1-(4-Nitro-2-phenylphenyl)pyrrolidine | 251115-16-9

• 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: 1-(4-Nitro-2-phenylphenyl)pyrrolidine
• CAS: 251115-16-9
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: KIEDISKNKUEFDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  1-(4-Nitro-2-phenylphenyl)pyrrolidine 在 tin(II) chloride dihydrate 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 生成 6-Pyrrolidin-1-YL-biphenyl-3-ylamine
  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：

  四氢吡咯 、 2-phenyl-4-nitrobromobenzene 生成 1-(4-Nitro-2-phenylphenyl)pyrrolidine
  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

• 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.
• Structurally Simple Inhibitors of Lanosterol 14α-Demethylase Are Efficacious In a Rodent Model of Acute Chagas Disease
  作者：Praveen Kumar Suryadevara、Srinivas Olepu、Jeffrey W. Lockman、Junko Ohkanda、Mandana Karimi、Christophe L. M. J. Verlinde、James M. Kraus、Jan Schoepe、Wesley C. Van Voorhis、Andrew D. Hamilton、Frederick S. Buckner、Michael H. Gelb

  DOI：10.1021/jm900030h

  日期：2009.6.25

  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.