1-(3-chlorobenzyl)-imidazole | 56643-68-6

• 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: 1-(3-chlorobenzyl)-imidazole
• 英文别名: 1-(3-chlorobenzyl)-1H-imidazole；N-(3-chlorobenzyl)-imidazole；1-(3-chloro-benzyl)-1H-imidazole；1-(3-Chlorobenzyl)imidazole；1-[(3-chlorophenyl)methyl]imidazole
• CAS: 56643-68-6
• 化学式: C₁₀H₉ClN₂
• mdl: MFCD06421440
• 分子量: 192.648
• InChiKey: DARGVYVMURXBSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-chlorobenzyl)-imidazole 在 sodium 5-methyl-2-pyridonate 、 copper(l) chloride 作用下， 以 对二甲苯 为溶剂， 反应 20.0h， 以83%的产率得到1,1'-di(3-chlorobenzyl)-1H,1'H-2,2'-biimidazole
  参考文献：
  名称：

  通过铜（I）/ 2-吡啶酮催化体系的好氧氧化均质偶合，高效合成联唑。

  摘要：

  已经开发了一种高效且方便的CuCl / 2-吡啶酮催化体系，用于氧化制提供双唑产物的吡咯。利用该系统，在非常少量的铜催化剂（1.0摩尔％）的存在下，已经以良好至优异的收率有效地合成了多种联唑。使用空气作为绿色氧化剂是可行的。

  DOI：

  10.1039/c1cc15363c
• 作为产物：
  描述：

  咪唑 、 3-氯苄溴 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以32%的产率得到1-(3-chlorobenzyl)-imidazole
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Molecular Modeling of 1-Benzyl-1H-imidazoles as Selective Inhibitors of Aldosterone Synthase (CYP11B2)

  摘要：

  Reducing aldosterone action is beneficial in various major diseases such as heart failure. Currently, flits is achieved with mineralocorticoid receptor antagonists, however, aldosterone synthase (CYP11B2) inhibitors may offer a promising alternative. In this study, WC used three-dimensional modeling of CYP11B2 to model the binding modes of the natural substrate 18-hydroxycorticosterone and the recently published CYP11B2 inhibitor R-fadrozole as a rational guide to design 44 structurally simple and achiral 1-benzyl-1H-imidazoles. Their syntheses, in vitro inhibitor potencies, and in silico docking are described. Some promising CYP11B2 inhibitors were identified, with our novel lead MOERAS115 (4-((5-phenyl-1H-imidazol-1-y1)methyl)benzonitrile) displaying an IC50 for CYP11B2 of 1.7 nM, and a CYP11B2 (versus CYP11B1) selectivity of 16.5, comparable to R-fadrozole (IC50 for CYP11B2 6.0 nM. Selectivity 19.8). Molecular docking of the Inhibitors in the models enabled us to generate posthoc hypotheses oil their binding modes, providing a Valuable basis for future Studies and further design of CYP11B2 inhibitors.

  DOI：

  10.1021/jm901356d

文献信息

• Novel Imidazole Aldoximes with Broad-Spectrum Antimicrobial Potency against Multidrug Resistant Gram-Negative Bacteria
  作者：Mirjana Skočibušić、Renata Odžak、Alma Ramić、Tomislav Smolić、Tomica Hrenar、Ines Primožič

  DOI：10.3390/molecules23051212

  日期：——

  search for a new class of potential antimicrobial agents, five novel N-substituted imidazole 2-aldoximes and their six quaternary salts were evaluated. The antimicrobial activity was assessed against a panel of representative Gram-positive and Gram-negative bacteria, including multidrug resistant bacteria. All compounds demonstrated potent in vitro activity against the tested microorganisms, with MIC

  在寻找一类潜在的抗菌剂时，对五种新颖的N-取代的咪唑2-醛肟及其六种季盐进行了评估。针对一组代表性的革兰氏阳性和革兰氏阴性细菌（包括耐多药细菌）评估了抗菌活性。所有化合物均显示出对测试微生物的有效体外活性，MIC值为6.25至50.0μg/ mL。在测试的化合物中，两种季化合物（N-丁-3-烯基和间-（10）或对-N-氯苄基（11）咪唑鎓2-醛肟）对革兰氏反应均表现出最有效和最广谱的活性。阳性和革兰氏阴性细菌菌株。肉汤微稀释测定法还用于研究两种活性最高的化合物对一组肠杆菌科细菌分离株的抗药性，与八种临床相关抗生素相比，这些细菌带有多种广谱β-内酰胺酶（ESBLs）。N-丁-3-烯基-N-间氯苄基咪唑-2-醛肟被发现具有对广泛范围内产生β-内酰胺酶的菌株（MIC 2.0至16.0μg/ mL）具有良好的抗药性。该化合物针对大肠杆菌和阴沟肠杆菌产生的最佳结果是产生多种A型和C型分子的β-内酰胺
• Arylmethylazoles and their salts, processes for their preparation,
  申请人：Hoechst Aktiengesellschaft

  公开号：US04876354A1

  公开（公告）日：1989-10-24

  Arylmethylazoles of the formula I ##STR1## in which Aryl is (substituted) phenyl or naphthyl; Z is CH or N; R.sup.1 and Q are H or alkyl; R.sup.2 is H, alk(en)yl or alkynyl; R.sup.3 and R.sup.4 are H, alkyl or other hydrocarbons; or R.sup.3 and R.sup.4 together are a --(CH.sub.2).sub.2-11 chain or a bridged --(CH.sub.2).sub.4-5 chain, and their acid addition salts, stereoisomers and optically active enantiomers possess outstanding antimycotic and antidepressant activity. They are obtained, inter alia, from arylmethylazoles II ##STR2## which are reacted with a strong base and then with a carbonyl compound III O.dbd.CR.sup.3 R.sup.4 ; thereafter, the product is reacted with the protic acid or with an alkyl halide IV R.sup.2 Hal. If desired, the products are converted to the acid addition salts, or the stereoisomers or optically active enantiomers are resolved.

  Arylmethylazoles的化学式为I，其中Aryl是（取代）苯或萘；Z是CH或N；R.sup.1和Q是H或烷基；R.sup.2是H，烯丙基或炔基；R.sup.3和R.sup.4是H，烷基或其他碳氢化合物；或者R.sup.3和R.sup.4一起是一个--(CH.sub.2).sub.2-11链或一个桥联的--(CH.sub.2).sub.4-5链，它们的酸盐、立体异构体和光学活性对映异构体具有出色的抗真菌和抗抑郁活性。它们可以从Arylmethylazoles II中获得，该化合物与强碱反应，然后与一个醛化合物III O.dbd.CR.sup.3 R.sup.4反应；之后，将产物与质子酸或烷基卤化物IV R.sup.2 Hal反应。如果需要，将产物转化为酸盐，或者将立体异构体或光学活性对映异构体分离。
• 1-(1-aryl-2-hydroxyethyl)-imidazoles and salts thereof, medicaments
  申请人：Hoechst Aktiengesellschaft

  公开号：US04999352A1

  公开（公告）日：1991-03-12

  1-(1-Aryl-2-hydroxyethyl)-imidazoles and salts thereof, processes for the preparation thereof, medicaments containing these compounds, and the use thereof. The invention relates to 1-(1-aryl-2-hydroxyethyl)-imidazoles of the formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, Q, W, X and Y have the meanings specified, and also to medicaments based on these compounds, in particular those having an antimycotic and an antidepressive action.

  1-(1-芳基-2-羟基乙基)-咪唑及其盐，其制备方法，含有这些化合物的药物以及其用途。该发明涉及具有以下结构的1-(1-芳基-2-羟基乙基)-咪唑的化合物：其中R.sup.1、R.sup.2、R.sup.3、Q、W、X和Y具有特定含义，还涉及基于这些化合物的药物，特别是那些具有抗真菌和抗抑郁作用的药物。
• Arylmethylazole preparation processes
  申请人：Hoechst Aktiengesellschaft

  公开号：US05023357A1

  公开（公告）日：1991-06-11

  Arylmethylazoles of the formula I ##STR1## in which Aryl is (substituted) phenyl or naphthyl; Z is CH or N; R.sup.1 and Q are H or alkyl; R.sup.2 is H, alk(en)yl or alkynyl; R.sup.3 l and R.sup.4 are H, alkyl or other hydrocarbons; or R.sup.3 and R.sup.4 together are a --(CH.sub.2).sub.2-11 chain or a bridged --(CH.sub.2).sub.4-5 chain, and their acid addition salts, stereoisomers and optically active enantiomers possess outstanding antimycotic and antidepressant activity. They are obtained, inter alia, from arylmethylazoles II ##STR2## which are reacted with a strong base and then with a carbonyl compound III 0=CR.sup.3 R.sup.4 ; thereafter, the product is reacted with the protic acid or with an alkyl halide IV R.sup.2 Hal. If desired, the products are converted to the acid addition salts, or the stereoisomers or optically active enantiomers are resolved.

  式I的芳基甲基唑化合物##STR1## 其中Aryl是（取代）苯基或萘基；Z是CH或N；R1和Q是H或烷基；R2是H、烷基或炔基；R3和R4是H、烷基或其他碳氢化合物；或者R3和R4一起是一个--（CH2）2-11链或一个桥接的--（CH2）4-5链，以及它们的酸加成盐、立体异构体和光学活性对映体具有出色的抗真菌和抗抑郁活性。它们可以从芳基甲基唑化合物II##STR2##获得，该化合物与强碱反应，然后与一个羰基化合物III 0=CR3R4反应；然后，产物与质子酸或烷基卤化物IV R2Hal反应。如果需要，产物可以转化为酸加成盐，或者立体异构体或光学活性对映体可以被分离。
• Arylmethylazoles and their salts, agents which contain these compounds,
  申请人：Hoechst Aktiengesellschaft

  公开号：US05100890A1

  公开（公告）日：1992-03-31

  Arylmethylazoles of the formula I ##STR1## in which Aryl is (substituted) phenyl or naphthyl; Z is CH or N; R.sup.1 and Q are H or alkyl; R.sup.2 is H, alk(en)yl or alkynyl; R.sup.3 and R.sup.4 are H, alkyl or other hydrocarbons; or R.sup.3 and R.sup.4 together are a--(CH.sub.2).sub.2-11 chain or a bridged--(CH.sub.2).sub.4-5 chain, and their acid addition salts, stereoisomers and optically active enantiomers possess outstanding antimycotic and antidepressant activity. They are obtained, inter alia, from arylmethylazoles II ##STR2## which are reacted with a strong base and then with a carbonyl compound III O.dbd.CR.sup.3 R.sup.4 ; thereafter, the product is reacted with the protic acid or with an alkyl halide IV R.sup.2 Hal. If desired, the products are converted to the acid addition salts, or the stereoisomers or optically active enantiomes are resolved.

  化学式I的芳基甲基咪唑化合物如下：##STR1## 其中Aryl为（取代）苯基或萘基；Z为CH或N；R.sup.1和Q为H或烷基；R.sup.2为H，烷基或炔基；R.sup.3和R.sup.4为H，烷基或其他碳氢化合物；或者R.sup.3和R.sup.4一起是一个-（CH.sub.2）.sub.2-11链或一个桥式-（CH.sub.2）.sub.4-5链，它们的酸加合物盐，立体异构体和光学活性对映体具有杰出的抗真菌和抗抑郁活性。它们可以从芳基甲基咪唑化合物II中获得，如下所示：##STR2## 其中，化合物II与强碱反应，然后与羰基化合物III O.dbd.CR.sup.3 R.sup.4反应；然后，产物与质子酸或烷基卤化物IV R.sup.2 Hal反应。如果需要，可以将产物转化为酸加合物盐，或者分离其立体异构体或光学活性对映体。