2-[(2-oxonaphthalen-1-ylidene)methylamino]benzamide | 106910-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[(2-oxonaphthalen-1-ylidene)methylamino]benzamide
• 英文别名: o-(2-hydroxy-1-naphthylmethyleneamino)benzamide
• CAS: 106910-71-8
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: ACZOPDXPANCKJA-RGVLZGJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.68
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-氨基苯甲酰胺 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 生成 2-[(2-oxonaphthalen-1-ylidene)methylamino]benzamide
  参考文献：
  名称：

  苯并环化的N-水杨基苯胺及其邻-C（O）X衍生物（X = CH 3，NH 2，OCH 3）的键固定对溶液中互变异构平衡的影响

  摘要：

  1 H，13 C，和15 ÑNMR光谱显示一个邻位（-C O）X本组中的分子Ñ -salicylideneanthranilamide（X = NH 2），甲基Ñ -salicylideneanthranilate（X = OCH 3），ñ -水杨基-邻-氨基苯乙酮（X = CH 3）及其苯并类似物对溶液中的互变异构OH / NH平衡只有很小的影响。仅检测到三种可能的互变异构体中的两种。理论计算证明了该缺席形式的不可靠性。计算的能量表明，烯醇胺形式（OH）的稳定性比烯胺酮（OH）不稳定。NH）形式仅适用于二苯并环化的N-水杨基苯胺。发现互变异构混合物中每种物质的种群与其能量成反比。基于几何学的芳香性指数HOMA的应用表明，分子中不同环中π电子离域的有效性主要取决于苯并环化的位置。两个NH ... O和N···HO氢键存在于NH和OH互变异构体，分别增加quasirings HO-C的芳香C-C

  DOI：

  10.1021/jo070454f

文献信息

• Sirtuin Inhibiting Compounds
  申请人：Sinclair David A

  公开号：US20090137681A1

  公开（公告）日：2009-05-28

  Provided herein are compositions and methods for treating or preventing cancer and autoimmune diseases. Compositions comprise a sirtuin inhibitory compound that decreases the activity of a sirtuin, such as SIRT1 or Sir2. Exemplary methods comprise contacting a cell or a molecule with a sirtuin inhibitory compound that decreases the activity of a sirtuin and thereby reduces the life span of a cell, kills the cell or renders it susceptible to certain cell stresses including radiation and chemotherapy. Other methods include treating pathogens expressing a sirtuin.

  本文提供了治疗或预防癌症和自身免疫疾病的组合物和方法。组合物包括抑制sirtuin的化合物，降低sirtuin的活性，如SIRT1或Sir2。示例方法包括将细胞或分子与抑制sirtuin的化合物接触，降低sirtuin的活性，从而缩短细胞的寿命，杀死细胞或使其对包括放射治疗和化疗在内的某些细胞应激变得敏感。其他方法包括治疗表达sirtuin的病原体。
• Design, Synthesis, and Biological Evaluation of Sirtinol Analogues as Class III Histone/Protein Deacetylase (Sirtuin) Inhibitors
  作者：Antonello Mai、Silvio Massa、Siva Lavu、Riccardo Pezzi、Silvia Simeoni、Rino Ragno、Francesca R. Mariotti、Francesco Chiani、Giorgio Camilloni、David A. Sinclair

  DOI：10.1021/jm050100l

  日期：2005.12.1

  In a search for potent inhibitors of class III histone/protein deacetylases (sirtuins), a series of sirtinol analogues have been synthesized and the degree of inhibition was assessed in vitro using recombinant yeast Sir2, human SIRT1, and human SIRT2 and in vivo with a yeast phenotypic assay. Two analogues, namely, 3- and 4-[(2-hydroxy-1-naphthalenylmethylene)amino] -N-(l-phenylethyl)benzamide (i.e., in- and p-sirtinol), were 2- to 10-fold more potent than sirtinol against human SIRT1 and SIRT2 enzymes. In yeast in vivo assay, these two small molecules were as potent as sirtinol. Compounds lacking the 2-hydroxy group at the naphthalene moiety or bearing several modifications at the benzene 2'-position of the aniline portion (carbethoxy, carboxy, and cyano) were 1.3-13 times less potent than sirtinol, whereas the 2'carboxamido analogue was totally inactive. Both (R)- and (S)-sirtinol had similar inhibitory effects on the yeast and human enzymes, demonstrating no enantioselective inhibitory effect.
• PARG INHIBITORS AND METHOD OF USE THEREOF
  申请人：City of Hope

  公开号：US20220002231A1

  公开（公告）日：2022-01-06

  Provided herein are, inter alia, compounds inhibiting poly(ADP-ribose) Glycohydrolase (PARG) in a cancer cell and methods of treating cancer using compounds of the invention.
• Influence of Bond Fixation in Benzo-Annulated <i>N</i>-Salicylideneanilines and Their <i>ortho</i>-C(O)X Derivatives (X = CH₃, NH₂, OCH₃) on Tautomeric Equilibria in Solution
  作者：Ryszard Gawinecki、Agnieszka Kuczek、Erkki Kolehmainen、Borys Ośmiałowski、Tadeusz M. Krygowski、Reijo Kauppinen

  DOI：10.1021/jo070454f

  日期：2007.7.1

  minor effect on the tautomeric OH/NH-equilibrium in solution. Only two of three possible tautomers were detected. Lability of the absent form was proved by theoretical calculations. Calculated energies show that the enolimino form (OH) is less stable than the enaminone (NH) form only for dibenzo-annulated N-salicylideneanilines. The population of each species in the tautomeric mixture was found to

  1 H，13 C，和15 ÑNMR光谱显示一个邻位（-C O）X本组中的分子Ñ -salicylideneanthranilamide（X = NH 2），甲基Ñ -salicylideneanthranilate（X = OCH 3），ñ -水杨基-邻-氨基苯乙酮（X = CH 3）及其苯并类似物对溶液中的互变异构OH / NH平衡只有很小的影响。仅检测到三种可能的互变异构体中的两种。理论计算证明了该缺席形式的不可靠性。计算的能量表明，烯醇胺形式（OH）的稳定性比烯胺酮（OH）不稳定。NH）形式仅适用于二苯并环化的N-水杨基苯胺。发现互变异构混合物中每种物质的种群与其能量成反比。基于几何学的芳香性指数HOMA的应用表明，分子中不同环中π电子离域的有效性主要取决于苯并环化的位置。两个NH ... O和N···HO氢键存在于NH和OH互变异构体，分别增加quasirings HO-C的芳香C-C