1-(4-fluorophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one | 395072-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(4-fluorophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
• CAS: 395072-47-6
• 化学式: C₁₇H₁₂FNO
• 分子量: 265.287
• InChiKey: WWPQCBWWSLFQME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one 在 aluminum oxide 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 0.23h， 以74.62%的产率得到5-(1H-indol-3-yl)-3-(4-fluorophenyl)-4,5-dihydroisoxazoline
  参考文献：
  名称：

  An Efficient Method for the Synthesis of Isoxazolines Under Microwave Irradiation and Solvent-Free Conditions

  摘要：

  报道了一种在无溶剂条件下从取代的 1-(1H-吲哚-3-基)-3-(取代的芳基)-丙-1-烯-3-酮和盐酸羟胺开始合成新异恶唑啉衍生物的简便方法条件和微波辐射。与传统合成方法相比，该方法具有反应时间短、产率中等至优异等优点。化合物的结构经1H NMR、IR、质谱和元素（C、H、N）分析证实。

  DOI：

  10.14233/ajchem.2013.13662
• 作为产物：
  描述：

  3-吲哚甲醛 、 4-氟苯乙酮 在 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 1-(4-fluorophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, Characterisation, Molecular Docking, Anti-microbial and Anti-diabetic Screening of Substituted 4-indolylphenyl-6-arylpyrimidine-2-imine Derivatives

  摘要：

  研究的目的是合成一系列新颖的(E)-2-(4-(1H-吲哚-3-基)-6-对取代苯基嘧啶-2-基)二甲基胍衍生物，评估它们的分子对接研究、抗菌和抗糖尿病活性。在所有合成的化合物（11a-g）中，化合物11a表现出优异的CDOCKER能量（-11.36 kcal/mol）。整个化合物（11a-g）对被测试的微生物表现出非常好的抗菌活性。在体外抗糖尿病研究中，化合物（11a、11c和11g）表现出更高的α-淀粉酶和α-葡萄糖苷酶抑制活性。在体内抗糖尿病活动中，合成的化合物（11a-g）（10 mg/kg, 口服）通过成年雄性白化病鼠通过链脲佐菌素（60 mg/kg, ip）-烟酰胺（120 mg/kg, 口服）诱导模型进行研究，这些衍生物在空腹血糖水平方面与甲双胍盐酸盐（一种有效且知名的抗糖尿病药物）相比表现出显著的效果。

  DOI：

  10.1055/s-0043-106444

文献信息

• Metal-free C(sp3)–H bond activation: first synthesis of diaryl-pyridinium-azaarene-butenolate zwitterionic salts on chalcones
  作者：Atul Kumar、Lalit Prakash Gupta、Mukesh Kumar

  DOI：10.1039/c3ra42761g

  日期：——

  An efficient route for the synthesis of diaryl-pyridinium-azaarene-butenolate zwitterionic derivatives via metal-free, iodine-mediated C(sp3)–H bond activation of alkyl-azaarenes on addition to the α,β-unsaturated carbonyls has been reported.

  报道了一种高效路线，用于通过无金属、碘介导的C(sp3)–H键活化，合成二芳基吡啶鎓-氮杂烯-丁烯酸酯的两性离子衍生物，反应是在烷基氮杂芳烃与α,β-不饱和羰基化合物反应时进行的。
• Synthesis and carbonic anhydrase inhibition studies of sulfonamide based indole-1,2,3-triazole chalcone hybrids
  作者：Priti Singh、Baijayantimala Swain、Pavitra S. Thacker、Dilep Kumar Sigalapalli、P. Purnachander Yadav、Andrea Angeli、Claudiu T. Supuran、Mohammed Arifuddin

  DOI：10.1016/j.bioorg.2020.103839

  日期：2020.6

  classes of classical carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. A novel series of indolylchalcones incorporating benzenesulfonamide-1,2,3-triazole (6a-q) has been synthesized by click chemistry reaction and investigated for hCA inhibitory activity against a panel of human carbonic anhydrases (hCAs). Most of these newly synthesized compounds exhibited interesting inhibition constants, in the nanomolar

  磺酰胺是最有前景的经典碳酸酐酶（CA，EC 4.2.1.1）抑制剂之一。通过点击化学反应合成了一系列新的吲哚基查耳酮并入苯磺酰胺-1，2，3-三唑（6a-q），并研究了其对人类碳酸酐酶（hCAs）的抑制作用。这些新合成的化合物大多数在纳摩尔范围内表现出令人感兴趣的抑制常数，其中一些衍生物对hCA I亚型的作用比标准药物乙酰唑胺（AAZ）强。在测试的化合物中，化合物6d（18.8 nM），6q（38.3 nM）和6e（50.4 nM）的效价分别比AAZ抗hCA I同工型高13、6和5倍。化合物6o，6m和6f有效抑制同工型hCA XII，KI的范围为10-41.9 nM。几种化合物还对同工型hCA II和hCA IX具有活性，KIs低于100 nM。这些吲哚基查耳酮-苯磺酰胺-1,2,3-三唑杂化物可能被认为是hCA I-选择性抑制剂的潜在先导。
• Acid-Modulated Construction of Cyclopenta[<i>b</i>]indole and Cyclohepta[<i>b</i>]indole via Unprecedented C3/C2 Carbocation Rearrangement
  作者：Shao-Cong Zhan、Jing Sun、Qiu Sun、Ying Han、Chao-Guo Yan

  DOI：10.1021/acs.joc.2c03094

  日期：2023.5.5

  p-TsOH-catalyzed cycloaddition of various 3-vinylindoles and (indol-2-yl)diphenylmethanols in acetonitrile gave the functionalized cyclopenta[b]indoles in good yields and with high diastereoselectivity via [3 + 2] cycloaddition reaction. More importantly, FeCl3-catalyzed annulation reaction afforded unexpected functionalized cyclohepta[1,2-b:4,5-b′]diindoles in satisfactory yields, in which a formal [4 + 3] cycloaddition

  p -TsOH 催化的各种 3-乙烯基吲哚和 (indol-2-yl) 二苯基甲醇在乙腈中的环加成反应以良好的产率和高非对映选择性通过 [3 + 2] 环加成反应得到官能化的环戊[ b ] 吲哚。更重要的是，FeCl 3催化的环化反应以令人满意的产率提供了意想不到的功能化环庚[1,2- b :4,5- b ']二吲哚，其中正式的 [4 + 3] 环加成和前所未有的 C3/C2 碳阳离子重排首先通过单晶结构的测定来证实。
• Synthesis and biological evaluation of indolyl chalcones as antitumor agents
  作者：Dalip Kumar、N. Maruthi Kumar、Kanako Akamatsu、Eriko Kusaka、Hiroshi Harada、Takeo Ito

  DOI：10.1016/j.bmcl.2010.05.016

  日期：2010.7

  A series of indolyl chalcones were synthesized and evaluated in vitro for their anticancer activity against three human cancer cell lines. Compounds 3b-d, 3h, 3j, 3l, 3m, 4g, and 4j showed significant cytotoxicity, particularly, indolyl chalcones 3l and 3m were identified as the most potent and selective anticancer agents with IC50 values 0.03 and 0.09 mu M, against PaCa-2 cell line, respectively. (c) 2010 Elsevier Ltd. All rights reserved.
• First‐in‐class pyrido[2,3‐ <i>d</i> ]pyrimidine‐2,4(1 <i>H</i> ,3 <i>H</i> )‐diones against leishmaniasis and tuberculosis: Rationale, in vitro, ex vivo studies and mechanistic insights
  作者：Deepthi Ramesh、Deblina Sarkar、Annu Joji、Monica Singh、Amaresh K. Mohanty、Balaji G. Vijayakumar、Mitali Chatterjee、Dharmarajan Sriram、Suresh K. Muthuvel、Tharanikkarasu Kannan

  DOI：10.1002/ardp.202100440

  日期：2022.4

  AbstractPyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones were synthesized, for the first time, from indole chalcones and 6‐aminouracil, and their ability to inhibit leishmaniasis and tuberculosis (Tb) infections was evaluated. The in vitro antileishmanial activity against promastigotes of Leishmania donovani revealed exceptional activities of compounds 3, 12 and 13, with IC50 values ranging from 10.23 ± 1.50 to 15.58 ± 1.67 µg/ml, which is better than the IC50 value of the standard drug pentostam of 500 μg/ml. The selectivity of the compounds towards Leishmania parasites was evaluated via ex vivo studies in Swiss albino mice. The efficiency of these compounds against Tb infection was then evaluated using the in vitro anti‐Tb microplate Alamar Blue assay. Five compounds, 3, 7, 8, 9 and 12, showed MIC100 values against the Mycobacterium tuberculosis H37Rv strain at 25 µg/ml, and compound 20 yielded an MIC100 value of 50 µg/ml. Molecular modelling of these compounds highlighted interactions with binding sites of dihydrofolate reductase, pteridine reductase and thymidylate kinase, thus establishing the rationale of their pharmacological activity against both pathogens, which is consistent with the in vitro results. From the above results, it is clear that compounds 3 and 12 are promising lead candidates for Leishmania and Mycobacterium infections and may be promising for coinfections.