N-Acetyl-2-hydroxy-4-aminobiphenyl | 146474-27-3

• 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: N-Acetyl-2-hydroxy-4-aminobiphenyl
• 英文别名: 3-hydroxy-4-phenylacetanilide；4-(Acetylamino)-2-hydroxybiphenyl；4-(methylcarbonylamino)biphenyl-2-ol；Acetamide, N-(2-hydroxy(1,1'-bipheny)-4-yl)-；N-(3-hydroxy-4-phenylphenyl)acetamide
• CAS: 146474-27-3
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: MKLPFZZCJWZDMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-二氯并[1,2,4]噻唑并[4,3-b]哒嗪 、 N-Acetyl-2-hydroxy-4-aminobiphenyl 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以37%的产率得到3-chloro-6-(4-acetamidobiphenyl-2-yloxy)-[1,2,4]triazolo[4,3-b]pyridazine
  参考文献：
  名称：

  [EN] DERIVATIVES OF 6-SUBSTITUTED TRIAZOLOPYRIDAZINES AS REV-ERB AGONISTS
  [FR] DÉRIVÉS DE TRIAZOLOPYRIDAZINES 6-SUBSTITUÉES EN TANT QU'AGONISTES DE REV-ERB

  摘要：

  本发明提供了新颖的激动Rev-Erb的6-取代[1,2,4]三唑并[4,3-b]吡啶嗪化合物。这些化合物以及包含它们的药物组合物是治疗任何激活Rev-Erb具有治疗效果的疾病的合适手段，例如在炎症和昼夜节律相关疾病或心脏代谢疾病中。

  公开号：

  WO2013045519A1
• 作为产物：
  描述：

  2-Hydroxy-4-nitrobiphenyl 在 platinum on activated charcoal 氢气 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 N-Acetyl-2-hydroxy-4-aminobiphenyl
  参考文献：
  名称：

  The electrochemical preparation and kinetic and product studies of acylated quinol and quinol ether imines. In search of the hydrolysis products of the ultimate carcinogen of N-acetyl-2-aminofluorene

  摘要：

  The N-acetyl and benzoyl derivatives of 4-methoxy-4-phenyl-2,5-cyclohexadienone imine and the N-benzoyl derivative of 4-hydroxy-4-phenyl-2,5-cyclohexadienone imine (1a-c) have been prepared via anodic oxidation of the corresponding amide of 4-aminobiphenyl in either methanol or water/acetonitrile, respectively. The products and the kinetics of the acidic and basic hydrolyses of these compounds were studied and the results compared with other N-acylquinol imine derivatives, including N-acetyl-4-hydroxy-4-phenyl-2,5-cyclohexadienone imine (1d), generated by solvolytic routes. The chemistry of these compounds was dependent upon the pH and the substituents on the quinol imine derivative. The major reaction pathways were hydrolysis of the imine linkage to afford the respective dienone and phenyl migration to afford the amides of 2-hydroxy- or 2-methoxy-5-aminobiphenyl. The reactivity of the quinol imine derivatives follows the order: 4-hydroxyl more reactive than 4-methoxyl compounds and N-acetyl more reactive than N-benzoyl derivatives. The higher reactivity for the former compounds is attributed to the greater electron-donating ability of the 4-hydroxyl versus the 4-methoxyl group. The higher reactivity of the N-acetyl relative to the N-benzoyl derivatives is attributed to the ca. 30-fold increase in basicity of the N-acetyl functionality. The additive effect of the 4-hydroxyl and N-acetyl functionality on the basic quinol imine moiety makes compounds having both of the groups difficult to isolate in aqueous media. This serves as a limitation for the preparation of the quinol imine derivative of N-acetyl-2-aminofluorene via the anodic oxidation methods reported herein.

  DOI：

  10.1021/jo00056a019

文献信息

• DERIVATIVES OF 6-SUBSTITUTED TRIAZOLOPYRIDAZINES AS REV-ERB AGONISTS
  申请人：GENFIT

  公开号：US20150038503A1

  公开（公告）日：2015-02-05

  The present invention provides novel 6-substituted [1,2,4]triazolo[4,3-b]pyridazines that are agonists of Rev-Erb. These compounds, and pharmaceutical compositions comprising the same, are suitable means for treating any disease wherein the activation of Rev-Erb has therapeutic effects, for instance in inflammatory and circadian rhythm-related disorders or cardiometabolic diseases.

  本发明提供了新型的6-取代[1,2,4]三唑并[4,3-b]吡啶嗪，这些化合物是Rev-Erb激动剂。这些化合物及其含有的药物组合物是治疗任何需要Rev-Erb激活具有治疗效果的疾病的适当手段，例如炎症和昼夜节律相关疾病或心脏代谢疾病。
• Derivatives of 6-substituted triazolopyridazines as Rev-Erb agonists
  申请人：GENFIT

  公开号：US10799510B2

  公开（公告）日：2020-10-13

  The present invention provides novel 6-substituted [1,2,4]triazolo[4,3-b]pyridazines that are agonists of Rev-Erb. These compounds, and pharmaceutical compositions comprising the same, are suitable means for treating any disease wherein the activation of Rev-Erb has therapeutic effects, for instance in inflammatory and circadian rhythm-related disorders or cardiometabolic diseases.

  本发明提供了新型 6-取代的[1,2,4]三唑并[4,3-b]哒嗪，它们是 Rev-Erb 的激动剂。这些化合物以及包含这些化合物的药物组合物适用于治疗任何激活 Rev-Erb 具有治疗效果的疾病，例如炎症和昼夜节律相关疾病或心脏代谢疾病。
• Nucleophilic aromatic substitution on ester derivatives of carcinogenic N-arylhydroxamic acids by aniline and N,N-dimethylaniline
  作者：Michael Novak、Kanchugarakoppal S. Rangappa、Rebecca K. Manitsas

  DOI：10.1021/jo00079a028

  日期：1993.12

  Decomposition of N-(pivaloyloxy)-2-(acetylamino)fluorene (1b) and N-(sulfonatooxy)-4-(acetylamino)-biphenyl (2a) in MeOH occurs predominately via N-0 bond cleavage to yield oxazoles (5, 6, 23), methoxy adducts (7,8,24,25,26), and rearrangement products (10b,11b,28). Minor ester methanolysis paths lead to the N-arylhydroxamic acids (9, 27). In the presence of 0.1 M aniline (3), 1b yields a number of adducts (14-18) identical to those previously obtained from the reaction of 3 with N-(sulfonatooxy)-2-(acetylamino)fluorene (1a). This occurs with no change in the rate constant for decomposition of 1b. At 0.1 M 3 all solvolysis products of 1b, except the rearrangement products 10 band 11b, are reduced below detectable levels. Similar results were obtained for 2a, which yields the adducts 30-35 in the presence of 3 and 36-38 in the presence of N,N-dimethylaniline (4). These results are consistent with a mechanism (Scheme V) in which the N-O bond heterolysis leads to a tight ion pair that can undergo internal return to yield the rearrangement products or diffusional separation to yield the free ion. The free nitrenium ion can be trapped by solvent or added nucleophiles. Both the N-acetyl-N-(4-biphenylyl)nitrenium ion (45) and the N-acetyl-N-(2-fluorenyl)nitrenium ion (48) react slowly enough with the solvent to undergo selective reaction with strong nucleophiles. Since 1a, 1b, and 2a span the reactivity range of the ester derivatives of the common N-arylhydroxamic acids which undergo N-O bond heterolysis in H2O, it appears that all of the carcinogenic esters will react with simple aromatic amines via an S(N)1 mechanism.
• Adriaan Davidse; Kahley, Mary Jo; McClelland, Robert A., Journal of the American Chemical Society, 1994, vol. 116, # 10, p. 4513 - 4514
  作者：Adriaan Davidse、Kahley, Mary Jo、McClelland, Robert A.、Novak, Michael

  DOI：——

  日期：——
• Novak Michael, Rangappa Kanchugarakoppal, Manitsas Rebecca K., J. Org. Chem, 58 (1993) N 27, S 7813- 7821
  作者：Novak Michael, Rangappa Kanchugarakoppal, Manitsas Rebecca K.

  DOI：——

  日期：——