2-Propen-1-one, 3-(1H-indol-3-yl)-1-(3-nitrophenyl)-, (E)- | 151390-86-2

• 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: 2-Propen-1-one, 3-(1H-indol-3-yl)-1-(3-nitrophenyl)-, (E)-
• 英文别名: 3-(1H-indol-3-yl)-1-(3-nitrophenyl)prop-2-en-1-one
• CAS: 151390-86-2
• 化学式: C₁₇H₁₂N₂O₃
• 分子量: 292.294
• InChiKey: XCHYJMLZAJKYMN-UHFFFAOYSA-N

物化性质

• 沸点：
  540.8±50.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 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：
  78.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氨基-2,6-二羟基嘧啶 、 2-Propen-1-one, 3-(1H-indol-3-yl)-1-(3-nitrophenyl)-, (E)- 在 溶剂黄146 作用下， 反应 6.0h， 以88%的产率得到7‐(3‐nitrophenyl)pyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐dione
  参考文献：
  名称：

  First‐in‐class pyrido[2,3‐ d ]pyrimidine‐2,4(1 H ,3 H )‐diones against leishmaniasis and tuberculosis: Rationale, in vitro, ex vivo studies and mechanistic insights

  摘要：

  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.

  DOI：

  10.1002/ardp.202100440
• 作为产物：
  描述：

  3-吲哚甲醛 、 间硝基苯乙酮 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 2-Propen-1-one, 3-(1H-indol-3-yl)-1-(3-nitrophenyl)-, (E)-
  参考文献：
  名称：

  发现一系列新型吲哚基查耳酮-苯磺酰胺杂化物作为选择性碳酸酐酶 II 抑制剂

  摘要：

  伯磺酰胺基团是设计碳酸酐酶 (CA、EC 4.2.1.1) 抑制剂时最有效的锌结合基团 (ZBG) 之一。在本研究中，设计了与吲哚基查尔酮连接的伯磺酰胺。新合成的分子 ( 5a-r ) 针对四种人 (h) CA 同工型（hCA I、hCA II、hCA IX 和 hCA XIII）进行了检查。这些磺胺类药物对同种型 hCA I、hCA II 和 hCA XIII 显示出良好的抑制活性。化合物5i (2.3 nM)、 5m (2.4 nM)、 5o (3.6 nM) 和5q (7.0 nM) 分别比标准药物 AAZ (12.1 nM) 更有效地对抗异构体 hCA II。本系列中的大多数其他化合物在 50 nM – 100 nM 范围内抑制 hCA XIII 和 hCA IX。

  DOI：

  10.1016/j.bioorg.2021.104647

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.
• Discovery of a novel series of indolylchalcone-benzenesulfonamide hybrids acting as selective carbonic anhydrase II inhibitors
  作者：Priti Singh、Parvatha Purnachander Yadav、Baijayantimala Swain、Pavitra S. Thacker、Andrea Angeli、Claudiu T. Supuran、Mohammed Arifuddin

  DOI：10.1016/j.bioorg.2021.104647

  日期：2021.3

  efficient zinc binding group (ZBG) for designing carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. In the present study primary sulfonamide linked with indolylchalcone were designed. The newly synthesized molecules (5a-r) were examined against four human (h) CA isoforms (hCA I, hCA II, hCA IX and hCA XIII). These sulfonamides showed good inhibition activity against isoforms hCA I, hCA II and hCA XIII.

  伯磺酰胺基团是设计碳酸酐酶 (CA、EC 4.2.1.1) 抑制剂时最有效的锌结合基团 (ZBG) 之一。在本研究中，设计了与吲哚基查尔酮连接的伯磺酰胺。新合成的分子 ( 5a-r ) 针对四种人 (h) CA 同工型（hCA I、hCA II、hCA IX 和 hCA XIII）进行了检查。这些磺胺类药物对同种型 hCA I、hCA II 和 hCA XIII 显示出良好的抑制活性。化合物5i (2.3 nM)、 5m (2.4 nM)、 5o (3.6 nM) 和5q (7.0 nM) 分别比标准药物 AAZ (12.1 nM) 更有效地对抗异构体 hCA II。本系列中的大多数其他化合物在 50 nM – 100 nM 范围内抑制 hCA XIII 和 hCA IX。