3-(furan-2-yl)-1-(4-hydroxyphenyl)prop-2-en-1-one

• 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: 3-(furan-2-yl)-1-(4-hydroxyphenyl)prop-2-en-1-one
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: UROHUHJEHDQADU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(furan-2-yl)-1-(4-hydroxyphenyl)prop-2-en-1-one 在 水 作用下， 以 乙醇 为溶剂， 生成 3-[1-(4-carbamoyl-2-methylphenyl)-5-(4-hydroxyphenyl)-1H-pyrrol-2-yl]propionic acid ethyl ester
  参考文献：
  名称：

  Discovery of S-Nitrosoglutathione Reductase Inhibitors: Potential Agents for the Treatment of Asthma and Other Inflammatory Diseases

  摘要：

  S-Nitrosoglutathione reductase (GSNOR) regulates S-nitrosothiols (SNOs) and nitric oxide (NO) in vivo through catabolism of S-nitrosoglutathione (GSNO). GSNOR and the anti-inflammatory and smooth muscle relaxant activities of SNOs, GSNO, and NO play significant roles in pulmonary, cardiovascular, and gastrointestinal function. In GSNOR knockout mice, basal airway tone is reduced and the response to challenge with bronchoconstrictors or airway allergens is attenuated. Consequently, GSNOR has emerged as an attractive therapeutic target for several clinically important human diseases. As such, small molecule inhibitors of GSNOR were developed. These GSNOR inhibitors were potent, selective, and efficacious in animal models of inflammatory disease characterized by reduced levels of GSNO and bioavailable NO. N6022, a potent and reversible GSNOR inhibitor, reduced bronchoconstriction and pulmonary inflammation in a mouse model of asthma and demonstrated an acceptable safety profile. N6022 is currently in clinical development as a potential agent for the treatment of acute asthma.

  DOI：

  10.1021/ml200045s
• 作为产物：
  描述：

  1-(4-溴苯基)-3-(呋喃-2-基)丙-2-烯-1-酮 在 bis(η3-allyl-μ-chloropalladium(II)) 、 caesium carbonate 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(furan-2-yl)-1-(4-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  醛肟和羟基功能化查耳酮作为高效和选择性的单胺氧化酶 B 抑制剂

  摘要：

  评估了一组 30 种查尔酮衍生物，包括 19 种醛肟-查尔酮醚 (ACE) 和 11 种羟基-查尔酮 (HC)，这些衍生物之前使用 Pd 催化的 C-O 交叉偶联方法合成，用于评估它们对单胺氧化酶的抑制活性。 MAO)、胆碱酯酶 (ChE) 和 β-分泌酶 (BACE-1)。HC6 是最有效的 MAO-B 抑制剂，IC 50值为 0.0046 µM，选择性指数 (SI) 为 1,113。HC3 还有效抑制 MAO-B (IC 50  = 0.0067 µM) 并具有最高的 SI (1,455)。ACE7 和 ACE15 也是有效的 MAO-B 抑制剂（IC 50 分别 为 0.012 和 0.018 µM），SI 分别为 260 和 1,161。HC3 和 HC6 是 MAO-B 的可逆竞争性抑制剂，K i值分别为 0.0036 和 0.0013 μM。构效关系表明甲基和氟取代基有助于增加抑制和选择性。ACE7

  DOI：

  10.1016/j.molstruc.2021.131817

文献信息

• Phosphate transport inhibitors
  申请人：GelTex Pharmaceuticals, Inc.

  公开号：US20040019113A1

  公开（公告）日：2004-01-29

  Disclosed are compounds which have been identified as inhibitors of phosphate transport. Many of the compounds are represented by Structural Formula (I): Ar 1 —W—X—Y—Ar 2 ; or a pharmaceutically acceptable salt thereof. Ar 1 and Ar 2 are independently a substituted or unsubstituted aryl group or an optionally substituted five membered or six membered non-aromatic heterocylic group fused to an optionally substituted monocylic aryl group. W and Y are independently a covalent bond or a C1-C3 substituted or unsubstituted alkylene group. X is a heteroatom-containing functional group, an aromatic heterocyclic group, substituted aromatic heterocyclic group, non-aromatic heterocyclic group, substituted non-aromatic heterocyclic group, an olefin group or a substituted olefin group. Also disclosed are methods of treating a subject with a disease associated with hyperphosphatemia, as well as a disease mediated by phosphate-transport function. The methods comprise the step of administering an effective amount of the one of the compounds described above.

  本文披露了被识别为磷酸盐转运抑制剂的化合物。许多化合物由结构式(I)表示：Ar1—W—X—Y—Ar2；或其药用可接受的盐。Ar1和Ar2独立地是取代或未取代的芳基或可取代的五元或六元非芳香杂环基与可取代的单环芳基融合。W和Y独立地是共价键或C1-C3取代或未取代的烷基基团。X是含杂原子的官能团、芳香杂环基、取代芳香杂环基、非芳香杂环基、取代非芳香杂环基、烯烃基或取代烯烃基。还披露了治疗与高磷血症相关疾病以及磷酸盐转运功能介导的疾病的方法。该方法包括给予上述化合物之一的有效量。
• Synthesis,<i>in Vitro, and in Vivo</i>Biological Evaluation and Molecular Docking Analysis of Novel 3-(3-oxo-substitutedphenyl-3-)4-(2-(piperidinyl)ethoxy)phenyl)propyl)-2H-chromen-2-one Derivatives as Anti-breast Cancer Agents
  作者：Pritam N. Dube、Madhuri N. Waghmare、Santosh N. Mokale

  DOI：10.1111/cbdd.12696

  日期：2016.4

  coumarin–chalcones have been reported to exhibit antineoplastic, anti‐allergic, antihepatoprotective, and estrogenic activity. Herein, we have reported 3‐(3‐oxo‐substitutedphenyl‐3‐)4‐(2‐(piperidinyl)ethoxy)phenyl)propyl)‐2H‐chromen‐2‐one derivatives as a new class of compounds that exhibit selectivity for ER‐α binding along with antiproliferative and cytotoxic activity on human breast cancer cell line

  据报道，香豆素–查耳酮的类似物具有抗肿瘤，抗过敏，抗肝保护和雌激素活性。在本文中，我们报道了3-（3-氧代-取代苯基-3-）4-（2-（哌啶基乙氧基）苯基）丙基）-2-H-铬-2-2-1衍生物是一类对...具有选择性的新化合物。 ER‐ α结合以及对人乳腺癌细胞系的抗增殖和细胞毒性活性。对体内表现出显着抗雌激素受体α阳性（ER +）人乳腺癌细胞MCF-7和Zr-75-1活性的化合物进行体内筛选。Glide XP对接是针对设计的支架进行的，以优化其对ER- α抑制的结构要求。
• The synthesis and screening of the antimicrobial activity of some novel 3-(furan-2-yl)-1-(aryl)-3-(phenylthio) propan-1-one derivatives
  作者：Mustafa Ceylan、Meliha Burcu Gürdere、İsa Karaman、Hayreddin Gezegen

  DOI：10.1007/s00044-009-9279-4

  日期：2011.1

  addition of thiophenol to chalcones (1a–m) in the presence of a catalytic amount of KOt-Bu in solvent free conditions. In addition, the antibacterial and antifungal in vitro properties were tested against some human pathogenic microorganisms by employing the disk diffusion technique. A majority of compounds were remarkably active against several of the microorganisms. Compound 3i was determined to be the

  在无溶剂条件下，在催化量的KO t -Bu存在下，将硫代苯酚加到查耳酮（1a - m）中，制备了一系列苯硫酚加合物（3a - m）。此外，通过使用圆盘扩散技术测试了对某些人类病原微生物的抗菌和抗真菌体外性能。大多数化合物对几种微生物具有显着的活性。确定化合物3i是最具活性的化合物。
• Synthesis and in-vivo hypolipidemic activity of some novel substituted phenyl isoxazol phenoxy acetic acid derivatives
  作者：Santosh N. Mokale、Manjusha C. Nevase、Nikhil S. Sakle、Pritam N. Dube、Vishakha R. Shelke、Swati A. Bhavale、Afreen Begum

  DOI：10.1016/j.bmcl.2014.03.030

  日期：2014.5

  The present study was undertaken to evaluate in-vivo hypolipidemic activity of a novel series of 2-methyl-2-(substituted phenyl isoxazol)phenoxyacetic acid derivatives by triton induced hyperlipidemia in rats. The newly synthesized compounds 5a, 5d and 5g showed significant decrease in the serum TCH, TG, LDL and VLDL along with an increase in serum HDL levels as compared to standard drug Fenofibrate

  进行本研究以评价Triton诱导的高脂血症大鼠体内一系列新的2-甲基-2-（取代的苯基异恶唑）苯氧基乙酸衍生物的体内降血脂活性。与标准药物非诺贝特相比，新合成的化合物5a，5d和5g血清TCH，TG，LDL和VLDL显着降低，同时血清HDL水平升高。与对照组相比，治疗组的动脉粥样硬化指数也显着降低，而保护活性的百分比提高。
• An expeditious one-pot microwave facilitated versus conventional syntheses: in vivo biological screening and molecular docking studies of some 3,5-disubstituted-4,5-dihydro-(1H)-pyrazole derivatives
  作者：Avinash C. Tripathi、Savita Upadhyay、Sarvesh Paliwal、Shailendra K. Saraf

  DOI：10.1007/s00044-015-1489-3

  日期：2016.3

  order to ascertain the binding interactions of the synthesized derivatives to the MAO-A target protein, molecular docking was employed which demonstrated the key interactions with the amino acid residues Asn181, Phe208, Tyr69, Tyr197, Tyr444 and Met445 at the binding site. In addition, the most active derivatives 2i and 2b showed some imperative conserved interactions of the PDB co-crystal ligand 2Z5X

  通过使不同的芳族/杂芳族醛和酮发生反应，通过克莱森·史密特（Claisen Schmidt）缩合分两步反应，然后将生成的查耳酮与肼环合，合成了一系列3,5-二取代-2-吡唑啉衍生物（2a – 2t）使用常规方法和微波方法在碱存在下将水合。通过各种物理化学方法对合成的衍生物进行了表征，并通过红外，质谱，1 H-NMR，13 C-NMR光谱数据和元素分析确定了它们的化学结构。使用合适的动物模型评估了具有尾部悬浮试验和强迫游泳试验的抗抑郁药以及具有Elevated Plus Maze试验活性的抗焦虑药。化合物2i和2j通过减少两种试验中的固定时间来显示出显着的抗抑郁活性，而化合物2a和2b被发现具有良好的抗焦虑活性，方法是增加试验剂量下的手臂进入次数和开放手臂探索时间（ 50和100 mg / kg bw），分别与标准药物丙咪嗪和地西epa相比。为了确定合成的衍生物与MAO-A靶蛋白的结合相互作