(S)-N-(1-(4-tert-butylphenyl)-2-fluoroethyl)-2-methoxyacetamide

• 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: (S)-N-(1-(4-tert-butylphenyl)-2-fluoroethyl)-2-methoxyacetamide
• 英文别名: N-[(1S)-1-(4-tert-butylphenyl)-2-fluoroethyl]-2-methoxyacetamide
• 化学式: C₁₅H₂₂FNO₂
• 分子量: 267.344
• InChiKey: AKGNDPMVMVIZPS-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-(4-tert-butylphenyl)-2-fluoroethyl)-2-methoxyacetamide 在 Candida antarctica lipase B immobilised on immobead 150 and Novozyme 435 作用下， 以 aq. phosphate buffer 为溶剂， 反应 48.0h， 以77%的产率得到(S)-1-(4-tert-butylphenyl)-2-fluoroethanamine
  参考文献：
  名称：

  Chiral N-benzyl-N-methyl-1-(naphthalen-1-yl)ethanamines and their in vitro antifungal activity against Cryptococcus neoformans, Trichophyton mentagrophytes and Trichophyton rubrum

  摘要：

  In the search for new antifungal compounds and to explore structure activity relationships, a series of 24 chiral benzyl amine type antifungals was synthesised and characterised. In vitro testing against the human pathogen Cryptococcus neoformans revealed that several derivatives had MIC50 values similar to that of the commercial drug Butenafine. All of these contained a bulky group in the para position of the benzyl fragment. Eighteen compounds were also tested for activity against the dermatophytes Trichophyton mentagrophytes and Trichophyton rubrum. Of these (R)-N-(4-tert-butylbenzyI)-N-methyl-1-(naphthalen-1-yl)ethanamine (MIC50,: 0.06 mu g/mL) and a para-benzyloxy substituted derivative (MIC50: 0.125 mu g/mL) possessed high activity. Testing of derivatives with a stereocentre at the benzylic carbon, revealed that (S)-stereochemistry was required for potency: a MIC50 value of 1 mu g/mL was obtained for (S)-1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)ethanamine. Preparation of the corresponding fluoromethyl compound was achieved employing lipase B from Candida antarctica as catalyst in the key step. A low antifungal activity was observed for the fluorinated derivative indicating the importance of the amine basicity for the antifungal potency of these compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.043
• 作为产物：
  描述：

  对叔丁基苯乙酮 在 ammonium acetate 、 sodium cyanoborohydride 、 Selectfluor 作用下， 以 甲醇 、 正己烷 、 水 为溶剂， 反应 43.5h， 生成 (S)-N-(1-(4-tert-butylphenyl)-2-fluoroethyl)-2-methoxyacetamide
  参考文献：
  名称：

  Chiral N-benzyl-N-methyl-1-(naphthalen-1-yl)ethanamines and their in vitro antifungal activity against Cryptococcus neoformans, Trichophyton mentagrophytes and Trichophyton rubrum

  摘要：

  In the search for new antifungal compounds and to explore structure activity relationships, a series of 24 chiral benzyl amine type antifungals was synthesised and characterised. In vitro testing against the human pathogen Cryptococcus neoformans revealed that several derivatives had MIC50 values similar to that of the commercial drug Butenafine. All of these contained a bulky group in the para position of the benzyl fragment. Eighteen compounds were also tested for activity against the dermatophytes Trichophyton mentagrophytes and Trichophyton rubrum. Of these (R)-N-(4-tert-butylbenzyI)-N-methyl-1-(naphthalen-1-yl)ethanamine (MIC50,: 0.06 mu g/mL) and a para-benzyloxy substituted derivative (MIC50: 0.125 mu g/mL) possessed high activity. Testing of derivatives with a stereocentre at the benzylic carbon, revealed that (S)-stereochemistry was required for potency: a MIC50 value of 1 mu g/mL was obtained for (S)-1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)ethanamine. Preparation of the corresponding fluoromethyl compound was achieved employing lipase B from Candida antarctica as catalyst in the key step. A low antifungal activity was observed for the fluorinated derivative indicating the importance of the amine basicity for the antifungal potency of these compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.043

文献信息

• Chiral N-benzyl-N-methyl-1-(naphthalen-1-yl)ethanamines and their in vitro antifungal activity against Cryptococcus neoformans, Trichophyton mentagrophytes and Trichophyton rubrum
  作者：Thor H. Krane Thvedt、Kristin Kaasa、Eirik Sundby、Colin Charnock、Bård Helge Hoff

  DOI：10.1016/j.ejmech.2013.07.043

  日期：2013.10

  In the search for new antifungal compounds and to explore structure activity relationships, a series of 24 chiral benzyl amine type antifungals was synthesised and characterised. In vitro testing against the human pathogen Cryptococcus neoformans revealed that several derivatives had MIC50 values similar to that of the commercial drug Butenafine. All of these contained a bulky group in the para position of the benzyl fragment. Eighteen compounds were also tested for activity against the dermatophytes Trichophyton mentagrophytes and Trichophyton rubrum. Of these (R)-N-(4-tert-butylbenzyI)-N-methyl-1-(naphthalen-1-yl)ethanamine (MIC50,: 0.06 mu g/mL) and a para-benzyloxy substituted derivative (MIC50: 0.125 mu g/mL) possessed high activity. Testing of derivatives with a stereocentre at the benzylic carbon, revealed that (S)-stereochemistry was required for potency: a MIC50 value of 1 mu g/mL was obtained for (S)-1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)ethanamine. Preparation of the corresponding fluoromethyl compound was achieved employing lipase B from Candida antarctica as catalyst in the key step. A low antifungal activity was observed for the fluorinated derivative indicating the importance of the amine basicity for the antifungal potency of these compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.