3-(4-hydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one | 19143-12-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(4-hydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one
• 英文别名: 3-(4-Hydroxyphenyl)-1-thiophen-2-ylprop-2-en-1-one
• CAS: 19143-12-5
• 化学式: C₁₃H₁₀O₂S
• 分子量: 230.287
• InChiKey: MCMNCKMDUDICKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one 在 一水合肼 、 三乙胺 作用下， 以 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 5.0h， 生成 Piperidine-1-carbodithioic acid 2-[5-(4-hydroxy-phenyl)-3-thiophen-2-yl-4,5-dihydro-pyrazol-1-yl]-2-oxo-ethyl ester
  参考文献：
  名称：

  部分1-[(N,N-二取代硫代甲酰氨基甲酰硫基)乙酰基]-3-(2-噻吩基)-5-芳基-2-吡唑啉衍生物的合成及抗菌抗真菌活性研究

  摘要：

  14 种新的 1 - [(N, N - 二取代硫代氨基甲酰硫基) 乙酰基] -3- (2- 噻吩基) -5- 芳基 - 2- 吡唑啉衍生物 (7a - n) 通过与 1- (氯乙酰基) -3- ( 2-噻吩基）-5-芳基-2-吡唑啉（5a-g）和适当的N，N-二取代二硫代氨基甲酸（6a，b）的钠盐。通过元素分析、UV、IR、1H-NMR和FAB+-MS光谱数据确认合成化合物的结构。它们对普通变形杆菌 (NRRL B-123)、大肠杆菌 (NRRL B-3704)、嗜水气单胞菌（安卡拉大学兽医学院）、鼠伤寒沙门氏菌 (NRRL B-4420)、粪链球菌 (NRRL B-1461) 的抗菌活性), 藤黄微球菌 (NRLL B-4375) 进行了调查，在本次调查中，说明了显着的活性水平。发现这些化合物对白色念珠菌和球形念珠菌（从 Osmangazi Uni. Fac. Of Medicine 获

  DOI：

  10.1002/ardp.200400935
• 作为产物：
  描述：

  4-(四氢-吡喃-2-基氧基)-苯甲醛 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 生成 3-(4-hydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent

  摘要：

  In this study, thirty-eight chalcone analogs were synthesized and evaluated for nitric oxide (NO) inhibition activity on RAW 264.7 cells. Among these compounds, chalcones bearing furanyl group showed remarkable anti-inflammatory activity. Both compounds 2d and 2j were identified as the most potent NO inhibitor on IFN-gamma/LPS-activated RAW 264.7 cells. In order to examine the structure-activity relationship, a 3D QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method on the selected chalcones. Partial least square analysis produced a statistically coherent model with good predictive value, r (2) = 0.989 and a good cross validated value, q (2) = 0.583.

  DOI：

  10.1007/s00044-011-9706-1

文献信息

• Microwave-assisted synthesis and bioevaluation of new sulfonamides
  作者：Halise Inci Gul、Cem Yamali、Fatma Yesilyurt、Hiroshi Sakagami、Kaan Kucukoglu、Ilhami Gulcin、Mustafa Gul、Claudiu T. Supuran

  DOI：10.1080/14756366.2016.1254207

  日期：2017.1.1

  In this study, 4-[5-(4-hydroxyphenyl)-3-aryl-4,5-dihydro-1H-pyrazol-1-yl]benzenesulfonamide derivatives (8-14) were synthesized for the first time by microwave irradiation and their chemical structures were confirmed by 1H NMR, 13C NMR and HRMS. Cytotoxic activities and inhibitory effects on carbonic anhydrase I and II isoenzymes of the compounds were investigated. The compounds 9 (PSE = 4.2), 12 (PSE = 4

  在这项研究中，首次通过微波辐射合成了4- [5-（4-羟基苯基）-3-芳基-4,5-二氢-1H-吡唑-1-基]苯磺酰胺衍生物（8-14），它们的化学结构通过1 H NMR，13 C NMR和HRMS证实。研究了该化合物的细胞毒性活性及其对碳酸酐酶I和II同工酶的抑制作用。在细胞毒性实验中具有最高效能选择性表达（PSE）值的化合物9（PSE = 4.2），化合物12（PSE = 4.1）和13（PSE = 3.9）和化合物13（针对hCA I的Ki（3.73±0.91 nM））在CA抑制研究中，具有最低Ki值的14个化合物（对hCA II而言，Ki = 3.85±0.57 nM）可被视为进一步研究的先导化合物。
• Synthesis, Pharmacological, and Biological Screening of Novel Derivatives of Benzodiazepines
  作者：K. Ishwar Bhat、Manoj Kumar Singh Chauhan、Abhishek Kumar、Pankaj Kumar

  DOI：10.1002/jhet.1722

  日期：2014.7

  A series of novel 4‐(substituted phenyl)‐2‐(thiophen‐2‐yl)‐2,3‐dihydro‐1H‐benzo[b][1,4]diazepine have been synthesized from 3‐(substituted phenyl)‐1‐(thiophen‐2‐yl)prop‐2‐en‐1‐one. 3‐(Substituted phenyl)‐1‐(thiophen‐2‐yl)prop‐2‐en‐1‐one was prepared by condensing 2‐acetyl thiophene with various aromatic aldehydes in the presence of 20% NaOH as base. Different 3‐(substituted phenyl)‐1‐(thiophen‐2‐yl)prop‐2‐en‐1‐one

  由3-（取代的苯基）合成了一系列新颖的4-（取代的苯基）-2-（噻吩-2-基）-2,3-二氢-1 H-苯并[b] [1,4]二氮杂-1（噻吩-2-基）prop-2-en-1。3-（取代的苯基）-1-（噻吩-2-基）丙-2-烯-1-酮是通过在20％NaOH为碱的情况下将2-乙酰基噻吩与各种芳香醛缩合而制得的。在NaOH为碱的情况下，用邻苯二胺环化不同的3-（取代的苯基）-1-（噻吩-2-基）丙-2-烯-1-烯-生成4-（取代的苯基）-2- （噻吩-2-基）-2,3-二氢-1 H-苯并[b] [1,4]二氮杂derivatives衍生物。合成化合物的结构通过IR确证，11 H NMR，质谱和元素分析。已对所有化合物的抗微生物，止痛和抗炎活性进行了筛选。
• Thieny/Furanyl-hydroxyphenylpropenones as Inhibitors of LPS-induced ROS and NO Production in RAW 264.7 Macrophages, and Their Structure-Activity Relationship Study
  作者：Tara Man Kadayat、Mi Jin Kim、Tae-Gyu Nam、Pil-Hoon Park、Eung-Seok Lee

  DOI：10.5012/bkcs.2014.35.8.2481

  日期：2014.8.20

  Twelve thienyl/furanyl-hydroxyphenylpropenones were systematically designed and synthesized, and evaluated for their inhibitory effect on LPS-induced ROS and NO production in RAW 264.7 macrophages. Compound 11 displayed the most significant inhibitory activity of LPS-induced ROS and NO production in RAW 264.7 macrophages. Structure-activity relationship study indicated that para-hydroxyphenyl moiety plays an important role for inhibitory activities on both LPS-induced ROS and NO production as well as 3-thienyl moiety on molecule.

  系统设计并合成了十二种噻吩/呋喃羟基苯丙烯酮，并评估其对LPS诱导的RAW 264.7巨噬细胞中ROS和NO产生的抑制作用。化合物11在抑制LPS诱导的RAW 264.7巨噬细胞中ROS和NO产生方面表现出最显著的抑制活性。结构-活性关系研究表明，para-羟基苯基部分在抑制LPS诱导的ROS和NO产生方面起着重要作用，而分子中的3-噻吩部分也同样关键。
• Mechanochemical synthesis of cyclohexenones and indazoles as potential antimicrobial agents
  作者：Abdullah S. Al-Bogami

  DOI：10.1007/s11164-015-2379-5

  日期：2016.6

  Mechanical force from ball milling was used for efficient and quantitative preparation of a series of cyclohexenones and indazoles. The method is environmentally friendly, simple, short, and solventless. Unambiguous structural assignments of the obtained cyclohexenones were achieved based on single-crystal X-ray diffraction. The structures of the indazoles were characterized using Fourier-transform infrared spectroscopy, hydrogen and carbon nuclear magnetic resonance (NMR) spectroscopy, homonuclear correlation spectroscopy, distortionless enhancement by polarization transfer (DEPT) NMR, and gas chromatography–mass spectrometry. The synthesized compounds were screened for antimicrobial activity against two Gram-positive bacteria (methicillin-resistant staphylococcus aureus and Micrococcus luteus), three Gram-negative bacteria (Klebsiella oxytoca, Salmonella typhimurium, and Shigella sonnei), and three fungi (Candida albicans, Aspergillus niger, and A. flavus). The effects that different substituents on the synthesized compounds had on the antibacterial and antifungal activities were evaluated. Cyclohexenone derivatives with thiophene moiety at 4-position showed antibacterial activity comparable to the antibiotic tetracycline.

  利用球磨产生的机械力高效、定量地制备了一系列环己烯酮和吲唑。该方法环保、简便、时间短且无溶剂。根据单晶 X 射线衍射，获得的环己烯酮的结构分配非常明确。利用傅立叶变换红外光谱、氢和碳核磁共振（NMR）光谱、同核相关光谱、无畸变极化传递增强（DEPT）NMR 和气相色谱-质谱法对吲唑类化合物的结构进行了表征。对合成的化合物进行了抗菌活性筛选，以检测其对两种革兰氏阳性菌（耐甲氧西林金黄色葡萄球菌和黄体微球菌）、三种革兰氏阴性菌（克雷伯菌、鼠伤寒沙门氏菌和宋内志贺氏菌）以及三种真菌（白色念珠菌、黑曲霉和黄曲霉）的抗菌活性。评估了不同取代基对合成化合物抗菌和抗真菌活性的影响。在 4 位上带有噻吩分子的环己酮衍生物显示出与抗生素四环素相当的抗菌活性。
• Mesomorphism Dependence of Chalconyl Derivatives on Position of -CH=CH- Unit
  作者：P. K. Rakhasia、G. N. Bhola、U. C. Bhoya

  DOI：10.1080/15421406.2015.1106280

  日期：2016.2.11

  effects of molecular structure on liquid crystal (LC) properties and the degree of liquid crystallinity. The C1 to C6 homologues are not liquid crystals, the C7 homologue is enantiotropic nematic, the C8 to C16 homologues are smectogenic in addition to nematogenic (C8 & C10 monotropic smectic). The texture of nematic phases are threaded or Schlieren and that of the smectic phase are fan-shaped smectic-A

  摘要 为了理解和确定分子结构对液晶 (LC) 特性和液晶度的影响，合成并研究了一系列新的同源杂环查尔酮酯（C1 至 C16）。C1 至 C6 同系物不是液晶，C7 同系物是对映向列型，C8 至 C16 同系物除了致线虫（C8 和 C10 单向近晶）外，还具有近近相。向列相的织构为螺纹或纹影，近晶相的织构为扇形近晶-A或近晶-C型。转变温度和中间相的织构由配备加热台的光学偏光显微镜确定。相图中显示系列相行为的过渡曲线 Cr-I/M、Sm-N/N-Sm 和 NI 表现正常。近晶和向列的热稳定性分别为 115.66°C 和 126.83°C，它们的中间相长度最小到最大分别为 6.3 到 12.9°C 和 6.9°C 到 17.4°C。分析和光谱数据证实了同系物的分子结构。将当前新型系列的 LC 特性与结构相似的其他报道系列进行比较。