1-吗啉-4-基-2-(3-硝基苯基)乙酮 | 19281-20-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-吗啉-4-基-2-(3-硝基苯基)乙酮
• 英文名称: 4-[(3-nitro-phenyl)-acetyl]-morpholine
• 英文别名: 1-morpholin-4-yl-2-(3-nitro-phenyl)-ethanone；1-(Morpholin-4-yl)-2-(3-nitrophenyl)ethan-1-one；1-morpholin-4-yl-2-(3-nitrophenyl)ethanone
• CAS: 19281-20-0
• 化学式: C₁₂H₁₄N₂O₄
• 分子量: 250.254
• InChiKey: YCLQRUDKGXDPHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  476.3±45.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-吗啉-4-基-2-(3-硝基苯基)乙酮 在 sodium tetrahydroborate 、 10% palladium on activated charcoal 、 三氟化硼乙醚 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 3-(2-morpholin-4-ylethyl)-aniline
  参考文献：
  名称：

  Synthesis and biological evaluation of new 4β-anilino-4′-O-demethyl-4-desoxypodophyllotoxin derivatives as potential antitumor agents

  摘要：

  A series of new 4 beta-anilino-4'-O-demethyl-4-desoxypodophyllotoxin derivatives were prepared and evaluated for their cytotoxicities against four human cancer cell lines including KB, KB/VCR, A549 and 95D. Most compounds showed better growth-inhibition activities against tested cell lines than that of etoposide (VP-16). Preliminary structure-activity relationships (SARs) were concluded and it indicated that the side chains substituted at 4 beta position of podophyllotoxin significantly influenced the cytotoxic activity, especially for the drug resistance profile. In vivo studies of compound 26c on highly metastatic human lung cancer xenograft in nude mice showed that it can significantly inhibit tumor growth with administrating by oral route. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.016
• 作为产物：
  描述：

  间硝基苯甲醛 在 水 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 1-吗啉-4-基-2-(3-硝基苯基)乙酮
  参考文献：
  名称：

  Synthesis and biological evaluation of new 4β-anilino-4′-O-demethyl-4-desoxypodophyllotoxin derivatives as potential antitumor agents

  摘要：

  A series of new 4 beta-anilino-4'-O-demethyl-4-desoxypodophyllotoxin derivatives were prepared and evaluated for their cytotoxicities against four human cancer cell lines including KB, KB/VCR, A549 and 95D. Most compounds showed better growth-inhibition activities against tested cell lines than that of etoposide (VP-16). Preliminary structure-activity relationships (SARs) were concluded and it indicated that the side chains substituted at 4 beta position of podophyllotoxin significantly influenced the cytotoxic activity, especially for the drug resistance profile. In vivo studies of compound 26c on highly metastatic human lung cancer xenograft in nude mice showed that it can significantly inhibit tumor growth with administrating by oral route. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.016

文献信息

• <i>N</i>-Phenylamidines as Selective Inhibitors of Human Neuronal Nitric Oxide Synthase:  Structure−Activity Studies and Demonstration of in Vivo Activity
  作者：Jon L. Collins、Barry G. Shearer、Jeffrey A. Oplinger、Shuliang Lee、Edward P. Garvey、Mark Salter、Claire Duffy、Thimysta C. Burnette、Eric S. Furfine

  DOI：10.1021/jm980072p

  日期：1998.7.1

  the amidine nitrogen and phenyl ring to give N-(3-(aminomethyl)phenyl)acetamidine (14) dramatically altered the selectivity to give a neuronal selective nitric oxide synthase (nNOS) inhibitor. Part of this large shift in selectivity was due to 14 being a rapidly reversible inhibitor of iNOS in contrast to the essentially irreversible inhibition of iNOS observed with 13. Structure-activity studies revealed

  与内皮和诱导型亚型相比，可能需要选择性抑制一氧化氮合酶（NOS）的神经元亚型，以治疗由一氧化氮过量产生引起的神经系统疾病。最近，我们将N-（3-（氨基甲基）苄基）乙am（13）描述为一种缓慢，紧密结合的抑制剂，对人诱导型一氧化氮合酶（iNOS）具有高度选择性。除去the氮和苯环之间的单个亚甲基桥以得到N-（3-（氨基甲基）苯基）乙am（14）极大地改变了选择性，从而得到了神经元选择性一氧化氮合酶（nNOS）抑制剂。选择性大幅度变化的部分原因是14是iNOS的快速可逆抑制剂，而13观察到的iNOS基本上不可逆的抑制。结构活性研究表明，与芳香环相连的碱性胺官能团和空间紧凑的idine是此类NOS抑制剂的关键药效​​团。用N-（3-（氨基甲基）苯基）-2-呋喃基idine啶（77）可获得最大的nNOS抑制能力（Ki-nNOS = 0.006 microM; Ki-eNOS = 0.35 microM;
• Anti-inflammatory medicaments
  申请人：Flynn L. Daniel

  公开号：US20050288286A1

  公开（公告）日：2005-12-29

  Novel compounds and methods of using those compounds for the treatment of inflammatory conditions are provided. In a preferred embodiment, modulation of the activation state of p38 kinase protein comprises the step of contacting the kinase protein with the novel compounds.

  提供了用于治疗炎症性疾病的新化合物和使用这些化合物的方法。在一个首选实施例中，调节p38激酶蛋白的活化状态包括将该激酶蛋白与新化合物接触的步骤。
• MODULATION OF PROTEIN FUNCTIONALITIES
  申请人：Flynn Daniel L.

  公开号：US20080248548A1

  公开（公告）日：2008-10-09

  New methods for the rational identification of molecules capable of interacting with specific naturally occurring proteins are provided, in order to yield new pharmacologically important compounds and treatment modalities. Broadly, the method comprises the steps of identifying a switch control ligand forming a part of a particular protein of interest, and also identifying a complemental switch control pocket forming a part of the protein and which interacts with said switch control ligand. The ligand interacts in vivo with the pocket to regulate the conformation and biological activity of the protein such that the protein assumes a first conformation and a first biological activity upon the ligand-pocket interaction, and assumes a second, different conformation and biological activity in the absence of the ligand-pocket interaction. Next, respective samples of said protein in the first and second conformations are provided, and these are screened against one or more candidate molecules by contacting the molecules and the samples. Thereupon, small molecules which bind with the protein at the region of the pocket may be identified. Novel protein-modulator adducts and methods of altering protein activity are also provided.

  提供了一种新的方法，用于理性地识别能够与特定天然蛋白质相互作用的分子，以产生新的在药理学上重要的化合物和治疗方式。广义上，该方法包括以下步骤：识别构成感兴趣特定蛋白质一部分的开关控制配体，同时识别构成该蛋白质一部分并与该开关控制配体相互作用的互补开关控制口袋。该配体在体内与口袋相互作用，以调节蛋白质的构象和生物活性，使得蛋白质在配体-口袋相互作用时呈现第一构象和第一生物活性，并在缺乏配体-口袋相互作用时呈现第二不同构象和生物活性。接下来，提供了处于第一和第二构象的蛋白质的各自样本，并通过接触分子和样本对这些样本进行筛选。然后，可以识别与口袋区域的蛋白质结合的小分子。还提供了新颖的蛋白质调节剂加合物和改变蛋白质活性的方法。
• Modulation of protein functionalities
  申请人：——

  公开号：US20040171075A1

  公开（公告）日：2004-09-02

  New methods for the rational identification of molecules capable of interacting with specific naturally occurring proteins are provided, in order to yield new pharmacologically important compounds and treatment modalities. Broadly, the method comprises the steps of identifying a switch control ligand forming a part of a particular protein of interest, and also identifying a complemental switch control pocket forming a part of the protein and which interacts with said switch control ligand. The ligand interacts in vivo with the pocket to regulate the conformation and biological activity of the protein such that the protein assumes a first conformation and a first biological activity upon the ligand-pocket interaction, and assumes a second, different conformation and biological activity in the absence of the ligand-pocket interaction. Next, respective samples of said protein in the first and second conformations are provided, and these are screened against one or more candidate molecules by contacting the molecules and the samples. Thereupon, small molecules which bind with the protein at the region of the pocket may be identified. Novel protein-modulator adducts and methods of altering protein activity are also provided.

  提供了一种合理鉴定能够与特定自然存在的蛋白质相互作用的分子的新方法，以产生新的药理学重要化合物和治疗方法。广泛地说，该方法包括以下步骤：鉴定一个开关控制配体，其构成所需蛋白质的一部分，以及鉴定一个补充的开关控制口袋，其构成所需蛋白质的一部分，并与所述开关控制配体相互作用。配体在体内与口袋相互作用，以调节蛋白质的构象和生物活性，使蛋白质在配体-口袋相互作用时呈现第一构象和第一生物活性，并在缺乏配体-口袋相互作用时呈现第二种不同的构象和生物活性。接下来，提供所述蛋白质的第一和第二构象的各个样品，并通过接触分子和样品筛选一个或多个候选分子。然后，可以鉴定与口袋区域的蛋白质结合的小分子。还提供了新的蛋白质调节剂加合物和改变蛋白质活性的方法。
• ANTI-INFLAMMATORY MEDICAMENTS
  申请人：Flynn Daniel L.

  公开号：US20090312349A1

  公开（公告）日：2009-12-17

  Novel compounds and methods of using those compounds for the treatment of inflammatory conditions, hyperproliferative diseases, cancer, and diseases characterized by hyper-vascularization are provided. In a preferred embodiment, modulation of the activation state of p38 kinase protein, abl kinase protein, bcr-abl kinase protein, braf kinase protein, VEGFR kinase protein, or PDGFR kinase protein comprises the step of contacting said kinase protein with the novel compounds.

  本发明提供了新型化合物及其使用方法，用于治疗炎症状况、过度增殖性疾病、癌症和以高血管化为特征的疾病。在一个优选实施例中，调节p38激酶蛋白、abl激酶蛋白、bcr-abl激酶蛋白、braf激酶蛋白、VEGFR激酶蛋白或PDGFR激酶蛋白的活化状态包括将该激酶蛋白与新型化合物接触的步骤。