3-(m-methoxyphenyl)-4-methoxybenzaldehyde | 628711-36-4

• 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-(m-methoxyphenyl)-4-methoxybenzaldehyde
• 英文别名: 4-methoxy-3-(3-methoxyphenyl)benzenecarboxaldehyde；4-methoxy-3-(3-methoxyphenyl)benzaldehyde
• CAS: 628711-36-4
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: RUQVQHUMYBUHFH-UHFFFAOYSA-N

物化性质

• 沸点：
  374.6±32.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  3-氨基吡啶 、 3-(m-methoxyphenyl)-4-methoxybenzaldehyde 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 以60%的产率得到N-(pyridin-3-yl)-3-m-methoxyphenyl-4-methoxybenzylamine
  参考文献：
  名称：

  Discovery of arylbenzylamines as PDE4 inhibitors with potential neuroprotective effect

  摘要：

  Growing evidence confirms the potential of PDE4 inhibitors for the treatment of Parkinson's disease. Our reported PDE4 inhibitors FCPR16 and FCPR03 have displayed neuroprotective effects in SH-SY5Y cells, but have very low oral bioavailability. To access analogues with improved bioavailability, a new series of arylbenzylamine derivatives were designed and synthesized. Preliminary screening results of the series showed that arylbenzylamine derivatives bearing a pyridin-3-amine side chain displayed good inhibitory activities against human PDE4B1 and PDE4D7 isoforms. Moreover, kinetic studies revealed that the most potent compounds 11r and 11s with mid-nanomolar IC50 values partially bind to PDE4B1 (I-max = 93% and 90% respectively). Molecular docking results revealed the possible interactions of compounds 11r and 11s with upstream conserved region 2 (UCR2) of PDE4B1, which illuminate possible reasons for their partial inhibition against PDE4. Using a cell-based model of PD, compounds lir and Us were found to alleviate cellular apoptosis in SH-SY5Y cells induced by MPP+ (1-methyl-4-phenylpyridinium), with this neuroprotective effect being greater than PDE4 inhibitor rolipram. Furthermore, compound 11r displayed nearly sevenfold oral bioavailability (8.20%) than FCPR03 (1.23%). (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.02.026
• 作为产物：
  描述：

  3-溴-4-甲氧基苯甲醛 、 3-甲氧基苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 以80%的产率得到3-(m-methoxyphenyl)-4-methoxybenzaldehyde
  参考文献：
  名称：

  Discovery of arylbenzylamines as PDE4 inhibitors with potential neuroprotective effect

  摘要：

  Growing evidence confirms the potential of PDE4 inhibitors for the treatment of Parkinson's disease. Our reported PDE4 inhibitors FCPR16 and FCPR03 have displayed neuroprotective effects in SH-SY5Y cells, but have very low oral bioavailability. To access analogues with improved bioavailability, a new series of arylbenzylamine derivatives were designed and synthesized. Preliminary screening results of the series showed that arylbenzylamine derivatives bearing a pyridin-3-amine side chain displayed good inhibitory activities against human PDE4B1 and PDE4D7 isoforms. Moreover, kinetic studies revealed that the most potent compounds 11r and 11s with mid-nanomolar IC50 values partially bind to PDE4B1 (I-max = 93% and 90% respectively). Molecular docking results revealed the possible interactions of compounds 11r and 11s with upstream conserved region 2 (UCR2) of PDE4B1, which illuminate possible reasons for their partial inhibition against PDE4. Using a cell-based model of PD, compounds lir and Us were found to alleviate cellular apoptosis in SH-SY5Y cells induced by MPP+ (1-methyl-4-phenylpyridinium), with this neuroprotective effect being greater than PDE4 inhibitor rolipram. Furthermore, compound 11r displayed nearly sevenfold oral bioavailability (8.20%) than FCPR03 (1.23%). (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.02.026

文献信息

• [EN] CALCIUM RECEPTOR MODULATING ARYLALKYLAMINES<br/>[FR] ARYLALKYLAMINES MODULANT UN RECEPTEUR CALCIQUE
  申请人：AMGEN INC

  公开号：WO2003099776A1

  公开（公告）日：2003-12-04

  The compounds of the invention are represented by the following general structure (I) or a pharmaceutically acceptable salt thereof, and compositions containing them, wherein the variables are defined herein, and their use to reduce or inhibit PTH secretion, including methods for reducing or inhibiting PTH secretion and methods for treatment or prophylaxis of diseases associated with bone disorders, such as osteoporosis, or associated with excessive secretion of PTH, such as hyperparathyroidism. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  该发明的化合物由以下一般结构（I）或其药用可接受盐所代表，以及含有它们的组合物，其中变量在此处定义，并且它们的用途是减少或抑制PTH分泌，包括减少或抑制PTH分泌的方法以及用于治疗或预防与骨骼疾病相关的疾病的方法，例如骨质疏松症，或与PTH过度分泌相关的疾病，例如甲状旁腺功能亢进症。该主题发明还涉及制备此类化合物的过程，以及在此类过程中有用的中间体。
• Calcium receptor modulating agents
  申请人：——

  公开号：US20040082625A1

  公开（公告）日：2004-04-29

  The compounds of the invention are represented by the following general structure 1 or a pharmaceutically acceptable salt thereof, and compositions containing them, wherein the variables are defined herein, and their use to reduce or inhibit PTH secretion, including methods for reducing or inhibiting PTH secretion and methods for treatment or prophylaxis of diseases associated with bone disorders, such as osteoporosis, or associated with excessive secretion of PTH, such as hyperparathyroidism. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  本发明的化合物由以下一般结构1或其药学上可接受的盐所代表，并且含有这些化合物的组合物，其中变量在此定义，并且它们的用途是减少或抑制PTH分泌，包括减少或抑制PTH分泌的方法以及用于治疗或预防与骨疾病相关的疾病，如骨质疏松症，或与PTH过度分泌相关的疾病，如甲状旁腺功能亢进症。本发明还涉及制备这些化合物的过程，以及在这些过程中有用的中间体。
• HSP90 FAMILY PROTEIN INHIBITORS
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：EP1642880B1

  公开（公告）日：2013-09-04
• CALCIUM RECEPTOR MODULATING ARYLALKYLAMINES
  申请人：Amgen Inc.

  公开号：EP1509497A1

  公开（公告）日：2005-03-02
• NOVOBIOCIN ANALOGUES HAVING MODIFIED SUGAR MOIETIES
  申请人：UNIVERSITY OF KANSAS

  公开号：EP2438078B1

  公开（公告）日：2017-10-25