1-[1-oxo-3-(3,4-methylenedioxyphenyl)propan]-piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-[1-oxo-3-(3,4-methylenedioxyphenyl)propan]-piperidine
• 英文别名: 3-benzo[1,3]dioxol-5-yl-1-piperidin-1-yl-propan-1-one；N-[3-(3,4-methylenedioxyphenyl)propionyl]piperidine；3-benzo-1,3-dioxol-5-ylpropionic acid piperidide；3-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpropan-1-one
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: XCBIVSYMPNVWRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-(亚甲二氧)肉桂酸 、 氢气 、 、 1-[1-oxo-3-(3,4-methylenedioxyphenyl)propan]-piperidine 在 钯 作用下， 以 乙醇 为溶剂， 反应 0.67h， 生成 3-[3,4-(亚甲二氧基)苯基]丙酸
  参考文献：
  名称：

  Treatment of skin conditions

  摘要：

  本发明提供了辣椒碱及其类似物或衍生物，用于治疗可通过刺激黑色素细胞增殖治疗的皮肤病，如白癜风，并用于治疗皮肤癌。辣椒碱及其类似物或衍生物也可用于美容上促进或增强皮肤的自然色彩。

  公开号：

  US07122561B2
• 作为产物：
  描述：

  3-[3,4-(亚甲二氧基)苯基]丙酸 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-[1-oxo-3-(3,4-methylenedioxyphenyl)propan]-piperidine
  参考文献：
  名称：

  New orally effective 3-(2-nitro)phenylpropanamide analgesic derivatives: Synthesis and antinociceptive evaluation

  摘要：

  A series of substituted 6-nitrophenylpropanamide derivatives (1-20) were synthesized using either the TDAE strategy or classical organic reactions. All these compounds were characterized by fusion point, 1H NMR,13C NMR, elemental analysis or mass spectrometry data. Because of their structural analogy with recently published compounds possessing antinociceptive properties, our derivatives were screened for peripheral analgesic activities on acetic acid-induced writhing in mice. Compound 13 showed the best result at 100 junol/kg ip (50% inhibition vs 59% for aspirin). This antinociceptive activity was maintained after oral administration (40% inhibition vs 31.6% for aspirin). Both hot-plate and actimetry-based tests were non-significant suggesting the analgesic activity of 13 linked to a peripheral mechanism. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.041

文献信息

• Amides from Piper capense with CNS Activity – A Preliminary SAR Analysis
  作者：Mikael Pedersen、Bjørn Metzler、Gary Stafford、Johannes Van Staden、Anna Jäger、Hasse Rasmussen

  DOI：10.3390/molecules14093833

  日期：——

  Piper capense L.f. (Piperaceae) is used traditionally in South Africa as a sleep inducing remedy. Bioassay-guided fractionation of the roots of P. capense led to the isolation of piperine (1) and 4,5-dihydropiperine (2), which showed moderate affinity for the benzodiazepine site on the GABAA receptor (IC50 values of 1.2 mM and 1.0 mM, respectively). The present study suggests that strict structural properties of the amides are essential for affinity. Taken together, these observations suggest that the carbon chain must contain not less than four carbons, and that a conjugated double bond, adjacent to the amide group, is necessary for binding to the receptor and that the amine part should be bulky.

  Piper capense L.f.（胡椒科）在南非传统上被用作催眠药。P. capense根部的生物测定引导分离出白胡椒碱（piperine，1）和4,5-二氢白胡椒碱（4,5-dihydropiperine，2），它们对GABAA受体的苯二氮平位点表现出中等亲和力（IC50值分别为1.2 mM和1.0 mM）。本研究表明，酰胺的严格结构特性对于亲和力至关重要。综合这些观察结果表明，碳链必须至少含有四个碳原子，并且靠近酰胺基团的共轭双键对于与受体结合是必要的，同时胺部分应较为庞大。
• DIHYDROCAFFEIC ACID AMIDE DERIVATIVE AND APPLICATION THEREOF AS MEDICINE
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0495998A1

  公开（公告）日：1992-07-29

  A medicine for treating central nervous system diseases containing a dihydrocaffeic acid amide derivative represented by general formula (I), which has an activity of inducing a nerve growth factor and is efficacious in treating or preventing the progression of central nervous system diseases.

  一种治疗中枢神经系统疾病的药物，含有通式（I）代表的二氢咖啡酸酰胺衍生物，该衍生物具有诱导神经生长因子的活性，可有效治疗或预防中枢神经系统疾病的恶化。
• Effects of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation
  作者：Radhakrishnan Venkatasamy、Laura Faas、Antony R Young、Amala Raman、Robert C Hider

  DOI：10.1016/j.bmc.2004.01.036

  日期：2004.4

  A wide range of piperine analogues has been synthesised in order to undertake a structure-activity study of their ability to stimulate melanocyte proliferation. Results demonstrate that an aromatic ring containing at least one ether function and a carbonyl group containing side chain is essential for this activity. A number of highly active piperine analogues have been identified, for instance 1-(3,4-methylenedioxyphenyl)-penta-2E,4E-dienoic acid methyl ester (3a), 1-E,E-piperinoyl-isobutylamine (4f) and 1-(3,4-methylenedioxyphenyl)-pentanoic acid cyclohexyl amide (20). A selection of analogues has also been evaluated for their effect on melanocyte morphology and melanogenesis. The piperine analogues altered cell morphology by increasing dendrite formation leading to bi-, tri- and quadripolar cells. These same analogues were found to increase total melanin in cell cultures, although melanin content per cell was not significantly altered from control in the presence of these compounds. (C) 2004 Elsevier Ltd. All rights reserved.
• US5338745A
  申请人：——

  公开号：US5338745A

  公开（公告）日：1994-08-16