3-bromo-4-n-butoxy-5-methoxybenzaldehyde | 91766-70-0

• 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: 3-bromo-4-n-butoxy-5-methoxybenzaldehyde
• 英文别名: 5-Brom-3-methoxy-4-butyloxy-benzaldehyd；3-Bromo-4-butoxy-5-methoxybenzaldehyde
• CAS: 91766-70-0
• 化学式: C₁₂H₁₅BrO₃
• mdl: MFCD02256506
• 分子量: 287.153
• InChiKey: GJGQFZHAWOKPOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-nitrobenzylidene)cyclohexanone 、 3-bromo-4-n-butoxy-5-methoxybenzaldehyde 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以57%的产率得到(6E)-2-(3-bromo-4-n-butoxy-5-methoxybenzylidene)-6-(4-nitrobenzylidene)cyclohexanone
  参考文献：
  名称：

  Asymmetrical 2,6-bis(benzylidene)cyclohexanones: Synthesis, cytotoxic activity and QSAR study

  摘要：

  In order to develop novel anti-cancer agents, a series of asymmetrical 2,6-bis (benzylidene)cyclohexanone derivatives containing nitrobenzylidene moiety were synthesized and their cytotoxic activity were determined in vitro against MDA-MB 231, MCF-7 and SK-N-MC cell lines using MTT assay. Among the tested compounds, the highest activity against MDA-MB 231 cells was achieved by 2-(3-bromo-5-methoxy-4-propoxybenzylidene)-6-(2-nitrobenzylidene)cyclohexanone (compound 5d). Whereas, compound 5j (the 3-nitro analog of compound 5d) was the most potent compound against MCF-7 and SK-N-MC cell lines. The results indicated that the cytotoxic activity profile against different tumor cells can be optimized by desired 4-alkoxy-3-bromo-5-methoxybenzylidene scaffold. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.045
• 作为产物：
  描述：

  香草醛 在 溴 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 生成 3-bromo-4-n-butoxy-5-methoxybenzaldehyde
  参考文献：
  名称：

  Asymmetrical 2,6-bis(benzylidene)cyclohexanones: Synthesis, cytotoxic activity and QSAR study

  摘要：

  In order to develop novel anti-cancer agents, a series of asymmetrical 2,6-bis (benzylidene)cyclohexanone derivatives containing nitrobenzylidene moiety were synthesized and their cytotoxic activity were determined in vitro against MDA-MB 231, MCF-7 and SK-N-MC cell lines using MTT assay. Among the tested compounds, the highest activity against MDA-MB 231 cells was achieved by 2-(3-bromo-5-methoxy-4-propoxybenzylidene)-6-(2-nitrobenzylidene)cyclohexanone (compound 5d). Whereas, compound 5j (the 3-nitro analog of compound 5d) was the most potent compound against MCF-7 and SK-N-MC cell lines. The results indicated that the cytotoxic activity profile against different tumor cells can be optimized by desired 4-alkoxy-3-bromo-5-methoxybenzylidene scaffold. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.045

文献信息

• CHROMENE DERIVATIVES AND THEIR ANALOGA AS WNT PATHWAY ANTAGONISTS
  申请人：Boutros Michael

  公开号：US20130296344A1

  公开（公告）日：2013-11-07

  Compounds according to the general formula (I) wherein X 1 , X 2 , X 3 and X 4 independently from each other are N or CR 8 wherein R 8 may be same or different, and wherein up to 3 of the group X 1 , X 2 , X 3 and X 4 may be N; A is a 5- or 6-membered aromatic or heteroaromtic cycle containing 1 to 3 heteroatoms selected from the group consisting of N, O and S wherein A may be substituted by 1 to 5 substituents R which may be same or different; their solvates, hydrates, and pharmaceutically acceptable salts for the treatment of a disorder or disease associated with an aberrant activation of Wnt signalling in a mammal selected from a cell proliferative disorder, rheumatoid arthritis, increased bone density, aging or age-related disorders and/or diseases or Dupuytren disease (superficial fibromatosis).

  根据通式（I），其中X1、X2、X3和X4独立地为N或CR8，其中R8可以相同或不同，且X1、X2、X3和X4中最多3个可以为N；A是一个含有1至3个异原子（选自N、O和S）的5-或6元芳香或杂芳基环，其中A可以被1至5个基团R取代，这些基团可以相同或不同；它们的溶剂化物、水合物和药学上可接受的盐用于治疗与哺乳动物中Wnt信号通路异常激活相关的疾病或症状，包括细胞增殖性疾病、类风湿性关节炎、骨密度增加、衰老或与年龄相关的疾病或疾病或杜普伊特伦病（表浅性纤维瘤病）。
• CHROMENE DERIVATIVES AND THEIR ANALOGS AS WNT PATHWAY ANTAGONISTS
  申请人：Deutsches Krebsforschungszentrum

  公开号：US20160355496A1

  公开（公告）日：2016-12-08

  Compounds of formula (IIc); wherein X 3 and X 4 independently from each other are N or CR 8 wherein R 8 may be same or different; Y 1 , Y 2 , Y 3 and Y 4 independently from each other are N or CR 9 wherein R 9 may be same or different and wherein up to 3 of the group Y 1 , Y 2 , Y 3 and Y 4 may be N; their solvates, hydrates, and pharmaceutically acceptable salts, their use for modulating the Wnt signalling pathway activity and their use as a medicament, preferably for the treatment of cancer.
• US9371333B2
  申请人：——

  公开号：US9371333B2

  公开（公告）日：2016-06-21
• Asymmetrical 2,6-bis(benzylidene)cyclohexanones: Synthesis, cytotoxic activity and QSAR study
  作者：Maryam Nakhjiri、Maliheh Safavi、Eskandar Alipour、Saeed Emami、Amir Farzin Atash、Mona Jafari-Zavareh、Sussan K. Ardestani、Mehdi Khoshneviszadeh、Alireza Foroumadi、Abbas Shafiee

  DOI：10.1016/j.ejmech.2012.01.045

  日期：2012.4

  In order to develop novel anti-cancer agents, a series of asymmetrical 2,6-bis (benzylidene)cyclohexanone derivatives containing nitrobenzylidene moiety were synthesized and their cytotoxic activity were determined in vitro against MDA-MB 231, MCF-7 and SK-N-MC cell lines using MTT assay. Among the tested compounds, the highest activity against MDA-MB 231 cells was achieved by 2-(3-bromo-5-methoxy-4-propoxybenzylidene)-6-(2-nitrobenzylidene)cyclohexanone (compound 5d). Whereas, compound 5j (the 3-nitro analog of compound 5d) was the most potent compound against MCF-7 and SK-N-MC cell lines. The results indicated that the cytotoxic activity profile against different tumor cells can be optimized by desired 4-alkoxy-3-bromo-5-methoxybenzylidene scaffold. (C) 2012 Elsevier Masson SAS. All rights reserved.