[3-(Butanoylamino)phenyl] butanoate | 218134-83-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: [3-(Butanoylamino)phenyl] butanoate
• CAS: 218134-83-9
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: WHBOYBFIGBMRPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3-(Butanoylamino)phenyl] butanoate 在 aluminum (III) chloride 作用下， 以 邻二氯苯 为溶剂， 生成 N-(4-butyryl-3-hydroxy-phenyl)-butyramide
  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：

  丁酸酐 、 3-氨基苯酚 在 吡啶 作用下， 生成 [3-(Butanoylamino)phenyl] butanoate
  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

• PROCEDE DE PREPARATION DE COMPOSES DE TYPE 4-(ALKYL)-3-ALCOXY-ANILINES
  申请人：MERIAL

  公开号：EP0994846A1

  公开（公告）日：2000-04-26
• [EN] METHOD FOR PREPARING 4-(ALKYL)-3-ALKOXY-ANILINE COMPOUNDS<br/>[FR] PROCEDE DE PREPARATION DE COMPOSES DE TYPE 4-(ALKYL)-3-ALCOXY-ANILINES
  申请人：MERIAL

  公开号：WO1998057921A1

  公开（公告）日：1998-12-23

  (EN) The invention concerns a method for preparing a compound of formula (I) in which: R1 represents a C1-C10 alkyl group, linear or branched, an aralkyl group in which the alkyl part is linear and comprises 1 to 3 carbon atoms and the aryl part is selected among the phenyl groups, substituted or not, in particular by one or several C1-C3 alkyl groups, or by several halogen atoms or by one or several nitro radicals; R2 represents a C1-C16 alkyl group, linear or branched. The compounds of formula (I) are synthesis intermediates useful in particular for preparing quinoline or quinolone derivatives such as 4-hydroxyquinoline-3-carboxylic acid esters.(FR) La présente invention concerne un procédé de préparation d'un composé de formule (I), dans laquelle: R1 représente un groupe alkyle, linéaire ou ramifié, en C1-C10, un groupe aralkyle dans lequel la partie alkyle est linéaire et comprend de 1 à 3 atomes de carbone et la partie aryle est choisie parmi les groupes phényles, substitués ou non, notamment par un ou plusieurs groupes alkyles en C1 à C3, par un ou plusieurs atomes d'halogène ou par un ou plusieurs radicaux nitro. R2 représente un groupe alkyle, linéaire ou ramifié en C1-C16. Les composés de formule (I) sont des intermédiaires de synthèse utiles notamment pour la préparation de dérivés de quinoléine ou de quinolone tels que les esters d'acides 4-hydroxyquinoléine-3-carboxyliques.
• 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.