2-(((2,4-dimethylphenyl)amino)methylene)-5,5-dimethylcyclohexane-1,3-dione | 154640-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(((2,4-dimethylphenyl)amino)methylene)-5,5-dimethylcyclohexane-1,3-dione
• 英文别名: 2-[(2,4-dimethylanilino)methylidene]-5,5-dimethylcyclohexane-1,3-dione
• CAS: 154640-86-5
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: JQRGCEUKSUSXPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 原甲酸三乙酯 、 2,4-二甲基苯胺 以79%的产率得到2-(((2,4-dimethylphenyl)amino)methylene)-5,5-dimethylcyclohexane-1,3-dione
  参考文献：
  名称：

  特定抗结核药2-苯基氨基亚甲基-环己烷-1,3-二酮的合成，生物学评价及构效关系

  摘要：

  本研究利用基于全细胞的表型筛选数千种针对结核分枝杆菌H37Rv（M.tb.）的小分子，并将基于环己烷-1,3-二酮的结构5和6鉴定为命中。选定的命中分子用于进一步合成，并合成了四个家族下的37种化合物的文库，用于产生先导。评估抗结核分枝杆菌的文库可鉴定出三种主要的抗结核药（37、39和41）。最有潜力的化合物2-（（（（2-羟基苯基）氨基）亚甲基）-5,5-二甲基环己烷-1,3-二酮（39）的MIC为2.5 µg / mL，属于MICs范围内。已知的抗结核药物乙胺丁醇，链霉素和左氧氟沙星。此外，该化合物被证明是无毒的（< 在50μM浓度下对4种人类细胞系的抑制率为20％。像一线抗结核药（异烟肼，利福平和吡嗪酰胺）一样，该化合物对一般革兰氏阳性菌和革兰氏阴性菌甚至对耻垢分枝杆菌均​​无活性。从而反映出其高度特异性的抗结核活性。

  DOI：

  10.1039/c7md00350a

文献信息

• Development of Inhibitors of Salicylic Acid Signaling
  作者：Kai Jiang、Tetsuya Kurimoto、Eun-kyung Seo、Sho Miyazaki、Masatoshi Nakajima、Hidemitsu Nakamura、Tadao Asami

  DOI：10.1021/acs.jafc.5b01521

  日期：2015.8.19

  Salicylic acid (SA) plays important roles in the induction of systemic acquired resistance (SAR) in plants. Determining the mechanism of SAR will extend our understanding of plant defenses against pathogens. We recently reported that PAMD is an inhibitor of SA signaling, which suppresses the expression of the pathogenesis-related PR genes and is expected to facilitate the understanding of SA signaling. However, PAMD strongly inhibits plant growth. To minimize the side effects of PAMD, we synthesized a number of PAMD derivatives, and identified compound 4 that strongly suppresses the expression of the PR genes with fewer adverse effects on plant growth than PAMD. We further showed that the adverse effects on plant growth were partially caused the stabilization of DELLA, which is also related to the pathogen responses. These results indicate that compound 4 would facilitate our understanding of SA signaling and its cross talk with other plant hormones.
• PLANT ADDITIVES AND USES THEREOF TO MODULATE THE SYNTHESIS OF MEMBRANE GLYCEROLIPIDS IN PLANTS
  申请人：Commissariat à l'Énergie Atomique et aux Énergies Alternatives

  公开号：EP2477491B1

  公开（公告）日：2017-05-17
• Plant Additives and Uses Thereof to Modulate the Synthesis of Membrane Glycerolipids in Planta
  申请人：Clement Mathilde

  公开号：US20120283101A1

  公开（公告）日：2012-11-08

  The present invention pertains to plant additives containing a molecule selected in a family of compounds, wherein said molecule can modulate some molecular markers and physiological modifications observed in cases of phosphate deficiency. The family of compounds comprises the molecule MC2 of formula (I) as well as analogues thereof.
• US9028855B2
  申请人：——

  公开号：US9028855B2

  公开（公告）日：2015-05-12
• The synthesis, biological evaluation and structure–activity relationship of 2-phenylaminomethylene-cyclohexane-1,3-diones as specific anti-tuberculosis agents
  作者：Muzafar Ahmad Rather、Ali Mohd Lone、Bisma Teli、Zubair Shanib Bhat、Paramjeet Singh、Mubashir Maqbool、Bashir Ahmad Shairgojray、Mohd Jamal Dar、Shajrul Amin、Syed Khalid Yousuf、Bilal A. Bhat、Zahoor Ahmad

  DOI：10.1039/c7md00350a

  日期：——

  cyclohexane-1,3-dione based structures 5 and 6 as hits. The selected hit molecules were used for further synthesis and a library of 37 compounds under four families was synthesized for lead generation. Evaluation of the library against M. tuberculosis lead to the identification of three lead antituberculosis agents (37, 39 and 41). The most potential compound, 2-(((2-hydroxyphenyl)amino)methylene)-5,5-dimethylcyclohexane-1

  本研究利用基于全细胞的表型筛选数千种针对结核分枝杆菌H37Rv（M.tb.）的小分子，并将基于环己烷-1,3-二酮的结构5和6鉴定为命中。选定的命中分子用于进一步合成，并合成了四个家族下的37种化合物的文库，用于产生先导。评估抗结核分枝杆菌的文库可鉴定出三种主要的抗结核药（37、39和41）。最有潜力的化合物2-（（（（2-羟基苯基）氨基）亚甲基）-5,5-二甲基环己烷-1,3-二酮（39）的MIC为2.5 µg / mL，属于MICs范围内。已知的抗结核药物乙胺丁醇，链霉素和左氧氟沙星。此外，该化合物被证明是无毒的（< 在50μM浓度下对4种人类细胞系的抑制率为20％。像一线抗结核药（异烟肼，利福平和吡嗪酰胺）一样，该化合物对一般革兰氏阳性菌和革兰氏阴性菌甚至对耻垢分枝杆菌均​​无活性。从而反映出其高度特异性的抗结核活性。