ethyl 3-(2,4-dibenzyloxy)phenyl propen-2-oate | 122841-71-8

• 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: ethyl 3-(2,4-dibenzyloxy)phenyl propen-2-oate
• 英文别名: Ethyl 3-(2,4-dibenzyloxyphenyl)-2-propenoate；ethyl 3-[2,4-bis(phenylmethoxy)phenyl]prop-2-enoate
• CAS: 122841-71-8
• 化学式: C₂₅H₂₄O₄
• 分子量: 388.463
• InChiKey: JAHDPQAINNEHRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2,4-dibenzyloxy)phenyl propen-2-oate 在 silver trifluoromethanesulfonate 、 sodium hydride 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 三氟乙酸 为溶剂， 反应 19.25h， 生成 (6S*,12R*)-1,3,9-tris(benzyloxy)-4-decanoyl-12H-6,12-methanodibenzo[d,g][1,3]dioxocine
  参考文献：
  名称：

  （±）-myristicyclin A的首次合成。

  摘要：

  描述了从巴布亚新几内亚植物Horsfieldia spicata分离的肉豆蔻环素A的第一个合成。该合成的特征在于酸介导的加氢芳基化反应以形成二氢香豆素部分，在酸性条件下构造2,8-二氧杂双环[3.3.1]壬烷骨架，并在稍后阶段进行区域选择性Friedel-Crafts酰化。

  DOI：

  10.1080/09168451.2018.1495553
• 作为产物：
  描述：

  2,4-二羟基苯甲醛 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.25h， 生成 ethyl 3-(2,4-dibenzyloxy)phenyl propen-2-oate
  参考文献：
  名称：

  Selective endothelin A receptor ligands. 1. Discovery and structure-activity of 2,4-disubstituted benzoic acid derivatives

  摘要：

  This paper describes the discovery of a new non-peptide endothelin A (ETA) selective ligand, 2,4-dibenzyloxybenzoic acid 3, which inhibits the binding of [I-125]ET-1 to ETA receptors with an IC50 of 9 mu M (ET-1 = endothelin-1). Optimisation of 3 resulted in compound 52 which had an IC50 of 1 mu M. One of the analogues of 3, compound 15, was examined in a functional assay and shown to antagonise ET-1-induced contraction of rat aorta. The identification of 3 was made through the application of ChemDBS-3D searching of our corporate database. The 3D query, using an aromatic ring to a carboxylic acid group separated by 10.2 +/- 1.1 Angstrom, was derived from an examination of common pharmacophoric distances found in the low energy conformations of two known ETA antagonists, the cyclic pentapeptide BQ 123 1 and myriceron caffeoyl ester 2.

  DOI：

  10.1016/s0223-5234(97)81678-9

文献信息

• Substituted phenyl compounds
  申请人：Rhone-Poulenc Rorer Limited

  公开号：US06211234B1

  公开（公告）日：2001-04-03

  Compounds of formula (I) are described wherein R1 is hydrogen, -(lower alkyl)q(CO2R6 or OH), —CN, —C(R7)═NOR8, NO2, —O(lower alkyl)R9, —C≡C—R10, —CR11═C(R12)(R13), —C(═O)CH2C(═O)CO2H, —CO(R14), alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, thiocarbamoyl, substituted carbamoyl, substituted thiocarbamoyl, sulphamoyl or an optionally substituted nitrogen-containing ring, m, n, o and p are independently zero or 1 and R2, R3, R4 and R5 are various groups; and physiologically acceptable salts, N-oxides and prodrugs thereof. The compounds have endothelin antagonist activity and are useful as pharmaceuticals.

  式(I)的化合物描述如下，其中R1为氢，-(较低烷基)q(CO2R6或OH)，—CN，—C(R7)HNOR8，NO2，—O(较低烷基)R9，—C≡C—R10，—CR11CH(R12)(R13)，—C(O)CH2C(O)CO2H，—CO(R14)，烷基硫醚，烷基亚砜基，烷基磺酰基，氨基甲酰基，硫代氨基甲酰基，取代的氨基甲酰基，取代的硫代氨基甲酰基，磺酰胺基或可选择取代的含氮环，m、n、o和p独立地为零或1，R2、R3、R4和R5为各种基团；以及其生理学上可接受的盐、N-氧化物和前药。这些化合物具有内皮素拮抗活性，并可用作药物。
• Amide compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05047430A1

  公开（公告）日：1991-09-10

  A compound is provided which has the formula ##STR1## wherein m is an integer of 1 to 3; n is an integer of 1 or 2; p is an integer of 1 or 2; q is an integer of 1 to 6; x is an integer of 2 to 6; Ph is phenylene or a pharmceutically acceptable salt thereof. Also provided is a method for glutamate receptor inhibition which comprises administering to a mammal in need thereof an effective amount of said compound or a pharmaceutically acceptable salt thereof. Compositions for glutamate receptor inhibition are provided which contain an effective amount of said compound to provide a glutamate receptor inhibition effect, together with at least one pharmaceutically acceptable carrier, dilient or excipient therefor.

  提供一种化合物，其化学式为##STR1## 其中，m为1至3的整数；n为1或2的整数；p为1或2的整数；q为1至6的整数；x为2至6的整数；Ph为苯基或其药学上可接受的盐。还提供了一种谷氨酸受体抑制剂的方法，其包括向需要的哺乳动物中投与该化合物或其药学上可接受的盐的有效量。提供了一种用于谷氨酸受体抑制的组合物，其含有该化合物的有效量，以提供谷氨酸受体抑制效果，以及至少一种药学上可接受的载体、稀释剂或赋形剂。
• Selective endothelin A receptor ligands. 1. Discovery and structure-activity of 2,4-disubstituted benzoic acid derivatives
  作者：PC Astles、TJ Brown、CM Handscombe、MF Harper、NV Harris、RA Lewis、PM Lockey、C McCarthy、IM McLay、B Porter、AG Roach、C Smith、RJA Walsh

  DOI：10.1016/s0223-5234(97)81678-9

  日期：1997.5

  This paper describes the discovery of a new non-peptide endothelin A (ETA) selective ligand, 2,4-dibenzyloxybenzoic acid 3, which inhibits the binding of [I-125]ET-1 to ETA receptors with an IC50 of 9 mu M (ET-1 = endothelin-1). Optimisation of 3 resulted in compound 52 which had an IC50 of 1 mu M. One of the analogues of 3, compound 15, was examined in a functional assay and shown to antagonise ET-1-induced contraction of rat aorta. The identification of 3 was made through the application of ChemDBS-3D searching of our corporate database. The 3D query, using an aromatic ring to a carboxylic acid group separated by 10.2 +/- 1.1 Angstrom, was derived from an examination of common pharmacophoric distances found in the low energy conformations of two known ETA antagonists, the cyclic pentapeptide BQ 123 1 and myriceron caffeoyl ester 2.
• First synthesis of (±)-myristicyclin A
  作者：Shinichiro Kubo、Naoki Mori、Hidenori Watanabe、Hirosato Takikawa

  DOI：10.1080/09168451.2018.1495553

  日期：2018.11.2

  The first synthesis of myristicyclin A, which was isolated from the Papua New Guinean plant Horsfieldia spicata, is described. The synthesis features acid-mediated hydroarylation reaction to form a dihydrocoumarin moiety, construction of the 2,8-dioxabicyclo[3.3.1]nonane skeleton under acidic conditions, and regioselective Friedel-Crafts acylation at a later stage.

  描述了从巴布亚新几内亚植物Horsfieldia spicata分离的肉豆蔻环素A的第一个合成。该合成的特征在于酸介导的加氢芳基化反应以形成二氢香豆素部分，在酸性条件下构造2,8-二氧杂双环[3.3.1]壬烷骨架，并在稍后阶段进行区域选择性Friedel-Crafts酰化。