2-[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid methyl ester | 125599-58-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid methyl ester
• 英文别名: Methyl 2-(3,4-dimethoxy-benzylidene)acetoacetate；methyl 2-[(3,4-dimethoxyphenyl)methylidene]-3-oxobutanoate
• CAS: 125599-58-8
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: YPOIZCADKLVXLB-UHFFFAOYSA-N

物化性质

• 沸点：
  392.2±37.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid methyl ester 在 palladium on activated charcoal 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (E) Methyl 2-(3,4-dimethoxybenzyl)-acetoacetate
  参考文献：
  名称：

  Studies on Disease-Modifying Antirheumatic Drugs. II. Synthesis and Activity of the Metabolites of Ethyl 4-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate (TAK-603).

  摘要：

  我们制备了 4-(3,4-二甲氧基苯基)-6,7-二甲氧基-2-(1,2,4-三唑-1-基甲基)喹啉-3-羧酸乙酯（1，TAK-603）的代谢物，以确认其结构并研究其药理特性。在鉴定出的代谢物中，发现 4-（4-羟基-3-甲氧基苯基）衍生物（2c，M-I）在佐剂关节炎大鼠模型中具有抗炎作用，尽管其在该模型中的效力略低于母体化合物。

  DOI：

  10.1248/cpb.46.1130
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 乙酰乙酸甲酯 在 哌啶 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid methyl ester
  参考文献：
  名称：

  通过金属化手性烷基乙酰乙酸的对映选择性汉茨二氢吡啶的合成1

  摘要：

  描述了4-芳基-1,4-二氢吡啶（ee = 84-98％）（重要的生物活性化合物（例如，作为钙通道阻滞剂））的汉茨合成的有效的整体对映选择性变体。新方法的关键步骤是将金属化手性烷基乙酰乙酸（）-不对称迈克尔加成到Knoevenagel受体上。还报道了确定手性二氢吡啶的对映体过量的准确方法。

  DOI：

  10.1016/s0040-4039(00)82366-7

文献信息

• FeCl 3 ·6H 2 O-catalyzed selective conjugate reduction of alkylidene- β -keto esters and alkylidene-1,3-diketones
  作者：Lakshmi V.R. Babu Syamala、Trimbak B. Mete、Ramakrishna G. Bhat

  DOI：10.1016/j.tetlet.2018.07.041

  日期：2018.8

  system is successfully developed for the selective conjugate reduction of carbon-carbon double bond of Michael acceptor-alkylidene-β-keto esters and alkylidene-1,3-diketones under mild reaction conditions to afford the corresponding saturated β-keto esters and 1,3-diketones. The process involves the iron-catalyzed hydrosilylation, followed by in situ hydrolysis of silyl enol ether. The optimal reaction

  成功开发了FeCl 3 ·6H 2 O /三乙基硅烷复合催化剂体系，用于在温和的反应条件下选择性共轭还原迈克尔受体-亚烷基-β-酮酯和亚烷基-1,3-二酮的碳-碳双键，从而得到相应的饱和β-酮酯和1,3-二酮。该方法涉及铁催化的氢化硅烷化，然后原位水解甲硅烷基烯醇醚。最佳反应条件包括20 mol％的FeCl 3 ·6H 2室温下在二氯甲烷中加入O和三乙基硅烷。各种各样的底物以1、4选择性的方式还原，从而以极好的收率得到相应的饱和化合物。
• 1,4-dihydropyridine-4-aryl-2,6-dimethyl-3,5-dicarboxylates useful as
  申请人：Ajinomoto Co., Inc.

  公开号：US05216172A1

  公开（公告）日：1993-06-01

  Agents against drug-resistant tumor cells comprising a 1,4-dihydropyridine derivative represented by the following formula (I): ##STR1## wherein R.sup.1 is an aryl group which may be substituted; R.sup.2 and R.sup.3, which may be the same or different, each is a member selected from the group consisting of an alkyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an aralkyloxycarbonyl group, an aminocarbonyl group, a hydroxycarbonyl group, a formyl group, and a cyano group, each of which may be substituted; R.sup.4 and R.sup.5 is a hydrogen atom or a member selected from the group consisting of a lower alkyl group, a hydroxymethyl group, a cyano group, an amino group, a formyl group, and a halogen atom; and R.sup.6 is a member selected from the group consisting of an alkyl group, an aralkyl group, an alkoxycarbonyl group and an aralkyloxycarbonyl group, each of which may be substituted and the alkyl moiety in each may also contain a double bond, a triple bond or a hetero atom and combinations thereof with anti-cancer agents.

  抗耐药肿瘤细胞的药剂包括下述式(I)所代表的1,4-二氢吡啶衍生物： ##STR1## 其中，R1是可以被取代的芳基基团；R2和R3，可以相同或不同，每个是从下列组中选择的一种成员：烷基基团、烷氧羰基基团、芳氧羰基基团、芳基烷氧羰基基团、氨基羰基基团、羟基羰基基团、甲酰基基团和氰基基团，每个基团可以被取代；R4和R5是氢原子或从下列组中选择的一种成员：低烷基基团、羟甲基基团、氰基基团、氨基基团、甲酰基基团和卤素原子；R6是从下列组中选择的一种成员：烷基基团、芳基烷基团、烷氧羰基基团和芳基烷氧羰基基团，每个基团可以被取代，每个烷基基团中也可以包含双键、三键或杂原子，以及与抗癌药物的组合。
• The Hantzsch Synthesis with 6-Aminouracils: One Step Synthesis of Pyrido[2,3-d]pyrimidines
  作者：Masahiro Kajino、Kanji Meguro

  DOI：10.3987/com-90-5554

  日期：——

  A one-step synthesis of new pyrido [2,3-d]pyrimidine derivatives (III) was achieved through the Hantzsch synthesis using 6-aminouracils (I) as enamine nucleophiles.
• Thieno[2,3-b]pyridines—A new class of multidrug resistance (MDR) modulators
  作者：Aivars Krauze、Signe Grinberga、Laura Krasnova、Ilze Adlere、Elina Sokolova、Ilona Domracheva、Irina Shestakova、Zigmars Andzans、Gunars Duburs

  DOI：10.1016/j.bmc.2014.09.023

  日期：2014.11

  To identify new potent multidrug resistance modulators, we have synthesized a series of novel thieno[ 2,3-b]pyridines and furo[2,3-b] pyridines, and examined their stucture-activity relationships. All synthesized compounds were tested to determine BCRP1, P-gp, and MRP1 inhibitor activity, and most potent MDR modulators were also screened for their toxicity, cytotoxicity and Ca2+ channel antagonist activity. Among these compounds, thieno[2,3-b] pyridine (6r) was found to exhibit a potent P-gp inhibitory action with EC50 = 0.3 +/- 0.2 mu M, MRP1 inhibitory action with EC50 = 1.1 +/- 0.1 mu M and BCRP1 inhibitory action with EC50 = 0.2 +/- 0.05 mu M and may represent suitable candidate for further pharmacological studies. (C) 2014 Elsevier Ltd. All rights reserved.