Methyl 3-methyl-2-[(4-nitrobenzoyl)amino]butanoate | 35519-07-4

• 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: Methyl 3-methyl-2-[(4-nitrobenzoyl)amino]butanoate
• CAS: 35519-07-4
• 化学式: C₁₃H₁₆N₂O₅
• 分子量: 280.28
• InChiKey: QBPDXAKLGUSASG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3-methyl-2-[(4-nitrobenzoyl)amino]butanoate 在 一水合肼 作用下， 以 甲醇 为溶剂， 生成 N-(1-hydrazineyl-3-methyl-1-oxobutan-2-yl)-4-nitrobenzamide
  参考文献：
  名称：

  Synthesis and antitumor evaluation of some 1,3,4-oxadiazole-2(3H)-thione and 1,2,4-triazole-5(1H)-thione derivatives

  摘要：

  A series of 1,3,4-oxadiazole-2-thione and 1,2,4-triazole-5-thione derivatives have been successfully synthesized and studied for their antitumor activity. These compounds were prepared from carboxylic acids and chiral aminoacid esters. The prepared compounds were evaluated for their cytotoxicity against cancer in vitro using hydroxyurea (HU) as positive control. A fair number of compounds were found to have significant antitumor activity. To study the molecular basis of interaction and affinity of binding of the target molecules, all the compounds were docked into the ATPase domain of TP-II and tubulin using Schrodinger.

  DOI：

  10.1007/s00044-010-9544-6
• 作为产物：
  描述：

  DL-缬氨酸甲酯盐酸盐 、 4-硝基苯甲酰氯 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以68%的产率得到Methyl 3-methyl-2-[(4-nitrobenzoyl)amino]butanoate
  参考文献：
  名称：

  The effect of substituents on the chiral solvating properties of (S)-1,6-dialkylpiperazine-2,5-diones

  摘要：

  The effect of substituents on the chiral solvating properties of 13 different (S)-1,6-dialkylpiperazine-2,5-diones (S)-1a-m and five (35,6S)-1,3,6-trialkyl analogues (S,S)-1n-r was studied by NMR in CDCl(3) with methyl (RS)-N-benzoylleucinate (RS)-2a as the model analyte. Most diketopiperazines exhibited typical resolution, Delta Delta delta(-20)(RS) similar to 0.1 ppm. Increased performance was observed with 6-CH(2)R substituted compounds (S)-1h-j. The best resolution of the NH protons of (R)-2a and (S)-2a, Delta Delta delta(-2)(RS)0 = 0.227 ppm, was obtained with (S)-1-isopropyl-6-(4-nitrobenzyl)piperazine-2,5-dione (S)-1j. An additional syn-oriented substituent at the C(3) position decreased the enantioselectivity. Association constants for the binding of (S)-1j to each enantiomer of (RS)-2a in CDCl(3) at -20 degrees C were determined by NMR titration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.019

文献信息

• Substituent Effect on Acidity of Substituted 2-(4-Nitrobenzoylamino)alkanamides in Methanol-Dimethyl Sulfoxide Mixtures
  作者：Petr Mitaš、Miloš Sedlák、Jaromír Kaválek

  DOI：10.1135/cccc19980085

  日期：——

  The dissociation constants of substituted 2-(4-nitrobenzoylamino)alkanamides, N-[2-(4-nitrobenzoylamino)alkanoyl]pyrrolidines, and N-alkyl-4-nitrobenzamides have been measured spectrophotometrically in 60 and 80% v/v DMSO. The pK_A values of these N-acids are discussed from the point of view of substituents at the acetamide α-carbon atom.

  已发送中文翻译结果。如果您有任何其他问题或需要进一步帮助，请随时告诉我。谢谢！
• Synthesis and evaluation of new 4(3H)-Quinazolinone derivatives as potential anticancer agents
  作者：Srikanth Gatadi、Gauthami Pulivendala、Jitendra Gour、Satyaveni Malasala、Sushmitha Bujji、Ramulu Parupalli、Mujahid Shaikh、Chandraiah Godugu、Srinivas Nanduri

  DOI：10.1016/j.molstruc.2019.127097

  日期：2020.1

  Abstract A series of new 4(3H)-quinazolinones were synthesized and evaluated for their cytotoxic activity against a set of human cancer cell lines MDA-MB-231 and MCF-7 (breast), HCT-116 and HT-29 (colon) and A549 (lung). Among the tested compounds, 22a exhibited promising cytotoxic activity against MDA-MB-231 (IC50: 3.21 μM) and HT-29 (IC50: 7.23 μM) cell lines. The mechanism of action and the apoptosis

  摘要 合成了一系列新的 4(3H)-喹唑啉酮并评估了它们对一组人癌细胞系 MDA-MB-231 和 MCF-7（乳腺）、HCT-116 和 HT-29（结肠）的细胞毒活性。和 A549（肺）。在测试的化合物中，22a 对 MDA-MB-231 (IC50: 3.21 μM) 和 HT-29 (IC50: 7.23 μM) 细胞系表现出有希望的细胞毒活性。使用乳腺癌细胞系MDA-MB-231研究了化合物22a的作用机制和细胞凋亡诱导作用。用化合物 22a 处理 MDA-MB-231 细胞系显示出典型的细胞凋亡形态，如细胞收缩、染色质凝聚和马蹄形细胞核形成。流式细胞术分析表明，该化合物以剂量依赖性方式诱导细胞周期停滞的 G0/G1 期。
• Synthesis and antitumor evaluation of some 1,3,4-oxadiazole-2(3H)-thione and 1,2,4-triazole-5(1H)-thione derivatives
  作者：ChengTao Feng、LingDong Wang、YuGang Yan、Jian Liu、ShaoHua Li

  DOI：10.1007/s00044-010-9544-6

  日期：2012.3

  A series of 1,3,4-oxadiazole-2-thione and 1,2,4-triazole-5-thione derivatives have been successfully synthesized and studied for their antitumor activity. These compounds were prepared from carboxylic acids and chiral aminoacid esters. The prepared compounds were evaluated for their cytotoxicity against cancer in vitro using hydroxyurea (HU) as positive control. A fair number of compounds were found to have significant antitumor activity. To study the molecular basis of interaction and affinity of binding of the target molecules, all the compounds were docked into the ATPase domain of TP-II and tubulin using Schrodinger.
• The effect of substituents on the chiral solvating properties of (S)-1,6-dialkylpiperazine-2,5-diones
  作者：Črt Malavašič、Branko Stanovnik、Jernej Wagger、Jurij Svete

  DOI：10.1016/j.tetasy.2011.07.019

  日期：2011.6

  The effect of substituents on the chiral solvating properties of 13 different (S)-1,6-dialkylpiperazine-2,5-diones (S)-1a-m and five (35,6S)-1,3,6-trialkyl analogues (S,S)-1n-r was studied by NMR in CDCl(3) with methyl (RS)-N-benzoylleucinate (RS)-2a as the model analyte. Most diketopiperazines exhibited typical resolution, Delta Delta delta(-20)(RS) similar to 0.1 ppm. Increased performance was observed with 6-CH(2)R substituted compounds (S)-1h-j. The best resolution of the NH protons of (R)-2a and (S)-2a, Delta Delta delta(-2)(RS)0 = 0.227 ppm, was obtained with (S)-1-isopropyl-6-(4-nitrobenzyl)piperazine-2,5-dione (S)-1j. An additional syn-oriented substituent at the C(3) position decreased the enantioselectivity. Association constants for the binding of (S)-1j to each enantiomer of (RS)-2a in CDCl(3) at -20 degrees C were determined by NMR titration. (C) 2011 Elsevier Ltd. All rights reserved.