2-benzamido-5-methoxyacetophenone

• 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-benzamido-5-methoxyacetophenone
• 英文别名: N-(2-acetyl-4-methoxyphenyl)benzamide；benzoic acid-(2-acetyl-4-methoxy-anilide)；Benzoesaeure-(2-acetyl-4-methoxy-anilid)；1-(6-Benzamino-3-methoxy-phenyl)-aethanon-(1)
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: WESUKIYSAVUASW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzamido-5-methoxyacetophenone 在 四丁基碘化铵 劳森试剂 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 甲苯 为溶剂， 生成 LDN-209964
  参考文献：
  名称：

  [EN] ACRIDINES AS INHIBITORS OF HASPIN AND DYRK KINASES
  [FR] ACRIDINES EN TANT QU'INHIBITEURS DES KINASES HASPINE ET DYRK

  摘要：

  公开号：

  WO2011127406A3
• 作为产物：
  描述：

  N-(2-acetyl-4-nitro-phenyl)-acetamide 在 吡啶 、 盐酸 、 sodium hydroxide 、 copper(I) sulfate 、 硫酸 、 铁粉 、 copper(II) sulfate 、 溶剂黄146 、 sodium nitrite 作用下， 生成 2-benzamido-5-methoxyacetophenone
  参考文献：
  名称：

  Simpson et al., Journal of the Chemical Society, 1945, p. 646,655

  摘要：

  DOI：

文献信息

• Oxidative Cleavage of Indoles Mediated by Urea Hydrogen Peroxide or H ₂ O ₂ in Polar Solvents
  作者：Natalia Llopis、Patricia Gisbert、Alejandro Baeza

  DOI：10.1002/adsc.202100214

  日期：2021.7

  The oxidative cleavage of indoles (Witkop oxidation) involving the use of H2O2 or urea hydrogen peroxide in combination with a polar solvent has been described. Among these solvents, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) stands out as the one affording the corresponding 2-ketoacetanilides generally in higher yields The protocol described has also enabled the oxidation of different pyrroles and furans

  已经描述了涉及使用 H 2 O 2或过氧化氢尿素与极性溶剂的吲哚的氧化裂解（Witkop 氧化）。在这些溶剂中，1,1,1,3,3,3-六氟异丙醇 (HFIP) 脱颖而出，通常以更高的产率提供相应的 2-酮乙酰苯胺。所描述的协议还能够氧化不同的吡咯和呋喃衍生物。此外，该程序是大规模实施的，从反应混合物中蒸馏出 HFIP 并重复使用（最多 4 个循环），而不会显着损害反应结果，这说明了其可持续性和适用性。
• Acridines As Inhibitors Of Haspin And DYRK Kinases
  申请人：Higgins Jonathan

  公开号：US20130102627A1

  公开（公告）日：2013-04-25

  The present disclosure is directed to compounds of Formula I: which are inhibitors of Haspin kinase and DYRK kinases. The compounds of the present disclosure, and compositions thereof, are useful in the treatment of disease related to Haspin kinase and DYRK kinase expression and/or activity.

  本公开涉及I式化合物，它们是Haspin激酶和DYRK激酶的抑制剂。本公开的化合物及其组合物在治疗与Haspin激酶和DYRK激酶表达和/或活性相关的疾病方面是有用的。
• Structure–activity relationship study of acridine analogs as haspin and DYRK2 kinase inhibitors
  作者：Gregory D. Cuny、Maxime Robin、Natalia P. Ulyanova、Debasis Patnaik、Valerie Pique、Gilles Casano、Ji-Feng Liu、Xiangjie Lin、Jun Xian、Marcie A. Glicksman、Ross L. Stein、Jonathan M.G. Higgins

  DOI：10.1016/j.bmcl.2010.04.150

  日期：2010.6

  Haspin is a serine/threonine kinase required for completion of normal mitosis that is highly expressed during cell proliferation, including in a number of neoplasms. Consequently, it has emerged as a potential therapeutic target in oncology. A high throughput screen of approximately 140,000 compounds identified an acridine analog as a potent haspin kinase inhibitor. Profiling against a panel of 270 kinases revealed that the compound also exhibited potent inhibitory activity for DYRK2, another serine/threonine kinase. An optimization study of the acridine series revealed that the structure-activity relationship (SAR) of the acridine series for haspin and DYRK2 inhibition had many similarities. However, several structural differences were noted that allowed generation of a potent haspin kinase inhibitor (33, IC(50) <60 nM) with 180fold selectivity over DYRK2. In addition, a moderately potent DYRK2 inhibitor (41, IC(50) <400 nM) with a 5.4-fold selectivity over haspin was also identified. (C) 2010 Elsevier Ltd. All rights reserved.
• Beer et al., Journal of the Chemical Society, 1954, p. 4139,4141
  作者：Beer et al.

  DOI：——

  日期：——
• Dioxygen transfer from 4a-hydroperoxyflavin anion. 3. Oxygen transfer to the 3-position of substituted indoles
  作者：Shigeaki Muto、Thomas C. Bruice

  DOI：10.1021/ja00545a028

  日期：1980.12