2-{3-[methyl(phenyl)amino]-2-oxopropyl}-1H-isoindole-1,3(2H)-dione | 82585-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-{3-[methyl(phenyl)amino]-2-oxopropyl}-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-[3-(N-methylanilino)-2-oxopropyl]isoindole-1,3-dione
• CAS: 82585-28-2
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: LQBUZOZETYVVMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.69
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-{2-hydroxy-3-[methyl(phenyl)amino]propyl}-1H-isoindole-1,3(2H)-dione 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86%的产率得到2-{3-[methyl(phenyl)amino]-2-oxopropyl}-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  A straightforward and general access to α-phthalimido-α′-substituted propan-2-ones

  摘要：

  The regioselective ring opening of the commercially available N-(2,3-epoxypropyl)phthalimide with different nucleophiles, to obtain the corresponding phthalimidopropan-2-ols (including a challenging fluorohydrin) followed by the Dess-Martin periodinane oxidation, constitutes a general and widely applicable protocol for the preparation of differently functionalized alpha-phthalimido-alpha'-substituted propan-2-ones. The incorporation of the substituent in the alpha' position takes place in an early stage of the process, thus furnishing a divergent and valuable approach. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.045

文献信息

• New anticancer agents: synthesis of 1,2-dihydropyrido[3,4-b]pyrazines (1-deaza-7,8-dihydropteridines)
  作者：Carroll Temple、Glynn P. Wheeler、Robert D. Elliott、Jerry D. Rose、Conrad L. Kussner、Robert N. Comber、John A. Montgomery

  DOI：10.1021/jm00351a008

  日期：1982.9

  Reaction of alpha-aminoacetophenone oximes (2) with ethyl 6-amino-4-chloro-5-nitropyridine-2-carbamate (1) gave ethyl 6-amino-5-nitro-4-[(2-oxo-2-phenylethyl)amino]pyridine-2-carbamate oximes (3), which were hydrolyzed under acidic conditions to give the corresponding ketones (4). Related pyridines substituted with a keto side chain were prepared from 1 and 1,3-diaminopropanone oximes and by oxidation of the side-chain hydroxy group of ethyl 6-amino-4- [[3-(N-methyl-N-phenylamino)-2-hydroxypropyl]amino]-5-nitropyridine-7- carbamates (6). Catalytic hydrogenation of the nitro group of 4 over Raney nickel in a large volume of ethanol gave the 1-deaza-7,8-dihydropteridines (7). Several of the oximes 3 were successfully hydrogenated to give 7 directly. The resulting 1-deaza-7,8-dihydropteridines showed potent cytotoxicity against cultured L1210 cells and significant anticancer activity against lymphocytic leukemia P-388 in mice. These biological activities are attributed to the accumulation of cells at mitosis.