3-methoxy-4-<2'-(methoxyethoxy)methoxy>-benzaldehyde | 78765-31-8

• 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: 3-methoxy-4-<2'-(methoxyethoxy)methoxy>-benzaldehyde
• 英文别名: 3-methoxy-4-((2-methoxyethoxy)methoxy)benzaldehyde；3-methoxy-4-[(2-methoxyethoxy)methoxy]benzaldehyde；4-((2-methoxyethoxy)methoxy)-3-methoxybenzaldehyde；3-methoxy-4-[2'-(methoxyethoxy)methoxy]-benzaldehyde；3-methoxy-4-(2-methoxyethoxymethoxy)benzaldehyde
• CAS: 78765-31-8
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: CBODASVMPGADDB-UHFFFAOYSA-N

物化性质

• 沸点：
  366.7±37.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methoxy-4-<2'-(methoxyethoxy)methoxy>-benzaldehyde 在 盐酸 、 sodium periodate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 55.0h， 生成 金圣草(黄)素
  参考文献：
  名称：

  Modulation of human neutrophils' oxidative burst by flavonoids

  摘要：

  Inflammation is a normal response towards tissue injury, but may become deleterious to the organism if uncontrolled. The overproduction of reactive species during the inflammatory process may cause or magnify the damage at inflammatory sites. Flavonoids have been suggested as therapeutic agents to avoid such damage, as these compounds exhibit anti-inflammatory activity, through the modulation of oxidative stress and signalling pathways. Both effects may attenuate neutrophils' activities at inflammatory sites. In this study, we investigated the structure/activity relationship of a series of flavonoids on the oxidative burst of human neutrophils in vitro, as a measure of its anti-inflammatory potential. Neutrophils were stimulated with phorbol-12-myristate-13-acetate, and fluorescence and chemiluminescence techniques were used to evaluate the generation of reactive oxygen species. All the tested flavonoids revealed the ability to modulate the neutrophil's oxidative burst. From the obtained results, the pivotal role of the catechol group in the B-ring was evidenced as well as the minor importance of the hydroxylations in the A-ring, which did not appear to be determinant for the activity, although clearly influencing the lipophilicity of the tested flavonoids. It is also clarified the importance of the methylation in the OH group at the B-ring catechol moiety. In conclusion, the obtained results uncover new possible strategies for the resolution of inflammatory processes, using flavonoids to modulate neutrophil's oxidative burst. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.019
• 作为产物：
  描述：

  2-甲氧基乙氧基甲基氯 、 香草醛 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以0.69 g的产率得到3-methoxy-4-<2'-(methoxyethoxy)methoxy>-benzaldehyde
  参考文献：
  名称：

  作为有效胰腺脂肪酶抑制剂的烷氧基黄酮的设计、合成、生物学评价和分子对接

  摘要：

  橙酮是黄酮类化合物的一个小亚类。与查尔酮、黄酮和异黄酮等其他亚类不同，橙酮作为胰腺脂肪酶抑制剂尚未得到广泛研究。在这项工作中，我们研究了合成Aurone衍生物的胰腺脂肪酶抑制效力。设计并合成了属于四个系列（4,6-二羟基黄酮、6-羟基黄酮、4,6-二烷氧基黄酮和6-烷氧基黄酮）的36个化合物。通过分光光度法测定其体外抑制活性，并与槲皮素和奥利司他进行比较。具有长链（6-10 个碳）烷氧基取代基的烷氧基橙酮衍生物显示出更大的效力。其中，相对于槲皮素（IC50为86.98±3.859μM）和奥利司他（IC50为0.0334±0.0015μM），4,6-二烷氧基橙酮8表现出最高的抗胰腺脂肪酶活性（IC50为1.945±0.520μM）。荧光猝灭测量证实了烷氧基黄酮衍生物对胰腺脂肪酶的亲和力。动力学研究表明，8 通过竞争机制抑制脂肪酶（Ki 为 1.288 ± 0.282 µM）。分子对接结果阐明了

  DOI：

  10.1016/j.bmcl.2023.129574

文献信息

• [EN] 3-PHENYL-N- ((1, 3, 4) THIADIAZOL-2-YL) -ACRYLAMIDE DERIVATIVES AND RELATED COMPOUNDS AS MODULATORS OF ESTROGEN-RELATED RECEPTORS FOR THE TREATMENT OF E.G. CANCER, RHEUMATOID ARTHRITIS OR NEUROLOGICAL DISORDERS<br/>[FR] DERIVES DE 3-PHENYL-N- ((1, 3, 4) THIADIAZOL-2-YL) -ACRYLAMIDE ET COMPOSES APPARENTES UTILES COMME MODULATEURS DES RECEPTEURS LIES A L'OESTROGENE DANS LE TRAITEMENT DU CANCER, DE L'ARTHRITE RHUMATOIDE OU DE TROUBLES NEUROLOGIQUES
  申请人：X CEPTOR THERAPEUTICS INC

  公开号：WO2005072731A1

  公开（公告）日：2005-08-11

  Compounds of formula (I) are provided as well as compositions and methods of using compounds of formula (I) for modulating the activity of the estrogen-related receptors and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder related to the activity of the estrogen-related receptor. Considering the wide range of activity of the nuclear hormone receptor ERRα, the compounds described herein which are capable of modulating ERRα activity, are useful for treating a range of disease states including cancer, diabetes, obesity, hyperlipidermia, arthritis, atherosclerosis, osteoporosis, anxiety, depression, Parkinson’s disease and Alzheimer’s disease. Formula (I). The substituents are defined in the claims.

  提供了化学式（I）的化合物，以及使用化学式（I）的化合物调节雌激素相关受体活性的组合物和方法，用于治疗、预防或改善与雌激素相关受体活性有关的一种或多种疾病或紊乱的症状。考虑到核激素受体ERRα的广泛活性范围，本文描述的能够调节ERRα活性的化合物，可用于治疗包括癌症、糖尿病、肥胖、高脂血症、关节炎、动脉粥样硬化、骨质疏松症、焦虑、抑郁症、帕金森病和阿尔茨海默病在内的一系列疾病状态。化学式（I）。取代基在权利要求中有定义。
• (2E,4E)-N-(4-(1H-Indol-3-yl)piperidin-1-yl)alkyl-5-(substituted phenyl)-2,4-pentadienamides as Antiallergic Agents with Antihistaminic and Anti Slow-Reacting Substance (SRS) Activities
  作者：Shinji Shigenaga、Takashi Manabe、Hiroshi Matsuda、Takashi Fujii、Masaaki Matsuo

  DOI：10.1002/ardp.19963290103

  日期：——

  compound with dual activities against histamine and slow‐reacting substance (SRS), we synthesized two types of indolylpiperidine derivatives, 3 and 4–20. Testing for in vivo antianaphylactic activity and for in vitro anti‐SRS activity revealed that (2E,4E)‐5‐(3,5‐dimethoxy‐4‐hydroxyphenyl)‐N‐(2‐(4‐(1H‐indol‐3‐yl)piperidin‐1‐yl)ethyl)‐2,4‐pentadienamide (11) exhibited potent dual activities with ED50 = 0

  作为我们研究的延伸，旨在发现一种对组胺和慢反应物质 (SRS) 具有双重活性的新型化合物，我们合成了两种类型的吲哚哌啶衍生物，3 和 4-20。体内抗过敏活性和体外抗 SRS 活性测试表明 (2E, 4E) -5- (3,5 - 二甲氧基 - 4 - 羟基苯基) -N- (2- (4- (1H - indole - 3 ‐Yl) 哌啶 ‐ 1 ‐ yl) 乙基) ‐2,4 - 戊二烯酰胺 (11) 表现出有效的双重活性，分别为 ED50 = 0.89 mg / kg 和 IC50 = 1.43 μM。然而，当在豚鼠中口服给药时，未改变的 11 的血浆浓度非常低。这一结果可以通过快速形成葡萄糖醛酸结合物来解释。
• Exploring cinnamic acid scaffold: development of promising neuroprotective lipophilic antioxidants
  作者：Daniel Chavarria、Tiago Silva、Daniel Martins、Joana Bravo、Teresa Summavielle、Jorge Garrido、Fernanda Borges

  DOI：10.1039/c5md00018a

  日期：——

  New lipophilic hydroxycinnamic acid based derivatives were designed and synthesized and their antioxidant and neuroprotective activities evaluated.

  设计并合成了新的亲脂性羟基肉桂酸衍生物，并评估了它们的抗氧化和神经保护活性。
• Breast cancer resistance protein (bcrp) inhibitor
  申请人：Yamazaki Ryuta

  公开号：US20060128636A1

  公开（公告）日：2006-06-15

  The invention provides a drug which inhibits BCRP. A breast cancer resistance protein inhibitor containing, as an active ingredient, a diphenylacrylonitrile derivative represented by the following formula (1): [wherein, each of 8 R's, which are the same or different from one another, represents a hydrogen atom, a hydroxyl group, a nitro group, an amino group, an acetylamino group (—NHCOCH 3 group); a cyano group (—CN group); a formyl group (—CHO group), —COOR 1 (R 1 is hydrogen or C1-C4 alkyl), —O(CH 2 ) n COOR 2 (n=1−7: R 2 is hydrogen or C1-C4 alkyl), —OOCCH 2 CH 2 COOR 3 (R 3 is hydrogen, C1-C4 alkyl, (Z)-2-(3,4-dimethoxy-phenyl)-3-(4-hydroxy-phenyl)-acrylonitrile, or glycopyranosyl), a C1-C8 alkoxy group, a C1-C4 alkyl group, a halogen atom, a C1-C4 alkoxy C1-C4 alkoxy C1-C4 alkoxy group, a C2-C8 acyloxy group, a C2-C8 halogenoacyloxy group, a methylenedioxy group, a trifluoromethyl group, a phosphate group (i.e., —OP(O) (OH) 2 ) or a salt thereof, a sulfate group (i.e., —OSO 3 H) or a salt thereof, a glycopyranosyl group or a salt thereof, a phosphate ester of a glycopyranosyl group or a salt of the ester, a sulfate ester of a glycopyranosyl group or a salt of the ester, or a piperidinopiperidinocarbonyloxy group], an ester thereof, or a salt thereof.

  本发明提供了一种抑制BCRP的药物。一种含有以下式（1）所表示的二苯乙烯腈衍生物作为活性成分的乳腺癌耐药蛋白抑制剂：[其中，8个R分别表示氢原子、羟基、硝基、氨基、乙酰氨基（—NHCOCH3基）、氰基（—CN基）、甲酰基（—CHO基）、—COOR1（R1为氢或C1-C4烷基）、—O（CH2）nCOOR2（n = 1-7：R2为氢或C1-C4烷基）、—OOCCH2CH2COOR3（R3为氢、C1-C4烷基、（Z）-2-（3,4-二甲氧基苯基）-3-（4-羟基苯基）-丙烯腈或葡萄糖基）、C1-C8烷氧基、C1-C4烷基、卤原子、C1-C4烷氧基C1-C4烷氧基C1-C4烷氧基、C2-C8酰氧基、C2-C8卤代酰氧基、亚甲二氧基基团、三氟甲基基团、磷酸酯基团（即—OP（O）（OH）2）或其盐、硫酸酯基团（即—OSO3H）或其盐、葡萄糖基或其盐、葡萄糖基的磷酸酯或酯的盐、葡萄糖基的硫酸酯或酯的盐，或者是它的酯或盐。
• Breast cancer resistance protein (BCRP) inhibitor
  申请人：Kabushiki Kaisha Yakult Honsha

  公开号：US07371773B2

  公开（公告）日：2008-05-13

  The invention provides a drug which inhibits BCRP. A breast cancer resistance protein inhibitor containing, as an active ingredient, a diphenylacrylonitrile derivative represented by the following formula (1): [wherein, each of 8 R's, which are the same or different from one another, represents a hydrogen atom, a hydroxyl group, a nitro group, an amino group, an acetylamino group (—NHCOCH3 group); a cyano group (—CN group); a formyl group (—CHO group), —COOR1 (R1 is hydrogen or C1-C4 alkyl), —O(CH2)nCOOR2 (n=1−7: R2 is hydrogen or C1-C4 alkyl), —OOCCH2CH2COOR3 (R3 is hydrogen, C1-C4 alkyl, (Z)-2-(3,4-dimethoxy-phenyl)-3-(4-hydroxy-phenyl)-acrylonitrile, or glycopyranosyl), a C1-C8 alkoxy group, a C1-C4 alkyl group, a halogen atom, a C1-C4 alkoxy C1-C4 alkoxy C1-C4 alkoxy group, a C2-C8 acyloxy group, a C2-C8 halogenoacyloxy group, a methylenedioxy group, a trifluoromethyl group, a phosphate group (i.e., —OP(O) (OH)2) or a salt thereof, a sulfate group (i.e., —OSO3H) or a salt thereof, a glycopyranosyl group or a salt thereof, a phosphate ester of a glycopyranosyl group or a salt of the ester, a sulfate ester of a glycopyranosyl group or a salt of the ester, or a piperidinopiperidinocarbonyloxy group], an ester thereof, or a salt thereof.

  该发明提供了一种抑制BCRP的药物。一种含有以下式（1）所表示的二苯丙烯腈衍生物作为活性成分的乳腺癌耐药蛋白抑制剂：[其中，8个R，它们相同或不同，分别表示氢原子，羟基，硝基，氨基，乙酰氨基（—NHCOCH3基），氰基（—CN基），甲酰基（—CHO基），—COOR1（R1为氢或C1-C4烷基），—O（CH2）nCOOR2（n = 1-7：R2为氢或C1-C4烷基），—OOCCH2CH2COOR3（R3为氢，C1-C4烷基，（Z）-2-（3,4-二甲氧基苯基）-3-（4-羟基苯基）-丙烯腈或甘露糖基），C1-C8烷氧基，C1-C4烷基，卤原子，C1-C4烷氧基C1-C4烷氧基C1-C4烷氧基，C2-C8酰氧基，C2-C8卤代酰氧基，亚甲二氧基基团，三氟甲基基团，磷酸盐基（即—OP（O）（OH）2）或其盐，硫酸盐基（即—OSO3H）或其盐，甘露糖基或其盐，甘露糖基的磷酸酯或其盐，甘露糖基的硫酸酯或其盐，或哌啶基哌啶羧酰氧基]，其酯或其盐。