3-[(2,4-二氯苯氧基)甲基]-5-苯基-1,2,4-恶二唑 | 4780-17-0

• 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
• 中文名称: 3-[(2,4-二氯苯氧基)甲基]-5-苯基-1,2,4-恶二唑
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-isocyanato-β-D-glucopyranose
• 英文别名: [(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-isocyanatooxan-2-yl]methyl acetate
• CAS: 4780-17-0
• 化学式: C₁₅H₁₉NO₁₀
• 分子量: 373.317
• InChiKey: RDYCVABPKPHWHC-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3-[(2,4-二氯苯氧基)甲基]-5-苯基-1,2,4-恶二唑 以 二氯甲烷 为溶剂， 生成 1-(4-bromophenyl)-3-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranos-2-yl)imidazolidine-2,4,5-trione
  参考文献：
  名称：

  Synthesis of Novel Glycosyl Imidazolidine-2,4,5-Trione Derivatives

  摘要：

  通过缩合过-O-乙酰化氨基葡萄糖、三光气、胺和草酰氯，制备了一系列糖基咪唑烷-2,4,5-三酮衍生物。这种简便高效的方法可以得到所需的产物，而且收率极高。所有化合物都获得了令人满意的红外光谱、1H NMR、13C NMR 和 ESI-MS 图谱。

  DOI：

  10.14233/ajchem.2015.16824
• 作为产物：
  描述：

  2-deoxy-2-[p-methoxybenzylidene(amino)]-β-D-glucopyranose 在 吡啶 、 盐酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 3-[(2,4-二氯苯氧基)甲基]-5-苯基-1,2,4-恶二唑
  参考文献：
  名称：

  乙酰氨基葡萄糖基咪唑-2,4,5-三酮的合成方法 与抑菌用途

  摘要：

  本发明是一种乙酰氨基葡萄糖基咪唑-2,4,5-三酮。本发明还公开了乙酰氨基葡萄糖基咪唑-2,4,5-三酮的合成方法与用途。本发明合成方法是一种快速，高效，产率高的方法，在合成乙酰氨基葡萄糖基咪唑-2,4,5-三酮以市售氨基葡萄糖盐酸盐、固体光气、芳胺类和草酰氯为原料，原料廉价易得，降低了成本；反应条件采用传统加热模式，实验步骤简单，后处理简便环保，拓宽了该方法的适用范围；采用廉价易得原料作为反应物，降低了成本；在合成的目标化合物中引入乙酰氨基葡萄糖基团，有望得到生物活性更高的物质；合成的目标化合物对大肠杆菌、金黄色葡萄球菌、枯草芽孢杆菌均有较好的抑菌效果。

  公开号：

  CN103626816B

文献信息

• Synthesis of Sugar Isocyanates and Their Application to the Formation of Ureido-Linked Disaccharides
  作者：Martín Ávalos、Reyes Babiano、Pedro Cintas、Michael B. Hursthouse、José L. Jiménez、Mark E. Light、Juan C. Palacios、Esther M. S. Pérez

  DOI：10.1002/ejoc.200500601

  日期：2006.2

  The present work describes a facile and practical route to carbohydrate-based isocyanates, a reactive and appealing family of chiral heterocumulenes, wich can be easily converted into disaccharides and pseudodisaccharides interconnected by urea moieties. A full characterization of these substances by X-ray diffraction analysis and spectroscopic methods reveals further insights into their structures

  目前的工作描述了一种简便实用的基于碳水化合物的异氰酸酯的途径，这是一种反应性和吸引人的手性杂草烯家族，可以很容易地转化为通过尿素部分相互连接的二糖和假二糖。通过 X 射线衍射分析和光谱方法对这些物质进行全面表征，可以进一步了解它们的结构和优选构象。
• Engineering Light-Mediated Bistable Azobenzene Switches Bearing Urea<scp>d</scp>-Aminoglucose Units for Chiral Discrimination of Carboxylates
  作者：Kajetan Dąbrowa、Patryk Niedbała、Janusz Jurczak

  DOI：10.1021/acs.joc.6b00200

  日期：2016.5.6

  The symmetrical molecular receptors 1a and 1b consisting of a photochemically addressable azobenzene tether functionalized with urea hydrogen-bonding groups and d-carbohydrates as chiral selectors were developed to achieve control over the chiral recognition of α-amino acid-derived carboxylates. The photo- and thermally interconvertible planar E-1 and concaved Z-1 were found to exhibit different affinities

  对称分子受体1a和1b由光化学可寻址的偶氮苯系链组成，该束链被尿素氢键基团和d-碳水化合物作为手性选择剂官能化，从而实现了对α-氨基酸衍生的羧酸盐的手性识别的控制。发现在高极性介质（DMSO + 0.5％H 2 O）中，光和热可相互转换的平面E - 1和凹形Z - 1对这些生物学上重要的阴离子表现出不同的亲和力，选择性和结合模式。相同对映体纯客体的结合亲和力比E高3倍- 1比ž - 1（参见参数β）。另外，发现热Z → E异构化的速率取决于Z- 1的手性结合能力，即，更牢固地结合的羧酸盐对映异构体以及更高的对映异构体浓度导致更快地松弛至E- 1。
• Synthesis and antifungal activity of d-glucopyranosyl ureas and d-glucofurano-imidazolidine-2-ones
  作者：Xuan Tang、Feng Xue、Hongju Ma、Xiufang Cao、Changshui Chen、Xuegang Li

  DOI：10.1007/s11164-012-0596-8

  日期：2013.3

  A series of N-β-d-glucopyranosyl-N’-substituted phenyl ureas were synthesized by reaction of glucosyl isocyanate with arylamines and glycosamine with aryl isocyanates, and a series of d-glucofurano-imidazolidine-2-ones were obtained via deacetylation of glycosylureas. Although some of the compounds have already been described, most were prepared for the first time in this work. The structures of all the compounds synthesized were confirmed by IR, 1H NMR, and, in part, by 13C NMR. Antifungal activity of the title compounds was determined against four kinds of plant pathogenic fungi, Sclerotinia sclerotiorum, Fusarium graminearum, Fusarium oxysporum, and Bipolaris maydis. Preliminary bioassay indicates that most of glycosylureas had some activity against S. sclerotiorum; for some, the antifungal activity was strong. However, most of the imidazolidine-2-ones had weak antifungal activity.

  通过葡萄糖基异氰酸酯与芳基胺和糖胺与芳基异氰酸酯的反应，合成了一系列 N-β-d-glucopyranosyl-N'-substituted phenyl 脲；通过糖基脲的脱乙酰化，得到了一系列 d-glucofurano-imidazolidine-2-one。虽然其中一些化合物已经被描述过，但大多数化合物都是在这项工作中首次制备的。所有合成化合物的结构都通过红外光谱、1H NMR 以及部分 13C NMR 进行了确认。测定了标题化合物对四种植物病原真菌--硬核菌、禾谷镰刀菌、氧孢镰刀菌和五月双孢蘑菇--的抗真菌活性。初步生物测定表明，大多数糖基脲类对硬菌有一定的活性；其中一些糖基脲类的抗真菌活性很强。然而，大多数咪唑烷-2-酮的抗真菌活性较弱。
• [EN] SMALL MOLECULE ANTAGONISTS OF PF4<br/>[FR] ANTAGONISTES À PETITES MOLÉCULES DE PF4
  申请人：NEW YORK BLOOD CENTER INC

  公开号：WO2022073003A1

  公开（公告）日：2022-04-07

  The present application provides a compound of Formula (I) or a pharmaceutically acceptable salt thereof, wherein Y, R1, R2, R3and R4are described herein. The methods of using these compounds to inhibit tetramerization of PF4 and to treat the associated diseases and conditions, such as heparin-induced thrombocytopenia and thrombosis (HITT) and vaccine-induced immune thrombotic thrombocytopenia (VITT), methods of making these compounds, and pharmaceutical compositions containing these compounds are also disclosed.

  本申请提供了式（I）的化合物或其药学上可接受的盐，其中Y，R1，R2，R3和R4如本文所述。还公开了使用这些化合物抑制PF4四聚体化和治疗相关疾病和状况的方法，例如肝素诱导的血小板减少和血栓形成（HITT）和疫苗诱导的免疫性血栓性血小板减少症（VITT），制备这些化合物的方法以及含有这些化合物的制药组合物。
• New synthetic approaches to sugar ureas. Access to ureido-β-cyclodextrins
  作者：Óscar López、Susana Maza、Inés Maya、José Fuentes、José G. Fernández-Bolaños

  DOI：10.1016/j.tet.2005.07.041

  日期：2005.9

  An efficient method for the preparation of urea-bridged cyclodextrins using triphosgene in the isocyanation step in an aqueous two-phase system is reported. Per-O-acetylated glycopyranosylamines and 2-amino-2-deoxy-alpha and beta-D-glucose were also transformed into the corresponding isocyanates using either an aqueous two-phase or an anhydrous dichloromethane medium, and converted in situ into ureas. An alternative method for the preparation of sugar-derived ureas consisting of desulfurization of sugar thioureas with mercury oxide is also presented. (c) 2005 Elsevier Ltd. All rights reserved.