4-(4-hydroxybenzoyl)benzonitrile | 27645-61-0

• 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: 4-(4-hydroxybenzoyl)benzonitrile
• 英文别名: 4-cyano-4'-hydroxybenzophenone；4-(4-hydroxy-benzoyl)-benzonitrile
• CAS: 27645-61-0
• 化学式: C₁₄H₉NO₂
• 分子量: 223.231
• InChiKey: CZYTUQCWOMSDFL-UHFFFAOYSA-N

物化性质

• 熔点：
  192.5-194 °C
• 沸点：
  451.1±30.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-hydroxybenzoyl)benzonitrile 在 三正丁基叠氮化锡 、 potassium tert-butylate 、 sodium iodide 作用下， 以 乙醇 、 乙二醇二乙醚 为溶剂， 反应 126.0h， 生成 1-[2-hydroxy-3-propyl-4-({4-[4-(1H-tetrazol-5-yl)-benzoyl]phenoxy}methyl)phenyl]ethanone
  参考文献：
  名称：

  (Phenylmethoxy)phenyl derivatives of w-oxo- and w-tetrazolylalkanoic acids and related tetrazoles. Synthesis and evaluation as leukotriene D4 receptor antagonists

  摘要：

  Two series of (phenylmethoxy)phenyl compounds derived from the structure of LY163443 were synthesized and evaluated as leukotriene D4 receptor antagonists. In the OMEGA-[(phenylmethoxy)phenyl]-OMEGA-oxoalkanoic acid series, 5-[4-[(4-acetyl-2-ethyl-3-hydroxyphenyl)methoxy]phenyl]-3,3-dimethyl-5-oxopentanoic acid (8) was the most potent antagonist of LTD4-induced contractions of guinea pig ileum (pK(B) of 7.60) and LTD4 pressor response in pithed rats (ED50 of 1.4 mg/kg iv). Replacing the carboxylic acid function with 5-tetrazole gave slightly more potent compounds. In the OMEGA-[5-[[(phenylmethoxy)phenyl]alkyl]tetrazolyl]alkanoic acid series, replacing the carboxylic acid with 5-tetrazole gave compounds that were equally effective in the guinea pig ileum but more potent in vivo against the LTD4 pressor response in rat. The pK(B) value in the guinea pig ileum for 1-[2-hydroxy-3-propyl-4-[[4-[[2-[3-(1H-tetrazol-5-yl)propyl]-2H-tetrazol-5-yl]methyl]phenoxy]methyl]phenyl]ethanone (25) was 7.87 and the ED50 for antagonism of the LTD4 pressor response was 4.0 mg/kg iv. The sodium salts of 8 (9) and 25 (26) given by the iv route of administration antagonized LTD4-induced cardiovascular alterations in anesthetized rat and LTD4-induced bronchoconstriction in guinea pig in a dose-dependent manner. Oral activity was also demonstrated against the LTD4-induced bronchoconstriction in guinea pig.

  DOI：

  10.1021/jm00113a014
• 作为产物：
  描述：

  4-(4-甲氧基苯甲酰基)苯甲腈 在 吡啶盐酸盐 作用下， 反应 0.33h， 以60%的产率得到4-(4-hydroxybenzoyl)benzonitrile
  参考文献：
  名称：

  来曲唑模板中的手性芳香酶和双重芳香酶-甾族硫酸酯酶抑制剂：合成，绝对构型和体外活性。

  摘要：

  为了探索芳香酶的抑制作用并拓宽双重芳香酶-硫酸酯酶抑制剂（DASIs）的结构多样性，我们将甾族硫酸酯酶（STS）抑制药效团引入了来曲唑。制备带有或不具有相邻取代基的双氨基磺酸盐或单氨基磺酸盐的来曲唑衍生物。最有效的非手性和外消旋芳香酶抑制剂为40（IC 50 = 3.0 nM）。通过手性HPLC分离其酚类前体39，并使用振动和电子圆二色性与预测光谱的计算相结合来确定每种对映体的绝对构型。在两种对映异构体中，（R）-苯酚（39a）是最有效的芳香化酶抑制剂（IC 50 = 0.6 nM，与来曲唑相当），而（S）-氨基磺酸盐（40b）最有效地抑制STS（IC 50 = 553 nM）。

  DOI：

  10.1021/jm800168s

文献信息

• Quinoline and quinazoline derivatives inhibiting platelet-derived growth
  申请人：Kirin Beer Kabushiki Kaisha

  公开号：US06143764A1

  公开（公告）日：2000-11-07

  The present invention relates to novel quinoline derivatives and quinazoline derivatives represented by the following formula (I): ##STR1## [wherein R.sub.1 and R.sub.2 are each independently H or C.sub.1 -C.sub.4 -alkyl, or R.sub.1 and R.sub.2 together form C.sub.1 -C.sub.3 -alkylene, X is O, S or CH.sub.2, W is CH or N, and Q is a substituted aryl group or substituted heteroaryl group] and their pharmaceutically acceptable salts, having platelet-derived growth factor receptor autophosphorylation inhibitory activity, to pharmaceutical compositions containing these compounds, and to methods for the treatment of diseases associated with abnormal cell growth such as tumors.

  本发明涉及由以下式（I）表示的新型喹啉衍生物和喹唑啉衍生物：[其中R.sub.1和R.sub.2分别独立地为H或C.sub.1 -C.sub.4 -烷基，或R.sub.1和R.sub.2一起形成C.sub.1 -C.sub.3 -烷基，X为O、S或CH.sub.2，W为CH或N，Q为取代芳基或取代杂芳基]及其在药学上可接受的盐，具有血小板源性生长因子受体自磷酸化抑制活性，用于含有这些化合物的药物组合物，以及用于治疗与异常细胞生长（如肿瘤）相关的疾病的方法。
• Benzophenone alpha-d-glycopyranosides, preparation and therapeutic use
  申请人：——

  公开号：US20030139349A1

  公开（公告）日：2003-07-24

  The invention concerns (i) [4-(4-cyanobenzyl)phenyl]&agr;-D-glycopyranosides of formula (I) wherein: the group &agr;-D-glycopyranosyl R represents a &agr;-D-glycopyranosyl, &agr;-D-galactopyranosyl. &agr;-D-mannopyranosyl, &agr;-D-arabinopyranosyl, &agr;-D-lyxopyranosyl, or &agr;-D-ribopyranosyl group: (ii) their esters resulting from the esterification of at least a OH function of each pyranosyl group with a C 2 -C 4 alkanoic or a cycloalkanoic acid, as novel industrial products. Said novel [4-(4-cyanobenzyl)phenyl]&agr;-D-glycopyranosides are useful in therapy for fighting against atheromatous plaque.

  该发明涉及公式(I)中的(4-(4-氰基苄基)苯基)α-D-葡萄糖苷，其中：α-D-葡萄糖苷R代表α-D-葡萄糖苷，α-D-半乳糖苷，α-D-阿拉伯糖苷，α-D-利索糖苷或α-D-核糖苷基团：(ii)它们是通过将每个吡喃糖基的至少一个OH功能与C2-C4烷酸或环烷酸酯化而得到的酯，作为新的工业产品。这些新型(4-(4-氰基苄基)苯基)α-D-葡萄糖苷在治疗动脉粥样硬化斑块方面具有用途。
• Novel .beta.-D-phenylthioxylosides, their method of preparation and
  申请人：Fournier Innovation et Synergie

  公开号：US04877808A1

  公开（公告）日：1989-10-31

  The present invention relates, by way of novel industrial products, to osides selected from the group consisting of: (i) the .beta.-D-phenylthioxylosides of the formula: ##STR1## in which: R represents a hydrogen atom, a halogen atom, a nitro group or a cyano group, A represents the sulfur atom or the oxygen atom, B represents a CH.sub.2, CHOH or CO group and Y represents the hydrogen atom or an acyl group; and (ii) epimers thereof when B is CHOH. These products are useful in therapy as antithrombotics.

  本发明涉及一种新型工业产品，属于从以下组中选择的糖苷类物质：(i) 公式为：##STR1## 其中：R代表氢原子、卤素原子、硝基或氰基；A代表硫原子或氧原子；B代表CH.sub.2、CHOH或CO基团；Y代表氢原子或酰基；以及(ii) 当B为CHOH时的对映体。这些产品在治疗中作为抗血栓药物非常有用。
• Benzophenone glycopyranosides, preparation and therapeutic use
  申请人：——

  公开号：US20030100515A1

  公开（公告）日：2003-05-29

  The invention concerns: (i) [4-(4-cyanobenzyl)phenyl]glycopyranosides of formula (I) wherein; the glycopyranosyl group R represents a &bgr;-D arabinopyranosyl, &bgr;-D-lyxopyranosyl, &bgr;-D-ribopyranosyl, &bgr;-D-mannopyranosyl, &bgr;-L-arabinopyranosyl, &bgr;-L-xylopyranosyl, &agr;-L-arabinopyranosyl, &agr;-L-xylopyranosyl or &bgr;-L-rhamnopyranosyl group; and (ii) their esters resulting from esterification of at least a OH function of each glycopyranosyl group with a C 2 -C 4 alkanoic or cycloalkanoic acid, as novel industrial products. Said novel [4-(4-cyanobenzyl)phenyl]glycopyranosides are useful in therapy for fighting against athermatous plaque.

  本发明涉及以下内容：（i）公式（I）中的[4-（4-氰基苯基）苷基吡喃糖苷]，其中；糖苷基R代表&bgr;-D阿拉伯糖苷、&bgr;-D-莱克糖苷、&bgr;-D-核糖苷、&bgr;-D-甘露糖苷、&bgr;-L-阿拉伯糖苷、&bgr;-L-木糖苷、&agr;-L-阿拉伯糖苷、&agr;-L-木糖苷或&bgr;-L-鼠李糖苷基团；以及（ii）它们的酯，所述酯是由至少一个糖苷基团的每个OH功能与C2-C4烷基或环烷基酸酯化而成的新型工业产品。这些新型的[4-（4-氰基苯基）苷基吡喃糖苷]在治疗抗动脉粥样硬化斑块方面具有用途。
• Photocatalytic oxidative coupling of terminal alkynes with p-benzoquinone to diaryl ketones by the Cu(I)-PS-POM assembling system through synergistic effect
  作者：Ting Zhang、Jiachen Jiao、Kaixin Guo、Lei Zhang、Chuanbao Zhang、Qiuxia Han

  DOI：10.1016/j.jcat.2023.115287

  日期：2024.1

  3,5-triazine (TPT) and binuclear Cu(I) units. CuW–TPT exhibits excellent light absorption ability and unique conductivity due to the coordination bond, strong π∙∙∙π interactions and H-bonding among Cu(I) ions, TPT moieties and [WO] in the defined spatial. The abundant exposed Cu(I) catalytic centres are conductive to activate phenylacetylene in situ formation Cu(I)-phenylacetylide, which then undergoes

  光催化C-C键形成是合成重要药物中间体二芳基酮的有效方法。在此，通过将氧化催化剂[WO]组装到由光敏剂（PS）4,6-三（4-吡啶基）-1构建的光活性MOF中，合成了一种新的基于多金属氧酸盐的金属有机框架（POMOF）CuW-TPT。 ,3,5-三嗪 (TPT) 和双核 Cu(I) 单元。由于Cu(I)离子、TPT部分和[WO]在特定空间内的配位键、强π∙∙∙π相互作用和H键，CuW-TPT表现出优异的光吸收能力和独特的电导率。丰富的暴露的Cu(I)催化中心有利于激活苯乙炔原位形成Cu(I)-苯乙酰化物，然后经过还原单电子转移(SET)过程得到Paterno的关键中间体Cu(II)-苯乙化物-Buchi (2+2) 与苯醌环加成形成不稳定的 Cu(II)-氧杂环丁烷环。它是从简单的起始原料（例如末端炔烃与对苯醌）合成带有羟基的二芳基酮的直接路线。