4-(2',4'-dimethoxybenzylidene)-2-phenyloxazole-5(4H)-one | 118555-99-0

• 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
• 英文名称: 4-(2',4'-dimethoxybenzylidene)-2-phenyloxazole-5(4H)-one
• 英文别名: 4-[(2,4-Dimethoxyphenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 118555-99-0
• 化学式: C₁₈H₁₅NO₄
• mdl: MFCD00578685
• 分子量: 309.321
• InChiKey: XYASTVNLIUEYBR-UHFFFAOYSA-N

物化性质

• 熔点：
  169-180 °C(Solv: ethanol (64-17-5))
• 沸点：
  470.8±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4-(2',4'-dimethoxybenzylidene)-2-phenyloxazole-5(4H)-one 在 palladium on activated charcoal 、 氢气 、 三溴化硼 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 DL-N-Benzoyl-η-2,4-dihydroxy-phenyl-alanin
  参考文献：
  名称：

  Interactions of phenylalanine derivatives with human tyrosinase: lessons from experimental and theoretical studies

  摘要：

  The pigmentation of the skin, modulated by different actors in melanogenesis, is mainly due to the melanins (protective pigments). In humans, these pigments’ precursors are synthetized by an enzyme known as tyrosinase (TyH). The regulation of the enzyme activity by specific modulators (inhibitors or activators) can offer a means to fight hypo‐ and hyper‐pigmentations responsible for medical, psychological and societal handicaps. Herein, we report the investigation of phenylalanine derivatives as TyH modulators. Interacting with the binuclear copper active site of the enzyme, phenylalanine derivatives combine effects induced by combination with known resorcinol inhibitors and natural substrate/intermediate (amino acid part). Computational studies including docking, molecular dynamics and free energy calculations combined with biological activity assays on isolated TyH and in human melanoma MNT‐1 cells, and X‐ray crystallography analyses with the TyH analogue Tyrp1, provide conclusive evidence of the interactions of phenylalanine derivatives with human tyrosinase. In particular, our findings indicate that an analogue of L‐DOPA, namely (S)‐3‐amino‐tyrosine, stands out as an amino phenol derivative with inhibitory properties against TyH.

  DOI：

  10.1002/cbic.202400235
• 作为产物：
  描述：

  马尿酸 、 2,4-二甲氧基苯甲醛 在 乙酸酐 、 N,N-二异丙基乙胺 作用下， 反应 3.0h， 生成 4-(2',4'-dimethoxybenzylidene)-2-phenyloxazole-5(4H)-one
  参考文献：
  名称：

  新型的基于二酰胺的苯甲磺酰胺作为具有抗肿瘤活性的选择性碳酸酐酶IX抑制剂：合成，生物学评估和计算机模拟的见解。

  摘要：

  在这项工作中，我们介绍了作为金属酶碳酸酐酶（CA，EC 4.2.1.1）同工型hCA I，II，IX和XII抑制剂的新型基于二酰胺的苯磺酰胺5a–h系列的合成和生物学评估。不可否认，与靶标肿瘤相关的同工型hCA IX和XII是受影响最严重的同工型（KIs：分别为8.3–123.3和9.8–134.5 nM）。值得注意的是，二酰胺5a和5h以一位数的纳摩尔hCA IX抑制剂（KIs = 8.8和8.3 nM）脱颖而出。SAR结果表明，用化合物2h的杂2-呋喃基部分对亚苄基化合物5a-g进行生物等位取代，实现了最佳的IX / I和IX / II选择性，SI分别为985和13.8。在CA IX活性位点内制备的二酰胺的分子对接模拟显示5h在杂环氧和HE / Gln67之间建立额外的H键的能力。此外，评价了苯磺酰胺5a，5b和5h对肾癌UO-31细胞系的抗肿瘤活性。化合物5h是最有效的衍生物，其增强活性（IC50

  DOI：

  10.3390/ijms20102484

文献信息

• A new, efficient and chemoselective one-pot protocol for synthesis of 4-arylidene-2-phenyl-5(4<i>H</i>)-oxazolones from aryl aldehyde bisulfite adducts promoted by POCL₃
  作者：Ahmad R. Khosropour、Mohammad M. Khodaei、Seyed J. Hoseini Jomor

  DOI：10.1002/jhet.5570450308

  日期：2008.5

  A one-pot procedure for the synthesis of 4-arylidene-2-phenyl-5(4H)oxazolones directly from aryl aldehyde bisulfite adducts in the absence of Ac2O in good to excellent yields using phosphoryl chloride is reported. In addition, the observed chemoselectivity can be considered as a noteworthy advantage of this method.

  据报道，在不存在Ac 2 O的情况下，使用磷酰氯可以一锅法直接从芳基醛亚硫酸氢盐加合物合成4-亚芳基-2-苯基-5（4 H）恶唑酮。另外，观察到的化学选择性可以认为是该方法的显着优点。
• Organocatalytic asymmetric synthesis of pyrrolo[3,2-c]quinolines via a formal [3+2] cycloaddition-lactamization cascade reaction using a bifunctional squaramide catalyst
  作者：Pratibha Mahto、Khyati Shukla、Arko Das、Vinod K. Singh

  DOI：10.1016/j.tet.2021.132115

  日期：2021.5

  A simple organocatalytic strategy for the asymmetric synthesis of pyrrolo[3,2-c]quinolines has been developed using N-protected o-amino aromatic aldimines and α,β-unsaturated azlactones in the presence of a cinchona-based H-bonding bifunctional squaramide catalyst via a formal [3 + 2] cycloaddition-lactamization cascade reaction. The chiral pyrrolo[3,2-c]quinoline derivatives are obtained in good yields

  已经开发了一种简单的有机催化策略，用于不对称合成吡咯并[3,2-c]喹啉，该方法使用N-保护的邻氨基芳族醛亚胺和α，β-不饱和的内酯在基于金鸡纳的H键双功能方酸酰胺的存在下催化剂通过正式的[3 + 2]环加成-内酰胺化级联反应进行反应。手性吡咯并[3，2-c]喹啉衍生物以良好的产率，中等的对映选择性和优异的非对映选择性获得。首次报道了利用氢键双官能团有机催化的不对称合成吡咯并[3,2-c]喹诺酮。
• A New Approach to the Synthesis of Poly-Functionalized Pyrano[2,3-<i>d</i>]Pyrimidines Derivatives via Microwave-Assisted Multi-Component Reactions without Catalyst
  作者：Runhong Jia、Juhua Peng、Bo Jiang、Junyong Zhang、Shu-Jiang Tu

  DOI：10.1002/jhet.2017

  日期：2015.1

  A facile microwave‐assisted synthesis of pyrano[2,3‐d]pyrimidines derivatives is accomplished via reactions of 4‐arylmethylene‐2‐phenyloxazol‐5(4H)‐ones with pyrimidine‐4,6‐diol in ethylene glycol. The reaction is simple to perform and occurs under mild conditions with broad scope of applicability.

  通过4-芳基亚甲基-2-苯基恶唑-5（4 H）-酮与嘧啶-4,6-二醇在乙二醇中的反应可轻松完成微波辅助的吡喃并[2,3- d ]嘧啶衍生物的合成。该反应易于进行，并且在温和条件下进行，适用范围广。
• Sulfanilic Acid-Catalyzed Green Synthesis of 4-Arylidene-2-phenyl-5(4H)-oxazolones
  作者：Hamzeh Kiyani、Shiva Aslanpour

  DOI：10.3987/com-17-13847

  日期：——
• Madje, Balaji R.; Ubale, Milind B.; Bharad, Jagdish V., South African Journal of Chemistry, 2010, vol. 63, p. 158 - 161
  作者：Madje, Balaji R.、Ubale, Milind B.、Bharad, Jagdish V.、Shingare, Murlidhar S.

  DOI：——

  日期：——