4-(3,4-dimethoxybenzylidene)-2-methyloxazol-5(4H)-one | 41888-65-7

• 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-(3,4-dimethoxybenzylidene)-2-methyloxazol-5(4H)-one
• 英文别名: 4-(3',4'-Dimethoxybenzylidene)-2-methyl-5(4h)-oxazolone；4-[(3,4-dimethoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one
• CAS: 41888-65-7
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: ABAKBSGPUNJZIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  167.0-167.5 °C
• 沸点：
  374.3±52.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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-(3,4-dimethoxybenzylidene)-2-methyloxazol-5(4H)-one 在 盐酸 、 水 作用下， 以62%的产率得到(3,4-二甲氧基苯基)丙酮酸
  参考文献：
  名称：

  Defining the Mechanism of Action and Enzymatic Selectivity of Psammaplin A against Its Epigenetic Targets

  摘要：

  Psammaplin A (11c) is a marine metabolite previously reported to be a potent inhibitor of two classes of epigenetic enzymes: histone deacetylases and DNA methyltransferases. The design and synthesis of a focused library based on the psammaplin A core has been carried out to probe the molecular features of this molecule responsible for its activity. By direct in vitro assay of the free thiol generated upon reduction of the dimeric psammaplin scaffold, we have unambiguously demonstrated that 11c functions as a natural prodrug, with the reduced form being highly potent against HDAC1 in vitro (IC50 0.9 nM). Furthermore, we have shown it to have high isoform selectivity, being 360-fold selective for HDAC1 over HDAC6 and more than 1000-fold less potent against HDAC7 and HDAC8. SAR around our focused library revealed a number of features, most notably the oxime functionality to be important to this selectivity. Many of the compounds show significant cytotoxicity in A549, MCF7, and W138 cells, with the SAR of cytotcodcity correlating to HDAC inhibition. Furthermore, compound treatment causes upregulation of histone acetylation but little effect on tubulin acetylation. Finally, we have found no evidence for 11c functioning as a DNMT inhibitor.

  DOI：

  10.1021/jm2016182
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 N-乙酰甘氨酸 在 sodium acetate 、 乙酸酐 作用下， 生成 4-(3,4-dimethoxybenzylidene)-2-methyloxazol-5(4H)-one
  参考文献：
  名称：

  磁性圆二色性分析合成荧光蛋白发色团中的电子跃迁

  摘要：

  荧光发色团的详细电子结构对其在活细胞成像中的应用很重要。通过磁性圆二色性（MCD）光谱检查了一系列绿色荧光蛋白发色团衍生物，与普通吸收和荧光光谱相比，该光谱可分辨更多条带。借助随时间变化的密度泛函理论（TDDFT）计算和状态总和（SOS）形式主义，可以合理化所观察到的光谱模式，这也揭示了MCD强度对发色团构象的显着依赖性。有机化学和理论化学与光谱技术的结合在荧光标记的合理设计和生色团性质的理解中也很有用。例如，

  DOI：

  10.1002/cphc.201600313

文献信息

• Resolving Electronic Transitions in Synthetic Fluorescent Protein Chromophores by Magnetic Circular Dichroism
  作者：Petr Štěpánek、Thomas Y. Cowie、Martin Šafařík、Jaroslav Šebestík、Radek Pohl、Petr Bouř

  DOI：10.1002/cphc.201600313

  日期：2016.8.4

  bands than plain absorption and fluorescence. Observed spectral patterns are rationalized with the aid of time‐dependent density functional theory (TDDFT) computations and the sum‐over‐state (SOS) formalism, which also reveals a significant dependence of MCD intensities on chromophore conformation. The combination of organic and theoretical chemistry with spectroscopic techniques also appears useful in

  荧光发色团的详细电子结构对其在活细胞成像中的应用很重要。通过磁性圆二色性（MCD）光谱检查了一系列绿色荧光蛋白发色团衍生物，与普通吸收和荧光光谱相比，该光谱可分辨更多条带。借助随时间变化的密度泛函理论（TDDFT）计算和状态总和（SOS）形式主义，可以合理化所观察到的光谱模式，这也揭示了MCD强度对发色团构象的显着依赖性。有机化学和理论化学与光谱技术的结合在荧光标记的合理设计和生色团性质的理解中也很有用。例如，
• A facile synthesis of 2-alkyl-3-α-carboxy-α-styryl/heterylvinyl quinazolin-4(3H)-ones and 3-arylidene/heterylmethylidene-4-aroyl-1H-[1,4]benzodiazepine-2,5(3H,4H)-diones and their transformation into novel heterocyclyl and heterocyclo analogues
  作者：Poonam Gupta、Archana Sharma、R. L. Sharma

  DOI：10.1002/jhet.756

  日期：2012.1

  formation of two entirely different heterocyclic systems, differently substituted quinazoline compounds, 2‐methyl‐/2‐ethyl‐3‐α‐carboxy‐α‐styryl‐/β‐heteryl‐α‐carboxyvinyl‐quinazolin‐4(3H)‐ones 3a–3e and 3′a–3′e and differently substituted 1,4‐benzodiazepine compounds, 3‐arylidene‐/heteryl methylidene‐4‐aroyl‐1H‐[1,4]benzodiazepine‐2,5(3H,4H)‐diones 7a–7e and 7′a–7′e. Compounds 3a–3e and 3′a–3′e have been converted

  导致2-甲基-2-乙基和2-苯基-/对甲苯基-4-芳基-亚芳基/杂甲基亚甲基-2-恶唑啉-5-酮（γ-内酯）2与邻氨基苯甲酰胺1在乙酸中缩合在形成两个完全不同的杂环系统时，取代基不同的喹唑啉化合物2-甲基-2-乙基-3-3-α-羧基-α-苯乙烯基/β-杂基-α-羧基乙烯基-喹唑啉-4（3 H）一个3a-3e和3'a-3'e以及不同取代的1,4-苯并二氮杂化合物，3-亚芳基-/杂甲叉基-4-芳基-1 H- [1,4]苯并二氮杂-2,5（3 H，4 H）-diones 7a-7e和7′a-7′e。化合物3a–3e和3'a-3'e已被转换为化合物4a-4e和4'a-4'e；5a-5e和5′a-5′e；和6a-6e和6′a-6′e通过不同的变换。与邻苯二胺缩合后的苯二氮卓类化合物7a-7e和7'a-7'e生成了三个新颖的杂环系统8a-8e和8'a-8'e；9a-9e和9′a-9′e；和10a-10e和10′a-10′e。J
• ＴＲＰＶ４活性抑制剤
  申请人：花王株式会社

  公开号：JP2020059675A

  公开（公告）日：2020-04-16

  【課題】ＴＲＰＶ４の活性を抑制し、過活動膀胱や過敏性腸症候群等の予防又は改善に有用な化合物の提供。【解決手段】下式（Ｉａ）〜（Ｉｄ）から選ばれるロズマリン酸誘導体又はその塩を有効成分とするＴＲＰＶ４活性抑制剤。【選択図】なし

  提供抑制TRPV4活性的化合物，用于预防或改善过度活动膀胱或过敏性肠综合征等。选取自下式（Ia）至（Id）的迷迭香酸衍生物或其盐作为有效成分的TRPV4活性抑制剂。【选择图】无
• Asymmetric Synthesis of Unnatural Amino Acids and Tamsulosin Chiral Intermediate
  作者：Veera Reddy Arava、Srinivasulu Reddy Amasa、Bharat Kumar Goud Bhatthula、Laxmi Srinivas Kompella、Venkata Prasad Matta、M. C. S. Subha

  DOI：10.1080/00397911.2012.748075

  日期：2013.11.2

  An efficient and enantioselective hydrogenation of N-acetylamino phenyl acrylic acids was successfully developed by using ruthenium catalyst. This methodology is important in the field of pharmaceuticals and provides a new process for the preparation of unnatural amino acids and tamsulosin chiral intermediate. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]
• Trivedi; Kubawat; Parekh, Journal of the Indian Chemical Society, 2002, vol. 79, # 3, p. 282 - 283
  作者：Trivedi、Kubawat、Parekh

  DOI：——

  日期：——