1-allylpyrrolidine-2,3-dione | 106180-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-allylpyrrolidine-2,3-dione
• 英文别名: 2,3-Pyrrolidinedione, 1-(2-propenyl)-；1-prop-2-enylpyrrolidine-2,3-dione
• CAS: 106180-90-9
• 化学式: C₇H₉NO₂
• 分子量: 139.154
• InChiKey: BDQGQHQBNPRPPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-allylpyrrolidine-2,3-dione 在 原乙酸三甲酯 、 三甲基氯硅烷 、 AD-mix-β 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 47.0h， 生成 2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1,2-dihydropyrrolo[3,4-b]quinolin-3-one
  参考文献：
  名称：

  Chemoenzymatic synthesis with lipase catalyzed resolution and evaluation of antitumor activity of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one

  摘要：

  Synthesis, characterization, resolution and evaluation of novel (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one derivatives are described. Enantiomerically pure compounds were isolated in good to excellent yield with high enantiomeric excess under mild reaction conditions by using Candida antarctica B (CAL-B) and Candida rugosa (CRL) Lipases. Newly synthesized and resolved compounds were screened for their antitumor activity against cancer cells such as human neuroblastoma SK-N-SH and human lung carcinoma A549 cell line in vitro. The results have shown that the compound 1 S-(-) alcohol was more effective in inhibiting the tumor cell growth. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.069
• 作为产物：
  描述：

  3-(烯丙基氨基)丙酸乙酯 在 盐酸 、 sodium 作用下， 以 甲醇 、 异丙醚 、 水 为溶剂， 反应 16.0h， 生成 1-allylpyrrolidine-2,3-dione
  参考文献：
  名称：

  [EN] SMALL MOLECULE INHIBITORS OF NF-kB INDUCING KINASE
  [FR] INHIBITEURS À PETITE MOLÉCULE DE KINASE INDUISANT NF-KB

  摘要：

  本发明涉及抑制NIK的化合物，以及包含这些化合物的药物组合物和使用方法。这些化合物和药物组合物预期能用于预防或治疗癌症（如包括白血病、淋巴瘤和多发性骨髓瘤的B细胞恶性肿瘤）、炎症性疾病、自身免疫疾病、免疫皮肤病学疾病（如掌跖脓疱病和化脓性汗腺炎）以及代谢紊乱疾病（如肥胖和糖尿病）。

  公开号：

  WO2020239999A1

文献信息

• α-Oxo-γ-Butyrolactam, <i>N</i>-Containing Pronucleophile in Organocatalytic One-Pot Assembly of Butyrolactam-Fused Indoloquinolizidines
  作者：Hai-Liang Zhu、Jun-Bing Ling、Peng-Fei Xu

  DOI：10.1021/jo301192d

  日期：2012.9.7

  sequence. The synthetically interesting and medicinally important pentacyclic butyrolactam-fused indoloquinolizidines can be efficiently constructed in a highly stereocontrolled manner. Importantly, the chemistry described herein provides a general catalytic method for the enantioselective synthesis of butyrolactam-incorporated chemical entities.

  已经在有机催化一锅Michael / Pictet-Spengler序列中探索了α-氧代-γ-丁内酰胺的环境反应性。可以以高度立体可控的方式有效地构建合成上有趣且对医学有重要意义的五环丁内酰胺融合的吲哚并喹喔啉。重要的是，本文所述的化学方法为掺入丁内酰胺的化学实体的对映选择性合成提供了一种通用的催化方法。
• Synthesis of novel building blocks of 1H-pyrrolo[3,4-b]quinolin-3(2H)-one and evaluation of their antitumor activity
  作者：Lingaiah Nagarapua、Hanmant K. Gaikwad、Sheeba Rani Manikonda、Rajashaker Bantu、Krishna Madhuri Manda、Shasi Vardhan Kalivendi

  DOI：10.1007/s00044-012-0018-x

  日期：2013.1

  A series of new building blocks consisting of 1H-pyrrolo[3,4-b]quinolin-3(2H)-one with potential as selective antitumor agents is described. Compounds were synthesized by using Heck reaction of N-allyl-1H-pyrrolo[3,4-b]quinolin-3(2H)-one with p-bromophenyl acetic acid followed by formation of amide (1a-h, 2a-d) by reaction with several secondary amines in good yields. The cytotoxicity of these compounds was evaluated against human cancer cell lines in vitro (SK-N-NH, A549). Studies suggest that most of these compounds were effective in inhibiting neuroblastoma cell growth, compound 1d was the most potent one (% IC50 = 8.62 mu M).
• Sundberg, Richard J.; Pearce, Bradley C.; Laurino, Joseph P., Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 537 - 539
  作者：Sundberg, Richard J.、Pearce, Bradley C.、Laurino, Joseph P.

  DOI：——

  日期：——
• Lewis acid-assisted olefin cross-metathesis reaction: an efficient approach for the synthesis of glycosidic-pyrroloquinolinone based novel building blocks of camptothecin and evaluation of their antitumor activity
  作者：Lingaiah Nagarapu、Hanmant K. Gaikwad、Rajashaker Bantu、Sheeba Rani Manikonda、C. Ganesh Kumar、Sujitha Pombala

  DOI：10.1016/j.tetlet.2012.01.001

  日期：2012.3

  A series of glycosidic-pyrroloquinolinone based novel building blocks of camptothecin (2a-g) were synthesized via Lewis acid-assisted olefin cross-metathesis reaction using Ti((OPr)-Pr-i)(4) 30 mol % and 10 mol % of Grubb's second generation catalyst with good to excellent yields. Most of these compounds exhibited significant growth inhibitory effects on all the tested cancer cell lines and three compounds (2c, 2d and ze) showed potent cytotoxic activity. (C) 2012 Elsevier Ltd. All rights reserved.
• A new synthesis of the cytotoxic alkaloid Luotonine A
  作者：Sabrina Dallavalle、Lucio Merlini

  DOI：10.1016/s0040-4039(02)00140-5

  日期：2002.3

  A convenient synthesis of the cytotoxic alkaloid Luotonine A has been achieved using cheap and readily accessible reagents. The key intermediate in the synthesis is the tricyclic Compound 2,3-dihydro[1H]-pyrrolo[3,4-b]quinolin-3-one (5). (C) 2002 Elsevier Science Ltd. All rights reserved.