4-cyclohexyloxy-3-methoxybenzaldehyde | 112207-51-9

• 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: 4-cyclohexyloxy-3-methoxybenzaldehyde
• CAS: 112207-51-9
• 化学式: C₁₄H₁₈O₃
• mdl: MFCD00444183
• 分子量: 234.295
• InChiKey: WSPHCCYQWWGCFS-UHFFFAOYSA-N

物化性质

• 熔点：
  42-43 °C(Solv: ligroine (8032-32-4))
• 沸点：
  142-143 °C(Press: 0.25 Torr)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4-cyclohexyloxy-3-methoxybenzaldehyde 、 2-(羧基乙酰氨基)苯甲酸 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以60%的产率得到(E)-2-{[3-(4-cyclohexyloxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid
  参考文献：
  名称：

  Evaluation and optimization of antifibrotic activity of cinnamoyl anthranilates

  摘要：

  Tranilast is an anti-inflammatory drug in use for asthma and atopic dermatitis. In studies over the last decade it has been revealed that tranilast can reduce fibrosis occurring in the kidney during diabetes, thereby delaying and/or preventing kidney dysfunction. We report a structure-activity study aimed at optimizing the antifibrotic activity of tranilast. A series of cinnamoyl anthranilates were prepared and assessed for their ability to prevent TGF-beta-stimulated production of collagen in cultured renal mesangial cells. We reveal derivatives with improved potency and reduced cellular toxicity relative to tranilast. 3-Methoxy-4-propargyloxycinnamoyl anthranilate reduces albuminuria in a rat model of progressive diabetes, and thus has potential as an innovative treatment for diabetic nephropathy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.120
• 作为产物：
  描述：

  溴代环己烷 、 香草醛 在 potassium carbonate 、 sodium iodide 作用下， 以 乙醇 为溶剂， 反应 64.0h， 以37%的产率得到4-cyclohexyloxy-3-methoxybenzaldehyde
  参考文献：
  名称：

  Evaluation and optimization of antifibrotic activity of cinnamoyl anthranilates

  摘要：

  Tranilast is an anti-inflammatory drug in use for asthma and atopic dermatitis. In studies over the last decade it has been revealed that tranilast can reduce fibrosis occurring in the kidney during diabetes, thereby delaying and/or preventing kidney dysfunction. We report a structure-activity study aimed at optimizing the antifibrotic activity of tranilast. A series of cinnamoyl anthranilates were prepared and assessed for their ability to prevent TGF-beta-stimulated production of collagen in cultured renal mesangial cells. We reveal derivatives with improved potency and reduced cellular toxicity relative to tranilast. 3-Methoxy-4-propargyloxycinnamoyl anthranilate reduces albuminuria in a rat model of progressive diabetes, and thus has potential as an innovative treatment for diabetic nephropathy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.120

文献信息

• Imidazole derivatives show anticancer potential by inducing apoptosis and cellular senescence
  作者：Gangavaram V. M. Sharma、Adepu Ramesh、Ashita Singh、Gourishetty Srikanth、Vankudoth Jayaram、Divya Duscharla、Jung Ho Jun、Ramesh Ummanni、Sanjay V. Malhotra

  DOI：10.1039/c4md00277f

  日期：——

  discovery of new drugs. In the current study, we have synthesized a series of new 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles by multicomponent reaction (MCR). Vanillin and isovanillin derivatives were reacted with benzil/pyridil and diverse amines and ammonium acetate in acetic acid at 50–110 °C for 24 h to afford respective imidazoles in 55–70% yields. The series of molecules were evaluated

  基于咪唑的化合物是用于发现新药的新颖化学结构设计中的有吸引力的靶标。在当前的研究中，我们通过多组分反应（MCR）合成了一系列新的2,4,5-三取代和1,2,4,5-四取代的咪唑。香兰素和异香兰素衍生物在50-110°C的温度下，与苯甲酰/吡啶并与各种胺和乙酸铵在乙酸中反应24小时，从而以55-70％的产率提供各自的咪唑。评价了该系列分子对美国国家癌症研究所的60个人类癌细胞系的抗癌潜力。初步筛选突出了2,2'-（2-（3-（环戊氧基）-4-甲氧基苯基）-1-异丁基-1 H-咪唑-4,5-二基）二吡啶的抗癌潜力（NSC 771432）针对不同类型的癌细胞。A549细胞用体外以确定的动作模式NSC 771432对这些细胞的生长。该化合物抑制锚定独立生长和细胞迁移，并诱导细胞周期阻滞在G2 / M期。同样，A549细胞暴露于NSC 771432也会导致细胞衰老。
• Novel immunotherapeutic agents
  申请人：Muller W. George

  公开号：US20050096355A1

  公开（公告）日：2005-05-05

  Novel amides and imides are inhibitors of tumor necrosis factorα and phosphodiesterase and can be used to combat cachexia, endotoxic shock, retrovirus replication, asthma, and inflammatory conditions.

  新型酰胺和亚酰胺是肿瘤坏死因子α和磷酸二酯酶的抑制剂，可用于抵抗消瘦症、内毒素休克、逆转录病毒复制、哮喘和炎症病症。
• Topical compositions of cyclic amides as immunotherapeutic agents
  申请人：Muller W. George

  公开号：US20060003979A1

  公开（公告）日：2006-01-05

  Novel amides and imides are inhibitors of tumor necrosis factors and phosphodiesterase and can be used to combat cachexia, endotoxic shock, retrovirus replication, asthma, and inflammatory conditions.

  新型酰胺和亚胺类化合物是肿瘤坏死因子和磷酸二酯酶的抑制剂，可用于对抗恶病质、内毒素休克、逆转录病毒复制、哮喘和炎症等疾病。
• Methods of using cyclic amides
  申请人：Muller W. George

  公开号：US20060264477A1

  公开（公告）日：2006-11-23

  Novel amides and imides are inhibitors of tumor necrosis factors and phosphodiesterase and can be used to combat cachexia, endotoxic shock, retrovirus replication, asthma, and inflammatory conditions.

  新型酰胺和亚酰胺是肿瘤坏死因子和磷酸二酯酶的抑制剂，可用于对抗消瘦症、内毒素休克、逆转录病毒复制、哮喘和炎症状况。
• Therapeutic Compounds
  申请人：Williams Spencer John

  公开号：US20100130497A1

  公开（公告）日：2010-05-27

  Substituted cinnamoyl anthranilate compounds exhibiting anti-fibrotic activity; or derivatives thereof, analogues thereof, pharmaceutically acceptable salts thereof, and metabolites thereof; with the proviso that the compound is not Tranilast.

  具有抗纤维化活性的替代肉桂酰基蒽醇衍生物；或其衍生物、类似物、药学上可接受的盐和代谢物；但前提是该化合物不是曲安奈德。