1,2-二氢哒嗪-3,6-二酮,钠盐 | 73094-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,2-二氢哒嗪-3,6-二酮,钠盐
• 英文名称: (S)-1-(2-((4-chlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
• 英文别名: (S)-1-[2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole；(S)-econazole；econazole；1-[(2s)-2-[(4-Chlorobenzyl)oxy]-2-(2,4-Dichlorophenyl)ethyl]-1h-Imidazole；1-[(2S)-2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
• CAS: 73094-37-8
• 化学式: C₁₈H₁₅Cl₃N₂O
• 分子量: 381.689
• InChiKey: LEZWWPYKPKIXLL-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-二氢哒嗪-3,6-二酮,钠盐 、 硝酸 生成 (S)-econazole nitrate
  参考文献：
  名称：

  AASEN, ARNE JZHUSTORGEN;GROTN, PER, ACTA CHEM. SCAND., 41,(1987) N 9, 496-500

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2',4'-三氯苯乙酮 在 alcohol dehydrogenase from Rhodococcus rubber 、 水 、 potassium hydride 、 potassium carbonate 、 三苯基膦 、 异丙醇 、 还原型辅酶Ⅰ 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 mineral oil 为溶剂， 反应 48.0h， 生成 1,2-二氢哒嗪-3,6-二酮,钠盐
  参考文献：
  名称：

  Asymmetric Chemoenzymatic Synthesis of Miconazole and Econazole Enantiomers. The Importance of Chirality in Their Biological Evaluation

  摘要：

  A simple and novel chemoenzymatic route has been applied for the first time in the synthesis of miconazole and econazole single enantiomers. Lipases and oxidoreductases have been tested in stereoselective processes; the best results were attained with oxidoreductases for the introduction of chirality in an adequate intermediate. The behaviors of a series of ketones and racemic alcohols in bioreductions and acetylation procedures, respectively, have been investigated; the best results were found with alcohol dehydrogenases A and T, which allowed the production of (R)-2-chloro-1-(2,4-dichlorophenyl)ethanol in enantiopure form under very mild reaction conditions. Final chemical modifications have been performed in order to isolate the target fungicides miconazole and econazole both as racemates and as single enantiomers. Biological evaluation of the racemates and single enantiomers has shown remarkable differences against the growth of several microorganisms; while (R)-miconazole seemed to account for most of the biological activity of racemic miconazole on all the strains tested, both enantiomers of econazole showed considerable biological activities. In this manner, (R)-econazole showed higher values against Candida krusei, while higher values were observed for (S)-econazole against Cryptococcus neoformans, Penicillium chrysogenum, and Aspergillus niger.

  DOI：

  10.1021/jo102459w

文献信息

• Diamine-Tethered Bis(thiourea) Organocatalyst for Asymmetric Henry Reaction
  作者：Jan Otevrel、Pavel Bobal

  DOI：10.1021/acs.joc.7b00079

  日期：2017.8.18

  We have developed a novel multifunctional C2-symmetric biphenyl-based diamine-tethered bis(thiourea) organocatalyst, which was tested in the asymmetric Henry reaction. Under thoroughly optimized conditions, the catalyst provided exceptionally high yields and excellent enantioselectivities especially for electron-deficient aromatic and heterocyclic substrates. Due to a high affinity of the catalyst

  我们已经开发了一种新型的多功能的C 2对称联苯基二胺系双（硫脲）有机催化剂，在不对称亨利反应中进行了测试。在充分优化的条件下，该催化剂可提供极高的收率和出色的对映选择性，尤其是对于电子不足的芳族和杂环底物而言。由于催化剂对硅胶的亲和力高，因此简单的无色谱硝基硝基醇分离方法是可行的。进行了初步的动力学和光谱实验，以完成有机催化的硝基醛缩醛化过程的机理图。最后，已开发的合成策略成功地应用于对映纯的催化对映选择性合成（S）-益康唑和（R）-米拉贝隆是后期中间体。
• Stereospecific modulation of dimeric rhodopsin
  作者：Tamar Getter、Sahil Gulati、Remy Zimmerman、Yuanyuan Chen、Frans Vinberg、Krzysztof Palczewski

  DOI：10.1096/fj.201900443rr

  日期：2019.8

  challenged by the emerging evidence of GPCR dimerization and oligomerization. Rhodopsin (Rh) is the only GPCR whose native oligomeric arrangement was revealed by atomic force microscopy demonstrating that Rh exists as a dimer. However, the role of Rh dimerization in retinal physiology is currently unknown. In this study, we identified econazole and sulconazole, two small molecules that disrupt Rh dimer contacts

  GPCR 作为单体发挥作用的经典概念受到了新出现的 GPCR 二聚化和寡聚化证据的挑战。视紫红质 (Rh) 是唯一一种通过原子力显微镜揭示其天然寡聚排列的 GPCR，证明 Rh 以二聚体形式存在。然而，Rh 二聚化在视网膜生理学中的作用目前尚不清楚。在这项研究中，我们通过实施基于细胞的高通量筛选测定，鉴定了益康唑和磺康唑这两种破坏 Rh 二聚体接触的小分子。分离出已鉴定的先导化合物的外消旋混合物，并使用紫外可见光谱和照明后色氨酸 (Trp) 265 的固有荧光测试其与 Rh 的立体特异性结合。通过跟踪体外紫外可见光谱和Trp265荧光的变化，我们发现R-益康唑的结合调节了Meta III的形成并猝灭了Trp265的固有荧光。此外，电生理离体记录显示，R-益康唑减缓了光响应动力学，而S-益康唑降低了视杆细胞的敏感性，但不影响动力学。因此，这项研究提供了新的方法来识别一般破坏 GPCR 二聚化的化合物，并验证了第一个专门破坏
• Simplified Modular Access to Enantiopure 1,2-Aminoalcohols via Ni-Electrocatalytic Decarboxylative Arylation
  作者：Jiawei Sun、Hirofumi Endo、Megan A. Emmanuel、Martins S. Oderinde、Yu Kawamata、Phil S. Baran

  DOI：10.1021/jacs.3c14119

  日期：2024.3.6

  Chiral aminoalcohols are omnipresent in bioactive compounds. Conventional strategies to access this motif involve multiple-step reactions to install the requisite functionalities stereoselectively using conventional polar bond analysis. This study reveals that a simple chiral oxazolidine-based carboxylic acid can be readily transformed to substituted chiral aminoalcohols with high stereochemical control

  手性氨基醇在生物活性化合物中无处不在。获取该基序的传统策略涉及多步反应，以使用传统的极性键分析立体选择性地安装必要的功能。这项研究表明，通过镍电催化脱羧芳基化，简单的手性恶唑烷基羧酸可以很容易地转化为具有高度立体化学控制的取代手性氨基醇。这种通用、稳健且可扩展的偶联可用于合成多种重要的药用化合物，避免保护和官能团操作，从而大大简化其制备。
• Podolska, Marzena; Białecka, Wanda; Kulik, Anna, Acta poloniae pharmaceutica, 2017, vol. 74, # 3, p. 777 - 784
  作者：Podolska, Marzena、Białecka, Wanda、Kulik, Anna、Kwiatkowska-Puchniarz, Barbara、Mazurek, Aleksander

  DOI：——

  日期：——
• REGULATED BIOCIRCUIT SYSTEMS
  申请人：Obsidian Therapeutics, Inc.

  公开号：US20190192691A1

  公开（公告）日：2019-06-27

  The present invention provides regulatable biocircuit systems. Such systems provide modular and tunable protein expression systems in support of the discovery and development of therapeutic modalities.