2-bromo-3,4,5-trimethoxybenzaldehyde dimethylacetal | 87850-44-0

• 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: 2-bromo-3,4,5-trimethoxybenzaldehyde dimethylacetal
• 英文别名: 2-bromo-1-(dimethoxymethyl)-3,4,5-trimethoxybenzene
• CAS: 87850-44-0
• 化学式: C₁₂H₁₇BrO₅
• 分子量: 321.168
• InChiKey: KIRMKSWFOVIEPB-UHFFFAOYSA-N

物化性质

• 沸点：
  333.7±42.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-bromo-3,4,5-trimethoxybenzaldehyde dimethylacetal 在 正丁基锂 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 1-(3-bromo-4,5-dimethoxyphenyl)-6,7,8-trimethoxy-2,3-bis(methoxycarbonyl)naphthalene
  参考文献：
  名称：

  1-Arylnaphthalene Lignan:  A Novel Scaffold for Type 5 Phosphodiesterase Inhibitor

  摘要：

  1-Arylnaphthalene lignan, which had been reported as a PDE4 inhibitor by Iwasaki, was disclosed as a new structural class of PDE5 inhibitors. The structural requirements for potent and specific PDE5 inhibition were revealed in a 1-arylnaphthalene lignan series, in which 1-(3-bromo-4, 5-dimethoxyphenyl)-5-chloro-3-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl]-2-(methoxycarbonyl)naphthalene hydrochloride (27q) showed the most potent and specific inhibition (PDE5 inhibition IC50 = 6.2 nM, selectivity for PDE5 against PDE1, -2, -3, and -4 > 16 000). It is noteworthy that 27q has the best selectivities against PDE isoforms among PDE5 inhibitors so far reported. Compound 27q exhibited almost the same relaxant effects on rat aortic rings as sodium 1-[6-chloro-4-[(3,4-methylenedioxybenzyl)amino]quinazolin-2-yl]piperidine-4-carboxylate (35) (27q, EC50 = 0.10 mu M; 35, EC50 = 0.20 mu M) and was selected for further biological evaluation.

  DOI：

  10.1021/jm9807048
• 作为产物：
  描述：

  3,4,5-三甲氧基-2-溴苯甲醛 、 原甲酸三甲酯 在 Dowex 50W-X₈ acid exchange resin 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 2-bromo-3,4,5-trimethoxybenzaldehyde dimethylacetal
  参考文献：
  名称：

  Keay, Brian A.; Plaumann, Heinz P.; Rajapaksa, Dayananda, Canadian Journal of Chemistry, 1983, vol. 61, p. 1987 - 1995

  摘要：

  DOI：

文献信息

• Synthesis and Hypolipidemic Activity of Diesters of Arylnaphthalene Lignan and Their Heteroaromatic Analogs.
  作者：Tooru KURODA、Kazuhiko KONDO、Tameo IWASAKI、Akio OHTANI、Kohki TAKASHIMA

  DOI：10.1248/cpb.45.678

  日期：——

  A series of diesters of arylnaphthalene lignan and their heteroaromatic analogs were synthesized and evaluated for hypolipidemic activity. The disasters with modifications at C-3 showed excellent hypocholesterolemic and high-density lipoprotein (HDL) cholesterol-elevating activities. Structure-activity analysis indicated that the 2-pyridylmethyl ester 5l has the optimum activity.

  合成了一系列芳基萘木脂素二酯及其杂芳族类似物，并评估了其降血脂活性。在C-3处进行修改的灾难显示出出色的降胆固醇和高密度脂蛋白（HDL）胆固醇升高活动。结构活性分析表明2-吡啶基甲基酯5l具有最佳活性。
• Arylnaphthalene Lignans as Novel Series of Hypolipidemic Agents Raising High-Density Lipoprotein Level.
  作者：Tameo IWASAKI、Kazuhiko KONDO、Takashi NISHITANI、Tooru KURODA、Kazuyuki HIRAKOSO、Akio OHTANI、Kohki TAKASHIMA

  DOI：10.1248/cpb.43.1701

  日期：——

  A series of arylnaphthalene lignans were synthesized and tested for hypolipidemic activity. The most potent compound (4b) (TA-7552) not only reduced serum cholesterol, but also increased high-density lipoproteins cholesterol in rats. The effective dose of 4b is 100 times less than that of cholestyramine. Structure-activity relationships are discussed.

  合成了一系列芳基萘二聚体木质素，并测试了其降脂活性。最有效的化合物（4b）（TA-7552）不仅降低了大鼠的血清胆固醇，还增加了高密度脂蛋白胆固醇。4b的有效剂量是胆固醇吸附剂的100倍小。讨论了结构与活性之间的关系。
• Naphthalene derivatives and composition and methods of use, and aldehyde
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US05070103A1

  公开（公告）日：1991-12-03

  Naphthalene derivative of the formula: ##STR1## wherein R.sup.1 is hydrogen atom or a lower alkoxycarbonyl and R.sup.2 is a lower alkoxycarbonyl, or R.sup.1 and R.sup.2 are combined together to form a group of the formula: ##STR2## each of R.sup.3 and R.sup.4 is a lower alkoxy, or one of R.sup.3 and R.sup.4 is hydrogen atom and the other is a lower alkoxy, and Ring A is a substituted or unsubstituted benzene ring, and a pharmaceutically acceptable salt thereof are disclosed. Said naphthalene derivative (I) and its salt have excellent hypolipidemic activity and are useful for treatment or prophylaxis of hyperlipidemia and/or arteriosclerosis.

  萘衍生物的化学式：##STR1##其中R.sup.1是氢原子或较低的烷氧羰基，R.sup.2是较低的烷氧羰基，或者R.sup.1和R.sup.2结合在一起形成下述分子式的基团：##STR2##其中每个R.sup.3和R.sup.4是较低的烷氧基，或者R.sup.3和R.sup.4中的一个是氢原子，另一个是较低的烷氧基，环A是取代或未取代的苯环，以及其药用盐。所述的萘衍生物（I）及其盐具有出色的降脂活性，可用于治疗或预防高脂血症和/或动脉硬化。
• Alkoxynaphthalene derivatives
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US04771072A1

  公开（公告）日：1988-09-13

  Naphthalene derivative of the formula: ##STR1## wherein R.sup.1 is hydrogen atom or a lower alkoxycarbonyl and R.sup.2 is a lower alkoxycarbonyl, or R.sup.1 and R.sup.2 are combined together to form a group of the formula: ##STR2## each of R.sup.3 and R.sup.4 is a lower alkoxy, or one of R.sup.3 and R.sup.4 is hydrogen atom and the other is a lower alkoxy, and Ring A is a substituted or unsubstituted benzene ring, and a pharmaceutically acceptable salt thereof are disclosed. Said naphthalene derivative (I) and its salt have excellent hypolipidemic activity and are useful for treatment or prophylaxis of hyperlipidemia and/or arteriosclerosis.

  萘衍生物的化学式如下：##STR1## 其中 R.sup.1 是氢原子或较低的烷氧羰基，R.sup.2 是较低的烷氧羰基，或者 R.sup.1 和 R.sup.2 结合在一起形成下列化合物：##STR2## 每个 R.sup.3 和 R.sup.4 是较低的烷氧基，或者 R.sup.3 和 R.sup.4 中的一个是氢原子，另一个是较低的烷氧基，环 A 是取代或未取代的苯环，以及其药用可接受的盐。所述的萘衍生物（I）及其盐具有出色的降脂活性，可用于治疗或预防高血脂症和/或动脉硬化。
• Novel naphthalene derivative
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US04840951A1

  公开（公告）日：1989-06-20

  Naphthalene derivative of the formula: ##STR1## wherein Ring A is a substituted or unsubstituted benzene ring; each of R.sup.1 and R.sup.2 is a group of the formula: --OR.sup.5, --NHR.sup.5 or ##STR2## or either one of R.sup.1 and R.sup.2 is a lower alkoxy group and the other one is a group of the formula: --OR.sup.5, --NHR.sup.5 or ##STR3## each of R.sup.3 and R.sup.4 is a lower alkoxy group, or one of R.sup.3 and R.sup.4 is a lower alkoxy group and the other is a hydrogen atom; R.sup.5 is a substituted alkyl group, a heterocyclic group, a cycloalkyl group, an alkyl group of at least 5 carbon atoms or alkenyl group; and each of R.sup.6 and R.sup.7 is hydrogen atom or a lower alkyl group and salts thereof are disclosed. Said naphthalene derivative (I) and its salts have excellent hypolipidemic activity and are useful for treatment or prophylaxis of hyperlipidemia and/or arteriosclerosis.

  萘衍生物的化学式为：##STR1## 其中环A是一个取代或未取代的苯环；R.sup.1和R.sup.2中的每一个是以下化学式的基团：--OR.sup.5，--NHR.sup.5或##STR2## 或者R.sup.1和R.sup.2中的一个是较低的烷氧基团，另一个是以下化学式的基团：--OR.sup.5，--NHR.sup.5或##STR3## R.sup.3和R.sup.4中的每一个是较低的烷氧基团，或者R.sup.3和R.sup.4中的一个是较低的烷氧基团，另一个是氢原子；R.sup.5是一个取代的烷基团，一个杂环基团，一个环烷基团，至少有5个碳原子的烷基团或烯烃基团；R.sup.6和R.sup.7中的每一个是氢原子或较低的烷基团，以及其盐。所述的萘衍生物(I)及其盐具有出色的降脂作用，可用于治疗或预防高脂血症和/或动脉硬化。