6-chloro-acetamidopiperonal | 89967-40-8

• 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: 6-chloro-acetamidopiperonal
• 英文别名: 2-Chloro-N-(6-formyl-2H-1,3-benzodioxol-5-yl)acetamide；2-chloro-N-(6-formyl-1,3-benzodioxol-5-yl)acetamide
• CAS: 89967-40-8
• 化学式: C₁₀H₈ClNO₄
• 分子量: 241.631
• InChiKey: JSKNVAVZJJYWBJ-UHFFFAOYSA-N

物化性质

• 熔点：
  145-146 °C(Solv: ethanol (64-17-5))
• 沸点：
  460.6±45.0 °C(Predicted)
• 密度：
  1.541±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氨基硫脲 、 6-chloro-acetamidopiperonal 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以95%的产率得到3,4-methylenedioxy-6-chloroacetylamino-benzaldehyde thiosemicarbazone
  参考文献：
  名称：

  Novel 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones: Synthesis and antileishmanial effects against Leishmania amazonensis

  摘要：

  A series of eleven 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones (16-27) was synthesised as part of a study to search for potential new drugs with a leishmanicidal effect. The thiosemicarbazones, ten of which are new compounds, were prepared in good yields (85-98%) by the reaction of 3,4-methylenedioxyde-6-benzaldehydes (6-X-piperonal), previously synthesised for this work by several methodologies, and thiosemicarbazide in ethanol with a few drops of H2SO4. These compounds were evaluated against Leishmania amazonensis promastigotes, and derivatives where X = I (22) and X = CN (23) moieties showed impressive results, having IC50 = 20.74 mu M and 16.40 mu M, respectively. The intracellular amastigotes assays showed IC50 = 22.00 mu M (22) and 17.00 mu M (23), and selectivity index >5.7 and >7.4, respectively, with a lower toxicity compared to pentamidine (positive control, SI = 4.5). The results obtained from the preliminary QSAR study indicated the hydrophobicity (log P) as a fundamental parameter for the 2D-QSAR linear model. A molecular docking study demonstrated that both compounds interact with flavin mononucleotide (FMN), important binding site of NO synthase. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.009
• 作为产物：
  描述：

  6-硝基胡椒醛 在 吡啶 、 ammonium hydroxide 、 硫酸 、 iron(II) sulfate 、 sodium nitrite 作用下， 以 乙醚 、 水 为溶剂， 反应 11.17h， 生成 6-chloro-acetamidopiperonal
  参考文献：
  名称：

  Novel 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones: Synthesis and antileishmanial effects against Leishmania amazonensis

  摘要：

  A series of eleven 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones (16-27) was synthesised as part of a study to search for potential new drugs with a leishmanicidal effect. The thiosemicarbazones, ten of which are new compounds, were prepared in good yields (85-98%) by the reaction of 3,4-methylenedioxyde-6-benzaldehydes (6-X-piperonal), previously synthesised for this work by several methodologies, and thiosemicarbazide in ethanol with a few drops of H2SO4. These compounds were evaluated against Leishmania amazonensis promastigotes, and derivatives where X = I (22) and X = CN (23) moieties showed impressive results, having IC50 = 20.74 mu M and 16.40 mu M, respectively. The intracellular amastigotes assays showed IC50 = 22.00 mu M (22) and 17.00 mu M (23), and selectivity index >5.7 and >7.4, respectively, with a lower toxicity compared to pentamidine (positive control, SI = 4.5). The results obtained from the preliminary QSAR study indicated the hydrophobicity (log P) as a fundamental parameter for the 2D-QSAR linear model. A molecular docking study demonstrated that both compounds interact with flavin mononucleotide (FMN), important binding site of NO synthase. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.009

文献信息

• 8,9-Methylenedioxy-3,4-dihydro-1,4,5-benzotriazocin-2(1H)-ones
  作者：Whei Oh Lin、Edson de Souza Coutinho

  DOI：10.1007/bf00799937

  日期：1983.11
• LIN, WHEI, OH;SOUZA, COUTINHO, E. DE, MONATSH. CHEM., 1983, 114, N 11, 1231-1235
  作者：LIN, WHEI, OH、SOUZA, COUTINHO, E. DE

  DOI：——

  日期：——
• Novel 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones: Synthesis and antileishmanial effects against Leishmania amazonensis
  作者：Jorge Luiz R. de Melos、Eduardo Caio Torres-Santos、Viviane dos S. Faiões、Catarina de Nigris Del Cistia、Carlos Maurício R. Sant'Anna、Cláudio Eduardo Rodrigues-Santos、Aurea Echevarria

  DOI：10.1016/j.ejmech.2015.09.009

  日期：2015.10

  A series of eleven 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones (16-27) was synthesised as part of a study to search for potential new drugs with a leishmanicidal effect. The thiosemicarbazones, ten of which are new compounds, were prepared in good yields (85-98%) by the reaction of 3,4-methylenedioxyde-6-benzaldehydes (6-X-piperonal), previously synthesised for this work by several methodologies, and thiosemicarbazide in ethanol with a few drops of H2SO4. These compounds were evaluated against Leishmania amazonensis promastigotes, and derivatives where X = I (22) and X = CN (23) moieties showed impressive results, having IC50 = 20.74 mu M and 16.40 mu M, respectively. The intracellular amastigotes assays showed IC50 = 22.00 mu M (22) and 17.00 mu M (23), and selectivity index >5.7 and >7.4, respectively, with a lower toxicity compared to pentamidine (positive control, SI = 4.5). The results obtained from the preliminary QSAR study indicated the hydrophobicity (log P) as a fundamental parameter for the 2D-QSAR linear model. A molecular docking study demonstrated that both compounds interact with flavin mononucleotide (FMN), important binding site of NO synthase. (C) 2015 Elsevier Masson SAS. All rights reserved.