2-butyl-4-chloro-1-methyl-1H-imidazole-5-carbaldehyde | 1332222-81-7

• 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-methyl-1H-imidazole-5-carbaldehyde
• 英文别名: 2-butyl-5-chloro-3-methylimidazole-4-carbaldehyde
• CAS: 1332222-81-7
• 化学式: C₉H₁₃ClN₂O
• 分子量: 200.668
• InChiKey: SRWUGJIGAMYGLE-UHFFFAOYSA-N

物化性质

• 沸点：
  345.2±22.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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-methyl-1H-imidazole-5-carbaldehyde 在 sodium methylate 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 1-(5-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone
  参考文献：
  名称：

  Synthesis and evaluation of novel 2-butyl-4-chloro-1-methylimidazole embedded chalcones and pyrazoles as angiotensin converting enzyme (ACE) inhibitors

  摘要：

  A series of novel 2-butyl-4-chloro-1-methylimidazole embedded aryl and heteroaryl derived chalcones and pyrazoles were synthesized and evaluated for their angiotensin converting enzyme (ACE) inhibitory activity. The condensation of 2-butyl-4-chloro-1-methylimidazole-5-carboxaldehyde with various aryl and heteroaryl methyl ketones in the presence of 10% aqueous NaOH in methanol proceeded efficiently to give the respective chalcones in very good yields. Further, the reaction of chalcones with hydrazine hydrate in acetic acid gave substituted pyrazole analogues. Screening all 36 new compounds using ACE inhibition assay, resulted chalcones with better ACE inhibitory activity compared to the respective pyrazole analogues. Among the chalcones 4a-r, three compounds, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(5-chlorothiophen-2-yl)prop-2-enone 4i, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(1H-pyrrol-2-yl)prop-2-enone 4l, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(dibenzo[b,d] thiophen-2-yl)prop-2-enone 4q were resulted as most active ACE inhibitors with IC50 of 3.60 mu M, 2.24 mu M, and 2.68 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.085
• 作为产物：
  描述：

  溴甲烷 、 咪唑醛 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 2-butyl-4-chloro-1-methyl-1H-imidazole-5-carbaldehyde
  参考文献：
  名称：

  磺胺氨基膦酸盐作为新型大肠杆菌抗菌剂的设计与合成

  摘要：

  传统抗生素治疗耐药细菌的能力有限，需要新的治疗选择。通过一锅三组分反应合成了一类独特的磺胺氨基膦酸盐作为新的潜在抗微生物剂。值得注意的是，氟苄基衍生物 5d (MIC = 2 μg/mL) 对耐药性大肠杆菌感染有活性，对人类哺乳动物细胞没有明显的毒性。化合物5d还表现出良好的抗生物膜活性，诱导耐药性的可能性很小。机制研究阐明分子 5d 可以破坏大肠杆菌膜通过产生活性氧 (ROS) 然后嵌入脱氧核糖核酸 (DNA) 形成稳定的 5d-DNA 复合物，从而导致细菌死亡。这些结果表明磺胺氨基膦酸盐将有助于开发新的潜在抗菌剂。

  DOI：

  10.1002/cjoc.202100165

文献信息

• DEPROTECTION METHOD FOR TETRAZOLE COMPOUND
  申请人：API CORPORATION

  公开号：US20150239854A1

  公开（公告）日：2015-08-27

  The present invention relates to a method of deprotecting a tetrazole compound, useful as an intermediate for angiotensin II receptor blockers, and provides a novel production method of angiotensin II receptor blockers. Provided is a production method of a compound represented by the formula [3] or [4] or a salt thereof, including (i) reducing a compound represented by the formula [1] or [2] or a salt thereof in the presence of a metal catalyst and an alkaline earth metal salt, or (ii) reacting the compound with a particular amount of Brønsted acid: wherein each symbol is as defined in the present specification.

  本发明涉及一种去保护四唑化合物的方法，该方法作为血管紧张素II受体拮抗剂的中间体，并提供了一种新颖的血管紧张素II受体拮抗剂的生产方法。 提供了一种由式[3]或[4]表示的化合物或其盐的生产方法，包括(i)在金属催化剂和碱土金属盐的存在下还原式[1]或[2]表示的化合物或其盐，或(ii)将该化合物与特定量的Brønsted酸反应： 其中每个符号如本说明书中所定义。
• Synthesis of Novel 2-Butyl-1H-Benzo [4, 5] Imidazo [1, 2-A] Imidazo [4, 5-E] Pyridine-5-Carbonitrile Derivatives and Evaluation of Their Anticancer Activity
  作者：Achanta Venkata Hanumantha Rao、Rayam Parsharamulu、Malthum Shankaraiah、Vadali Lakshman Rao、Anireddy Jaya Shree

  DOI：10.13005/ojc/320312

  日期：2016.6.28

  A series of new 2-butyl-1H-benzo[4,5]imidazo[1,2-a]imidazo[4,5-e]pyridine-5-carbonitrile derivatives  were synthesized by the self cyclisation of (E)-2-(1H-benzo[d]imidazol-2-yl)-3-(2-butyl-4-chloro-1H-imidazol-5-yl)acrylonitrile in the presence of piperidine as catalyst, which in turn were prepared by the condensation of substituted N-alkyl 2-butyl-4-chloro-1H-imidazole-5-carbaldehydes with 2-cyanomethylbenzimidazole  in the presence of catalytic amount of L-proline in ethanol or by using piperidine as a base. Newly synthesized compounds which incorporate a variety of N-substituent moieties were characterized by spectral data and screened for anticancer activity against MCF-7 breast cancer cell line. The results showed that compounds 3b, 3a and 4b possess significant anti proliferative activity with IC50 values 26.59 and 27.98, 36.95 µM respectively.

  一系列新的2-丁基-1H-苯并[4,5]咪唑[1,2-a]咪唑[4,5-e]吡啶-5-腈衍生物是通过在哌啶催化剂存在下自环化(E)-2-(1H-苯并[d]咪唑-2-基)-3-(2-丁基-4-氯-1H-咪唑-5-基)丙烯腈合成的，而后者是通过在乙醇中使用催化量的L-脯氨酸或哌啶作为碱与取代的N-烷基2-丁基-4-氯-1H-咪唑-5-醛与2-氰甲基苯并咪唑缩合而成。新合成的化合物包含多种N-取代基团，通过光谱数据进行表征，并针对MCF-7乳腺癌细胞系筛选其抗癌活性。结果表明，化合物3b、3a和4b具有显著的抑制增殖活性，IC50值分别为26.59、27.98和36.95 µM。
• Design, synthesis and evaluation of novel 2-butyl-4-chloroimidazole derived peptidomimetics as Angiotensin Converting Enzyme (ACE) inhibitors
  作者：Anvesh Jallapally、Dinesh Addla、Pankaj Bagul、Balasubramanian Sridhar、Sanjay K. Banerjee、Srinivas Kantevari

  DOI：10.1016/j.bmc.2015.04.024

  日期：2015.7

  A series of novel 2-butyl-4-chloro-1-methylimidazole derived peptidomimetics were designed, synthesized and evaluated for their Angiotensin Converting Enzyme (ACE) inhibitor activity. 2-Butyl-4-chloro-1-methylimidazole-5-carboxylic acid 2 obtained after oxidation of respective carboxaldehyde 1, was condensed with various amino acid methyl esters 3a–k to give imidazole–amino acid conjugates 4a–k in

  设计，合成和评估了一系列新颖的2-丁基-4-氯-1-甲基咪唑衍生的拟肽，并评估了它们的血管紧张素转化酶（ACE）抑制剂活性。氧化相应的甲醛1之后得到的2-丁基-4-氯-1-甲基咪唑-5-羧酸2与各种氨基酸甲基酯3a - k缩合，以非常好的收率得到咪唑-氨基酸共轭物4a - k。用LiOH水溶液将4a - k酯水解，得到所需的拟肽5a - k。筛选所有新化合物4a – k和5a - k使用ACE抑制试验，得到了五种化合物4i，4k，5e，5h和5i作为有效的ACE抑制剂，IC 50为0.647、0.531、1.12、0.657和0.100μM，毒性最小。其中，5i成为最活跃的ACE抑制剂，其功效比市售药物利诺普利，雷米普利和与贝那普利，奎那普利和依那普利相对等价。
• Novel Schiff base-bridged multi-component sulfonamide imidazole hybrids as potentially highly selective DNA-targeting membrane active repressors against methicillin-resistant Staphylococcus aureus
  作者：Yuanyuan Hu、Guangxing Pan、Zhixiong Yang、Tiejun Li、Juan Wang、Mohammad Fawad Ansari、Chunfang Hu、Rammohan R. Yadav Bheemanaboina、Yu Cheng、Chenghe Zhou、Jiaheng Zhang

  DOI：10.1016/j.bioorg.2020.104575

  日期：2021.2

  multi-component sulfonamide imidazole hybrids with antimicrobial potential was developed. Some target compounds showed significant antibacterial potency. Observably, butylene hybrids 4h exhibited remarkable inhibitory efficacy against clinical MRSA (MIC = 1 µg/mL), but had no significant toxic effect on normal mammalian cells (RAW 264.7). The highly active molecule 4h was revealed by molecular modeling study that

  开发了一种具有抗菌潜力的新型席夫碱桥连多组分磺酰胺咪唑杂化物。一些目标化合物显示出显着的抗菌效力。可观察到，丁烯杂化物4h对临床 MRSA 表现出显着的抑制效果（MIC = 1 µg/mL），但对正常哺乳动物细胞没有显着的毒性作用（RAW 264.7）。分子模型研究表明，高活性分子4h可以插入DNA六聚体双链体的碱基对中，并通过氢键与人碳酸酐酶同工酶II的ASN-62残基结合。此外，进一步的初步抗菌机制实验证实，化合物4h能有效干扰MRSA膜并通过非共价键插入从临床MRSA菌株中分离的细菌DNA中产生超分子复合物，从而通过阻碍DNA复制发挥其强大的抗菌功效。这些发现强烈暗示高活性杂交4h可用作潜在的 DNA 靶向模板，用于开发有价值的抗菌剂。
• 腙基桥连的萘酰亚胺咪唑类化合物及其制备方法和应用
  申请人：西南大学

  公开号：CN111087388A

  公开（公告）日：2020-05-01

  本发明涉及腙基桥连的萘酰亚胺咪唑类化合物及其制备方法和应用，属于化学合成技术领域，腙基桥连的萘酰亚胺咪唑类化合物如通式I所示，该类化合物对革兰阳性菌、革兰阴性菌和/或真菌中的一种或多种具有一定抑制活性，可以用于制备抗细菌和/或抗真菌药物，从而有机会为临床抗微生物治疗提供更多安全、高效的多样化候选药物。其制备原料简单，廉价易得，合成路线短，在抗感染方面的应用具有重要意义。