tert-butyl N-[(3,5-dimethoxyphenyl)methylamino]carbamate | 1372807-89-0

• 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: tert-butyl N-[(3,5-dimethoxyphenyl)methylamino]carbamate
• CAS: 1372807-89-0
• 化学式: C₁₄H₂₂N₂O₄
• 分子量: 282.34
• InChiKey: CGELODRGNSNDAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(3,5-dimethoxyphenyl)methylamino]carbamate 在 光气 、 三光气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Combinatorial Aid for Underprivileged Scaffolds: Solution and Solid-phase Strategies for a Rapid and Efficient Access To Novel Aza-diketopiperazines (Aza-DKP)

  摘要：

  An efficient solution-phase synthesis of aza-diketopiperazines (aza-DKP, triazinediones) is reported. A structurally diverse collection of c-[aza-alkylGly-Pro] derivatives and yet unreported 2,4,5-trisubstituted-1,2,4-triazine-3,6-diones has been synthesized starting from Fmoc-L-Pro-OH and various Fmoc-L-amino acids. To extend the practical value of this class of dipeptidomimetics, a general solid-phase synthesis approach amenable to library production was developed on both Wang-PS and HMBA-PS resins. The final acidic treatment of the resins in TFA/water mixture at room temperature enabled the rapid and quantitative cyclization/release highly pure triazinediones. The conformational preferences and the spatial organization of the three substituents of a representative 2,4,5-trisubstituted-1,2,4-triazine-3,6-dione were investigated by X-ray diffraction and H-1 NMR spectroscopy.

  DOI：

  10.1021/co300015k
• 作为产物：
  描述：

  3,5-Dimethoxybenzaldehyde t-Butoxycarbohydrazone 在 palladium 10% on activated carbon 、 sodium formate 作用下， 以 乙醇 、 水 为溶剂， 以65%的产率得到tert-butyl N-[(3,5-dimethoxyphenyl)methylamino]carbamate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Hydrazone Derivatives as Antifungal Agents

  摘要：

  新兴酵母菌是系统性感染中最常见的病原体之一，死亡率极高，因此迫切需要开发具有特异性、有效且无毒的抗真菌药物来应对这一问题。本研究中，我们获得了35种醛类、肼类和酰肼类化合物，并在体外筛选中评估了它们对Candida属（C. parapsilosis、C. tropicalis、C. krusei、C. albicans、C. glabrata和C. lusitaneae）和Trichosporon asahii的抗真菌活性。我们对筛选出的活性化合物对10株临床分离的C. parapsilosis和10株T. asahii的最低抑菌浓度（MICs）进行了测定。化合物4-吡啶-2-基苯甲醛（13a）和叔丁基-(2Z)-2-(3,4,5-三羟基苄脒)酰肼羧酸酯（7b）分别在16-32 μg/mL和8-16 μg/mL的范围内显示出最有希望的MIC值。我们评估了这些化合物对细胞膜和细胞壁稳定性的影响，结果表明这些化合物作用于真菌细胞膜。通过细胞活力测定和碱性彗星试验评价了其细胞毒性。化合物13a在活性浓度下不具有细胞毒性。这些结果支持了发现有希望的候选药物用于开发新型抗真菌药物。

  DOI：

  10.3390/molecules20059229

文献信息

• Synthesis and Biological Evaluation of Hydrazone Derivatives as Antifungal Agents
  作者：Bruna Casanova、Mauro Muniz、Thayse de Oliveira、Luís de Oliveira、Michel Machado、Alexandre Fuentefria、Grace Gosmann、Simone Gnoatto

  DOI：10.3390/molecules20059229

  日期：——

  Emerging yeasts are among the most prevalent causes of systemic infections with high mortality rates and there is an urgent need to develop specific, effective and non-toxic antifungal agents to respond to this issue. In this study 35 aldehydes, hydrazones and hydrazines were obtained and their antifungal activity was evaluated against Candida species (C. parapsilosis, C. tropicalis, C. krusei, C. albicans, C. glabrata and C. lusitaneae) and Trichosporon asahii, in an in vitro screening. The minimum inhibitory concentrations (MICs) of the active compounds in the screening was determined against 10 clinical isolates of C. parapsilosis and 10 of T. asahii. The compounds 4-pyridin-2-ylbenzaldehyde] (13a) and tert-butyl-(2Z)-2-(3,4,5-trihydroxybenzylidine)hydrazine carboxylate (7b) showed the most promising MIC values in the range of 16–32 μg/mL and 8–16 μg/mL, respectively. The compounds’ action on the stability of the cell membrane and cell wall was evaluated, which suggested the action of the compounds on the fungal cell membrane. Cell viability of leukocytes and an alkaline comet assay were performed to evaluate the cytotoxicity. Compound 13a was not cytotoxic at the active concentrations. These results support the discovery of promising candidates for the development of new antifungal agents.

  新兴酵母菌是系统性感染中最常见的病原体之一，死亡率极高，因此迫切需要开发具有特异性、有效且无毒的抗真菌药物来应对这一问题。本研究中，我们获得了35种醛类、肼类和酰肼类化合物，并在体外筛选中评估了它们对Candida属（C. parapsilosis、C. tropicalis、C. krusei、C. albicans、C. glabrata和C. lusitaneae）和Trichosporon asahii的抗真菌活性。我们对筛选出的活性化合物对10株临床分离的C. parapsilosis和10株T. asahii的最低抑菌浓度（MICs）进行了测定。化合物4-吡啶-2-基苯甲醛（13a）和叔丁基-(2Z)-2-(3,4,5-三羟基苄脒)酰肼羧酸酯（7b）分别在16-32 μg/mL和8-16 μg/mL的范围内显示出最有希望的MIC值。我们评估了这些化合物对细胞膜和细胞壁稳定性的影响，结果表明这些化合物作用于真菌细胞膜。通过细胞活力测定和碱性彗星试验评价了其细胞毒性。化合物13a在活性浓度下不具有细胞毒性。这些结果支持了发现有希望的候选药物用于开发新型抗真菌药物。
• Combinatorial Aid for Underprivileged Scaffolds: Solution and Solid-phase Strategies for a Rapid and Efficient Access To Novel Aza-diketopiperazines (Aza-DKP)
  作者：Dominique Bonnet、Jean-François Margathe、Sally Radford、Elsa Pflimlin、Stéphanie Riché、Pete Doman、Marcel Hibert、A. Ganesan

  DOI：10.1021/co300015k

  日期：2012.5.14

  An efficient solution-phase synthesis of aza-diketopiperazines (aza-DKP, triazinediones) is reported. A structurally diverse collection of c-[aza-alkylGly-Pro] derivatives and yet unreported 2,4,5-trisubstituted-1,2,4-triazine-3,6-diones has been synthesized starting from Fmoc-L-Pro-OH and various Fmoc-L-amino acids. To extend the practical value of this class of dipeptidomimetics, a general solid-phase synthesis approach amenable to library production was developed on both Wang-PS and HMBA-PS resins. The final acidic treatment of the resins in TFA/water mixture at room temperature enabled the rapid and quantitative cyclization/release highly pure triazinediones. The conformational preferences and the spatial organization of the three substituents of a representative 2,4,5-trisubstituted-1,2,4-triazine-3,6-dione were investigated by X-ray diffraction and H-1 NMR spectroscopy.