N,4-dimethyl-3-nitrobenzenamine | 33992-16-4

• 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: N,4-dimethyl-3-nitrobenzenamine
• 英文别名: N,4-dimethyl-3-nitroaniline；p-Methyl-m-nitro-N-methylanilin；N.4-Dimethyl-3-nitrobenzolamin；N-Methyl-2-nitro-p-toluidin；4,N-dimethyl-3-nitro-aniline；4,N-Dimethyl-3-nitro-anilin；2-Nitro-4-methylamino-toluol；3-Nitro-4,N-dimethyl-anilin；Methyl-(4-methyl-3-nitro-phenyl)-amine
• CAS: 33992-16-4
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: IYEKTRISTOHSPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,4-dimethyl-3-nitrobenzenamine 在 盐酸 、 一水合肼 、 溶剂黄146 、 copper(l) chloride 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 、 异丙醇 、 甲苯 为溶剂， 反应 75.67h， 生成 3-(2-(methyl(4-methyl-3-nitrophenyl)amino)ethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide
  参考文献：
  名称：

  Synthesis and Quantitative Structure–Activity Relationship of Imidazotetrazine Prodrugs with Activity Independent of O6-Methylguanine-DNA-methyltransferase, DNA Mismatch Repair, and p53

  摘要：

  The antitumor prodrug temozolomide is compromised by its dependence for activity on DNA mismatch repair (MMR) and the repair of the chemosensitive DNA lesion, O6-methylguanine (O6-MeG), by O6-methylguanine-DNA-methyltransferase (E.C. 2.1.1.63, MGMT). Tumor response is also dependent on wild-type p53. Novel 3-(2-anilinoethyl)-substituted imidazotetrazines are reported that have activity independent of MGMT, MMR, and p53. This is achieved through a switch of mechanism so that bioactivity derives from imidazotetrazine-generated arylaziridinium ions that principally modify guanine-N7 sites on DNA. Mono- and bifunctional analogues are reported, and a quantitative structure-activity relationship (QSAR) study identified the p-tolyl-substituted bifunctional congener as optimized for potency, MGMT-independence, and MMR-independence. NCI60 data show the tumor cell response is distinct from other imidazotetrazines and DNA-guanine-N7 active agents such as nitrogen mustards and cisplatin. The new imidazotetrazine compounds are promising agents for further development, and their improved in vitro activity validates the principles on which they were designed.

  DOI：

  10.1021/jm401121k
• 作为产物：
  描述：

  N-甲基-对甲基苯胺 在 硫酸 、 硝酸 作用下， 生成 N,4-dimethyl-3-nitrobenzenamine
  参考文献：
  名称：

  Pinnow, Chemische Berichte, 1895, vol. 28, p. 3039,3041

  摘要：

  DOI：

文献信息

• Acetic Acid Accelerated Visible-Light Photoredox Catalyzed<i>N</i>-Demethylation of<i>N,N</i>-Dimethylaminophenyl Derivatives
  作者：Guolin Wu、Yazhen Li、Xuemei Yu、Yu Gao、Haijun Chen

  DOI：10.1002/adsc.201601108

  日期：2017.2.20

  N,N‐Dimethylaminophenyl moiety is a common fragment in medicinal chemistry as several pharmaceuticals bearing this privileged motif are on the market and under clinical evaluation. Oxidative N‐demethylation is generally regarded as the major metabolic pathway. However, pharmacokinetics, metabolites studies as well as the further structural modification are precluded by the impracticality of chemical

  N，N-二甲基氨基苯基部分是药物化学中的常见片段，因为带有这种特权基序的几种药物已在市场上出售并正在临床评估中。氧化性N-去甲基化通常被认为是主要的代谢途径。但是，化学合成的不切实际性排除了药代动力学，代谢产物的研究以及进一步的结构修饰。这里，我们报告，乙酸可以加速显著可见光photoredox催化Ñ的-demethylation N，N- -dimethylaminophenyl衍生物。这种方法很容易进行大规模反应，甚至可能用于潜在的工业生产。
• Observation of a single-pot aromatic reductive denitration
  作者：Angelo G. Giumanini、Giancarlo Verardo

  DOI：10.1139/v97-054

  日期：1997.4.1

  4,N,N-Trimethyl-3-nitrobenzenamine gave reductive denitration products (ca. 28%) upon treatment with n-butyl nitrite in the presence of catalytic amounts of ammonium chloride and water in an unprecedented one-reagent single-pot process. The three isomeric N,N-dimethylnitrobenzenamines showed the same behaviour to a much lesser extent; the ortho isomer was partially (7%) transformed into 1-methylbenzotriazole. Keywords: aromatic protolytic denitration, nitroaromatics, n-butyl nitrite, E- and Z-nitrosamine.

  4，N，N-三甲基-3-硝基苯胺在氯化铵和水存在下，与正丁硝酸酯处理后产生还原脱硝产物（约28%）在一个前所未有的单试剂单锅过程中。三种同分异构的N，N-二甲基硝基苯胺以较小程度显示相同行为；邻位异构体部分（7%）转化为1-甲基苯并三唑。关键词：芳香质子化脱硝，硝基芳烃，正丁硝酸酯，E-和Z-亚硝胺。
• Synthesen in der Lumiflavinreihe IV
  作者：P. Hemmerich、B. Prijs、H. Erlenmeyer

  DOI：10.1002/hlca.19590420522

  日期：——

  2,4-Substituted flavins (isoalloxazines) bearing an NH2-group in 8-position were found to be stable and easily accessible. In particular the 2- and 4-imino-, resp. 2,4-diimino-compounds are similar to riboflavin in colour and fluorescence, but readily water-soluble. The chemical behaviour of this new class of flavins is discussed.

  发现在8位上带有NH 2基团的2,4-取代的黄素（异四恶嗪）稳定且易于获得。特别是2-和4-亚氨基-。2,4-二亚氨基化合物的颜色和荧光与核黄素相似，但易溶于水。讨论了这类新黄酮的化学行为。
• Discovery of a Chemical Probe Bisamide (CCT251236): An Orally Bioavailable Efficacious Pirin Ligand from a Heat Shock Transcription Factor 1 (HSF1) Phenotypic Screen
  作者：Matthew D. Cheeseman、Nicola E. A. Chessum、Carl S. Rye、A. Elisa Pasqua、Michael J. Tucker、Birgit Wilding、Lindsay E. Evans、Susan Lepri、Meirion Richards、Swee Y. Sharp、Salyha Ali、Martin Rowlands、Lisa O’Fee、Asadh Miah、Angela Hayes、Alan T. Henley、Marissa Powers、Robert te Poele、Emmanuel De Billy、Loredana Pellegrino、Florence Raynaud、Rosemary Burke、Rob L. M. van Montfort、Suzanne A. Eccles、Paul Workman、Keith Jones

  DOI：10.1021/acs.jmedchem.6b01055

  日期：2017.1.12

  Phenotypic screens, which focus on measuring and quantifying discrete cellular changes rather than affinity for individual recombinant proteins, have recently attracted renewed interest as an efficient strategy for drug discovery. In this article, we describe the discovery of a new chemical probe, bisamide (CCT251236), identified using an unbiased phenotypic screen to detect inhibitors of the HSF1 stress pathway. The chemical probe is orally bioavailable and displays efficacy in a human ovarian carcinoma xenograft model. By developing cell:based SAP. and using chemical proteomics, we identified pirin as a high affinity molecular target, which was confirmed by SPR and crystallography.
• Jaubert, Bulletin de la Societe Chimique de France, 1899, vol. <3>21, p. 20
  作者：Jaubert

  DOI：——

  日期：——