1-(2-phenylethyl)imidazolidin-2-one | 21053-54-3

• 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: 1-(2-phenylethyl)imidazolidin-2-one
• 英文别名: 1-phenethyl-imidazolidin-2-one；1-Phenaethyl-imidazolidin-2-on；1-Phenethyl-2-imidazolin
• CAS: 21053-54-3
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: WFLORUBCDPGIFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-phenylethyl)imidazolidin-2-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以50%的产率得到1-(2-phenylethyl)imidazolidine-2-thione
  参考文献：
  名称：

  Inhibitory effect of novel tetrahydropyrimidine-2(1H)-thiones on melanogenesis

  摘要：

  The series of imidazoldine-2-thiones 2 and tetrahydropyrimidine-2-thiones 3 were discovered as inhibitor of alpha-MSH-induced melanin production in melanoma B16 cells. The primary bioassay showed that 1-(4-ethylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3e (> 100% inhibition at 10 mu M, IC50 = 1.2 mu M) and 1-(4-tert-butylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3f (> 100% inhibition at 10 mu M, IC50 = 0.76 mu M) exhibited potent inhibitory effect against alpha-MSH-induced melanin production. Compounds 3 inhibit the biosynthesis of tyrosinase without affecting its catalytic activity in melanogenesis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.044
• 作为产物：
  描述：

  2-(2-phenylethylamino)ethylcarbamic acid tert-butyl ester 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以62%的产率得到1-(2-phenylethyl)imidazolidin-2-one
  参考文献：
  名称：

  Inhibitory effect of novel tetrahydropyrimidine-2(1H)-thiones on melanogenesis

  摘要：

  The series of imidazoldine-2-thiones 2 and tetrahydropyrimidine-2-thiones 3 were discovered as inhibitor of alpha-MSH-induced melanin production in melanoma B16 cells. The primary bioassay showed that 1-(4-ethylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3e (> 100% inhibition at 10 mu M, IC50 = 1.2 mu M) and 1-(4-tert-butylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3f (> 100% inhibition at 10 mu M, IC50 = 0.76 mu M) exhibited potent inhibitory effect against alpha-MSH-induced melanin production. Compounds 3 inhibit the biosynthesis of tyrosinase without affecting its catalytic activity in melanogenesis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.044

文献信息

• Synthesis in the diazasteroid group. XIV. Synthesis of the 13,15-diazasteroid system.
  作者：KATSUHIDE MATOBA、TOSHIO IMAI、YOSHIE NISHINO、HIROKI TAKAHATA、YOSHIRO HIRAI、TAKAO YAMAZAKI

  DOI：10.1248/cpb.28.1810

  日期：——

  A 13, 15-diazasteroid system was synthesized from 2-(6-methoxynaphthyl) ethyl tosylate (steroidal segment of the A, B rings) and ethylene urea (steroidal segment of the D ring) in 24.3% overall yield. The tosylate formed a 1 : 1 adduct with ethylene urea in 44% yield, using 2 molar equivalents of ethylene urea in the presence of sodium hydride in benzene. The adduct was cyclized to 13, 15-diazasteroid hydrochloride in 69.7% yield by prolonged heating in the presence of phosphorus pentoxide in phosphorus oxychloride. The hydrochloride was neutralized to provide the 13, 15-diazasteroid in 79.1% yield by treatment with potassium hydroxide solution. The biological activity of the hydrochloride of the 13, 15-diazasteroid is now being examined.

  从2-（6-甲氧基萘基）乙基甲苯磺酸酯（A、B环的甾体部分）和乙烯脲（D环的甾体部分）合成了一个13,15-二氮杂甾体系统，总产率为24.3%。在苯中加入氢化钠的情况下使用两当量的乙烯脲，甲苯磺酸酯与乙烯脲以1:1的比例形成加成物，产率为44%。在磷酰氯中加入五氧化二磷的条件下，通过延长加热，加成物环化为13,15-二氮杂甾体盐酸盐，产率为69.7%。通过用氢氧化钾处理，盐酸盐中性的13,15-二氮杂甾体产率为79.1%。现在正在研究13,15-二氮杂甾体盐酸盐的生物活性。
• Cyclourea Compounds as Calcium Channel Blockers
  申请人：ZHOU Xiaoming

  公开号：US20120322830A1

  公开（公告）日：2012-12-20

  The invention relates to cyclourea compounds of Formula I: or a pharmaceutically acceptable salt or solvate thereof, wherein R 1 -R 3 and Z are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula I to treat, prevent or ameliorate a disorder responsive to the blockade of calcium channels, and particularly N-type calcium channels. Compounds of the present invention are especially useful for treating pain.

  本发明涉及公式I的环脲化合物：或其药学上可接受的盐或溶剂，其中R1-R3和Z如规范中所述。本发明还涉及使用公式I的化合物来治疗、预防或改善对钙通道阻滞有反应的疾病，特别是N型钙通道。本发明的化合物特别适用于治疗疼痛。
• Calcium independent camp phosphodiestrerase inhibitor antidepressant
  申请人：PFIZER INC.

  公开号：EP0247725B1

  公开（公告）日：1994-03-02
• Najer et al., Bulletin de la Societe Chimique de France, 1957, p. 1069,1071
  作者：Najer et al.

  DOI：——

  日期：——
• CYCLOUREA COMPOUNDS AS CALCIUM CHANNEL BLOCKERS
  申请人：EURO-CELTIQUE S.A.

  公开号：EP1987009A1

  公开（公告）日：2008-11-05