1H-苯并咪唑-2-基甲基乙酸酯 | 33809-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1H-苯并咪唑-2-基甲基乙酸酯
• 英文名称: 2-acetoxymethylbenzimidazole
• 英文别名: (1H-benzo[d]imidazol-2-yl)methyl acetate；AMBi；2-Acetoxymethyl-benzimidazol；2-acetoxymethyl-1H-benzoimidazole；acetic acid-(1H-benzimidazol-2-ylmethyl ester)；Essigsaeure-(1H-benzimidazol-2-ylmethylester)；1H-benzimidazol-2-ylmethyl acetate
• CAS: 33809-91-5
• 化学式: C₁₀H₁₀N₂O₂
• mdl: MFCD24388430
• 分子量: 190.202
• InChiKey: KTLXBVGBWNYAQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1H-苯并咪唑-2-基甲基乙酸酯 在 氯化亚砜 、 lithium hydroxide monohydrate 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 11.75h， 生成 1-(4-chlorobenzyl)-2-(chloromethyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Evaluation of Cytotoxic Activity of New Benzimidazole-Piperazine Hybrids Against Human MCF-7 and A549 Cancer Cells

  摘要：

  一系列苯并咪唑-哌嗪杂化物（14-37）被设计、合成并评估其对人肺（A549）和乳腺（MCF-7）癌细胞系的细胞毒性活性。初步评估显示，大多数这些杂化分子（即16-25）对人肺癌（A549）表现出显著且优先的抗增殖效果，IC50值为2.8-7.8 μM。在合成的分子中，化合物17对肺（A549）和乳腺（MCF-7）癌细胞的细胞毒性效果最为均衡，IC50值分别为5.4和4.2 μM。为了探讨与观察到的活性相关的机制方面，进一步对化合物16、17和22进行了生物学研究。此外，这些化合物诱导了PARP-1裂解和凋亡酶7激活，造成处理细胞的形态变化，如气泡形成，并显著增加了核碎裂。综合来看，我们的研究结果表明，新合成的苯并咪唑-哌嗪杂化物的细胞毒性活性是通过诱导凋亡细胞死亡介导的。这些苯并咪唑衍生物具有进一步开发作为抗癌药物的潜力。

  DOI：

  10.1007/s11094-020-02119-9
• 作为产物：
  描述：

  2-羟甲基苯并咪唑 在 水 作用下， 反应 2.0h， 生成 1H-苯并咪唑-2-基甲基乙酸酯
  参考文献：
  名称：

  Alternate Method for the Synthesis of N‐Alkyl/aralkyl‐2‐(α‐hydroxy Alkyl/aralkyl)benzimidazoles via Regiospecific Acetylation

  摘要：

  Acetylation of 1H-2-(alpha-hydroxyalkyl/aryl) benzimidazoles 2 with Ac2O results in the regiospecific formation of O-acetoxy derivative 3, which on alkylation with alkylating agents in nonaqueous media under phase-transfer catalytic conditions affords N-alkyl derivatives 4. The latter, on hydrolysis in an aqueous basic medium, results in the title compounds 5 in good yields in high purity. Alternatively, 5 can also be obtained by reduction of 1-substituted-2-acetyl/benzoylbenzimidazoles 8 using NaBH4.

  DOI：

  10.1080/00397910701265556

文献信息

• 6-beta(substituted)-(S)-hydroxymethylpenicillanic acids and derivatives
  申请人：Pfizer Inc.

  公开号：US04782050A1

  公开（公告）日：1988-11-01

  Antibacterial penicillins of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein R.sup.1 is a heterocyclic group and R is hydrogen, the residue of certian carboxy protecting groups or the residue of an ester group readily hydrolyzable in vivo having activity against resistant organisms.

  公式为##STR1##的抗菌青霉素，或其药学上可接受的盐，其中R.sup.1是杂环基团，R是氢，某些羧保护基团的残基或易在体内水解的酯基团的残基，具有对抗耐药菌的活性。
• Synthesis, Cytotoxicity, and DNA Interactions of New Cisplatin Analogues Containing Substituted Benzimidazole Ligands
  作者：Fatma Gümüş、Gökçen Eren、Leyla Açık、Ayten Çelebi、Fatma Öztürk、Şükran Yılmaz、Rahşan Ilıkçı Saǧkan、Sibel Gür、Aykut Özkul、Ayhan Elmalı、Yalçın Elerman

  DOI：10.1021/jm8000983

  日期：2009.3.12

  Six new platinum(II) complexes with 1-H or methyl-2-chloromethyl or acetoxymethyl or 2'-hydroxyethylbenzimidazole carrier ligands were synthesized and evaluated for their reactivity against model nucleophile I-, cellular uptake, and in vitro anti proliferative activities against the human MCF-7 breast and HeLa cervix cancer cell lines. The effect of the compounds on pBR322 plasmid DNA was studied by gel electrophoretic mobility measurements. Flow cytometric analysis was also carried out to study the effect of representative compounds 1 and 2, bearing 2-chloromethyl or -acetoxymethylbenzimidazole carrier ligands, on the cell cycle distribution of MCF-7 and HeLa cells, respectively. In general, it was found that Pt(II) complexes were less cytotoxic than cisplatin and were comparable to carboplatin. The results of the plasmid DNA interaction and the restriction studies suggest that changing the chemical structure of the benzimidazole ligands may modulate DNA binding mode and the sequence selectivity. Compounds I and 2 had no significant effect on the cell cycle profile of the cells used. However, Compound 2 induced a significant increase in the SubG1 cell population at a concentration of 20 mu M.
• Vinyl protecting group for benzimidazole nitrogen: Synthesis of benzimidazole-penam alcohol
  作者：Yuhpyng L. Chen、Kirk G. Hedberg、Karen J. Guarino

  DOI：10.1016/s0040-4039(01)80360-9

  日期：1989.1
• Sacharowa et al., Zhurnal Obshchei Khimii, 1953, vol. 23, p. 1225,1229; engl. Ausg. S. 1289, 1292
  作者：Sacharowa et al.

  DOI：——

  日期：——
• A novel Trans-Pt(II) complex bearing 2-acetoxymethylbenzimidazole as a non-leaving ligand (trans-[Pt(AMBi)2Cl2]): Synthesis, antiproliferative activity, DNA interaction and molecular docking studies compared with its cis isomer (cis-[Pt(AMBi)2Cl2])
  作者：Gokcen Eren、Esra Emerce、Leyla Acik、Betul Aydin、Fatma Gumus

  DOI：10.1016/j.molstruc.2019.02.066

  日期：2019.5

  Trans-[Pt(AMBi)(2)Cl-2 (1) in which AMBi is 2-acetoxymethylbenzimidazole, was synthesized and characterized by spectroscopic methods. Novel complex 1 was evaluated for its potential antiproliferative effect against three human cancer cell lines, including HeLa (human cervix cancer), MCF-7 (human breast cancer) and A549 (human non-small-cell lung cancer) in comparison with those of cis-[Pt(AMBi)(2)Cl-2 (2) and cisplatin by means of the MTT assay. Interaction of complexes 1, 2 and cisplatin with pBR322 plasmid DNA and their restriction endonuclease reactions by BamHI and HindIII enzymes were studied by agarose gel electrophoresis. Cytotoxicity tests showed that complex 1 exhibited similar in vitro cytotoxicity profile as compared with cisplatin whereas better than corresponding cis isomer against MCF-7 and A549 human cancer cell lines. The electrophoretic mobility shift assay showed that although no comigration of the Form I and II bands of plasmid DNA was observed for complex 1 at the concentrations tested, the binding of complex 1 was able to prevent partially BamHI digestion for concentrations ranging from 40 to 160 mu M while having no inhibitory effect on HindIII activity in the digestion studies with restriction enzymes. Molecular docking studies on DNA were carried out to explore the binding mode and the best orientation of the complexes 1 and 2 to DNA. (C) 2019 Elsevier B.V. All rights reserved.