Benzo[1,3]dioxol-5-yl-((E)-3,7-dimethyl-octa-2,6-dienyl)-amine | 42933-35-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Benzo[1,3]dioxol-5-yl-((E)-3,7-dimethyl-octa-2,6-dienyl)-amine
• 英文别名: N-[(2E)-3,7-dimethylocta-2,6-dienyl]-1,3-benzodioxol-5-amine
• CAS: 42933-35-7
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: PATGXYVWXKSLNJ-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-3,7-二甲基-2,6-辛二烯醛 、 3,4-亚甲二氧基苯胺 在 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以72%的产率得到Benzo[1,3]dioxol-5-yl-((E)-3,7-dimethyl-octa-2,6-dienyl)-amine
  参考文献：
  名称：

  4-Nerolidylcatechol and its synthetic analogues: Antioxidant activity and toxicity evaluation

  摘要：

  4-Nerolidylcatechol (1) is a secondary metabolite of plants and is described as a promising anti-inflammatory, antimalarial, antiulcerogenic, analgesic and cytotoxic compound possibly due to its antioxidant profile. In this study, we evaluated the pharmacologic activity and the antioxidant and toxicological profiles of compound (1) and its synthetic analogues (2-6). The synthetic analogues were designed from the lead compound, (1), using a molecular-simplification strategy. Compound 5 showed, by 1,1-diphenyl-2-picrylhydrazyl (DPPH) and beta-carotene systems, similar antioxidant activity when compared to compound (1). The oxidative stress in erythrocyte membrane demonstrated the highly protective effect of compounds (4), (5) and (6) and high antioxidant/pro-oxidant activity in relation to the concentrations of compounds (1) and (3). Compounds (2), (4), (5) and (6) were haemobiocompatible. All compounds (1-6) showed cytotoxic effects in 3T3 cells, but compounds (2) and (6) were highly cytotoxic in this lineage when compared to compound (1). Compound (5) had a lower myelosuppressive effect in haematopoietic progenitor cells compared to (1). Both compounds, (1) and (5), showed low genotoxic effects in vitro, on human lymphocyte cells. In addition, these compounds also showed low-toxicity in vivo as defined a LD50 > 2000 mg/kg. In this assay, we did not observe death in the animals exposed to treatment with (1) and (5) compound. In conclusion, the structural design of the analogues as validated once compound (5) was found to have an antioxidant profile that was as potent as the lead compound (1). In addition, considering the safety profile, these compounds are promising as preventive and/or therapeutic agents against oxidative damage. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.028

文献信息

• 4-Nerolidylcatechol and its synthetic analogues: Antioxidant activity and toxicity evaluation
  作者：Carla Rosane Mendanha da Cunha、Sebastião Antônio Mendanha Neto、Claudio Carlos da Silva、Alane Pereira Cortez、Marcelo do Nascimento Gomes、Fabiula Ines Martins、Antônio Alonso、Kênnia Rocha Rezende、Ricardo Menegatti、Mariana Torquato Quezado de Magalhães、Marize Campos Valadares

  DOI：10.1016/j.ejmech.2012.12.028

  日期：2013.4

  4-Nerolidylcatechol (1) is a secondary metabolite of plants and is described as a promising anti-inflammatory, antimalarial, antiulcerogenic, analgesic and cytotoxic compound possibly due to its antioxidant profile. In this study, we evaluated the pharmacologic activity and the antioxidant and toxicological profiles of compound (1) and its synthetic analogues (2-6). The synthetic analogues were designed from the lead compound, (1), using a molecular-simplification strategy. Compound 5 showed, by 1,1-diphenyl-2-picrylhydrazyl (DPPH) and beta-carotene systems, similar antioxidant activity when compared to compound (1). The oxidative stress in erythrocyte membrane demonstrated the highly protective effect of compounds (4), (5) and (6) and high antioxidant/pro-oxidant activity in relation to the concentrations of compounds (1) and (3). Compounds (2), (4), (5) and (6) were haemobiocompatible. All compounds (1-6) showed cytotoxic effects in 3T3 cells, but compounds (2) and (6) were highly cytotoxic in this lineage when compared to compound (1). Compound (5) had a lower myelosuppressive effect in haematopoietic progenitor cells compared to (1). Both compounds, (1) and (5), showed low genotoxic effects in vitro, on human lymphocyte cells. In addition, these compounds also showed low-toxicity in vivo as defined a LD50 > 2000 mg/kg. In this assay, we did not observe death in the animals exposed to treatment with (1) and (5) compound. In conclusion, the structural design of the analogues as validated once compound (5) was found to have an antioxidant profile that was as potent as the lead compound (1). In addition, considering the safety profile, these compounds are promising as preventive and/or therapeutic agents against oxidative damage. (C) 2013 Elsevier Masson SAS. All rights reserved.