3-(二甲氨基)-N-(4-硝基苯基)丙酰胺 | 854813-63-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3-(二甲氨基)-N-(4-硝基苯基)丙酰胺
• 英文名称: 3-dimethylamino-N-(4-nitro-phenyl)-propionamide
• 英文别名: 3-(dimethylamino)-N-(4-nitrophenyl)propanamide；N,N-dimethyl-β-alanine-(4-nitro-anilide)；N,N-Dimethyl-β-alanin-(4-nitro-anilid)
• CAS: 854813-63-1
• 化学式: C₁₁H₁₅N₃O₃
• 分子量: 237.258
• InChiKey: GJROBODIYOYWOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(二甲氨基)-N-(4-硝基苯基)丙酰胺 在 palladium on activated charcoal benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 甲酸铵 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 1,3-bis(3-(4-(3-(dimethylamino)propanamido)phenylcarbamoyl)phenyl)urea
  参考文献：
  名称：

  WO2008/122667

  摘要：

  公开号：
• 作为产物：
  描述：

  4-硝基苯胺 以 甲醇 为溶剂， 反应 16.0h， 生成 3-(二甲氨基)-N-(4-硝基苯基)丙酰胺
  参考文献：
  名称：

  高选择性配体通过点击化学稳定 G-四链体 DNA

  摘要：

  一系列 G-四链体稳定化合物已通过点击化学制备，采用 Cu(I) 催化的 Huisgen 反应。即使存在竞争性高浓度双链 DNA，这些化合物也能与 G-四链 DNA 紧密结合。此外，改进的 TRAP 分析表明，这些化合物中的一些还在低微摩尔浓度下抑制端粒酶。

  DOI：

  10.1021/ja0661919

文献信息

• Click chemistry assembly of G-quadruplex ligands incorporating a diarylurea scaffold and triazole linkers
  作者：William C. Drewe、Stephen Neidle

  DOI：10.1039/b814576h

  日期：——

  A series of diarylurea ligands were designed to interact selectively with G-quadruplexes and were synthesised using copper(I) catalysed ‘click’ chemistry to incorporate the 1,4-substituted 1,2,3-triazole ring into the core of the ligands; the optimal ligands demonstrate a high degree of selective telomeric G-quadruplex stabilisation and are not cytotoxic in several cancer cell lines.

  设计了一系列二芳基脲配体，以选择性地与G-四重螺旋相互作用，并采用铜(I)催化的“点击”化学合成这些配体，将1,4-取代的1,2,3-三唑环引入配体的核心；最佳配体在稳定端粒G-四重螺旋方面表现出高度选择性，并且在多种癌细胞系中无细胞毒性。
• Design and synthesis of potent antitumor water-soluble phenyl N-mustard-benzenealkylamide conjugates via a bioisostere approach
  作者：Satishkumar D. Tala、Tai-Hsin Ou、Yi-Wen Lin、Kiranben S. Tala、Shu-Hsin Chao、Ming-Hsi Wu、Tung-Hu Tsai、Rajesh Kakadiya、Sharda Suman、Ching-Huang Chen、Te-Chang Lee、Tsann-Long Su

  DOI：10.1016/j.ejmech.2014.02.018

  日期：2014.4

  A series of new, water-soluble phenyl N-mustard-benzenealkylamide conjugates containing hydrophilic ω-dialkylaminoalkylamide or ω-cyclic aminoalkylamide moieties were synthesized via a bioisostere approach. These compounds have a broad spectrum of antitumor activity against a panel of human tumor cell lines. Of these derivatives, compound 18b effectively suppressed the growth of colon cancer (HCT-116)

  通过生物等排方法合成了一系列新的，水溶性的苯基N-芥子-苯烷基酰胺共轭物，其中包含亲水性ω-二烷基氨基烷基酰胺或ω-环氨基烷基酰胺部分。这些化合物对一组人类肿瘤细胞系具有广泛的抗肿瘤活性。在这些衍生物中，化合物18b有效抑制结肠癌（HCT-116），前列腺癌（PC3）和肺癌（H460）异种移植物的生长。当与化合物18b和5-氟尿嘧啶共同处理时，HCT-116异种移植物的生长几乎被完全抑制。此外，化合物18b可以在G2 / M期诱导DNA交联和细胞周期停滞。早期的临床前研究，包括在大鼠中的药代动力学，对hERG的抑制以及14天的急性静脉内注射毒性，表明化合物18b是进行进一步临床前研究的有希望的候选者。
• Design, synthesis and evaluation of 4,5-di-substituted acridone ligands with high G-quadruplex affinity and selectivity, together with low toxicity to normal cells
  作者：Francisco Cuenca、Michael J.B. Moore、Karin Johnson、Bérangère Guyen、Anne De Cian、Stephen Neidle

  DOI：10.1016/j.bmcl.2009.07.033

  日期：2009.9

  A series of 4,5-di-substituted acridones have been designed and synthesized. Several compounds show high affinity for telomeric G-quadruplex DNA in classical and competition FRET assays, together with low duplex DNA affinity, although they do not show activity in a telomerase assay or evidence of telomere shortening. They have low toxicity against a panel of cancer cell lines and a normal human fibroblast

  已经设计和合成了一系列的4，5-二取代的cri啶。几种化合物在经典和竞争性FRET分析中显示出对端粒G-四链体DNA的高亲和力，而在低端双链DNA亲和性中则低，尽管它们在端粒酶分析中没有活性，也没有端粒缩短的迹象。它们对一组癌细胞系和正常人成纤维细胞系具有低毒性，并在MCF7和A549癌细胞系中产生有效的基于衰老的长期生长停滞。
• 3-SUBSTITUTED-1H-INDOLE COMPOUNDS, THEIR USE AS MTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES
  申请人：Bursavich Matthew Gregory

  公开号：US20090311217A1

  公开（公告）日：2009-12-17

  The invention relates to 3-substituted-1H-indole compounds of the Formula I: or a pharmaceutically acceptable salt thereof, wherein the constituent variables are as defined herein, compositions comprising the compounds, and methods for making and using the compounds.

  本发明涉及公式I的3-取代-1H-吲哚化合物或其药学上可接受的盐，其中组成变量如本文所定义，包括该化合物的组合物，以及制备和使用该化合物的方法。
• Rational Design of Substituted Diarylureas: A Scaffold for Binding to G-Quadruplex Motifs
  作者：William C. Drewe、Rupesh Nanjunda、Mekala Gunaratnam、Monica Beltran、Gary N. Parkinson、Anthony P. Reszka、W. David Wilson、Stephen Neidle

  DOI：10.1021/jm801245v

  日期：2008.12.25

  The design and synthesis of a series of urea-based nonpolycyclic aromatic ligands with alkylaminoanilino side chains as telomeric and genomic G-quadruplex DNA interacting agents are described. Their interactions with quadruplexes have been examined by means of fluorescent resonance energy transfer melting, circular dichroism, and surface plasmon resonance-based assays. These validate the design concept for such urea-based ligands and also show that they have significant selectivity over duplex DNA, as well as for particular G-quadruplexes. The ligand-quadruplex complexes were investigated by computational molecular modeling, providing further information on structure-activity relationships. Preliminary biological studies using shortterm cell growth inhibition assays show that some of the ligands have cancer cell selectivity, although they appear to have low potency for intracellular telomeric G-quadruplex structures, suggesting that their cellular targets may be other, possibly oncogene-related quadruplexes,