(E)-1-(2-hydroxyphenyl)-3-(thiophen-2-yl)prop-2-en-1-one | 2875-22-1

• 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: (E)-1-(2-hydroxyphenyl)-3-(thiophen-2-yl)prop-2-en-1-one
• 英文别名: 1-(2-Hydroxyphenyl)-3-(thiophen-2-yl)prop-2-en-1-one；(E)-1-(2-hydroxyphenyl)-3-thiophen-2-ylprop-2-en-1-one
• CAS: 2875-22-1
• 化学式: C₁₃H₁₀O₂S
• mdl: MFCD00175308
• 分子量: 230.287
• InChiKey: KROMWFWQAIFUPA-BQYQJAHWSA-N

物化性质

• 熔点：
  99-100 °C
• 沸点：
  407.1±45.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：

  (E)-1-(2-hydroxyphenyl)-3-(thiophen-2-yl)prop-2-en-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 5-(2-thienyl)-4,5-dihydro-3-(2-hydroxyphenyl)pyrazole
  参考文献：
  名称：

  Small molecules with structural similarities to siderophores as novel antimicrobials against Mycobacterium tuberculosis and Yersinia pestis

  摘要：

  Drugs inhibiting the iron scarcity-induced, siderophore-mediated iron-scavenging systems of Mycobacterium tuberculosis (Mtb) and Yersinia pestis (Yp) may provide new therapeutic lines of defense. Compounds with structural similarities to siderophores were synthesized and evaluated as antimicrobials against Mtb and Yp under iron-limiting conditions, which mimic the iron scarcity these pathogens encounter and must adapt to in the host, and under standard iron-rich conditions for comparison. New antimicrobials were identified, some of which warrant exploration as initial leads against potentially novel targets and small-molecule tools to assist in the elucidation of targets specific to iron-scarcity adapted Mtb and Yp. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.025
• 作为产物：
  描述：

  1-乙酰氧基-2-碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 对甲苯磺酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 48.0h， 生成 (E)-1-(2-hydroxyphenyl)-3-(thiophen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  De, Mahuya; Majumdar, Dyuti P.; Kundu, Nitya G., Journal of the Indian Chemical Society, 1999, vol. 76, # 11-12, p. 665 - 674

  摘要：

  DOI：

文献信息

• Screening of Biological Activities of a Series of Chalcone Derivatives against Human Pathogenic Microorganisms
  作者：İsa Karaman、Hayreddin Gezegen、M. Burcu Gürdere、Alparslan Dingil、Mustafa Ceylan

  DOI：10.1002/cbdv.200900027

  日期：2010.2

  In an effort to develop new antimicrobial agents, a series of chalcone derivatives, 3-60, were prepared by Claisen-Schmidt condensation of appropriate acetophenones and 2-furyl methyl ketones with appropriate aromatic aldehydes, furfural, and thiophene-2-carbaldehyde in an aqueous solution of NaOH and EtOH at room temperature. The synthesized compounds were characterized by means of their IR- and NMR-spectral

  为了开发新的抗菌剂，通过Claisen-Schmidt将适当的苯乙酮和2-呋喃基甲基酮与适当的芳族醛，糠醛和噻吩-2-甲醛缩合制备了一系列查尔酮衍生物3-60。室温下的NaOH和EtOH水溶液。合成的化合物通过其IR和NMR光谱数据以及元素分析进行​​表征。通过盘扩散法测试所有化合物的抗菌和抗真菌活性。对于活性最高的化合物，还确定了最低抑菌浓度（MIC）。
• Design, synthesis, and biological evaluation of <i>Helicobacter pylori</i> inosine 5′-monophosphate dehydrogenase (<i>Hp</i> IMPDH) inhibitors
  作者：Niteshkumar U. Sahu、Gayathri Purushothaman、Vijay Thiruvenkatam、Prashant S. Kharkar

  DOI：10.1002/ddr.21467

  日期：2019.2

  Inosine 5′‐monophosphate dehydrogenase (IMPDH) catalyzes a crucial step in the biosynthesis of guanine nucleotides. Being a validated target for immunosuppressive, antiviral, and anticancer drug development, lately it has been exploited as a promising target for antimicrobial therapy. Extending our previous work on Mycobacterium tuberculosis IMPDH, GuaB2, inhibitor development, we screened a set of

  肌苷5'-单磷酸脱氢酶（IMPDH）催化鸟嘌呤核苷酸生物合成中的关键步骤。作为免疫抑制，抗病毒和抗癌药物开发的有效靶标，最近它已被用作抗菌治疗的有希望的靶标。扩展了我们先前关于结核分枝杆菌IMPDH，GuaB2，抑制剂开发的工作，我们筛选了23种新的化学实体（NCE），它们被取代的黄酮（系列1）和1,2,3-三唑（系列2）核心结构所取代。体外幽门螺杆菌IMPDH（Hp IMPDH）和人IMPDH2（h IMPDH2）的抑制活性。所有NCE都具有可接受的分子，物理化学和毒性特性。的范围在10μM浓度下，Hp IMPDH和h IMPDH2的抑制分别为9–99.9％和16–57％。最有效的Hp IMPDH抑制剂25c的IC 50值为1.27μM ，无h IMPDH2抑制活性。中等强度，结构新颖的命中分子25c可作为进一步设计和开发高效Hp IMPDH抑制剂的先导。
• Extended Aromatic and Heteroaromatic Ring Systems in the Chalcone–Flavanone Molecular Switch Scaffold
  作者：Brian M. Muller、Theodore J. Litberg、Reid A. Yocum、Chanté A. Pniewski、Marc J. Adler

  DOI：10.1021/acs.joc.6b00986

  日期：2016.7.1

  substitutions alter the pH range in which rapid interconversion occurs. Herein, more impactful structural modifications were performed via alteration of the characteristic phenyl rings to alternative aromatic systems. It was determined that the scaffold was still viable after these changes and that the range of accessible midpoint pH values was markedly increased. To further explore the switch’s scope, scaffolds

  以前对邻羟基查耳酮/黄酮酮分子转换支架的研究表明，简单的取代改变了发生快速相互转化的pH范围。本文中，通过将特征性苯环改变为替代的芳族体系进行了更具影响力的结构修饰。确定在这些改变之后，支架仍然是可行的，并且可达到的中点pH值的范围显着增加。为了进一步探索开关的范围，还研究了能够发生多个开关事件的支架。
• Synthesis and Anti-Bacterial Activity of Some Heterocyclic Chalcone Derivatives Bearing Thiofuran, Furan, and Quinoline Moieties
  作者：Chang-Ji Zheng、Sheng-Ming Jiang、Zhen-Hua Chen、Bai-Jun Ye、Hu-Ri Piao

  DOI：10.1002/ardp.201100005

  日期：2011.10

  36 Novel heterocyclic chalcone derivatives were synthesized and tested for their anti‐bacterial activity. Some compounds presented good anti‐microbial activities against Gram‐positive bacteria (including the multidrug‐resistant clinical isolates). This class of compounds presented high potency against Streptococcus mutans, among which the derivatives F2 with an MIC of 2 µg/mL was as active as the standard

  合成了 36 种新型杂环查耳酮衍生物并测试了它们的抗菌活性。一些化合物对革兰氏阳性菌（包括耐多药临床分离株）具有良好的抗菌活性。这类化合物对变形链球菌表现出高效能，其中MIC为2 µg/mL的衍生物F2与标准药物（诺氟沙星）活性相同，但活性低于苯唑西林。所有化合物在 64 µg/mL 时均不抑制革兰氏阴性菌（大肠杆菌 CCARM 1924 或大肠杆菌 CCARM 1356）的生长。
• Design, Synthesis and Structural Confirmation of a Series of 2-(Thiophen-2-yl)- 4H-chromen-3-yl-sulfonate Derivatives and Preliminary Investigation of Their Antioxidant and Anticancer Potentials
  作者：Jialin Zang、Ming Bu、Jifang Yang、Lu Han、Zhen Lv

  DOI：10.21577/0103-5053.20210069

  日期：——

  series of novel 2-(thiophen-2-yl)-4H-chromen-3-yl-sulfonate derivatives (4a-4n) were synthesized and investigated for their in vitro free radical scavenging potential as well as cytotoxic efficacies against selected cancer cell lines. The cytotoxicity of the 4H-chromene derivatives (4a‑4n) was evaluated according to three human cancer cell lines (HepG2, A549, HeLa) by utilizing a 3-(4,5-dimethylthiazol-2-yl)-2

  一系列新颖的2-(噻吩-2-基)-4H-香豆素-3-基-磺酸酯衍生物（4a-4n）被合成并研究其体外自由基清除潜力以及对选定癌细胞系的细胞毒性效力。通过利用3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴化物（MTT）测定法评估了4H-香豆素衍生物（4a-4n）对三种人类癌细胞系（HepG2，A549，HeLa）的细胞毒性。因此，部分结果表明，与阳性对照物（4H-香豆素-4-酮和芹菜素）相比，某些化合物表现出更好的细胞毒性活性。其中，化合物4c-4g对三种人类癌细胞系表现出比阳性对照更好的训练（半数抑制浓度（IC50）= 3.87 ± 0.12至21.38 ± 0.52 μM）。此外，4H-香豆素衍生物（4a-4n）的提取物在抗氧化实验中对2,2-二苯基-1-苯基苦基肼（DPPH）和2,2'-双(3-乙基苯并噻唑啉-6-磺酸)（ABTS）表现出比阳性对照抗坏血酸更好的活性（IC50 = 12.72 ± 0.27，5.09 ± 0.21 μg mL-1）。因此，可以从生物测定结果中确认，整体结构设计以及适当的取代对于产生预期的生物效应至关重要。在这方面，还进行了光谱技术，如1H核磁共振（NMR）、13C NMR和高分辨质谱（HRMS）以确认最终结构。