4-(methyl(propyl)amino)benzaldehyde | 1078-18-8

• 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-(methyl(propyl)amino)benzaldehyde
• 英文别名: 4-[Methyl(propyl)amino]benzaldehyde
• CAS: 1078-18-8
• 化学式: C₁₁H₁₅NO
• mdl: MFCD11627332
• 分子量: 177.246
• InChiKey: QQDXNZZRGUITHW-UHFFFAOYSA-N

物化性质

• 沸点：
  189-191 °C(Press: 15 Torr)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Methoxy-6-(oxan-2-yloxy)-2,3-dihydroinden-1-one 、 4-(methyl(propyl)amino)benzaldehyde 在 盐酸 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 丁酮 为溶剂， 以77%的产率得到6-hydroxy-5-methoxy-2-(4-(methyl(propyl)amino)-benzylidene)-2,3-dihydro-1H-inden-1-one hydrochloride
  参考文献：
  名称：

  Multitarget-Directed Benzylideneindanone Derivatives: Anti-β-Amyloid (Aβ) Aggregation, Antioxidant, Metal Chelation, and Monoamine Oxidase B (MAO-B) Inhibition Properties against Alzheimer’s Disease

  摘要：

  A novel series of benzylideneindanone derivatives were designed, synthesized, and evaluated as multitarget-directed ligands against Alzheimer's disease. The in vitro studies showed that most of the molecules exhibited a significant ability to inhibit self-induced beta-amyloid (A beta(1-42)) aggregation (10.5-80.1%, 20 mu M) and MAO-B activity (IC50 of 7.5-40.5 mu M), to act as potential antioxidants (ORAC-FL value of 2.75-9.37), and to function as metal chelators. In particular, compound 41 had the greatest ability to inhibit A beta(1-42) aggregation (80.1%), and MAO-B (IC50 = 7.5 mu M) was also an excellent antioxidant and metal chelator. Moreover, it is capable of inhibiting Cu(II)-induced A beta(1-42) aggregation and disassembling the well-structured A beta fibrils. These results indicated that compound 41 is an excellent multifunctional agent for the treatment of AD.

  DOI：

  10.1021/jm300978h
• 作为产物：
  描述：

  对氟苯甲醛 在 甲酸 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 23.0h， 生成 4-(methyl(propyl)amino)benzaldehyde
  参考文献：
  名称：

  Multitarget-Directed Benzylideneindanone Derivatives: Anti-β-Amyloid (Aβ) Aggregation, Antioxidant, Metal Chelation, and Monoamine Oxidase B (MAO-B) Inhibition Properties against Alzheimer’s Disease

  摘要：

  A novel series of benzylideneindanone derivatives were designed, synthesized, and evaluated as multitarget-directed ligands against Alzheimer's disease. The in vitro studies showed that most of the molecules exhibited a significant ability to inhibit self-induced beta-amyloid (A beta(1-42)) aggregation (10.5-80.1%, 20 mu M) and MAO-B activity (IC50 of 7.5-40.5 mu M), to act as potential antioxidants (ORAC-FL value of 2.75-9.37), and to function as metal chelators. In particular, compound 41 had the greatest ability to inhibit A beta(1-42) aggregation (80.1%), and MAO-B (IC50 = 7.5 mu M) was also an excellent antioxidant and metal chelator. Moreover, it is capable of inhibiting Cu(II)-induced A beta(1-42) aggregation and disassembling the well-structured A beta fibrils. These results indicated that compound 41 is an excellent multifunctional agent for the treatment of AD.

  DOI：

  10.1021/jm300978h

文献信息

• NOVEL INHIBITORS
  申请人：Heiser Ulrich

  公开号：US20110092501A1

  公开（公告）日：2011-04-21

  The invention relates to novel pyrrolidine derivatives of formula (I): wherein R 1 , R 2 and R 3 are as defined herein, as inhibitors of glutaminyl cyclase (QC, EC 2.3.2.5). QC catalyzes the intramolecular cyclization of N-terminal glutamine residues into pyroglutamic acid (5-oxo-prolyl, pGlu*) under liberation of ammonia and the intramolecular cyclization of N-terminal glutamate residues into pyroglutamic acid under liberation of water.

  本发明涉及新颖的吡咯烷衍生物，其具有如下公式(I)：其中R1、R2和R3如本文所述定义，作为谷氨酰胺环化酶（QC，EC 2.3.2.5）的抑制剂。谷氨酰胺环化酶催化N末端谷氨酰胺残基形成焦谷氨酸（5-氧代脯氨酸，pGlu*）的分子内环化，并释放氨，以及催化N末端谷氨酸残基形成焦谷氨酸的分子内环化，并释放水。
• [EN] DYE COMPOSITION COMPRISING AT LEAST ONE COLORLESS DISULFIDE/THIOL PRECURSOR, AND DYEING PROCESS USING THE COMPOSITION<br/>[FR] COMPOSITION COLORANTE COMPRENANT AU MOINS UN PRÉCURSEUR DE DISULFURE/THIOL INCOLORE ET PROCÉDÉ DE TEINTURE UTILISANT LA COMPOSITION
  申请人：OREAL

  公开号：WO2009040354A1

  公开（公告）日：2009-04-02

  The present invention relates to the dyeing of keratin materials using two colorless dye precursors, at least one of which contains a disulfide/thiol unit, said precursors reacting together chemically to form the color in situ. The process according to the invention makes it possible in the context of certain variants to solve the problems caused by the color generated during the process, while at the same time not degrading the efficacy of the coloration, and especially of the lightening effect. The colorations obtained are moreover powerful, chromatic, sparingly selective, and fast with respect to external agents such as sunlight, perspiration and especially shampoo.

  本发明涉及使用两种无色染料前体对角蛋白材料进行染色，其中至少一种含有二硫化物/巯基单元，这些前体在化学上相互反应以在原位形成颜色。根据本发明的方法使得在某些变体情况下能够解决染色过程中产生的问题，同时不降低染色的功效，特别是减淡效果。所获得的染色品不仅强大、色彩鲜艳、选择性较少，而且对于阳光、汗水和尤其是洗发水等外部因素具有快速的耐久性。
• Discovery of indanone derivatives as multi-target-directed ligands against Alzheimer's disease
  作者：Ling Huang、Hui Miao、Yang Sun、Fanchao Meng、Xingshu Li

  DOI：10.1016/j.ejmech.2014.09.081

  日期：2014.11

  disease (AD) agents. The investigations assessed the activities of the agents for the inhibition of cholinesterases (AChE and BuChE), the inhibition of amyloid beta (Aβ) self-assembly, and the catalysis of the disassembly of preformed Aβ oligomers and measured their antioxidant activities. Our results demonstrate that most of the synthesized compounds demonstrated good inhibitory activity against AChE

  使用各种测定法设计，合成和测试了一系列茚满酮衍生物，以评估其作为抗阿尔茨海默氏病（AD）药物的潜力。研究评估了这些试剂对胆碱酯酶（AChE和BuChE）的抑制作用，对淀粉样β（Aβ）自组装的抑制作用以及对预先形成的Aβ低聚物分解的催化作用，并测量了它们的抗氧化活性。我们的结果表明，大多数合成的化合物对AChE表现出良好的抑制活性，IC 50值在纳摩尔范围内。特别是化合物9（IC 50  = 14.8 nM）和14（IC 50 = 18.6 nM）表现出比他克林明显更高的抑制活性以及与多奈哌齐相似的活性。另外，9和14显着抑制Aβ聚集（抑制率分别为85.5％和83.8％），催化由自诱导的Aβ聚集产生的Aβ纤维分解，并表现出抗氧化活性。此外，这两种化合物均可在体外穿过血脑屏障（BBB）。这些特性突出了这些新化合物被开发为治疗阿尔茨海默氏病的多功能药物的潜力。
• Identification of 4-(N,N-dipropylamino)benzaldehyde as a potent, reversible inhibitor of mouse and human class I aldehyde dehydrogenase
  作者：James Russo、Song Chung、Kristi Contreras、Brian Lian、Jon Lorenz、David Stevens、Wendy Trousdell

  DOI：10.1016/0006-2952(95)00138-p

  日期：1995.7

  structure-function studies identified dialkylamino substituted benzaldehyde compounds as a novel class of reversible inhibitors of class I ALDH. To examine further structural requirements for inhibition, we tested a series of 4-(N,N-dialkylamino)benzaldehyde analogs as inhibitors of propanal oxidation by mouse liver and human erythrocyte class I ALDH. 4-(N,N-dipropylamino)benzaldehyde (DPAB) was identified

  随着阐明了不同类别的醛脱氢酶（ALDH）酶的生理作用，特异性，可逆抑制剂的鉴定变得具有重要的药理学意义。先前的结构功能研究确定，二烷基氨基取代的苯甲醛化合物是一类新的I类ALDH可逆抑制剂。为了检查抑制的进一步结构要求，我们测试了一系列4-（N，N-二烷基氨基）苯甲醛类似物作为小鼠肝脏和人类I类红细胞ALDH的丙醛氧化抑制剂。在分光光度酶测定法中，I类ALDH将4-（N，N-二丙基氨基）苯甲醛（DPAB）鉴定为最有效，可逆的丙烷氧化抑制剂。在动力学研究中，DPAB对乙醛的醛底物表现出混合型抑制作用，苯乙醛，苯甲醛和醛基磷酰胺。DPAB对辅因子NAD表现出非竞争性抑制作用。根据狄克逊图测得的DPAB抑制常数（Ki）对小鼠ALDH为10 nM（丙醛）和77 nM（苯乙醛），对人ALDH为3 nM（丙醛）和70 nM（苯乙醛）。这些Ki值比报道的I类特异性抑制剂的Ki值低100倍。在低（<1 m
• DYE COMPOSITION COMPRISING AT LEAST ONE COLORLESS DISULFIDE/THIOL PRECURSOR, AND DYEING PROCESS USING THE COMPOSITION
  申请人：Greaves Andrew

  公开号：US20110016642A1

  公开（公告）日：2011-01-27

  The present invention relates to the dyeing of keratin materials using two colorless dye precursors, at least one of which contains a disulfide/thiol unit, said precursors reacting together chemically to form the color in situ. The process according to the invention makes it possible in the context of certain variants to solve the problems caused by the color generated during the process, while at the same time not degrading the efficacy of the coloration, and especially of the lightening effect. The colorations obtained are moreover powerful, chromatic, sparingly selective, and fast with respect to external agents such as sunlight, perspiration and especially shampoo.

  本发明涉及使用两种无色染料前体对角蛋白质材料进行染色，其中至少一种包含二硫键/巯基单元，这些前体在化学上相互反应以在现场形成颜色。根据本发明的方法，在某些变体的背景下，可以解决染色过程中产生的颜色引起的问题，同时不降低染色的功效，特别是减淡效果。所获得的染色色彩强烈、色彩饱和、选择性小、对阳光、汗水和尤其是洗发水等外部因素快速稳定。