have been synthesized in relatively good yield and characterized using different spectral techniques including single-crystal X-ray diffraction (XRD). β-Anomeric forms of sugar moiety in these derivatives were identified from (1)H NMR studies. The existence of inter- and intramolecular hydrogen bonding interactions were

  已经以相对较高的产率合成了一系列醚，取代的烷基或芳基连接的二糖衍生物，并使用包括单晶X射线衍射（XRD）在内的不同光谱技术对其进行了表征。这些衍生物中糖部分的β-端基异构形式是通过（1）H NMR研究确定的。从单晶XRD研究确定了分子间和分子内氢键相互作用的存在。
• Synthesis of isatin based N1-alkylated 3-β-C-glycoconjugated-oxopropylidene oxindoles as potent antiplasmodial agents
  作者：Ravi Kumar Thakur、Prince Joshi、Kapil Upadhyaya、Kartikey Singh、Gaurav Sharma、Sanjeev K. Shukla、Renu Tripathi、Rama Pati Tripathi

  DOI：10.1016/j.ejmech.2018.11.008

  日期：2019.1

  In an attempt to develop new antimalarial drugs, we have synthesized a new class of N-alkylated 3-glycoconjugated-oxopropylidene oxindoles starting from substituted isatins and glucopyranosyl propanone via a well-known cross-aldol reaction followed by dehydration. The newly synthesized compounds were screened for their in vitro antiplasmodial activity, and among all the compounds 9g, 9f, 9b, 8d, 9d

  为了开发新的抗疟疾药物，我们已经合成了新的一类N-烷基化的3-糖基共轭-氧亚丙基氧吲哚，它是由取代的靛红和葡萄糖基吡喃糖基丙酮通过众所周知的交叉羟醛反应然后脱水而合成的。筛选了新合成的化合物的体外抗血浆活性，在所有化合物9g，9f，9b，8d，9d，9c和9e中显示出有效的活性，对氯喹的IC 50值在0.1–0.3μM范围内（CQ）敏感的Pf 3D7菌株，而化合物9d，9b，9e，8c，8f，9c和9a显示出对CQ耐药的Pf K1菌株的IC 50值在0.1-0.4μM范围内的有希望的活性，甚至比标准药物氯喹的IC 50值为0.5更好。微米
• The concise synthesis and biological evaluation of C-glycosyl chalcone analogues inspired by the natural product aspalathin
  作者：Tao Zhang、Zhijie Fang

  DOI：10.1039/c6ra26969a

  日期：——

  We describe the synthesis and biological evaluation of C-glycosyl chalcone analogues of aspalathin. The DPPH radical scavenging method was used to detect their antioxidant activity and an MTT colorimetric assay was employed to test the anticancer activity against Hep-G2 liver carcinoma cells and MCF-7 human breast carcinoma cells. The antioxidant ability between C-furanosides and C-pyranosides was

  我们描述了天冬酰胺的C-糖基查耳酮类似物的合成和生物学评估。用DPPH自由基清除法检测其抗氧化活性，并用MTT比色法检测其对Hep-G2肝癌细胞和MCF-7人乳腺癌细胞的抗癌活性。比较了C-呋喃糖苷和C-吡喃糖苷之间的抗氧化能力。化合物3c'被证明是最有前途的化合物，具有良好的抗氧化能力和抑制Hep-G2和MCF-7细胞的能力，IC 50值分别为4.9μM和19μM。
• A novel fluorescent probe based on β - C- glycoside for quantification of bovine serum albumin
  作者：Xiaomin Gu、Qing Chen、Zhijie Fang

  DOI：10.1016/j.dyepig.2016.12.017

  日期：2017.4

  Two novel C-glycoside-coumarin fluorescent dyes are reported and their UV/Vis, fluorescence spectra and fluorescence-response to bovine serum albumin (BSA) are investigated and discussed. The fluorescence emission is red-shifted and quenched with the increase in polarity of solvents. Moreover, the fluorescence intensity of the dyes increased upon the addition of BSA in pH 7.4 phosphate buffer solution

  报道了两种新颖的C-糖苷-香豆素荧光染料，并研究和讨论了它们的UV / Vis，荧光光谱和对牛血清白蛋白（BSA）的荧光响应。随着溶剂极性的增加，荧光发射发生红移并猝灭。此外，在pH 7.4磷酸盐缓冲溶液中添加BSA后，染料的荧光强度增加。 化合物1的线性关系极好（R 2 = 0.99495）在荧光强度和牛血清白蛋白浓度之间获得。该方法对几种蛋白质，其他离子和氨基酸对BSA表现出良好的选择性和敏感性，被认为是生物科学中BSA定量的高选择性和灵敏荧光试剂。