N,N-dimethyl-5-nitro-[1,1'-biphenyl]-2-amine | 29608-77-3

• 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,N-dimethyl-5-nitro-[1,1'-biphenyl]-2-amine
• 英文别名: dimethyl-(5-nitro-biphenyl-2-yl)-amine；N,N-dimethyl-4-nitro-2-phenylaniline
• CAS: 29608-77-3
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: YQNUXMCUBCQQAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-5-nitro-[1,1'-biphenyl]-2-amine 在 tin(II) chloride dihydrate 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 生成 3-amino-6-dimethylaminobiphenyl
  参考文献：
  名称：

  Structurally Simple Inhibitors of Lanosterol 14α-Demethylase Are Efficacious In a Rodent Model of Acute Chagas Disease

  摘要：

  We report structure-activity studies of a large number of dialkyl imidazoles as inhibitors of Trypanosoma cruzi lanosterol-14 alpha-demethylase (L14DM). The compounds have a simple structure compared to posaconazole, another L14DM inhibitor that is an anti-Chagas drug candidate. Several compounds display potency for killing T cruzi amastigotes in vitro with values of EC50 in the 0.4-10 nM range. Two compounds were selected for efficacy studies in a mouse model of acute Chagas disease. At oral doses of 20-50 mg/kg given after establishment of parasite infection, the compounds reduced parasitemia in the blood to undetectable levels, and analysis of remaining parasites by PCR revealed a lack of parasites in the majority of animals. These dialkyl imidazoles are substantially less expensive to produce than posaconazole and are appropriate for further development toward an anti-Chagas disease clinical candidate.

  DOI：

  10.1021/jm900030h
• 作为产物：
  描述：

  聚合甲醛 、 2-苯基-4-硝基苯胺 在 sodium tetrahydroborate 、 硫酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以80%的产率得到N,N-dimethyl-5-nitro-[1,1'-biphenyl]-2-amine
  参考文献：
  名称：

  Structurally Simple Inhibitors of Lanosterol 14α-Demethylase Are Efficacious In a Rodent Model of Acute Chagas Disease

  摘要：

  We report structure-activity studies of a large number of dialkyl imidazoles as inhibitors of Trypanosoma cruzi lanosterol-14 alpha-demethylase (L14DM). The compounds have a simple structure compared to posaconazole, another L14DM inhibitor that is an anti-Chagas drug candidate. Several compounds display potency for killing T cruzi amastigotes in vitro with values of EC50 in the 0.4-10 nM range. Two compounds were selected for efficacy studies in a mouse model of acute Chagas disease. At oral doses of 20-50 mg/kg given after establishment of parasite infection, the compounds reduced parasitemia in the blood to undetectable levels, and analysis of remaining parasites by PCR revealed a lack of parasites in the majority of animals. These dialkyl imidazoles are substantially less expensive to produce than posaconazole and are appropriate for further development toward an anti-Chagas disease clinical candidate.

  DOI：

  10.1021/jm900030h

文献信息

• Pd/Cu-Catalyzed aerobic oxidative aromatic C–H bond activation/N-dealkylative carbonylation towards the synthesis of phenanthridinones
  作者：Renyi Shi、Huiying Niu、Lijun Lu、Aiwen Lei

  DOI：10.1039/c6cc08701a

  日期：——

  A straightforward Pd/Cu-catalyzed oxidative C–H bond activation/N-dealkylative carbonylation of tertiary [1,1′-biphenyl]-2-anilines towards the synthesis of various biologically important phenanthridin-6(5H)-ones has been developed. A wide range of functional groups are well tolerated in this transformation.

  一种直接的Pd/Cu催化氧化C-H键活化/N-去烷基羰基化反应已被开发，用于合成各种生物重要的苯并噻吩-6(5H)-酮。在这一转化中，广泛的官能团被很好地容忍。
• 2,5-DIAMINO-1-PHENYLBENZOL-DERIVATE ENTHALTENDE OXIDATIONSHAARFÄRBEMITTEL SOWIE NEUE 2,5-DIAMINO-1-PHENYLBENZOL-DERIVATE
  申请人：Wella Aktiengesellschaft

  公开号：EP1051143B1

  公开（公告）日：2004-07-21
• US6500213B1
  申请人：——

  公开号：US6500213B1

  公开（公告）日：2002-12-31
• [DE] 2,5-DIAMINO-1-PHENYLBENZOL-DERIVATE ENTHALTENDE OXIDATIONSHAARFÄRBEMITTEL SOWIE NEUE 2,5-DIAMINO-1-PHENYLBENZOL-DERIVATE<br/>[EN] OXIDIZING HAIR COLORING AGENTS CONTAINING 2,5-DIAMINO-1-PHENYLBENZENE DERIVATIVES AND NOVEL 2,5-DIAMINO-1-PHENYLBENZENE DERIVATIVES<br/>[FR] PRODUITS DE COLORATION OXYDANTE POUR LES CHEVEUX CONTENANT DES DERIVES DE 2,5-DIAMINO-1-PHENYLBENZOL ET NOUVEAUX DERIVES DE 2,5-DIAMINO-1-PHENYLBENZOL
  申请人：——

  公开号：WO1999059527A2

  公开（公告）日：1999-11-25

  [EN] The invention relates to oxidizing agents for coloration of keratin fibers, especially hair, based on a combination of developer-coupler substances, characterized in that they contain at least one 2,5-diamino-1-phenylbenzene derivative of general formula (I) as a developer substance. The invention also relates to novel 2,5-diamino-1-phenylbenzene derivatives according to formula (I), wherein at least one of the radicals R1-R10 is different from hydrogen.
  [FR] L'invention concerne des produits de coloration oxydante de fibres kératiniques, notamment de cheveux, à base d'une association substance copulatrice/substance révélatrice. Ces produits sont caractérisés en ce qu'ils contiennent comme substance révélatrice au moins un dérivé de 2,5-diamino-1-phénylbenzol de la formule générale (I). L'invention concerne également de nouveaux dérivés 2-5-diamino-1-phénylbenzol selon la formule (I), dans lesquels au moins un des restes R1 à R10 n'est pas de l'hydrogène.
  [DE] Gegenstand der vorliegenden Anmeldung sind Mittel zur oxidativen Färbung von Keratinfasern, insbesondere Haaren auf der Basis einer Entwicklersubstanz-Kupplersubstanz-Kombination, welche dadurch gekennzeichnet sind, dass sie als Entwicklersubstanz mindestens ein 2,5-Diamino-1-phenylbenzol-Derivat der allgemeinen Formel (I) enthalten, sowie neue 2,5-Diamino-1-phenylbenzol-Derivate gemäss Formel (I), in denen mindestens einer der Reste R1 bis R10 von Wasserstoff verschieden ist.