2-Methoxy-4-phenyl-4,5-dihydro-1H-imidazole | 185098-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Methoxy-4-phenyl-4,5-dihydro-1H-imidazole
• 英文别名: 2-methoxy-5-phenyl-4,5-dihydro-1H-imidazole
• CAS: 185098-72-0
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: QDHWDRYAHKUGGD-UHFFFAOYSA-N

物化性质

• 沸点：
  368.0±22.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Methoxy-4-phenyl-4,5-dihydro-1H-imidazole 在 吡啶 、 盐酸 、 sodium hydroxide 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 4-phenyl-1-[N-(4-nitrobenzoyl)indoline-5-sulfonyl]-4,5-dihydro-2-imidazolone
  参考文献：
  名称：

  Synthesis and antitumor activity of 4-phenyl-1-arylsulfonyl imidazolidinones

  摘要：

  Novel 1-(1-benzoylindoline-5-sulfonyl)-4-phenyl,5-dihydroimidazolones 3 synthesized show highly potent and broad cytotoxicities. Among them compound 3b (DW2143) exhibits much more potent cytotoxicities than doxorubicin and highly effective antitumor activities against murine (3LL, Colon 26) and human xenograft (NCI-H23, SW620) tumor models. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00261-3
• 作为产物：
  描述：

  苯乙烯 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 生成 2-Methoxy-4-phenyl-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  Structure–activity relationship studies of novel arylsulfonylimidazolidinones for their anticancer activity

  摘要：

  To define the SAR, a series of novel N-arylsulfonylimidazolidinone derivatives were evaluated for their in vitro anticancer activity against five human tumor cell lines, including A549, COLO205, KATO III, K562, SK-OV-3 and murine leukemia (P288D1) cell line. Among them, N-(2-chloroacetyl)-6-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,4-dihydroquinoline-1(2H)-carboxamide (4m) and N-cyclohexyl-6-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,4-dihydroquinoline-1(2H)-carboxamide (4n) exhibited comparable in vitro anticancer activity to doxorubicin against A549, KATO III and K562 cell lines and gave superior xenographic results against NCI-H23 and SW620 cancer cell lines. Regarding the structure activity relationship, two critical points were discovered; the steric congestion at 4-position of N-arylsulfonylimidazolidinone scaffold abolishes the activity and the bulkiness or hydrophobicity of acyl groups at 3,4-dihydroquinoline of 4, especially with carbamoyl moiety, enormously enhances the activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.042

文献信息

• Synthesis and evaluation of cytotoxic activity of novel arylsulfonylimidazolidinones
  作者：Sang-Hun Jung、Jae-Shin Song、Hui-Soon Lee、Sang-Un Choi、Chong-Ock Lee

  DOI：10.1016/0960-894x(96)00463-5

  日期：1996.11

  Synthesis of novel arylsulfonylimidazolidinones 3 and 4 containing sulfonylurea pharmacophore and evaluation of their in vitro cytotoxicity against human cell lines were investigated. As a result, a series of 4-phenyl-1(N)-arylsulfonylimidazolidinones have been found to be the potential anticancer agent. Copyright (C) 1996 Elsevier Science Ltd