2-(1H-imidazol-1-yl)-2'-hydroxyacetophenone | 85928-32-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1H-imidazol-1-yl)-2'-hydroxyacetophenone
• 英文别名: 2-hydroxy-α-(1-imidazolyl)-acetophenone；Ethanone, 1-(2-hydroxyphenyl)-2-(1H-imidazol-1-yl)-；1-(2-hydroxyphenyl)-2-imidazol-1-ylethanone
• CAS: 85928-32-1
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: GLQMBLXNRZTILO-UHFFFAOYSA-N

物化性质

• 沸点：
  428.5±25.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-imidazol-1-yl)-2'-hydroxyacetophenone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-(1-hydroxy-2-(1H-imidazol-1-yl)ethyl)phenol
  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
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(1H-imidazol-1-yl)-2'-hydroxyacetophenone
  参考文献：
  名称：

  Synthesis and Antifungal Activity of 1-[(2-Benzyloxy)Phenyl]-2-(Azol-1-yl)Ethanone Derivatives: Exploring the Scaffold Flexibility

  摘要：

  Based on the N‐(phenethyl)azole backbone of azole antifungals, we designed 1‐[(2‐benzyloxy)phenyl]‐2‐(azol‐1‐yl)ethanone derivatives 2 and 3, containing benzyloxyphenyl scaffold of croconazole. Also these compounds can be considered as flexible analogs, resulted from C2–C3 disconnection of 3′‐chloro‐3‐imidazolylflavanone 1, recently described as antifungal agent. Thus, in this report, we describe the synthesis of 1‐[(2‐benzyloxy)phenyl]‐2‐(azol‐1‐yl)ethanone derivatives 2 and 3 and their biological evaluation against different pathogenic fungi. By comparing the antifungal activity profile of flexible compounds 2 and 3 with that of rigid analog 1, it can be inferred that lower susceptibilities (higher minimum inhibitory concentrations) were observed with flexible compounds. However, among the synthesized compounds, 1‐[2‐(2,4‐dichlorobenzyloxy)phenyl]‐2‐(1H‐imidazol‐1‐yl)ethanone hydrochloride (2g) showed comparable or more potent antifungal activity in comparison with fluconazole as a standard drug.

  DOI：

  10.1111/j.1747-0285.2011.01243.x

文献信息

• Imidazole derivative
  申请人：SS Pharmaceutical Co., Ltd.

  公开号：US04925953A1

  公开（公告）日：1990-05-15

  Novel imidazole derivatives and their acid adducts are disclosed. The imidazole derivatives are represented by formula: ##STR1## wherein R.sub.1 represents an alkyl group, R.sub.2 represents a hydrogen atom, an alkyl group which may have a substituent, or an aralkyl group which may have a substituent, provided that R.sub.1 and R.sub.2 are not both methyl groups at the same time. They have strong antimicrobial activity, especially against those fungi belonging to the genera Candida, Trichophyton, Microsporum, and Epidermorphyton, as well as against Gram-positive bacteria, and thus are useful as an antimicrobial agent.

  披露了新型的咪唑衍生物及其酸加成物。这些咪唑衍生物可以用以下公式表示：##STR1## 其中R.sub.1代表烷基，R.sub.2代表氢原子、可能带有取代基的烷基或可能带有取代基的芳烷基，前提是R.sub.1和R.sub.2不同时为甲基。它们具有强烈的抗菌活性，特别是对属于念珠菌属、毛癣菌属、小孢子菌属和表皮癣菌属的真菌，以及对革兰氏阳性细菌，因此可用作抗菌剂。
• Imidazolyl derivatives of the chroman ring. 2
  作者：Paolo Cozzi、Antonio Pillan

  DOI：10.1002/jhet.5570220245

  日期：1985.3

  The synthesis of 3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-ones 2 and of 2-(1H-imidazol-1-yl)-4H-1-benzopyr-an-4-ones 11 are described. The former proceeds through chroman ring closure from 2-(1H-imidazol-1-yl)-2′-hydroxyacetophenones, the latter occurs reacting 3-bromo-4H-1-benzopyran-4-ones with imidazole and represents an example of a new synthesis of 2-heteroarylchromones. Compounds 2 can be easily

  3-（1 H-咪唑-1-基）-4 H -1-苯并吡喃-4-酮2和2-（1 H-咪唑-1-基）-4 H -1-苯并吡喃-an的合成-4-一11被描述。前者通过2-（1 H-咪唑-1-基）-2'-羟基苯乙酮的苯并二氢吡喃环封闭而进行，后者发生的是使3-溴-4 H -1-苯并吡喃-4-酮与咪唑反应，这是一个例子。 2-杂芳基色酮的新合成方法。化合物2可以很容易地还原为先前在第1部分中描述的相应的苯并二氢吡喃酮和苯并二氢吡喃醇。
• N-Imidazolyl-4-chromanones, N-imidazolyl-1-tetralones, and their alcohols as hypolipemic agents raising high-density lipoproteins
  作者：Paolo Cozzi、Umberto Branzoli、Pier Paolo Lovisolo、Gaetano Orsini、Germano Carganico、Antonio Pillan、Augusto Chiari

  DOI：10.1021/jm00153a016

  日期：1986.3

  3-(1-imidazolyl)chroman-4-ones and 2-(1-imidazolyl)-1-tetralones II, some of their alcohols, and some related compounds were synthesized and tested for hypolipidemic activity. Compounds II, bearing appropriate lipophilic substituents on the phenyl ring, strongly reduced total serum cholesterol while raising high-density lipoprotein cholesterol in diet-induced hypercholesterolemic rats. 3-(1-Imidazolyl)chroman-4-ols

  合成了一系列3-（1-咪唑基）苯并二氢吡喃-4-酮和2-（1-咪唑基）-1-四氢萘酮II，它们的一些醇和一些相关化合物，并测试了其降血脂活性。在饮食诱导的高胆固醇血症大鼠中，在苯环上带有适当亲脂性取代基的化合物II大大降低了血清总胆固醇，同时提高了高密度脂蛋白胆固醇。对应于II的3-（1-咪唑基）苯并吡喃-4-醇和2-（1-咪唑基）-1-四醇保留了降血脂活性，同时除去了与咪唑相邻的羰基或羟基，得到了惰性化合物。尽管许多活性化合物显着增加了肝脏的重量，但作为模型研究的一种化合物是6-氯-3-（1-咪唑基）-2,3-二氢-4H-1-苯并吡喃-4-酮（5）引起的。没有过氧化物酶体增殖。化合物5和相应的醇40，作为酮和醇系列的代表，在降血脂正常大鼠中显示出显着的降血脂活性。在胆固醇生物合成中检测到的某些化合物抑制乙酸盐的掺入，但没有抑制HMG-CoA还原酶。选择5-溴-6-羟基-2-（1-咪唑基）-3
• N-Imidazolyl derivatives of 1,2,3,4-tetrahydro-naphthalene and indan
  申请人：Farmitalia Carlo Erba S.p.A.

  公开号：US04492707A1

  公开（公告）日：1985-01-08

  Compounds of the formula ##STR1## where Z completes a bond or is a ##STR2## group; one of R.sub.1 and R.sub.2 is hydroxy and the other is hydrogen or alkyl, or R.sub.1 and R.sub.2, taken together, form an oxo group; and the remaining substituents are as defined in the specification. These compounds possess hypolipaemic properties.

  公式的化合物##STR1##，其中Z形成一个键或是一个##STR2##基团；R.sub.1和R.sub.2中的一个为羟基，另一个为氢或烷基，或者R.sub.1和R.sub.2共同形成一个氧代基团；其余取代基如说明书所定义。这些化合物具有降血脂性质。
• 3-Imidazolyl-Substituted Flavans as Potential Antifungal Agents: Synthesis, Stereochemical Properties, and Antifungal Activity
  作者：Saeed Emami、Alireza Foroumadi

  DOI：10.1002/ardp.200900024

  日期：2009.9

  3‐imidazolyl‐substituted flavan derivatives being equipped with a N‐(phenethyl)‐azole scaffold as the common pharmacophore of azole antifungals, were synthesized. The stereochemical and conformational properties of compounds were also characterized by 1H‐NMR data. The results of the antifungal evaluation of trans‐3‐imidazolyl‐substituted flavan‐4‐ones and (Z)‐trans‐3‐imidazolyl‐substituted flavan‐4‐one oximes

  合成了一系列新的 3-咪唑基取代的黄烷衍生物，其配备了 N-（苯乙基）-唑支架作为唑类抗真菌药的常见药效团。化合物的立体化学和构象特性也通过 1H-NMR 数据表征。反式-3-咪唑基取代的黄烷-4-酮和(Z)-反-3-咪唑基-取代的黄烷-4-酮肟与参比药物氟康唑的抗真菌评价结果表明，大多数目标化合物具有对受试真菌具有显着的体外抗真菌活性，与氟康唑相当或优于氟康唑。