(Z)-2-methyl-4-(naphthalen-2-ylmethylene)oxazol-5(4H)-one | 68100-02-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-2-methyl-4-(naphthalen-2-ylmethylene)oxazol-5(4H)-one
• 英文别名: Z-2-Methyl-4-(naphthalen-2-ylmethylene)oxazol-5(4H)-one；(4Z)-2-methyl-4-(naphthalen-2-ylmethylidene)-1,3-oxazol-5-one
• CAS: 68100-02-7
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: MPEYDEJAPRRZJZ-ZROIWOOFSA-N

物化性质

• 沸点：
  395.8±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-methyl-4-(naphthalen-2-ylmethylene)oxazol-5(4H)-one 在 盐酸 、 sodium hydroxide 作用下， 生成 2-氧代-3-(2-萘基)丙酸
  参考文献：
  名称：

  Potent, Selective Tetrahydro-β-carboline Antagonists of the Serotonin 2B (5HT_2B) Contractile Receptor in the Rat Stomach Fundus

  摘要：

  A series of potent, selective 5HT(2B) receptor antagonists has been identified based upon yohimbine, with SAR studies resulting in a 1000-fold increase in 5HT(2B) receptor affinity relative to the starting structure (-log K(B)s > 10.0 have been obtained). These high-affinity tetrahydro-beta-carboline antagonists are able to discriminate among the 5HT(2) family of serotonin receptors, with members of the series showing selectivities of more than 100-fold versus both the 5HT(2A) and 5HT(2C) receptors based upon radioligand binding and functional assays. As the first compounds reported with such selectivity and enhanced receptor affinity, these tetrahydro-beta-carboline antagonists are useful tools for elucidating the role of serotonin acting at the 5HT(2B) receptor in normal and disease physiology.

  DOI：

  10.1021/jm960062t
• 作为产物：
  描述：

  2-萘甲醛 、 N-乙酰甘氨酸 在 sodium acetate 、 乙酸酐 作用下， 以40%的产率得到(Z)-2-methyl-4-(naphthalen-2-ylmethylene)oxazol-5(4H)-one
  参考文献：
  名称：

  绿色荧光蛋白发色团衍生物作为新型醛糖还原酶抑制剂

  摘要：

  已合成了许多与水母绿色荧光蛋白（GFP）的荧光发色团有关的（Z）-4-芳基亚甲基-1 H-咪唑-5（4 H）-，并对其体外抑制作用进行了评估。重组人醛糖还原酶的活性首次获得证实。GFP生色团模型1a在4-亚苄基上具有对羟基，在N1位置上具有羧甲基，具有很强的生物活性，IC 50值为0.36μM。该功效高于已知的高效醛糖还原酶抑制剂山梨醇的功效。化合物1h，即1a的2-萘基亚甲基类似物，在被测化合物中表现出最佳的抑制作用，IC 50值为0.10μM 。结构-活性关系研究与对接模拟相结合，揭示了新合成的抑制剂与靶蛋白的相互作用模式以及获得高抑制活性所需的结构特征。总之，本研究中合成的GFP生色团模型化合物已被证明是糖尿病并发症的潜在药物。

  DOI：

  10.1016/j.ejmech.2016.10.016

文献信息

• The Preparation of Single Enantiomer 2-Naphthylalanine Derivatives Using Rhodium−Methyl <i>BoPhoz</i>-catalyzed Asymmetric Hydrogenation
  作者：Neil W. Boaz、Shannon E. Large、James A. Ponasik、Mary K. Moore、Theresa Barnette、W. Dell Nottingham

  DOI：10.1021/op050026g

  日期：2005.7.1

  The single enantiomers of 2-naphthylalanine and N-tert-butoxycarbonyl 2-naphthylalanine were prepared from 2-naphthaldehyde. The sequence has been optimized and run on multikilogram scale, with the key step the asymmetric hydrogenation of methyl 2-acetamido-3-(2-naphthyl)propenoate using the rhodium complex of the methyl BoPhoz ligand, which proceeded smoothly at scale with 97.9% ee. Enhancement to

  2-萘基丙氨酸和的单一对映体ñ -叔由2-萘甲醛制备丁氧羰基2-萘基。该序列已优化并以多千克规模运行，关键步骤是使用甲基BoPhoz的铑配合物不对称氢化2-乙酰氨基-3-（2-萘基）丙酸甲酯配体，以97.9％ee的规模顺利进行。通过使2-氨基-3-（2-萘基）丙酸甲酯甲磺酸加成盐结晶（氢化产物的酸性脱酰作用的产物），可以提高至> 99.5％ee。对于这些类型的氨基酸衍生物，用于增强对映体纯度的方案似乎是通用的。随后的转化不影响对映体纯度，以＞ 99.5％ee提供所需产物。
• Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C–H Bonds
  作者：Kyle Clagg、Haiyun Hou、Adam B. Weinstein、David Russell、Shannon S. Stahl、Stefan G. Koenig

  DOI：10.1021/acs.orglett.6b01592

  日期：2016.8.5

  A direct oxidative C–H amination affording 1-acetyl indolecarboxylates starting from 2-acetamido-3-arylacrylates has been achieved. Indole-2-carboxylates can be targeted with a straightforward deacetylation of the initial reaction products. The C–H amination reaction is carried out using a catalytic Pd(II) source with oxygen as the terminal oxidant. The scope and application of this chemistry is demonstrated

  已经实现了从 2-乙酰氨基-3-芳基丙烯酸酯开始直接氧化 C-H 胺化，得到 1-乙酰基吲哚甲酸酯。通过对初始反应产物进行直接脱乙酰化，可以靶向 2-吲哚羧酸酯。 C-H 胺化反应是使用催化 Pd(II) 源和氧气作为末端氧化剂进行的。这种化学的范围和应用已被证明对于许多富电子和贫电子底物具有良好到高的产率。所选产物通过铃木芳基化和脱乙酰化进行进一步反应，获得高度功能化的吲哚结构。
• Oxazolone-Based Photoswitches: Synthesis and Properties
  作者：Marina Blanco-Lomas、Ignacio Funes-Ardoiz、Pedro J. Campos、Diego Sampedro

  DOI：10.1002/ejoc.201300641

  日期：2013.10

  synthesis, photophysics and photochemistry of a family of molecular switches inspired by the green fluorescent protein (GFP) chromophore is presented. These compounds can be synthesized in one step and good yields, their photophysical properties may be tuned by the substituents, solvent and wavelength of irradiation, and they show very efficient and fast photoisomerization. Furthermore, their high thermal

  介绍了受绿色荧光蛋白 (GFP) 生色团启发的一系列分子开关的合成、光物理学和光化学。这些化合物可以一步合成，产率高，它们的光物理性质可以通过取代基、溶剂和照射波长进行调节，并且它们表现出非常有效和快速的光异构化。此外，它们的高热稳定性和有限的光分解可以使这些开关用于一系列应用。最后，恶唑酮光开关可以通过使用光激活，并通过热或不同波长的光停用。
• Synthesis of new simplified hemiasterlin derivatives with α,β-unsaturated carbonyl moiety
  作者：Chinh Pham The、Tuyet Anh Dang Thi、Thi Phuong Hoang、Quoc Anh Ngo、Duy Tien Doan、Thu Ha Nguyen Thi、Tham Pham Thi、Thu Ha Vu Thi、M. Jean、P. van de Weghe、Tuyen Nguyen Van

  DOI：10.1016/j.bmcl.2014.03.091

  日期：2014.5

  In this Letter, we report a convenient and efficient method for the synthesis of new simplified derivatives of hemiasterlin in which the α,α-dimethylbenzylic moiety A is replaced by α,β-unsaturated aryl groups as Michael acceptor. Most of these derivatives have a strong cytotoxic activity on three human tumor cell lines (KB, Hep-G2 and MCF7). Analogs 17b and 17f showed a high cytotoxicity against KB

  在这封信中，我们报告了一种方便而有效的方法，用于合成半精胺素的新的简化衍生物，其中α，α-二甲基苄基部分A被α，β-不饱和芳基取代为Michael受体。这些衍生物大多数对三种人类肿瘤细胞系（KB，Hep-G 2和MCF 7）具有很强的细胞毒活性。类似物17b和17f显示出与紫杉醇和玫瑰树碱相当的对KB和Hep-G 2癌细胞系的高细胞毒性。
• Pseudo-peptides derived from isomannide: inhibitors of serine proteases
  作者：Thalita G. Barros、Sergio Pinheiro、J. S. Williamson、Amílcar Tanuri、M. Gomes、Helena S. Pereira、R. M. Brindeiro、José B. A. Neto、O. A. C. Antunes、Estela M. F. Muri

  DOI：10.1007/s00726-009-0273-4

  日期：2010.3

  In this paper, we describe the synthesis of a novel class of pseudo-peptides derived from isomannide and several oxazolones as potential inhibitors of serine proteases as well as preliminary pharmacological assays for hepatitis C. Hepatitis C, dengue and West Nile fever are among the most important flaviviruses that share one important serine protease enzyme. Serine proteases belong to the most studied class of proteolytic enzymes and are a primary target in the drug development field. Several pseudo-peptides were obtained in good yields from the reaction of isomannide and oxazolones, and their anti-HCV potential using the HCV replicon-based assay was shown.