1-(2,4-dichlorobenzyl)-1H-imidazole | 42032-28-0

• 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-(2,4-dichlorobenzyl)-1H-imidazole
• 英文别名: 1-(2,4-Dichlorbenzyl)imidazol；N-(2,4-dichlorobenzyl)-imidazole；1-[(2,4-dichlorophenyl)methyl]imidazole
• CAS: 42032-28-0
• 化学式: C₁₀H₈Cl₂N₂
• mdl: MFCD06421441
• 分子量: 227.093
• InChiKey: OPCJKENNKLSJMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 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-(2,4-dichlorobenzyl)-1H-imidazole 在 正丁基锂 作用下， 以 乙醇 为溶剂， 反应 8.17h， 生成 1-[1,2-Bis-(2,4-dichloro-phenyl)-ethyl]-1H-imidazole; compound with naphthalene-1,5-disulfonic acid
  参考文献：
  名称：

  α-Lithiation ofN-Arylmethylimidazoles and Triazoles: A General Method for the Synthesis of 1,2-Diaryl-1-(N-azolyl)-ethanes

  摘要：

  DOI：

  10.1055/s-1985-31187
• 作为产物：
  描述：

  咪唑 、 2,4-二氯溴苄 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 14.17h， 以60%的产率得到1-(2,4-dichlorobenzyl)-1H-imidazole
  参考文献：
  名称：

  Detailed analysis and follow-up studies of a high-throughput screening for indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors

  摘要：

  Indoleamine 2,3-dioxygenase 1 (IDO1) is a key regulator of immune responses and therefore an important therapeutic target for the treatment of diseases that involve pathological immune escape, such as cancer. Here, we describe a robust and sensitive high-throughput screen (HTS) for IDO1 inhibitors using the Prestwick Chemical Library of 1200 FDA-approved drugs and the Maybridge HitFinder Collection of 14,000 small molecules. Of the 60 hits selected for follow-up studies, 14 displayed IC50 values below 20 μM under the secondary assay conditions, and 4 showed an activity in cellular tests. In view of the high attrition rate we used both experimental and computational techniques to identify and to characterize compounds inhibiting IDO1 through unspecific inhibition mechanisms such as chemical reactivity, redox cycling, or aggregation. One specific IDO1 inhibitor scaffold, the imidazole antifungal agents, was chosen for rational structure-based lead optimization, which led to more soluble and smaller compounds with micromolar activity.

  DOI：

  10.1016/j.ejmech.2014.06.078

文献信息

• 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。
• 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。
• Imidazole derivatives and salts thereof, their synthesis, and pharmaceutical formulations
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0003560A2

  公开（公告）日：1979-08-22

  Pharmaceutical formulations comprising an imidazole (or pharmaceutically acceptable salt thereof) of formula: wherein (i) A is an aliphatic hydrocarbon residue of from 1 to 4 carbon atoms and R is a naphthyl, tetrahydronaphthyl, heterocyclyl, arylthio, arylalkylthio, aryloxy, arylalkyloxy, arylhydroxymethylene, arylcarbonyl, arylalkylcarbonyl, alkyloxy, alkylthio or a substituted cycloalkyl or cycloalkenyl group or (ii) A is a -S02- group and R is aryl or heterocyclyl or (iii) A is a chemical bond and R is a heterocyclyl or substituted phenyl group, or (iv) A is an aliphatic hydrocarbon residue of from 1 to 3 carbon atoms and R is a halophenyl group. Some of these imidazoles and salts are novel. Methods of preparing the imidazoles are disclosed. The imidazoles and their salts are useful in the treatment or prophylaxis of thrombo-embolic conditions.

  药物制剂，包含式中的咪唑（或其药学上可接受的盐）： 其中 (i) A 是 1 至 4 个碳原子的脂族烃残基，R 是萘基、四氢萘基、杂环基、芳硫基、芳烷硫基、芳氧基、芳烷氧基、芳羟甲基、芳羰基、芳烷基羰基、烷氧基、烷硫基或取代的环烷基或环烯基，或 (ii) A 是-S02-基团，R 是芳基或杂环基，或 (iii) A 是化学键，R 是杂环基或取代苯基，或 (iv) A 是 1 至 3 个碳原子的脂肪烃残基，R 是卤代苯基。 其中一些咪唑和盐是新型的。 这些咪唑的制备方法已经公开。咪唑及其盐类可用于治疗或预防血栓栓塞。
• 1-(1,3-Dioxolan-2-ylmethyl)-azole, ihre Salze, Verfahren zu ihrer Herstellung und ihre Verwendung
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0050298A2

  公开（公告）日：1982-04-28

  Es werden 1-(1,3-Dioxolan-2-ylmethyl)-azole der allgemeinen Formel sowie ihre Stereoisomeren und ihre Salze mit physiologisch verträglichen Säuren beschrieben, die Herstellung dieser Verbindungen, sie enthaltende pharmazeutische Zubereitungen und ihre Verwendung gegen Mykosen, Protozoen und grampositive sowie gramnegative Bakterien.

  通式为 1-(1,3-二氧戊环-2-基甲基)-唑 以及它们的立体异构体和它们与生理上相容的酸的盐，描述了这些化合物的制备方法、含有它们的药物制剂以及它们对霉菌、原生动物、革兰氏阳性和革兰氏阴性细菌的作用。