methyl (E)-3-[5-(5-N-isopropylamidino-2-benzimidazolyl)-2-thienyl]-2-phenylacrylate hydrochloride | 1106772-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: methyl (E)-3-[5-(5-N-isopropylamidino-2-benzimidazolyl)-2-thienyl]-2-phenylacrylate hydrochloride
• 英文别名: methyl (E)-2-phenyl-3-[5-[6-(N'-propan-2-ylcarbamimidoyl)-1H-benzimidazol-2-yl]thiophen-2-yl]prop-2-enoate;hydrochloride
• CAS: 1106772-71-7
• 化学式: C₂₅H₂₄N₄O₂S*ClH
• 分子量: 481.018
• InChiKey: CRGFIRVLROCJDY-UGAWPWHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[5-(5-N-isopropylamidino-2-benzimidazolyl)-2-thienyl]-2-phenylacrylate hydrochloride 在 碘 、 氧气 作用下， 以 乙醇 为溶剂， 反应 40.0h， 以59%的产率得到methyl 2-[(5-N-isopropylamidino)benzimidazolyl]naphtho[2,1-b]thiophene-5-carboxylate hydrochloride
  参考文献：
  名称：

  Synthesis, antitumor evaluation and DNA binding studies of novel amidino-benzimidazolyl substituted derivatives of furyl-phenyl- and thienyl-phenyl-acrylates, naphthofurans and naphthothiophenes

  摘要：

  A series of amidino-substituted benzimidazoles, related to furyl-phenyl- and thienyl-phenyl-acrylates, naphthofurans and naphthothiophenes were prepared, their antitumor evaluation and interactions with ct-DNA have been investigated. All tested compounds show differential and strong antitumor activity without apparent difference depending on their structures. Interestingly, the MCF-7 tumor cell line is highly sensitive to all compounds. Compounds 6-9 showed noticeable selectivity in regard to normal fibroblasts (WI 38). Compounds 4-9 interact with ct-DNA by more binding modes, whose mutual distribution is dependent on the compound/DNA ratio. The "acyclic" 4-6 and "cyclic" compound 7 interact mostly within the minor groove of DNA, although partial intercalation of 6 and 7 cannot be excluded. The "cyclic" compounds 8 and 9 intercalate between DNA base pairs at high excess of DNA over compounds. (C) 2008 Elsevier Masson SAS. All fights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.010
• 作为产物：
  描述：

  methyl E-3-(5-formyl-2-thienyl)-2-phenylacrylate 、 3,4-diamino-N-isopropylbenzamidine hydrochloride 在 对苯醌 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以51%的产率得到methyl (E)-3-[5-(5-N-isopropylamidino-2-benzimidazolyl)-2-thienyl]-2-phenylacrylate hydrochloride
  参考文献：
  名称：

  Synthesis, antitumor evaluation and DNA binding studies of novel amidino-benzimidazolyl substituted derivatives of furyl-phenyl- and thienyl-phenyl-acrylates, naphthofurans and naphthothiophenes

  摘要：

  A series of amidino-substituted benzimidazoles, related to furyl-phenyl- and thienyl-phenyl-acrylates, naphthofurans and naphthothiophenes were prepared, their antitumor evaluation and interactions with ct-DNA have been investigated. All tested compounds show differential and strong antitumor activity without apparent difference depending on their structures. Interestingly, the MCF-7 tumor cell line is highly sensitive to all compounds. Compounds 6-9 showed noticeable selectivity in regard to normal fibroblasts (WI 38). Compounds 4-9 interact with ct-DNA by more binding modes, whose mutual distribution is dependent on the compound/DNA ratio. The "acyclic" 4-6 and "cyclic" compound 7 interact mostly within the minor groove of DNA, although partial intercalation of 6 and 7 cannot be excluded. The "cyclic" compounds 8 and 9 intercalate between DNA base pairs at high excess of DNA over compounds. (C) 2008 Elsevier Masson SAS. All fights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.010

文献信息

• Synthesis, antitumor evaluation and DNA binding studies of novel amidino-benzimidazolyl substituted derivatives of furyl-phenyl- and thienyl-phenyl-acrylates, naphthofurans and naphthothiophenes
  作者：Marijana Hranjec、Kristina Starčević、Ivo Piantanida、Marijeta Kralj、Marko Marjanović、Merima Hasani、Gunnar Westman、Grace Karminski-Zamola

  DOI：10.1016/j.ejmech.2008.02.010

  日期：2008.12

  A series of amidino-substituted benzimidazoles, related to furyl-phenyl- and thienyl-phenyl-acrylates, naphthofurans and naphthothiophenes were prepared, their antitumor evaluation and interactions with ct-DNA have been investigated. All tested compounds show differential and strong antitumor activity without apparent difference depending on their structures. Interestingly, the MCF-7 tumor cell line is highly sensitive to all compounds. Compounds 6-9 showed noticeable selectivity in regard to normal fibroblasts (WI 38). Compounds 4-9 interact with ct-DNA by more binding modes, whose mutual distribution is dependent on the compound/DNA ratio. The "acyclic" 4-6 and "cyclic" compound 7 interact mostly within the minor groove of DNA, although partial intercalation of 6 and 7 cannot be excluded. The "cyclic" compounds 8 and 9 intercalate between DNA base pairs at high excess of DNA over compounds. (C) 2008 Elsevier Masson SAS. All fights reserved.