3-ethoxy-4-pentyloxybenzaldehide | 79714-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-ethoxy-4-pentyloxybenzaldehide
• 英文别名: 3-Aethoxy-4-pentyloxy-benzaldehyd；3-Ethoxy-4-pentyloxybenzaldehyde；3-ethoxy-4-pentoxybenzaldehyde
• CAS: 79714-25-3
• 化学式: C₁₄H₂₀O₃
• mdl: MFCD08143639
• 分子量: 236.311
• InChiKey: BYYLQWYSRDRNLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• 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

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2912499000

反应信息

• 作为反应物：
  描述：

  3-ethoxy-4-pentyloxybenzaldehide 在 盐酸 、 氯化亚砜 、 sodium hydrogensulfite 作用下， 以 氯仿 、 水 、 乙酸乙酯 为溶剂， 反应 40.0h， 生成 5-(3-乙氧基-4-戊氧基苯基)-1,3-噻唑烷-2,4-二酮
  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：

  邻乙氧基苯酚 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 3-ethoxy-4-pentyloxybenzaldehide
  参考文献：
  名称：

  Über das Äthylvanillin I. Mitt.

  摘要：

  DOI：

  10.1002/ardp.19642970505

文献信息

• Thiazolidine derivatives and their production and medicinal compositions containing them
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0033617A2

  公开（公告）日：1981-08-12

  A thiazolidine derivatives of the formula: wherein R is a phenyl group having 2 nuclear substituent groups selected from the class consisting of a lower alkyl having 1 to 6 carbon atoms, a lower alkoxy having 1 to 7 carbon atoms, hydroxyl and a carboxylic acyloxy having 1 to4 carbon atoms or a phenyl group having a methylenedioxy group in adjacent positions on its ring; R' is H or an alkyl having 1 to 6 carbon atoms, or a physiologically acceptable salt thereof is a novel compound and is having the activity to control certain chronic symptoms due to diabetes, such as diabetic cataract, diabetic neuropathy and diabetic retinosis.

  一种式中的噻唑烷衍生物： 其中 R 是苯基，具有 2 个核取代基团，这些取代基团选自具有 1 至 6 个碳原子的低级烷基、具有 1 至 7 个碳原子的低级烷氧基、羟基和具有 1 至 4 个碳原子的羧基酰氧基或在其环上相邻位置具有亚甲二氧基的苯基；R'是 H 或具有 1 至 6 个碳原子的烷基，或其生理上可接受的盐，是一种新型化合物，具有控制糖尿病引起的某些慢性症状（如糖尿病性白内障、糖尿病性神经病变和糖尿病性视网膜病变）的活性。
• Use of 5-(3 ethoxy-4-pentyloxyphenyl)-2,4-thiazolidinedione for the preparation of an ophthalmic topical agent
  申请人：Senju Pharmaceutical Co., Ltd.

  公开号：EP0170237A2

  公开（公告）日：1986-02-05

  An ophthalmic topical agent for remedy of diseases of iris and ciliary body containing 5-(3-ethoxy-4-pentyloxyphenyl)-2,4-thiazolidinedion and/or a physiological acceptable salt as an active ingredient.

  一种用于治疗虹膜和睫状体疾病的眼科外用制剂，其活性成分含有 5-(3-乙氧基-4-戊氧基苯基)-2,4-噻唑烷二酮和/或生理上可接受的盐。
• Physicochemical-activity relationships in asymmetrical analogues of methoxychlor
  作者：Peter J. Goodford、Alan T. Hudson、G. Clive Sheppey、Raymond Wootton、Malcolm H. Black、Graeme J. Sutherland、John C. Wickham

  DOI：10.1021/jm00232a014

  日期：1976.10

  Compounds of the general formula 2-aryl-2-(p-methoxyphenyl)-1,1,1-trichloroethane have been prepared and tested for toxicity toward houseflies, pretreated for 1 h with 2mug of piperonyl butoxide. The majority of the compounds synthesized were chosen with the aid of computer programs designed to ensurewell-spread sets of minimally correlated physicochemical parameter values. A nonlinear two-dimensional representation was used to map the active region of physiochemical parameter space and a regression equation was obtained relating the observed toxicity to a combination of these physicochemical parameters. The equation indicates that toxicity increases with the hydrophobicity of the molecules but is decreased markedly by the introduction of bulky substituents into the ortho positions of the benzene ring and less markedly by bulky substituents in the meta and para positions. Substituents which donate electrons to the benzene ring by the "resonance" effect favor high toxicity. The equation performs well in forecasting the toxicity of further members of the series.
• Target Guided Synthesis of 5-Benzyl-2,4-diamonopyrimidines: Their Antimalarial Activities and Binding Affinities to Wild Type and Mutant Dihydrofolate Reductases from <i>Plasmodium falciparum</i>
  作者：Chawanee Sirichaiwat、Chakapong Intaraudom、Sumalee Kamchonwongpaisan、Jarunee Vanichtanankul、Yodhathai Thebtaranonth、Yongyuth Yuthavong

  DOI：10.1021/jm0303352

  日期：2004.1.1

  The resistance to pyrimethamine (PYR) of Plasmodium falciparum arising from mutation at position 108 of dihydrofolate reductase (pfDHFR) from serine to asparagine (S108N) is due to steric interaction between the bulky side chain of N108 and Cl atom of the 5-p-Cl aryl group of PYR, which consequently resulted in the reduction in binding affinity between the enzyme and inhibitor. Molecular modeling suggested that the flexible antifolate, such as trimethoprim (TMP) derivatives, could avoid this steric constraint and should be considered as new, potentially effective compounds. The hydrophobic interaction between the side chain of inhibitor and the active site of the enzyme around position 108 was enhanced by the introduction of a longer and more hydrophobic side chain on TMP's 5-benzyl moiety. The prepared compounds, especially those bearing aromatic substituents, exhibited better binding affinities to both wild type and mutant enzymes than the parent compound. Binding affinities of these compounds correlated well with their antimalarial. activities against both wild type and resistant parasites. Molecular modeling of the binding of such compounds with pfDHFR also supported the experimental data and clearly showed that aromatic substituents play an important role in enhancing binding affinity. In addition, some compounds with 6-alkyl substituents showed relatively less decrease in binding constants with the mutant enzymes and relatively good antimalarial. activities against the parasites bearing the mutant enzymes.
• KAVAMATSU, YUTAKA;YAMAMOTO, YUDZIRO
  作者：KAVAMATSU, YUTAKA、YAMAMOTO, YUDZIRO

  DOI：——

  日期：——