4-methoxy-3-n-pentyloxybenzaldehyde | 118791-48-3

• 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-methoxy-3-n-pentyloxybenzaldehyde
• 英文别名: 4-Methoxy-3-(pentyloxy)benzaldehyde；4-methoxy-3-pentoxybenzaldehyde
• CAS: 118791-48-3
• 化学式: C₁₃H₁₈O₃
• mdl: MFCD06742799
• 分子量: 222.284
• InChiKey: RBKOEPNLFQXHJD-UHFFFAOYSA-N

物化性质

• 沸点：
  334.9±22.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 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-methoxy-3-n-pentyloxybenzaldehyde 在 氯化亚砜 、 sodium hydrogensulfite 作用下， 以 氯仿 、 水 、 乙酸乙酯 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  Studies on antidiabetic agents. III. 5-Arylthiazolidine-2,4-diones as potent aldose reductase inhibitors.

  摘要：

  具有一个或两个取代基（如苯基、杂基和烷基）的噻唑烷-2,4-二酮衍生物在5位合成并评估为醛糖还原酶抑制剂。在鼠晶状体培养检测中，活性化合物的抑制作用也被测量。在这些化合物中，一系列5-(3,4-二烷氧基苯基)噻唑烷-2,4-二酮在两种检测中显示出显著的活性。结构-活性关系进行了讨论，并描述了一种合成5-芳基噻唑烷-2,4-二酮的新方法。

  DOI：

  10.1248/cpb.30.3601
• 作为产物：
  描述：

  异香兰素 、 1-溴戊烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-methoxy-3-n-pentyloxybenzaldehyde
  参考文献：
  名称：

  Studies on antidiabetic agents. III. 5-Arylthiazolidine-2,4-diones as potent aldose reductase inhibitors.

  摘要：

  具有一个或两个取代基（如苯基、杂基和烷基）的噻唑烷-2,4-二酮衍生物在5位合成并评估为醛糖还原酶抑制剂。在鼠晶状体培养检测中，活性化合物的抑制作用也被测量。在这些化合物中，一系列5-(3,4-二烷氧基苯基)噻唑烷-2,4-二酮在两种检测中显示出显著的活性。结构-活性关系进行了讨论，并描述了一种合成5-芳基噻唑烷-2,4-二酮的新方法。

  DOI：

  10.1248/cpb.30.3601

文献信息

• Benzimidazole derivatives and pharmacologically acceptable salts thereof
  申请人：Taiho Pharmaceutical Co., Ltd.

  公开号：US06248768B1

  公开（公告）日：2001-06-19

  This invention provides a compound having both IL-4 production inhibitory activity and PDE (IV) inhibitory activity, represented by formula (I): and a pharmaceutical composition or a therapeutic agent for acute and chronic inflammatory diseases and an anti-allergic or anti-inflammatory agent, each of which comprising an effective amount of the compound and a pharmacological carrier. It also provides use of the compound of formula (I) for the production of the aforementioned pharmaceutical composition or therapeutic agent for acute and chronic inflammatory diseases and anti-allergic or anti-inflammatory agent, and a method for treating acute and chronic inflammatory diseases.

  该发明提供了一种具有IL-4产生抑制活性和PDE（IV）抑制活性的化合物，其化学式表示为（I）：以及包含该化合物的有效量和药理载体的药物组合物或治疗剂，用于急性和慢性炎症性疾病和抗过敏或抗炎剂。还提供了使用化合物（I）的方法，用于制备上述药物组合物或治疗剂，用于急性和慢性炎症性疾病和抗过敏或抗炎剂，并提供了治疗急性和慢性炎症性疾病的方法。
• [EN] SYNTHESIS FOR THE PREPARATION OF COMPOUNDS FOR SCREENING AS POTENTIAL TUBULIN BINDING AGENTS<br/>[FR] SYNTHESE DESTINEE A LA PREPARATION DE COMPOSES DE CRIBLAGE UTILISES COMME AGENTS DE FIXATION A LA TUBULINE
  申请人：UNIV AUSTRALIAN

  公开号：WO2002060872A1

  公开（公告）日：2002-08-08

  The present invention relates to methods for the synthesis of chemical compounds for screening as potential tubulin polymerization inhibitors. The invention also provides chemical compounds with tubulin polymerization inhibitor activity.

  本发明涉及用于合成化学化合物以用作潜在的微管聚合抑制剂筛选的方法。本发明还提供了具有微管聚合抑制剂活性的化学化合物。
• Synthesis for the preparation of compounds for screening as potential tubulin binding agents
  申请人：Flynn Luke Bernard

  公开号：US20050130221A1

  公开（公告）日：2005-06-16

  The present invention relates to methods for the synthesis of chemical compounds for screening as potential tubulin polymerization inhibitors. The invention also provides chemical compounds with tubulin polymerization inhibitor activity.

  本发明涉及用于合成化学化合物的方法，用于筛选作为潜在微管聚合抑制剂的化合物。本发明还提供具有微管聚合抑制剂活性的化学化合物。
• BENZIMIDAZOLE DERIVATIVES AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF
  申请人：TAIHO PHARMACEUTICAL COMPANY, LIMITED

  公开号：EP0974589A1

  公开（公告）日：2000-01-26

  This invention provides a compound having both IL-4 production inhibitory activity and PDE (IV) inhibitory activity, represented by formula (I): [wherein A represents a triazole group; R1 and R2 may be the same or different from each other and each represents an aliphatic hydrocarbon radical which may have an alicyclic or aromatic hydrocarbon radical or an alicyclic hydrocarbon radical; R3 represents hydrogen atom or a substituent group; and R4 represents a hydrogen atom or a protective group of the nitrogen atom], and a pharmaceutical composition, a therapeutic or preventive agent for acute and chronic inflammatory diseases and an anti-allergic or anti-inflammatory agent, each of which comprising an effective amount of the compound and a pharmacological carrier. It also provides use of the compound of formula (I) for the production of the aforementioned pharmaceutical composition, therapeutic or preventive agent for acute and chronic inflammatory diseases and anti-allergic or anti-inflammatory agent, and a method for treating and/or preventing acute and chronic inflammatory diseases.

  本发明提供了一种同时具有IL-4产生抑制活性和PDE（IV）抑制活性的化合物，由式（I）表示： [其中 A 代表三唑基团；R1 和 R2 可以彼此相同或不同，并且各自代表脂肪族烃基，该烃基可以具有脂环族或芳香族烃基或脂环族烃基；R3 代表氢原子或取代基团；以及 R4 代表氢原子或氮原子的保护基团]，以及一种药物组合物、急性和慢性炎症性疾病的治疗剂或预防剂以及抗过敏剂或抗炎剂，其中每种药物组合物包括有效量的该化合物和药理学载体。本发明还提供了式（I）化合物用于生产上述药物组合物、急慢性炎症疾病的治疗或预防剂和抗过敏或抗炎剂的用途，以及治疗和/或预防急慢性炎症疾病的方法。
• Understanding the cytotoxic effects of new isovanillin derivatives through phospholipid Langmuir monolayers
  作者：Ana C. de Carvalho、Natália Girola、Carlos R. de Figueiredo、André C. Machado、Lívia S. de Medeiros、Rafael C. Guadagnin、Luciano Caseli、Thiago A.M. Veiga

  DOI：10.1016/j.bioorg.2018.10.029

  日期：2019.3

  Twenty-one isovanillin derivatives were prepared in order to evaluate their cytotoxic properties against the cancer cell lines B16F10-Nex2, HL-60, MCF-7, A2058 and HeLa. Among them, seven derivatives exhibited cytotoxic activity. We observed that for obtaining smaller IC50, values and for increasing the index of selectivity, two structural features are very important when compared with isovanillin (1); a hydroxymethyl group at C-1 and the replacement of the hydroxyl group at C-3 by different alkyl groups. As the lipophilicity of the compounds was changed, we decided to investigate the interaction of the cytotoxic isovallinin derivatives on cell membrane models through Langmuir monolayers by employing the lipids DPPC (1,2-diplamitoyl-sn-glycero-3-phosphocoline) and DPPS (1,2-diplamitoyl-sn-glycero-3-phosphoserine). The structural changes on the scaffold of the compounds modulated the interaction with the phospholipids at the air-water interface. These results were very important to understand the biophysical aspects related to the interaction of the cytotoxic compounds with the cancer cell membranes.