3-(2,4-dimethoxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one | 18594-20-2

• 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-(2,4-dimethoxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one
• 英文别名: 3-(2,4-dimethoxy-phenyl)-1-thiophen-2-yl-propenone；1-<2.4-Dimethoxy-phenyl>-3--propen-(1)-on-(3)；1--3-<2.4-dimethoxy-phenyl>-propenon-(1)；3-<2.4-Dimethoxy-phenyl>-1--propen-1-on；1-<2,4-Dimethoxy-phenyl>-3-thienyl-propen-(1)-on-(3)；1-(2-Thienyl)-3-(2.4-dimethoxyphenyl)-propen-1-on；3-(2,4-Dimethoxyphenyl)-1-thiophen-2-ylprop-2-en-1-one
• CAS: 18594-20-2
• 化学式: C₁₅H₁₄O₃S
• 分子量: 274.34
• InChiKey: FSCVMQMQVJOKED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(2,4-dimethoxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one 在 sodium 、 四氯化锡 作用下， 以 硝基苯 、 苯 为溶剂， 反应 18.0h， 生成 (4R,5R)-ethyl 4-(2,4-dimethoxyphenyl)-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-carboxylate
  参考文献：
  名称：

  Synthesis of lignan conjugates via cyclopropanation: Antimicrobial and antioxidant studies

  摘要：

  Ethyl 2-(4-methoxyphenyl)-3-(thiophene-2-carbonyl)cyclopropanecarboxylates 2(a-f) and ethyl 4-aryl-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-carboxylates 4(a-f) were synthesized by simple procedure. The synthesized new compounds were screened in vitro for their antimicrobial and antioxidant activities. The compounds 2b and 4f showed excellent antibacterial activity; while 2b and 4f showed remarkable antifungal properties. The results of antioxidant activity studies revealed that compounds 4b and 4f manifested profound antioxidant potential. The docking studies were done for the final compounds. The ADME result indicates that all these molecules possess pharmaceutical properties in the range of 95% of drugs. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.06.005
• 作为产物：
  描述：

  2-乙酰基噻吩 、 2,4-二甲氧基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 3-(2,4-dimethoxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  合成4-4- [5-芳基-3-（噻吩-2-基）-4-5-二氢-1H-吡唑-1-基]苯磺酰胺类化合物对乙酰胆碱酯酶，碳酸酐酶I和II的合成，分子建模和生物学评估

  摘要：

  在这项研究中，合成了4- [5-芳基-3-（噻吩-2-基）-4,5-二氢-1 H-吡唑-1-基]苯磺酰胺，并对AChE，hCA I和AChE具有抑制作用。 hCA II进行了评估。朝向hCA I的化合物的K i值在24.2±4.6-49.8±12.8 n m的范围内，而朝向hCA II的K i值在37.3±9.0-65.3±16.7 n m的范围内。两种同工酶的乙酰唑酰胺的K i值分别为282.1±19.7 n m和103.60±27.6 n m。化合物抑制的AChE与ķ我在22.7±10.3-109.1±27.0 n中的范围米，而他克林具有ķi值为66.5±13.8 n m。还进行了M06-L / 6-31 + G（d，p）// AM1水平的电子结构计算和分子对接研究，以启发抑制机理并支持实验结果。通过分子特性计算获得的结果表明，这些化合物符合药物样特性。在这项研究中获得的实验和计算结果可能有助于设计针对hCA

  DOI：

  10.1111/cbdd.13149

文献信息

• Synthesis of Heterocyclic Chalcone Derivatives and Their Radical Scavenging Ability Toward 2,2-Diphenyl-1-Picrylhydrazyl (DPPH) Free Radicals
  作者：Ki-Jun Hwang、Ho-Seok Kim、In-Cheol Han、Beom-Tae Kim

  DOI：10.5012/bkcs.2012.33.8.2585

  日期：2012.8.20

  A series of heterocyclic chalcone derivatives bearing heterocycles such as thiophene or furan ring as an isostere of benzene ring were carefully prepared, and the influence of heterocycles on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities was systematically investigated. Structure-activity relationships (SAR) analysis showed that the activities of thiophene ring-containing chalcones

  精心制备了一系列杂环杂环查耳酮衍生物，如苯环的等排体噻吩或呋喃环，并系统研究了杂环对2,2-二苯基-1-苦基肼（DPPH）自由基清除活性的影响。构效关系（SAR）分析表明，含噻吩环的查尔酮的活性高于含呋喃环的查尔酮，并且与未取代的杂环相比，杂环甲基取代基的存在对活性的影响明显相反。 , 噻吩环的 4'-甲基基团活性增加，呋喃环的 3'-甲基基团活性降低。杂环的独特等排效应（即，
• Synthesis, molecular modeling, and biological evaluation of 4-[5-aryl-3-(thiophen-2-yl)-4,5-dihydro-1<i>H</i>-pyrazol-1-yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes
  作者：Cem Yamali、Halise Inci Gul、Abdulilah Ece、Parham Taslimi、Ilhami Gulcin

  DOI：10.1111/cbdd.13149

  日期：2018.4

  In this study, 4‐[5‐aryl‐3‐(thiophen‐2‐yl)‐4,5‐dihydro‐1H‐pyrazol‐1‐yl] benzenesulfonamides were synthesized, and inhibition effects on AChE, hCA I, and hCA II were evaluated. Ki values of the compounds toward hCA I were in the range of 24.2 ± 4.6‐49.8 ± 12.8 nm, while they were in the range of 37.3 ± 9.0‐65.3 ± 16.7 nm toward hCA II. Ki values of the acetazolamide were 282.1 ± 19.7 nm and 103.60 ± 27

  在这项研究中，合成了4- [5-芳基-3-（噻吩-2-基）-4,5-二氢-1 H-吡唑-1-基]苯磺酰胺，并对AChE，hCA I和AChE具有抑制作用。 hCA II进行了评估。朝向hCA I的化合物的K i值在24.2±4.6-49.8±12.8 n m的范围内，而朝向hCA II的K i值在37.3±9.0-65.3±16.7 n m的范围内。两种同工酶的乙酰唑酰胺的K i值分别为282.1±19.7 n m和103.60±27.6 n m。化合物抑制的AChE与ķ我在22.7±10.3-109.1±27.0 n中的范围米，而他克林具有ķi值为66.5±13.8 n m。还进行了M06-L / 6-31 + G（d，p）// AM1水平的电子结构计算和分子对接研究，以启发抑制机理并支持实验结果。通过分子特性计算获得的结果表明，这些化合物符合药物样特性。在这项研究中获得的实验和计算结果可能有助于设计针对hCA
• Synthesis of lignan conjugates via cyclopropanation: Antimicrobial and antioxidant studies
  作者：Kanchipura Ramachandrappa Raghavendra、Nagamallu Renuka、Vivek H. Kameshwar、Bharath Srinivasan、Kariyappa Ajay Kumar、Sheena Shashikanth

  DOI：10.1016/j.bmcl.2016.06.005

  日期：2016.8

  Ethyl 2-(4-methoxyphenyl)-3-(thiophene-2-carbonyl)cyclopropanecarboxylates 2(a-f) and ethyl 4-aryl-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-carboxylates 4(a-f) were synthesized by simple procedure. The synthesized new compounds were screened in vitro for their antimicrobial and antioxidant activities. The compounds 2b and 4f showed excellent antibacterial activity; while 2b and 4f showed remarkable antifungal properties. The results of antioxidant activity studies revealed that compounds 4b and 4f manifested profound antioxidant potential. The docking studies were done for the final compounds. The ADME result indicates that all these molecules possess pharmaceutical properties in the range of 95% of drugs. (C) 2016 Elsevier Ltd. All rights reserved.
• Design and synthesis of isoniazid-based pyrazolines as potential inhibitors of Mycobacterium tuberculosis with promising radical scavenging action: In-vitro and in-silico evaluations
  作者：Jyoti Rasgania、Renu Gavadia、Mandira Varma-Basil、Varsha Chauhan、Sanjay Kumar、Satbir Mor、Devender Singh、Komal Jakhar

  DOI：10.1016/j.molstruc.2023.136657

  日期：2024.1