(Z)-5-(4-(thiophen-2-yl)benzylidene)imidazolidine-2,4-dione | 1134426-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (Z)-5-(4-(thiophen-2-yl)benzylidene)imidazolidine-2,4-dione
• 英文别名: (Z)-5-[4-(2-thienyl)benzylidene]imidazolidine-2,4-dione；(5Z)-5-[(4-thiophen-2-ylphenyl)methylidene]imidazolidine-2,4-dione
• CAS: 1134426-49-5
• 化学式: C₁₄H₁₀N₂O₂S
• 分子量: 270.312
• InChiKey: FFMNALVOYZWDTH-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  海因 、 4-(2-噻吩基)苯甲醛 在 碳酸氢钠 、 C.I.酸性橙108 作用下， 以 乙醇 、 水 为溶剂， 生成 (Z)-5-(4-(thiophen-2-yl)benzylidene)imidazolidine-2,4-dione
  参考文献：
  名称：

  Discovery, design, and synthesis of anti-metastatic lead phenylmethylene hydantoins inspired by marine natural products

  摘要：

  The Red Sea sponge Hemimycale arabica afforded the known (Z)-5-(4-hydroxybenzylidene)-hydantoin (1), (R)-5-(4-hydroxybenzyl) hydantoin (2), and (Z)-5-((6-bromo-1H-indol-3-yl)methylene)-hydantoin (3). The natural phenylmethylene hydantoin (PMH) 1 and the synthetic (Z)-5-(4-(ethylthio)benzylidene)hydantoin (4) showed potent in vitro anti-growth and anti-invasive properties against PC-3M prostate cancer cells in MTT and spheroid disaggregation assays. PMHs 1 and 4 also showed significant anti-invasive activities in orthotopic xenograft and transgenic mice models. To study the effect of electronic and lipophilic parameters on the activity, a wide array of several substituted aldehydes possessing electron-withdrawing (+sigma), lipophilic (+pi), electron-donating (-sigma), and less lipophilic substituents (-pi) were used to synthesize several PMHs. Few des-phenylmethylenehydantoins and 2-thiohydanoins were also synthesized and the anti-invasive activities of all compounds were evaluated. Comparative molecular field analysis (CoMFA) was then used to study the 3D QSAR. Predictive 3D QSAR model with conventional r(2) and cross validated coefficient (q(2)) values up to 0.910 and 0.651 were established. In conclusion, PMH is a novel antimetastatic lead class with potential to control metastatic prostate cancer. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.053

文献信息

• US8188130B1
  申请人：——

  公开号：US8188130B1

  公开（公告）日：2012-05-29
• Discovery, design, and synthesis of anti-metastatic lead phenylmethylene hydantoins inspired by marine natural products
  作者：Mudit Mudit、Mohammad Khanfar、Anbalagan Muralidharan、Shibu Thomas、Girish V. Shah、Rob W.M. van Soest、Khalid A. El Sayed

  DOI：10.1016/j.bmc.2008.12.053

  日期：2009.2

  The Red Sea sponge Hemimycale arabica afforded the known (Z)-5-(4-hydroxybenzylidene)-hydantoin (1), (R)-5-(4-hydroxybenzyl) hydantoin (2), and (Z)-5-((6-bromo-1H-indol-3-yl)methylene)-hydantoin (3). The natural phenylmethylene hydantoin (PMH) 1 and the synthetic (Z)-5-(4-(ethylthio)benzylidene)hydantoin (4) showed potent in vitro anti-growth and anti-invasive properties against PC-3M prostate cancer cells in MTT and spheroid disaggregation assays. PMHs 1 and 4 also showed significant anti-invasive activities in orthotopic xenograft and transgenic mice models. To study the effect of electronic and lipophilic parameters on the activity, a wide array of several substituted aldehydes possessing electron-withdrawing (+sigma), lipophilic (+pi), electron-donating (-sigma), and less lipophilic substituents (-pi) were used to synthesize several PMHs. Few des-phenylmethylenehydantoins and 2-thiohydanoins were also synthesized and the anti-invasive activities of all compounds were evaluated. Comparative molecular field analysis (CoMFA) was then used to study the 3D QSAR. Predictive 3D QSAR model with conventional r(2) and cross validated coefficient (q(2)) values up to 0.910 and 0.651 were established. In conclusion, PMH is a novel antimetastatic lead class with potential to control metastatic prostate cancer. (C) 2008 Elsevier Ltd. All rights reserved.