3-(3-indolyl)-2-ene-1-propanoyl-2'-thiophene | 22883-39-2

• 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: 3-(3-indolyl)-2-ene-1-propanoyl-2'-thiophene
• 英文别名: 3-indol-3-yl-1-thiophen-2-yl-propenone；1-(Thienyl-(2))-3-(indolyl-(3))-propenon-(1)；1-(3-Indolyl)-3-(2-thienyl)-1-propenon；3-(1H-indol-3-yl)-1-thiophen-2-ylprop-2-en-1-one
• CAS: 22883-39-2
• 化学式: C₁₅H₁₁NOS
• 分子量: 253.324
• InChiKey: JUIAOWGQECPCGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-indolyl)-2-ene-1-propanoyl-2'-thiophene 在 乙酸铵 、 三氯氧磷 作用下， 以 正丁醇 为溶剂， 反应 10.0h， 生成 2-chloro-3-cyano-4-(indole-3-yl)-6-(thien-2-yl)pyridine
  参考文献：
  名称：

  Kassem, E. M.; Mandour, A. H., Egyptian Journal of Chemistry, 1999, vol. 42, # 4, p. 387 - 402

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰基噻吩 、 3-吲哚甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以92%的产率得到3-(3-indolyl)-2-ene-1-propanoyl-2'-thiophene
  参考文献：
  名称：

  1-取代的氨基甲酰基和硫代氨基甲酰基-4,5-二氢-1H-吡唑类可能是细胞毒性和抗菌剂。

  摘要：

  通过分别用适当的异氰酸酯和异硫氰酸酯处理相应的吡唑，或通过将适当的二酮与适当的取代的氨基脲或硫代氨基脲缩合来制备两个系列的1-取代的氨基甲酰基和硫代氨基甲酰基衍生物。通过分析和光谱方法完全确定了所制备化合物的结构。对制备的化合物进行的初步生物学筛选显示，某些化合物具有显着的抗菌和细胞毒性活性。发现化合物4a2和4a3对人结肠癌HT29（分别为11.8和7.5μg/ mL）和人乳腺癌MCF 7（分别为3.4和2.6μg/ mL）最具活性。构效关系（SAR）和计算机病毒相关属性（HBD，HBA，tPSA，

  DOI：

  10.3109/14756366.2015.1057717

文献信息

• Regio- and diastereoselective construction of a new set of functionalized pyrrolidine, spiropyrrolidine and spiropyrrolizidine scaffolds appended with aryl- and heteroaryl moieties via the azomethine ylide cycloadditions
  作者：Vadla Rajkumar、Srinivasarao Arulananda Babu、Rayavarapu Padmavathi

  DOI：10.1016/j.tet.2016.07.053

  日期：2016.9

  Highly regio- and diastereoselective syntheses of a new set of functionalized pyrrolidines, spiro-pyrrolidine/pyrrolizidine oxindoles, spiroacenaphthylenolyl-pyrrolidines/pyrrolizidines and spiro-1,3-indandionolyl-pyrrolidines/pyrrolizidines appended with various aryl- and heteroaryl moieties via the azomethine ylide cycloaddition reaction are reported. The Ag-catalyzed [3+2] cycloaddition of azomethine

  一组新的功能化吡咯烷，螺并吡咯烷/吡咯并吡啶氧吲哚，螺并ac苯并菲咯啉基-吡咯烷/吡咯并吡啶和螺-1,3-吲哚并菲酰基-吡咯烷/吡咯并吡啶的高区域选择性和非对映选择性合成报道了环加成反应。Ag衍生自N的偶氮甲亚胺的[3 + 2]环加成反应用各种亚芳基/杂芳基亚甲基丙二酸-亚苄基亚氨基甘氨酸盐产生具有良好区域和非对映选择性的C-3，C-5-芳基/杂芳基取代的C-4，C-4-二氰基吡咯烷-2-羧酸酯支架。此外，研究了由不同的1,2-二羰基和α-氨基酸与基于吲哚/吡咯的偶极亲和剂的脱羧反应衍生的偶氮甲亚胺的[3 + 2]环加成反应。在丰富功能化的螺吡咯烷-和螺吡咯并吡啶骨架的文库的背景下，这些反应导致组装了各种螺并吡咯烷/吡咯并吡啶氧吲哚，螺并ena庚烯基-吡咯烷/吡咯并吡啶和螺-1,3-茚满二酮基-吡啶并吡啶在螺吡咯烷/吡咯烷环的C-3位的吲哚基和吡咯基部分。由甲亚胺叶立德环加成反应获得的图8
• 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.
• Synthesis of chalcone analogs and derivatives of 2-pyrazoline from 3-formylindole
  作者：S. V. Tsukerman、V. M. Nikitchenko、A. I. Bugai、V. F. Lavrushin

  DOI：10.1007/bf00943916

  日期：——
• 1-Substituted carbamoyl and thiocarbamoyl-4,5-dihydro-1H-pyrazoles as possible cytotoxic and antimicrobial agents
  作者：Khalid A. Khan、Hassan M. Faidallah

  DOI：10.3109/14756366.2015.1057717

  日期：2016.7.3

  appropriate isocyanate and isothiocyanate respectively, or alternatively by condensing the appropriate diketone with the proper substituted semicarbazide or thiosemicarbazide. The structures of the prepared compounds were fully determined by analytical and spectral methods. Preliminary biological screening of the prepared compounds revealed significant antibacterial and cytotoxic activities for some compounds

  通过分别用适当的异氰酸酯和异硫氰酸酯处理相应的吡唑，或通过将适当的二酮与适当的取代的氨基脲或硫代氨基脲缩合来制备两个系列的1-取代的氨基甲酰基和硫代氨基甲酰基衍生物。通过分析和光谱方法完全确定了所制备化合物的结构。对制备的化合物进行的初步生物学筛选显示，某些化合物具有显着的抗菌和细胞毒性活性。发现化合物4a2和4a3对人结肠癌HT29（分别为11.8和7.5μg/ mL）和人乳腺癌MCF 7（分别为3.4和2.6μg/ mL）最具活性。构效关系（SAR）和计算机病毒相关属性（HBD，HBA，tPSA，
• Kassem, E. M.; Mandour, A. H., Egyptian Journal of Chemistry, 1999, vol. 42, # 4, p. 387 - 402
  作者：Kassem, E. M.、Mandour, A. H.

  DOI：——

  日期：——