(Z)-4-(3,4-dimethoxybenzylidene)-2-methyloxazol-5 (4H)-one | 676626-91-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-4-(3,4-dimethoxybenzylidene)-2-methyloxazol-5 (4H)-one
• 英文别名: (4Z)-4-(3,4-dimethylbenzylidene)-2-methyl-1,3-oxazol-5(4H)-one；(4Z)-4-[(3,4-dimethylphenyl)methylidene]-2-methyl-1,3-oxazol-5-one
• CAS: 676626-91-8
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: ZAJZIYJBZNYOAS-GHXNOFRVSA-N

物化性质

• 沸点：
  330.6±52.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-4-(3,4-dimethoxybenzylidene)-2-methyloxazol-5 (4H)-one 在 盐酸 作用下， 反应 8.0h， 以89%的产率得到(Z)-3-(3,4-dimethoxyphenyl)-2-hydroxyacrylic acid
  参考文献：
  名称：

  Synthesis of derivatives of methyl rosmarinate and their inhibitory activities against matrix metalloproteinase-1 (MMP-1)

  摘要：

  A series of MMP-1 inhibitors have been identified based upon a methyl rosmarinate scaffold using structure-based drug design methods. The best compound in the series showed an IC50 value of 0.4 mu M. A docking study was conducted for compound (S)-10n in order to investigate its binding interactions with MMP-1. The structure activity relationships (SAR) were also briefly discussed. Useful SAR was established which provides important guidelines for the design of future generations of potent inhibitors against MMP-1. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.047
• 作为产物：
  描述：

  3,4-二甲基苯甲醛 、 N-乙酰甘氨酸 在 sodium acetate 、 乙酸酐 作用下， 反应 4.0h， 生成 (Z)-4-(3,4-dimethoxybenzylidene)-2-methyloxazol-5 (4H)-one
  参考文献：
  名称：

  Potent, Selective Tetrahydro-β-carboline Antagonists of the Serotonin 2B (5HT_2B) Contractile Receptor in the Rat Stomach Fundus

  摘要：

  A series of potent, selective 5HT(2B) receptor antagonists has been identified based upon yohimbine, with SAR studies resulting in a 1000-fold increase in 5HT(2B) receptor affinity relative to the starting structure (-log K(B)s > 10.0 have been obtained). These high-affinity tetrahydro-beta-carboline antagonists are able to discriminate among the 5HT(2) family of serotonin receptors, with members of the series showing selectivities of more than 100-fold versus both the 5HT(2A) and 5HT(2C) receptors based upon radioligand binding and functional assays. As the first compounds reported with such selectivity and enhanced receptor affinity, these tetrahydro-beta-carboline antagonists are useful tools for elucidating the role of serotonin acting at the 5HT(2B) receptor in normal and disease physiology.

  DOI：

  10.1021/jm960062t

文献信息

• Method of treating resistant tumors
  申请人：Wyeth Holdings Corporation

  公开号：US20040121965A1

  公开（公告）日：2004-06-24

  The invention provides a method of treating or inhibiting the growth of or eradicating a tumor in a mammal in need thereof wherein said tumor is resistant to at least one chemotherapeutic agent which method comprises providing to said mammal an effective amount of a compound of Formula II or a pharmaceutically acceptable salt thereof.

  本发明提供了一种治疗或抑制哺乳动物体内对至少一种化疗药物产生耐药性的肿瘤生长或根除肿瘤的方法，该方法包括向该哺乳动物提供有效量的公式II化合物或其药学上可接受的盐。
• Potent, Selective Tetrahydro-β-carboline Antagonists of the Serotonin 2B (5HT_2B) Contractile Receptor in the Rat Stomach Fundus
  作者：James E. Audia、Deborah A. Evrard、Gwyn R. Murdoch、James J. Droste、Jeffrey S. Nissen、Kathy W. Schenck、Pawel Fludzinski、Virginia L. Lucaites、David L. Nelson、Marlene L. Cohen

  DOI：10.1021/jm960062t

  日期：1996.1.1

  A series of potent, selective 5HT(2B) receptor antagonists has been identified based upon yohimbine, with SAR studies resulting in a 1000-fold increase in 5HT(2B) receptor affinity relative to the starting structure (-log K(B)s > 10.0 have been obtained). These high-affinity tetrahydro-beta-carboline antagonists are able to discriminate among the 5HT(2) family of serotonin receptors, with members of the series showing selectivities of more than 100-fold versus both the 5HT(2A) and 5HT(2C) receptors based upon radioligand binding and functional assays. As the first compounds reported with such selectivity and enhanced receptor affinity, these tetrahydro-beta-carboline antagonists are useful tools for elucidating the role of serotonin acting at the 5HT(2B) receptor in normal and disease physiology.
• “Pictet-Spengler-like” Synthesis of Tetrahydro-β-carbolines under Hydrolytic Conditions. Direct Use of Azalactones as Phenylacetaldehyde Equivalents
  作者：James E. Audia、James J. Droste、Jeffrey S. Nissen、Gwyn L. Murdoch、Deborah A. Evrard

  DOI：10.1021/jo9600868

  日期：1996.1.1
• [EN] METHOD OF TREATING RESISTANT TUMORS<br/>[FR] METHODE DE TRAITEMENT DE TUMEURS RESISTANTES
  申请人：WYETH CORP

  公开号：WO2004026293A2

  公开（公告）日：2004-04-01

  The invention provides a method of treating or inhibiting the growth of or eradicating a tumor in a mammal in need thereof wherein said tumor is resistant to at least one chemotherapeutic agents which method comprises providing to said mammal an effective amount of a compound of Formula II or a pharmaceutically acceptable salt thereof.
• Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment
  作者：Ayako Yamashita、Emily B. Norton、Joshua A. Kaplan、Chuan Niu、Frank Loganzo、Richard Hernandez、Carl F. Beyer、Tami Annable、Sylvia Musto、Carolyn Discafani、Arie Zask、Semiramis Ayral-Kaloustian

  DOI：10.1016/j.bmcl.2004.08.024

  日期：2004.11

  Analogs of hemiasterlin (1) and HTI-286 (2), which contain various aromatic rings in the A segment, were synthesized as potential inhibitors of tubulin polymerization. The structure-activity relationships related to stereo- and regio-chemical effects of substituents on the aromatic ring in the A segment were studied. Analogs, which carry a meta-substituted phenyl ring in the A segment show comparable activity for inhibition of tubulin polymerization to 2, as well as in the cell proliferation assay using KB cells containing P-glycoprotein, compared to those of 1 and 2. (C) 2004 Elsevier Ltd. All rights reserved.