3-(4-bromobenzyl)-5-chloro-2-phenyl-3H-imidazole-4-carbaldehyde | 210824-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-bromobenzyl)-5-chloro-2-phenyl-3H-imidazole-4-carbaldehyde
• 英文别名: 4-Chloro-1-[(4-bromophenyl)methyl]-5-formyl-2-phenylimidazole；3-[(4-bromophenyl)methyl]-5-chloro-2-phenylimidazole-4-carbaldehyde
• CAS: 210824-76-3
• 化学式: C₁₇H₁₂BrClN₂O
• 分子量: 375.652
• InChiKey: RVEDAYLTLJEIPA-UHFFFAOYSA-N

物化性质

• 沸点：
  555.8±60.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  3-(4-bromobenzyl)-5-chloro-2-phenyl-3H-imidazole-4-carbaldehyde 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 74.0h， 生成 3-[4-(4-chloro-5-formyl-2-phenyl-imidazol-1-ylmethyl)phenyl]-5-isobutylthiophene-2-(3-ethyl) sulfonylurea
  参考文献：
  名称：

  ¹⁴C-Labeled and Large-Scale Synthesis of the Angiotensin-(1−7)-receptor Agonist AVE 0991 by Cross-Coupling Reactions

  摘要：

  The synthesis of C-14-labeled AVE 0991 (C-14-1a) and large-scale synthesis of AVE 0991 (1a) are described. In the key step of the synthesis, the C-C coupling reaction of the imidazole (2) and thiophene (3) building blocks was studied under Suzuki and Stille reaction conditions, respectively. Suzuki reaction gave only moderate yields, whereas the best results were obtained under Stille reaction conditions with up to 64% yield.

  DOI：

  10.1021/jo034372c
• 作为产物：
  描述：

  对溴溴苄 、 5-氯-2-苯基-3H-咪唑-4-甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以3.9 g的产率得到3-(4-bromobenzyl)-5-chloro-2-phenyl-3H-imidazole-4-carbaldehyde
  参考文献：
  名称：

  Five-membered heterocycles having biphenylsulfonyl substitution, with sulfonylcyanamide side chain, compositions containing them, and methods of using them

  摘要：

  具有联苯磺酰基取代的五元杂环化合物，其制备方法，它们作为药物或诊断工具的用途，以及包含它们的药物。在式I的化合物中，符号具有索赔中指示的含义，具有出色的抗心律失常性能，并表现出心脏保护成分。它们可以预防性地抑制或大大减少在缺血诱导损伤形成过程中的病理生理过程，特别是在缺血诱导的心律失常的引发中。此外，它们对细胞增殖具有强大的抑制作用。

  公开号：

  US06335451B1

文献信息

• Five-membered heterocycles having biphenylsulfonyl substitution, with sulfonylcyanamide side chain, compositions containing them, and methods of using them
  申请人：Hoechst Aktiengesellschaft

  公开号：US06335451B1

  公开（公告）日：2002-01-01

  Five-membered heterocycles having biphenylsulfonyl substitution, process for their preparation, their use as a medicament or diagnostic, and medicament comprising them. Compounds of the formula I in which the symbols have the meanings indicated in the claims, have outstanding antiarrhythmic properties and exhibit a cardioprotective component. They can preventively inhibit or greatly decrease the pathophysiological processes in the formation of ischemically induced damage, in particular in the elicitation of ischemically induced cardiac arrhythmias. Moreover, they have a potent inhibitory action on the proliferation of cells.

  具有联苯磺酰基取代的五元杂环化合物，其制备方法，它们作为药物或诊断工具的用途，以及包含它们的药物。在式I的化合物中，符号具有索赔中指示的含义，具有出色的抗心律失常性能，并表现出心脏保护成分。它们可以预防性地抑制或大大减少在缺血诱导损伤形成过程中的病理生理过程，特别是在缺血诱导的心律失常的引发中。此外，它们对细胞增殖具有强大的抑制作用。
• 1-(p-thienylbenzyl)imidazoles as agonists of angiotensin (1-7) receptors, processes for their preparation, their use, and pharmaceutical preparations comprising them
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US06235766B1

  公开（公告）日：2001-05-22

  The invention relates to novel 1-(p-thienylbenzyl)imidazoles of formula (I) where the radicals R(1) to R(6), X, and Y have the meaning indicated in the description, which are potent agonists of angiotensin (1-7) receptors and owing to the production and release of the vasorelaxant, antithrombotic, and cardioprotective messengers cyclic 3′,5′-guanosine monophosphate (cGMP) and nitrogen monoxide (NO) associated with the stimulation of these receptors on endothelial cells are valuable pharmaceuticals for the treatment and prophylaxis of high blood pressure, cardiac hypertrophy, cardiac insufficiency, coronary heart diseases such as angina pectoris, cardiac infarct, vascular restenosis after angioplasty, cardiomyopathies, endothelial dysfunction or endothelial damage, e.g., as a result of arteriosclerotic processes or diabetes mellitus, and also of arterial and venous thromboses.

  该发明涉及具有以下式(I)的新型1-(对噻吩基苄)咪唑，其中基团R(1)到R(6)、X和Y的含义如描述中所示，这些化合物是强效的血管紧张素(1-7)受体激动剂，由于产生和释放导致血管舒张、抗血栓和心脏保护信使环3′,5′-鸟苷酸单磷酸(cGMP)和一氧化氮(NO)，这些与刺激内皮细胞上这些受体相关联的药物对于高血压、心脏肥大、心脏功能不全、如心绞痛、心肌梗死、血管成形术后的血管再狭窄、心肌病、内皮功能障碍或内皮损伤，例如由于动脉粥样硬化过程或糖尿病引起，以及动脉和静脉血栓形成的治疗和预防具有重要价值。
• [DE] 1-(P-THIENYLBENZYL)-IMIDAZOLE ALS AGONISTEN VON ANGIOTENSIN-(1-7)-REZEPTOREN, VERFAHREN ZU IHRER HERSTELLUNG, IHRE VERWENDUNG UND SIE ENTHALTENDE PHARMAZEUTISCHE PRÄPARATE<br/>[EN] 1-(P-THIENYLBENZYL)-IMIDAZOLES AS ANGIOTENSIN-(1-7) RECEPTOR AGONISTS, METHOD FOR THE PRODUCTION AND THE UTILIZATION THEREOF AND PHARMACEUTICAL PREPARATIONS CONTAINING SAID COMPOUNDS<br/>[FR] 1(P-THIENYLBENZYL)-IMIDAZOLES COMME AGONISTES DES RECEPTEURS DE L'ANGIOTENSINE (1-7), LEUR PROCEDE DE PRODUCTION, LEUR UTILISATION, ET PREPARATIONS PHARMACEUTIQUES LES CONTENANT
  申请人：AVENTIS PHARMA GMBH

  公开号：WO2000068226A1

  公开（公告）日：2000-11-16

  Die Erfindung betrifft neue 1-(p-Thienylbenzyl)-Imidazole der Formel (I), wobei die Reste R(1) bis R(6), X und Y die in der Beschreibung angegebene Bedeutung haben, die potente Agonisten von Angiotensin-(1-7)-Rezeptoren sind und durch die mit der Stimulation dieser Rezeptoren an Endothelzellen verbundene Produktion und Freisetzung der vasorelaxierenden, antithrombotischen und kardioprotektiven Botenstoffe cyclisches 3',5'-Guanosinmonophosphat (cGMP) und Stickstoffmonoxid (NO) wertvolle Arzneimittel zur Behandlung und Prophylaxe von Bluthochdruck, Herzhypertrophie, Herzinsuffizienz, koronaren Herzerkrankungen wie der Angina Pectoris, Herzinfarkt, vaskulärer Restenose nach Angioplastie, Kardiomyopathien, einer endothelialen Dysfunktion bzw. endothelialer Schädigungen, z.B. als Folge atheriosklerotischer Prozesse oder beim Diabetis mellitus, sowie von arterieller und venöser Thrombose darstellen.

  本发明涉及新的1-(p-噻吩基苄基)-咪唑(I)的化合物，其中基团R(1)至R(6)，X和Y在说明书中有所描述，是血管紧张素-(1-7)-受体的有效激动剂，通过刺激内皮细胞上的这些受体，产生和释放血管舒张、抗血栓和心脏保护作用的信使分子环磷酸鸟苷单磷酸(cGMP)和一氧化氮(NO)，可用于治疗和预防高血压、心肌肥厚、心力衰竭、冠状动脉疾病如心绞痛、心肌梗塞、血管成形术后的血管再狭窄、心肌病、内皮功能障碍或内皮损伤，例如动脉粥样硬化过程或糖尿病，以及动脉和静脉血栓的有价值药物。
• Five-membered heterocycles having biphenylsulfonyl substitution, process for their preparation, their use as a medicament or diagnostic, and medicament comprising them
  申请人：——

  公开号：US20020045761A1

  公开（公告）日：2002-04-18

  Five-membered heterocycles having biphenylsulfonyl substitution, process for their preparation, their use as a medicament or diagnostic, and medicament comprising them. Compounds of the formula I 1 in which the symbols have the meanings indicated in the claims, have outstanding antiarrhythmic properties and exhibit a cardioprotective component. They can preventively inhibit or greatly decrease the pathophysiological processes in the formation of ischemically induced damage, in particular in the elicitation of ischemically induced cardiac arrhythmias. Moreover, they have a potent inhibitory action on the proliferation of cells.

  五元杂环具有联苯磺酰基取代的化合物、其制备方法、作为药物或诊断试剂的用途以及含有它们的药物。式I1的化合物中，符号具有权利要求中所示的含义，具有出色的抗心律失常性能并表现出心脏保护成分。它们可以预防性地抑制或大大减少缺血性损伤形成的病理生理过程，特别是在缺血性诱导的心脏心律失常的引发中。此外，它们对细胞增殖具有强效的抑制作用。
• 1-(p-thienylbenzyl)imidazoles as agonists of angiotensin (1-7) receptors, processes for their preparation, their use, and pharmaceutical prepartions comprising them
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US20020077344A1

  公开（公告）日：2002-06-20

  The invention relates to novel 1-(p-thienylbenzyl)imidazoles of formula (I) 1 where the radicals R(1) to R(6), X, and Y have the meaning indicated in the description, which are potent agonists of angiotensin (1-7) receptors and owing to the production and release of the vasorelaxant, antithrombotic, and cardioprotective messengers cyclic 3′,5′-guanosine monophosphate (cGMP) and nitrogen monoxide (NO) associated with the stimulation of these receptors on endothelial cells are valuable pharmaceuticals for the treatment and prophylaxis of high blood pressure, cardiac hypertrophy, cardiac insufficiency, coronary heart diseases such as angina pectoris, cardiac infarct, vascular restenosis after angioplasty, cardiomyopathies, endothelial dysfunction or endothelial damage, e.g., as a result of arteriosclerotic processes or diabetes mellitus, and also of arterial and venous thromboses.

  本发明涉及一种新的1-(p-噻吩基苯基)咪唑类化合物，其化学式为(I)，其中基团R(1)到R(6)、X和Y的含义如说明书中所示。这些化合物是血管紧张素(1-7)受体的强效激动剂，并由于刺激内皮细胞上这些受体产生和释放血管舒张剂、抗血栓和心脏保护信使环磷酸鸟苷单磷酸(cGMP)和一氧化氮(NO)，因此对于治疗和预防高血压、心肌肥大、心力衰竭、冠心病如心绞痛、心肌梗死、血管成形术后的血管再狭窄、心肌病、内皮功能障碍或内皮损伤，如动脉硬化过程或糖尿病所致的，以及动脉和静脉血栓等方面具有重要的药物价值。