BMIM[BF4]: An Efficient Ionic Liquid Medium for the Synthesis of Chromeno[b]pyridines as Potential Anticancer Agents

被引:2
作者
Kalpana, K. [1 ]
Rani, V. A. [2 ]
Seshadri, S. [3 ]
Kiran, B. Ravi [1 ]
机构
[1] Gokaraju Rangaraju Inst Engn & Technol, Dept Humanities & Sci Chem, Hyderabad 500090, India
[2] Inst Aeronaut Engn, Dept Chem, Hyderabad 500043, India
[3] Nirma Univ, Inst Sci, Ahmadabad 382470, Gujarat, India
关键词
green synthesis; one-pot reaction; anticancer activity; molecular descriptors prediction; chromeno[4; 3-b]pyridines; DERIVATIVES;
D O I
10.1134/S1070428021090177
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 2-amino-4-aryl-5-oxochromeno[4,3-b]pyridine-3-carbonitriles have been synthesized with good yields (85-90%) by reacting 4-amino-2H-chromen-2-one, substituted benzaldehydes, and malono-nitrile at 80-85 degrees C for 90-120 min using 1-butyl-3-methylimidazolium tetrafluoroborate as an ionic liquid medium. The synthesized derivatives have been screened for their anticancer potential on SKOV-3 and PC-3 cell lines, and the results were found to be encouraging. In addition, molecular descriptor prediction was performed for the compounds in terms of Lipinski's rule of five; in particular, their topological polar surface areas (TPSA) and lipophilicities (iLogP) were found to be within an acceptable range.
引用
收藏
页码:1501 / 1507
页数:7
相关论文
共 50 条
  • [41] 1-Butyl-3-methylimidazolium Hydrogen Sulfate [bmim]HSO4: An Efficient Reusable Acidic Ionic Liquid for the Synthesis of 1,8-Dioxo-octahydroxanthenes
    Niknam, Khodabakhsh
    Damya, Maryam
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2009, 56 (03) : 659 - 665
  • [42] An efficient synthesis of novel 3-hydroxy-12-arylbenzo[a]xanthen-11-ones and 5,12-diarylxantheno[2,1-a]xanthene-4,12-diones using pTSA in [bmim] BF4
    Yadav, Sneha
    Nand, Bhaskara
    Khurana, Jitender M.
    CANADIAN JOURNAL OF CHEMISTRY, 2013, 91 (08) : 698 - 703
  • [43] Acidic Ionic Liquid [H-NP]HSO4 Promoted One-Pot Synthesis of Dihydro-1H-Indeno[1,2-b]pyridines and Polysubstituted Imidazoles
    Alinezhad, Heshmatollah
    Tajbakhsh, Mahmoud
    Maleki, Behrooz
    Pourshaban Oushibi, Fereshteh
    POLYCYCLIC AROMATIC COMPOUNDS, 2020, 40 (05) : 1485 - 1500
  • [44] [CMMIM][BF4-] Ionic Liquid-Catalyzed Facile, One-Pot Synthesis of Chromeno[4,3-d]pyrido[1,2-a]pyrimidin-6-ones: Evaluation of Their Photophysical Properties and Theoretical Calculations
    Pasuparthy, Sai Deepak
    Maiti, Barnali
    ACS OMEGA, 2022, 7 (43): : 39147 - 39158
  • [45] An Efficient and Facile Synthesis of tert-Butyl 2-(Methylamino)-3-nitro-5-oxo-4-aryl-7,8-dihydro-4H-pyrano[3,2-c]pyridine-6(5H)-carboxylate derivatives in [BMIM]BF4
    Pan, Zhengbing
    Xu, Hui
    Mao, Kaimin
    Dai, Lei
    Zhao, Liming
    Rong, Liangce
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (04) : 1393 - 1402
  • [46] Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents
    Moreno, Leydi M.
    Quiroga, Jairo
    Abonia, Rodrigo
    Crespo, Maria del P.
    Aranaga, Carlos
    Martinez-Martinez, Luis
    Sortino, Maximiliano
    Barreto, Mauricio
    Burbano, Maria E.
    Insuasty, Braulio
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2024, 25 (07)
  • [47] Basic ionic liquid grafted on magnetic nanoparticles: An efficient and highly active recyclable catalyst for the synthesis ofβ-nitroalcohols and 4H-benzo[b]pyrans
    Gupta, Padmini
    Rani, Swati
    Sah, Digvijay
    Surabhi, Bholey
    Shabir, Javaid
    Singh, Bholey
    Pani, Balaram
    Mozumdar, Subho
    JOURNAL OF MOLECULAR STRUCTURE, 2023, 1274
  • [48] [H-Pyrr][HSO4] as an Efficient Ionic Liquid Catalyst for the Synthesis of Xanthenes, Tetraketones, and Triazolo[2,1-b]quinazolinones
    Zabihzadeh, Mehdi
    Shirini, Farhad
    Tajik, Hassan
    Daneshvar, Nader
    POLYCYCLIC AROMATIC COMPOUNDS, 2021, 41 (09) : 1972 - 1987
  • [49] SYNTHESIS OF NEW 2, 5, 6-SUBSTITUTED IMIDAZO[2,1-B][1,3,4]THIADIAZOLE DERIVATIVES AS POTENTIAL ANTICANCER AGENTS
    Sethi, Navdeep Singh
    Noolvi, Malleshappa N.
    Kharb, Vandana
    Nathubhai, Vinay K.
    More, Uttam A.
    Avvaru, Stephen Paul
    Khairnar, Bhikan J.
    Desai, Shivali
    Thippeswamy, B. S.
    Al Otaibi, Faisal
    INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2020, 11 (11): : 5518 - 5529
  • [50] Fe3O4@SiO2-NH2 core-shell nanocomposite as an efficient and green catalyst for the multi-component synthesis of highly substituted chromeno[2,3-b]pyridines in aqueous ethanol media
    Ghasemzadeh, Mohammad Ali
    Abdollahi-Basir, Mohammad Hossein
    Babaei, Masoomeh
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2015, 8 (3-4) : 40 - 49