3-Oxo-1-(4-dimethylamino-phenyl)-3-(3-hydroxy-phenyl)-propen-(1) | 72700-07-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-Oxo-1-(4-dimethylamino-phenyl)-3-(3-hydroxy-phenyl)-propen-(1)
• 英文别名: 3-[4-(Dimethylamino)phenyl]-1-(3-hydroxyphenyl)-2-propen-1-one；3-[4-(dimethylamino)phenyl]-1-(3-hydroxyphenyl)prop-2-en-1-one
• CAS: 72700-07-3
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: VZXBTKOMYVEZHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Oxo-1-(4-dimethylamino-phenyl)-3-(3-hydroxy-phenyl)-propen-(1) 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 3-(5-(4-(dimethylamino)phenyl)-4,5-dihydroisoxazol-3-yl)phenol
  参考文献：
  名称：

  Synthesis, Characterization and Biological Evaluation of Some New Isoxazoline Derivatives

  摘要：

  异噁唑啉是一类独特的含氮和含氧的五元杂环化合物，这类化合物在生物化学中具有重要意义。异噁唑啉被认为是最有效的抗菌化合物之一。研究发现，异噁唑啉衍生物对结核分枝杆菌具有显著的抗结核活性。由于结核药物耐药性事件的增加，抗结核药物发现的目标变得更加具有挑战性。本研究旨在合成高效的抗结核异噁唑啉衍生物。通过在羟胺 hydrochloride 存在下对取代的查尔酮衍生物进行环化，合成了不同取代的异噁唑啉衍生物。合成的衍生物通过熔点、薄层色谱 (TLC)、傅里叶变换红外光谱 (FT-IR)、质子核磁共振 (1H NMR) 和质谱 (MS) 进行表征。合成的化合物在体外抗结核活性方面与异烟肼进行了比较，获得了相似的抗结核活性。

  DOI：

  10.14233/ajchem.2013.12899
• 作为产物：
  描述：

  3-羟基苯乙酮 、 对二甲氨基苯甲醛 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 3-Oxo-1-(4-dimethylamino-phenyl)-3-(3-hydroxy-phenyl)-propen-(1)
  参考文献：
  名称：

  Synthesis, Characterization and Biological Evaluation of Some New Isoxazoline Derivatives

  摘要：

  异噁唑啉是一类独特的含氮和含氧的五元杂环化合物，这类化合物在生物化学中具有重要意义。异噁唑啉被认为是最有效的抗菌化合物之一。研究发现，异噁唑啉衍生物对结核分枝杆菌具有显著的抗结核活性。由于结核药物耐药性事件的增加，抗结核药物发现的目标变得更加具有挑战性。本研究旨在合成高效的抗结核异噁唑啉衍生物。通过在羟胺 hydrochloride 存在下对取代的查尔酮衍生物进行环化，合成了不同取代的异噁唑啉衍生物。合成的衍生物通过熔点、薄层色谱 (TLC)、傅里叶变换红外光谱 (FT-IR)、质子核磁共振 (1H NMR) 和质谱 (MS) 进行表征。合成的化合物在体外抗结核活性方面与异烟肼进行了比较，获得了相似的抗结核活性。

  DOI：

  10.14233/ajchem.2013.12899

文献信息

• Structure-activity relationship study of antitrypanosomal chalcone derivatives using multivariate analysis
  作者：Kaio S. Gomes、Thais A. da Costa-Silva、Igor H. Oliveira、Andrea M. Aguilar、Diogo Oliveira-Silva、Miriam Uemi、Wender A. Silva、Lennine R. Melo、Carlos Kleber Z. Andrade、Andre G. Tempone、João L. Baldim、João Henrique G. Lago

  DOI：10.1016/j.bmcl.2019.04.020

  日期：2019.6

  a series of 36 chalcone derivatives were synthesized and tested against trypomastigotes of Trypanosoma cruzi. In addition, a detailed investigation on their molecular features was performed. The obtained results suggest that certain molecular features are fundamental for an efficient antitrypanosomal potential of chalcones, such as allylic groups, α,β-unsaturated carbonyl system, and aromatic hydroxyl

  恰加斯病是几种被忽视的疾病之一，其化学治疗药物的数量减少了，其中包括高毒性化合物苯硝唑和硝呋替莫。从这个意义上讲，天然产物代表了一种发现新的生物活性化合物的进口支架，其中查耳酮因其抗胰锥虫的潜力而成为有前途的代表。在这项工作中，合成了一系列36种查尔酮衍生物，并针对克氏锥虫的拟鞭毛体进行了测试。另外，对它们的分子特征进行了详细的研究。获得的结果表明，某些分子特征是有效的查耳酮类抗胰锥管潜在能力的基础，例如烯丙基，α，β-不饱和羰基体系和芳族羟基。
• Differential Effects of Structural Modifications on the Competition of Chalcones for the PIB Amyloid Imaging Ligand-Binding Site in Alzheimer’s Disease Brain and Synthetic Aβ Fibrils
  作者：Marina Y. Fosso、Katie McCarty、Elizabeth Head、Sylvie Garneau-Tsodikova、Harry LeVine

  DOI：10.1021/acschemneuro.5b00266

  日期：2016.2.17

  the parent member of the chalcone family generally improved the binding affinity of chalcones toward ADPBC and synthetic fibrils F40 and F42. Furthermore, any substitution on ring I at the ortho-position of the carbonyl group greatly decreases the binding affinity of the chalcones, potentially as a result of steric hindrance. Together with the finding that neither our chalcones nor PIB interact with the

  阿尔茨海默氏病（AD）是一种复杂的脑部疾病，至今仍不清楚。为了了解不同的临床体内成像配体与AD脑多态性病理特征结合的重要性，需要定义与其特异性结合位点相互作用的配体的分子特征。在这里，我们观察到tri化的匹兹堡化合物B（3 H-PIB）可以从合成的Aβ（1-40）和Aβ（1-42）纤维以及从人AD脑（ADPBC）纯化的分子结合的PIB结合复合物中置换出来包含查耳酮结构支架。我们评估了查耳酮支架上的取代如何改变其置换3的能力H-PIB来自合成纤维和ADPBC。通过比较未取代的核心查耳酮骨架以及在各个位置处溴和甲基取代的影响，我们发现在查耳酮家族母体的羰基（环I）附近的环上连接羟基通常会改善结合查耳酮对ADPBC和合成纤维F 40和F 42的亲和力。此外，邻位环I上的任何取代羰基的-位极大地降低了查耳酮的结合亲和力，这可能是空间位阻的结果。这些发现与我们的查尔酮或PIB都不与刚果红/ X-34
• Mesomorphic study of novel chalconyl-ester-based nonisomeric series: Synthesis and characterization
  作者：Vinay S. Sharma、R. B. Patel

  DOI：10.1080/15421406.2016.1262680

  日期：2017.1.22

  A newly designed homologues series: 3-(3-(4-(Dimethylamino) phenyl) acrylonyl) phenyl 3-(4-n-alkoxyphenyl) acrylate has been synthesized and studied through chalconyl ester linking group at (meta) position. The series consists of 13 compounds, in which C-1 to C-4 homologue are nonliquid crystal, while C-5 to C-18 exhibit nematic phase, and C-12 to C-18 shows smectic and nematic phase with enantiotropically manner. Mesophase image of present compounds are rod like, needle and threaded type textures investigated by POM. All this compounds were characterized by elemental analysis, FT-IR and H-1 NMR. The mesomorphism is measured by POM, DSC, and molecular packing is determined by XRD technique. The following synthesized chalconyl ester-based compounds C-5 to C-12 shows antibacterial as well as antifungal activity compared with corresponding standard drugs. Analytical and spectral data confirmed the molecular structures of homologous series.[GRAPHICS]
• Synthesis, Characterization and Biological Evaluation of Some New Isoxazoline Derivatives
  作者：Dinesh K. Jain、Neeraj Goyal、Upendra Bhadoriya

  DOI：10.14233/ajchem.2013.12899

  日期：——

  Isoxazoline represents a unique class of nitrogen- and oxygen-containing five-membered heterocycles, a class of compounds of great importance in biological chemistry. Isoxazoline is considered as one of the most potent antimicrobial compound. Isoxazoline derivatives have been found to possess appreciable antitubercular activity against Mycobacterium tuberculosis. The object of antitubercular drug discovery has become a subject of greater challenge due to increasing incidences of tubercular drug resistance. The study aimed to synthesize potent antitubercular isoxazline derivatives. Different substituted isoxazoline derivatives have been synthesized by cyclization of substituted chalcone derivatives in presence of hydroxylamine hydrochloride. Synthesized derivatives were characterized by melting point, TLC, FT-IR, 1H NMR and MS spectroscopy. Synthesized conjugates were evaluated for in vitro antitubercular activity against M. tuberculosis. Comparable antitubercular activity was obtained as compared to isoniazide.

  异噁唑啉是一类独特的含氮和含氧的五元杂环化合物，这类化合物在生物化学中具有重要意义。异噁唑啉被认为是最有效的抗菌化合物之一。研究发现，异噁唑啉衍生物对结核分枝杆菌具有显著的抗结核活性。由于结核药物耐药性事件的增加，抗结核药物发现的目标变得更加具有挑战性。本研究旨在合成高效的抗结核异噁唑啉衍生物。通过在羟胺 hydrochloride 存在下对取代的查尔酮衍生物进行环化，合成了不同取代的异噁唑啉衍生物。合成的衍生物通过熔点、薄层色谱 (TLC)、傅里叶变换红外光谱 (FT-IR)、质子核磁共振 (1H NMR) 和质谱 (MS) 进行表征。合成的化合物在体外抗结核活性方面与异烟肼进行了比较，获得了相似的抗结核活性。
• New chalcone-3-<i>O</i>-glycoside derivatives: Synthesis and characterization
  作者：Gonca Çelik

  DOI：10.1177/1747519820915165

  日期：2020.9

  Seven novel carbohydrate conjugates of new chalcone-3-O-glycosides were synthesized and characterized. Starting from the substituted 3′-hydroxyarylmethylacetophenone derivatives (chalcones) with α-acetobromoglucose in anhydrous acetone were synthesized 2,3,4,6-tetra-O-acetyl-3′-O-β-d-glucopyranosyloxychalcones. Deblocking the latter with CH3ONa in dry methanol results in substituted chalcone-3-O-glycosides

  合成并表征了七种新型查耳酮-3-O-糖苷的新型碳水化合物缀合物。从在无水丙酮中用α-乙酰溴葡萄糖取代的 3'-羟基芳甲基苯乙酮衍生物（查耳酮）开始合成 2,3,4,6-四-O-乙酰基-3'-O-β-d-吡喃葡萄糖氧基查耳酮。后者在无水甲醇中用 CH3ONa 解封会产生取代的查尔酮-3-O-糖苷（3'-O-β-d-吡喃葡萄糖基氧查尔酮）。新合成的查尔酮-3-O-糖苷的结构基于 1H 核磁共振、13C 核磁共振、质谱和傅里叶变换红外光谱进行了表征。