2-amino-5-acetamidoacetophenone | 42465-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-5-acetamidoacetophenone
• 英文别名: acetic acid-(3-acetyl-4-amino-anilide)；1-(6-Amino-3-acetamino-phenyl)-aethanon-(1)；Essigsaeure-(3-acetyl-4-amino-anilid)；N-(3-acetyl-4-aminophenyl)acetamide
• CAS: 42465-64-5
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: LNLMNPRFGRCPQG-UHFFFAOYSA-N

物化性质

• 熔点：
  175 °C
• 沸点：
  331.9±27.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-5-acetamidoacetophenone 在 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 22.5h， 生成 3'-methoxy-6-acetamido-2-phenyl-4-quinolone
  参考文献：
  名称：

  Antitumor Agents 155. Synthesis and Biological Evaluation of 3',6,7-Substituted 2-Phenyl-4-quinolones as Antimicrotubule Agents

  摘要：

  A series of 3',6,7-substituted 2-phenyl-4-quinolones were designed and synthesized as antimitotic antitumor agents. All compounds showed cytotoxic effects (log GI(50) less than or equal to -4.0; log drug molar concentration required to cause 50% inhibition) against the growth of a variety of human tumor cell lines, including those derived from solid tumors such as non-small cell lung, colon, central nervous system, ovary, prostate, and breast cancers, when evaluated in the National Cancer Institute's 60 human tumor cell line in vitro screen. The most potent compound (26) demonstrated strong cytotoxic effects with GI(50) values in the nanomolar or subnanomolar range in almost all the tumor cell lines. Compound 26 was also a potent inhibitor of tubulin polymerization and radiolabeled colchicine binding to tubulin, with activity comparable to those of the potent antimitotic natural products colchicine, podophyllotoxin, and combretastatin A-4.

  DOI：

  10.1021/jm00046a025
• 作为产物：
  描述：

  3-乙酰胺基苯乙酮 在 乙醇 、 硫酸 、 硝酸 、 铂 作用下， 生成 2-amino-5-acetamidoacetophenone
  参考文献：
  名称：

  五线谱; 氨基苯乙酮和氨基苯乙酮的合成。

  摘要：

  DOI：

  10.1021/jo01174a018

文献信息

• Antitumor compounds
  申请人：The University of North Carolina at Chapel Hill

  公开号：US05571822A1

  公开（公告）日：1996-11-05

  A method of inhibiting tumor-cell growth in a mammalian subject, by administering a therapeutically effective amount of a selected 2-phenyl-4-quinolone compound. The selected compound shows unexpectely high activity against a variety of solid tumor cells.

  通过向哺乳动物受试者施用所选2-苯基-4-喹啉酮化合物的治疗有效量，来抑制肿瘤细胞生长的方法。所选的化合物显示出对各种实体肿瘤细胞具有意外的高活性。
• US5571822A
  申请人：——

  公开号：US5571822A

  公开（公告）日：1996-11-05
• [EN] 2-ARYL-4-QUINOLONES AS ANTITUMOR COMPOUNDS<br/>[FR] 2-ARYL-4-QUINOLONES UTILISEES COMME AGENTS ANTITUMEUR
  申请人：THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：WO1996010563A1

  公开（公告）日：1996-04-11

  (EN) A method of inhibiting tumor-cell growth in a mammalian subject, by administering a therapeutically effective amount of selected 2-phenyl-4-quinolone compounds represented by formula (5), wherein X is selected from the group consisting of H, F, C1, Br, I, CH3, CF3, OH, OCH3, OCF3, OCH2CH3, NH2, NHCH3, N(CH3)2, O-benzyl, -C(=O)-R0, -C(=O)-OR0, where R0 is a lower alkyl group; and where R1 and R2 (i) are lower alkyl groups or (ii) taken together, form a chain having the form -(CH2)m Y(CH2)n-, where Y is CH2, O, or S; m and n are each greater than 1; and the sum of m and n is between 3 and 6.(FR) L'invention concerne un procédé pour inhiber la croissance des cellules de tumeurs chez les mammifères en administrant une quantité, suffisante pour avoir un effet thérapeutique, d'un composé 2-phényl-4-quinolone choisi, représenté par la formule (5). Dans cette formule, X est choisi parmi l'un des groupes H, F, CI, Br, I, CH3, CF3, OH, OCH3, OCF3, OCH2CH3, NH2, NHCH3N(CH3)2, O-benzyle, C(=O)-R0, -C(=O)-OR0, où R0 est un groupe alkyle inférieur et où R1 et R2 sont (i) des groupes alkyle inférieur ou (ii) forment ensemble une chaîne ayant la forme -(CH2)mY(CH2)n-, où Y est CH2, O ou S, et m et n sont, chacun, supérieurs à 1 et leur somme est comprise entre 3 et 6.
• CINNOLINES. I. SYNTHESIS OF AMINOACETOPHENONES AND AMINOPROPIOPHENONES¹
  作者：NELSON J. LEONARD、SAMUEL N. BOYD

  DOI：10.1021/jo01174a018

  日期：1946.7
• Antitumor Agents 155. Synthesis and Biological Evaluation of 3',6,7-Substituted 2-Phenyl-4-quinolones as Antimicrotubule Agents
  作者：Leping Li、Hui-Kang Wang、Sheng-Chu Kuo、Tian-Shung Wu、Anthony Mauger、Chii M. Lin、Ernest Hamel、Kuo-Hsiung Lee

  DOI：10.1021/jm00046a025

  日期：1994.9

  A series of 3',6,7-substituted 2-phenyl-4-quinolones were designed and synthesized as antimitotic antitumor agents. All compounds showed cytotoxic effects (log GI(50) less than or equal to -4.0; log drug molar concentration required to cause 50% inhibition) against the growth of a variety of human tumor cell lines, including those derived from solid tumors such as non-small cell lung, colon, central nervous system, ovary, prostate, and breast cancers, when evaluated in the National Cancer Institute's 60 human tumor cell line in vitro screen. The most potent compound (26) demonstrated strong cytotoxic effects with GI(50) values in the nanomolar or subnanomolar range in almost all the tumor cell lines. Compound 26 was also a potent inhibitor of tubulin polymerization and radiolabeled colchicine binding to tubulin, with activity comparable to those of the potent antimitotic natural products colchicine, podophyllotoxin, and combretastatin A-4.