4-(2-dimethylamino-ethoxy)-3',5'-dimethyl-biphenyl-3-carbaldehyde | 628306-36-5

• 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-(2-dimethylamino-ethoxy)-3',5'-dimethyl-biphenyl-3-carbaldehyde
• 英文别名: 2-[2-(Dimethylamino)ethoxy]-5-(3,5-dimethylphenyl)benzaldehyde
• CAS: 628306-36-5
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: PLNLZGAKNGEPIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-dimethylamino-ethoxy)-3',5'-dimethyl-biphenyl-3-carbaldehyde 、 邻氨基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 (E)-1-(2-aminophenyl)-3-[2-[2-(dimethylamino)ethoxy]-5-(3,5-dimethylphenyl)phenyl]prop-2-en-1-one
  参考文献：
  名称：

  Cationic Chalcone Antibiotics. Design, Synthesis, and Mechanism of Action

  摘要：

  This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the beta-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the A-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 mu M against methicillin resistant Staphylococus aureus.

  DOI：

  10.1021/jm049424k

文献信息

• [EN] QUATERNARY AMINO-FUNCTIONAL CHALCONES<br/>[FR] CHALCONES COMPORTANT DES FONCTIONS AMINE QUATERNAIRE
  申请人：LICA PHARMACEUTICALS AS

  公开号：WO2005042467A1

  公开（公告）日：2005-05-12

  The present invention provides novel quaternary amino-functional chalcone derivatives and analogues exhibiting interesting antibacterial activity. The compounds have the general formula (Y1)m-Ar1(X1)-C(=O)Var2(X2)-(Y2)p (I), wherein V designates -CH2-CH2-, -CH=CH-or -C=C; Ar1 and Ar2 independently are aryl and heteroary.; m=0, 2, p=0, 1, 2, m+p>0; each Y1 and Y2 independently is -Z-N+(R1)(R2)R4 Q-(A); -NR3-Z-N+(R1)(R2)R4 Q- (B), or O-Z-N+(R1)(R2)R4 Q- (C), R1, R2, R3, R4, X1, X2 are substituents, and Q- is an anion. The present invention also relates to the compounds for sue as pharmaceutically active agents, in particular against bacterial infections (such as Gram-negative and Gram-positive bacteria, including antibiotic-sensitive or resistant strains), and in the medical treatment of bacterial infections in mammals.

  本发明提供了新型季铵功能的香豆素衍生物和类似物，具有有趣的抗菌活性。这些化合物具有通式（Y1）m-Ar1（X1）-C（=O）Var2（X2）-（Y2）p（I），其中V代表-CH2-CH2-，-CH=CH-或-C=C；Ar1和Ar2独立地是芳基和杂芳基；m=0、2，p=0、1、2，m+p>0；每个Y1和Y2独立地是-Z-N+（R1）（R2）R4Q-（A）；-NR3-Z-N+（R1）（R2）R4Q-（B）或O-Z-N+（R1）（R2）R4Q-（C），其中R1、R2、R3、R4、X1、X2是取代基，Q-是阴离子。本发明还涉及这些化合物作为药物活性剂的用途，特别是对抗细菌感染（如革兰氏阴性和革兰氏阳性细菌，包括抗生素敏感或耐药菌株），以及在哺乳动物的医疗治疗中用于治疗细菌感染。
• Aminoalkoxy-functional chalcones
  申请人：Nielsen Feldbaek Simon

  公开号：US20050227990A1

  公开（公告）日：2005-10-13

  The invention provides novel alkoxyaminochalcone derivatives and analogues thereof. Use of the compounds, or compositions comprising them, as pharmaceutically active agents, in particular against bacterial and parasitic infections, is also disclosed. The invention further relates to a method for detecting inhibitory effects against e.g., bacteria, parasites, fungi, and helminths. The chalcones of the invention carry amino substituents and exhibit enhanced biological effects combined with improved metabolic and physicochemical properties, making the compounds useful as drug substances, in particular as antiparasitic, bacteriostatic, and bacteriocidal agents.

  本发明提供了新型的烷氧基氨基查尔酮衍生物及其类似物。本发明还揭示了将该化合物或包含它们的组合物用作药物活性剂，特别是用于对抗细菌和寄生虫感染。本发明还涉及一种检测抑制作用的方法，例如对细菌、寄生虫、真菌和蠕虫的抑制作用。本发明的查尔酮带有氨基取代基，并展示出增强的生物效应和改善的代谢和物理化学性质，使得该化合物可用作药物物质，特别是作为抗寄生虫、细菌静止和杀菌剂。
• QUATERNARY AMINO-FUNCTIONAL CHALCONES
  申请人：Lica Pharmaceuticals A/S

  公开号：EP1682486A1

  公开（公告）日：2006-07-26
• Quaternary Amino-Function Chalcones
  申请人：Nielsen Simon Feldbaek

  公开号：US20080027075A1

  公开（公告）日：2008-01-31

  The present invention provides novel quaternary amino-functional chalcone derivatives and analogues exhibiting interesting antibacterial activity. The compounds have the general formula (Y 1 ) m —Ar 1 (X 1 )—C(=O)VAr 2 (X 2 )−(Y 2 ) p (I), wherein V designates —CH 2 —CH 2 —, —CH═CH— or —C≡C—; Ar 1 and Ar 2 independently are aryl and heteroaryl; m=0, 1, 2, p=0, 1, 2, m+p>0; each Y 1 and Y 2 independently is -Z—N + (R 1 )(R 2 )R 4 Q − (A); —NR 3 -Z—N + (R 1 )(R 2 )R 4 Q − (B), or —O-Z—N + (R 1 )(R 2 )R 4 Q − (C), R 1 , R 2 , R 3 , R 4 , X 1 , X 2 are substituents, and Q − is an anion. The present invention also relates to the compounds for use as pharmaceutically active agents, in particular against bacterial infections (such as Gram-negative and Gram-positive bacteria, including antibiotic-sensitive or resistant strains), and in the medical treatment of bacterial infections in mammals.
• US7423181B2
  申请人：——

  公开号：US7423181B2

  公开（公告）日：2008-09-09