2-(4-Methoxyphenyl)amino-1-cyclohexencarbonsaeure-ethylester | 38778-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-Methoxyphenyl)amino-1-cyclohexencarbonsaeure-ethylester
• 英文别名: 2-p-anisidino-cyclohex-1-enecarboxylic acid ethyl ester；2-p-Anisidino-cyclohex-1-encarbonsaeure-aethylester；2-(4-Methoxy-phenylimino)-cyclohexan-carbonsaeure-(1)-aethylester；Ethyl 2-[(4-methoxyphenyl)amino]cyclohex-1-ene-1-carboxylate；ethyl 2-(4-methoxyanilino)cyclohexene-1-carboxylate
• CAS: 38778-80-2
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: JAYGQUHVWBWNKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-Methoxyphenyl)amino-1-cyclohexencarbonsaeure-ethylester 在 硫酸 作用下， 生成 7-methoxy-1,2,3,4-tetrahydroacridin-9(10H)-one
  参考文献：
  名称：

  Structure–activity relationship study of acridine analogs as haspin and DYRK2 kinase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.04.150
• 作为产物：
  描述：

  甲氧苯胺 、 2-环己酮甲酸乙酯 在 盐酸 作用下， 生成 2-(4-Methoxyphenyl)amino-1-cyclohexencarbonsaeure-ethylester
  参考文献：
  名称：

  硼和碳原子中的全构型相互作用和多构型自旋密度

  摘要：

  通过与全构型相互作用 (FCI) 计算的结果进行比较，检验了使用几种广泛使用的高斯基组获得的原子自旋密度的自旋极化方法结果的可靠性。使用自旋极化模型和其他一些方法通过这些基组获得的自旋密度与 FCI 处理不一致。由于 FCI 波函数对于给定的基础是精确的，因此自旋极化模型是否普遍可靠尚不清楚。大型活动空间多配置 (CASSCF) 计算被证明不足以替代 FCI 处理。至少在一定程度上考虑基函数完整空间中所有轨道的激发的重要性可以通过 CASSCF 结果随着活动空间大小的增加而非常缓慢地收敛来说明。

  DOI：

  10.1063/1.1288377

文献信息

• General, Mild and Efficient Synthesis of β-Enaminones Catalyzed by Ceric Ammonium Nitrate
  作者：J. Menéndez、Vellaisamy Sridharan、Carmen Avendaño

  DOI：10.1055/s-2007-973862

  日期：2007.4

  Ceric ammonium nitrate catalyzes the reaction between aromatic or aliphatic primary amines and a variety of β-dicarbonyl compounds, including β-ketoesters, β-ketothioesters and β-diketones. The reaction proceeds smoothly at room temperature in short reaction times and gives β-enaminones in good to excellent yields.

  铈铵硝酸盐催化芳香族或脂肪族初级胺与多种β-二羰基化合物的反应，包括β-酮酯、β-酮硫酯和β-二酮。该反应在室温下顺利进行，反应时间短，产物为β-烯酰胺，产率良好至优异。
• 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。
• Stephen et al., Journal of the Chemical Society, 1947, p. 1034,1037
  作者：Stephen et al.

  DOI：——

  日期：——
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  作者：Basu、Das-Gupta

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