2-butyl-4-chloro-1-(3-chloropropyl)-1H-imidazole-5-carbaldehyde | 1165931-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-butyl-4-chloro-1-(3-chloropropyl)-1H-imidazole-5-carbaldehyde
• 英文别名: 2-butyl-4-chloro-1-(3-chloropropyl)-1H-imidazole-5-carboxaldehyde；2-Butyl-5-chloro-3-(3-chloropropyl)imidazole-4-carbaldehyde
• CAS: 1165931-51-0
• 化学式: C₁₁H₁₆Cl₂N₂O
• 分子量: 263.167
• InChiKey: UNSZLZFEBZCQNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-butyl-4-chloro-1-(3-chloropropyl)-1H-imidazole-5-carbaldehyde 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 (E)-2-((2-butyl-4-chloro-1-(3-(4-(4-fluorobenzyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide
  参考文献：
  名称：

  2-Butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids as potent inhibitors of Mycobacterium tuberculosis

  摘要：

  Here a series of 2-butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids were designed by combining three different pharmacophoric fragments in single molecular architecture. 2-Butyl-4-chloro-1-(3-(4-substituted)piperazin-1-yl)propyl)-1H-imidazole-5-carbaldehydes (4a-p) prepared by reacting carboxaldehyde 2 with N-alkyl piperazines 3a-p which were condensed with thiosemicarbazine to give desired compounds 5a-p in very good yields. Among all sixteen compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB), two compounds (E)-2-((2-butyl-4-chloro-1-(3-(4-(o-tolyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide 5e and (E)-2-((2-butyl-4-chloro-1-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide 5f were found to be the most potent antitubercular agents (MIC: 3.13 mu g/mL) with low toxicity profile. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.084
• 作为产物：
  描述：

  咪唑醛 、 1-溴-3-氯丙烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以70%的产率得到2-butyl-4-chloro-1-(3-chloropropyl)-1H-imidazole-5-carbaldehyde
  参考文献：
  名称：

  新型4-苯胺基喹唑啉衍生物的合成及体外抗肿瘤活性

  摘要：

  设计了一系列6，7-二烷氧基-4-苯胺基喹唑啉，通过在喹唑啉的6-位取代不同的杂环和在4-位取代多种苯胺来合成。通过使用非过度表达的肿瘤细胞作为阴性对照（乳腺癌细胞系MCF-7），筛选了这些新型喹唑啉化合物对过表达表皮生长因子受体的皮肤表皮样癌细胞系（A431）的细胞毒性作用。2-丁基-4-氯-1- {3- [7-甲氧基-4-（3-（三氟甲基）苯基氨基）喹唑啉-6-酰氧基]-丙基} -1 H-咪唑-5-甲醛（30）和2-丁基-4-氯-1- {3- [4-（3-碘苯基氨基）-7-甲氧基喹唑啉-6-酰氧基]丙基} -1 H-咪唑-5-甲醛（33）被发现对A431细胞系（IC 50 3.5和3μM）更有效，其活性与吉非替尼相当。使用人EGFR酪氨酸激酶结构域（PDB id-2gs2）进行的计算机对接实验表明，与吉非替尼的33个对接在同一位置，涉及Val702，Ala719，Ser696和Lys721。

  DOI：

  10.1016/j.ejmech.2008.07.023

文献信息

• Synthesis and in vitro antitumor activities of novel 4-anilinoquinazoline derivatives
  作者：Venkateshappa Chandregowda、A.K. Kush、G. Chandrasekara Reddy

  DOI：10.1016/j.ejmech.2008.07.023

  日期：2009.7

  2-butyl-4-chloro-1-3-[4-(3-iodophenyl amino)-7-methoxyquinazolin-6-yloxy]propyl}-1H-imidazole-5-carboxaldehyde (33) were found to be more potent against A431 cell line (IC50 3.5 and 3 μM) and their activities are comparable to gefitinib. Insilico docking experiments with human EGFR Tyrosine kinase domain (PDB id-2gs2) indicated that 33 docks at the same position as that of gefitinib involving Val702,

  设计了一系列6，7-二烷氧基-4-苯胺基喹唑啉，通过在喹唑啉的6-位取代不同的杂环和在4-位取代多种苯胺来合成。通过使用非过度表达的肿瘤细胞作为阴性对照（乳腺癌细胞系MCF-7），筛选了这些新型喹唑啉化合物对过表达表皮生长因子受体的皮肤表皮样癌细胞系（A431）的细胞毒性作用。2-丁基-4-氯-1- 3- [7-甲氧基-4-（3-（三氟甲基）苯基氨基）喹唑啉-6-酰氧基]-丙基} -1 H-咪唑-5-甲醛（30）和2-丁基-4-氯-1- 3- [4-（3-碘苯基氨基）-7-甲氧基喹唑啉-6-酰氧基]丙基} -1 H-咪唑-5-甲醛（33）被发现对A431细胞系（IC 50 3.5和3μM）更有效，其活性与吉非替尼相当。使用人EGFR酪氨酸激酶结构域（PDB id-2gs2）进行的计算机对接实验表明，与吉非替尼的33个对接在同一位置，涉及Val702，Ala719，Ser696和Lys721。
• 2-Butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids as potent inhibitors of Mycobacterium tuberculosis
  作者：Anvesh Jallapally、Dinesh Addla、Perumal Yogeeswari、Dharmarajan Sriram、Srinivas Kantevari

  DOI：10.1016/j.bmcl.2014.09.084

  日期：2014.12

  Here a series of 2-butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids were designed by combining three different pharmacophoric fragments in single molecular architecture. 2-Butyl-4-chloro-1-(3-(4-substituted)piperazin-1-yl)propyl)-1H-imidazole-5-carbaldehydes (4a-p) prepared by reacting carboxaldehyde 2 with N-alkyl piperazines 3a-p which were condensed with thiosemicarbazine to give desired compounds 5a-p in very good yields. Among all sixteen compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB), two compounds (E)-2-((2-butyl-4-chloro-1-(3-(4-(o-tolyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide 5e and (E)-2-((2-butyl-4-chloro-1-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide 5f were found to be the most potent antitubercular agents (MIC: 3.13 mu g/mL) with low toxicity profile. (C) 2014 Elsevier Ltd. All rights reserved.