1-(4-methoxybenzyl)-5-phenyl-1H-imidazole | 1192811-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-methoxybenzyl)-5-phenyl-1H-imidazole
• 英文别名: 1-[(4-methoxyphenyl)methyl]-5-phenylimidazole
• CAS: 1192811-38-3
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: AZQFSYIIRUWICT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-methoxybenzyl)-5-phenyl-1H-imidazole 在 氢溴酸 作用下， 反应 16.0h， 以24%的产率得到4-((5-phenyl-1H-imidazol-1-yl)methyl)phenol
  参考文献：
  名称：

  IDO inhibitors

  摘要：

  目前提供的是按照化学式(I)或(II)提供的化合物以及含有这些化合物的药物组合物，其中R1、R4和R5在此有定义。这些化合物和组合物可用于调节吲哌醇胺2,3-二氧化酶的活性；治疗吲哌醇胺2,3-二氧化酶（IDO）介导的免疫抑制；治疗受益于抑制吲哌醇胺-2,3-二氧化酶酶活性的医疗状况；增强包括给予抗癌剂的抗癌治疗的有效性；治疗与癌症相关的肿瘤特异性免疫抑制；以及治疗与传染性疾病相关的免疫抑制。

  公开号：

  US09174942B2
• 作为产物：
  描述：

  在 水 、 溶剂黄146 、 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.17h， 以96 mg的产率得到1-(4-methoxybenzyl)-5-phenyl-1H-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

• IDO Inhibitors
  申请人：Mautino Mario R.

  公开号：US20110136796A1

  公开（公告）日：2011-06-09

  Presently provided are compounds according to the formula (I) or (II), and pharmaceutical compositions comprising the compounds, wherein R 1 , R 4 , and R 5 are defined herein. Such compounds and compositions are useful for modulating an activity of indoleamine 2,3-dioxygenase; treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression; treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine -2,3-dioxygenase; enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent; treating tumor-specific immunosuppression associated with cancer; and treating immunosupression associated with an infectious disease.

  目前提供了按照公式(I)或(II)定义的化合物以及含有这些化合物的药物组合物，其中R1、R4和R5的定义在此处。这些化合物和组合物对于调节吲哚胺2,3-二氧化酶的活性；治疗吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制；治疗从抑制吲哚胺-2,3-二氧化酶的酶活性中获益的医疗状况；增强包括给予抗癌剂的抗癌治疗的有效性；治疗与癌症相关的肿瘤特异性免疫抑制；以及治疗与传染性疾病相关的免疫抑制具有用处。
• Discovery and Preliminary Structure-Activity Investigation of 3-Substituted-1H-imidazol-5-yl-1H-indoles with In Vitro Activity towards Methicillin-Resistant Staphylococcus aureus
  作者：Steven A. Li、Rebecca J. Zheng、Kenneth Sue、Marie-Lise Bourguet-Kondracki、Azza Troudi、Jean Michel Brunel、Brent R. Copp、Melissa M. Cadelis

  DOI：10.3390/antibiotics11101450

  日期：——

  extensive library of analogues was prepared using the Van Leusen three-component reaction, biological evaluation of which led to the identification of two analogues (26 and 32) with favorable anti-MRSA activity (MIC ≤ 0.25 µg/mL) which also lacked cytotoxic or hemolytic properties. The screening campaign also identified two derivatives, a phenethyl-indole-imidazole 57 and a 5-phenyl-1H-imidazole 111 that

  抗生素能够治愈传染病并预防免疫功能低下者的感染，因此成为现代医学拯救生命的基石。它们的大量使用导致抗生素耐药细菌的发生率急剧增加，从而迫切需要具有新作用机制的抗生素。作为我们寻找新抗菌药物的一部分，我们筛选了内部化合物库，并确定了两种 3-取代-1 H -咪唑-5-基-1 H -吲哚作为弱生长抑制剂 (MIC 16 µg/mL)耐甲氧西林金黄色葡萄球菌(MRSA)。使用 Van Leusen 三组分反应制备了一个广泛的类似物库，对其进行生物学评估，鉴定出具有良好抗 MRSA 活性 (MIC ≤ 0.25 µg/mL) 且缺乏细胞毒性的两种类似物（ 26和32 ）或溶血特性。筛选活动还鉴定出两种衍生物，苯乙基吲哚咪唑57和 5-苯基-1 H-咪唑111 ，它们是针对新型隐球菌的无毒选择性抗真菌剂。这些结果已确定 3-取代-1 H -咪唑-5-基-1 H -吲哚和 5-苯基-1 H -咪唑作为新的结构支架，分别作为抗
• US8748469B2
  申请人：——

  公开号：US8748469B2

  公开（公告）日：2014-06-10
• US9174942B2
  申请人：——

  公开号：US9174942B2

  公开（公告）日：2015-11-03
• [EN] IDO INHIBITORS<br/>[FR] INHIBITEURS DE L'IDO
  申请人：NEWLINK GENETICS

  公开号：WO2009132238A2

  公开（公告）日：2009-10-29

  Presently provided are compounds according to the formula (I) or (II), and pharmaceutical compositions comprising the compounds, wherein R1, R4, and R5 are defined herein. Such compounds and compositions are useful for modulating an activity of indoleamine 2,3-dioxygenase; treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression; treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine -2,3-dioxygenase; enhancing the effectiveness of an anti- cancer treatment comprising administering an anti-cancer agent; treating tumor-specific immunosuppression associated with cancer; and treating immunosupression associated with an infectious disease.