Synthesis of novel 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives and their cytotoxic activity

被引：28
|
作者：
Rao, P. Sambasiva [1 ]
Kurumurthy, C. [1 ]
Veeraswamy, B. [1 ]
Poornachandra, Y. [2 ]
Kumar, C. Ganesh [2 ]
Narsaiah, B. [1 ]
机构：
[1] CSIR Indian Inst Chem Technol, Fluoroorgan Div, Hyderabad 500007, Andhra Pradesh, India
[2] CSIR Indian Inst Chem Technol, Med Chem & Pharmacol Div, Hyderabad 500007, Andhra Pradesh, India
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 05期
关键词：
Aldoxime; Isoxazole; Quinoline; Jones reagent; Cytotoxic activity; QUINOLINE; TRIFLATE;
D O I：
10.1016/j.bmcl.2014.01.038
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The propargyl alcohol on reaction with aldoxime and NaOCl in DCM gave exclusively (3-arylisoxazol-5-yl) methanol 1. The compound 1 was oxidized to an aldehyde 2 followed by reaction with aniline resulted in Schiff's base 3. The compounds 3 were further reacted with various aldehydes having a-hydrogen using molecular iodine as catalyst and which yielded 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives 4. All the final compounds 4 were screened against four human cancer cell lines (A549, COLO 205, MDA-MB 231 and PC-3) and among these compounds 4n showed potent cytotoxicity against all the cell lines at IC50 values of < 12 mu M. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1349 / 1351
页数：3
相关论文
共 50 条
  • [41] Methyl 3-aryl(pyridyl)-5-oxopyrrolidine-2-carboxylates: synthesis and structure
    Gorodnicheva, Natal'ya V.
    Vasil'eva, Olga S.
    Ostroglyadov, Evgeny S.
    Baichurin, Ruslan I.
    Litvinov, Igor A.
    Makarenko, Sergey V.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2023, 59 (1-2) : 48 - 53
  • [42] Synthesis and anti-angiogenetic activity evaluation of N-(3-aryl acryloyl)aminosaccharide derivatives
    Liu, Kun
    Yao, Shuowei
    Lou, Yinghan
    Xu, Yungen
    CARBOHYDRATE RESEARCH, 2013, 381 : 83 - 92
  • [43] Study on Synthesis and Biological Evaluation of 3-Aryl Substituted Xanthone Derivatives as Novel and Potent Tyrosinase Inhibitors
    Yu, Lihong
    Chen, Liandi
    Luo, Guolin
    Liu, Licai
    Zhu, Wenqi
    Yan, Pengke
    Zhang, Peiquan
    Zhang, Chao
    Wu, Wenhao
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2019, 67 (11) : 1232 - 1241
  • [44] Synthesis of functional derivatives of isothiazole and isoxazole basing on (5-arylizoxazol-3-yl)- and (4,5-dichloroisothiazol-3-yl)arylmethanol
    Potkin, V. I.
    Bumagin, N. A.
    Kletskov, A. V.
    Petkevich, S. K.
    Kurman, P. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (11) : 1661 - 1669
  • [45] Synthesis of functional isoxazole and isothiazole derivatives from [(5-arylisoxazol-3-yl)methoxy]arylmethanols
    Dikusar, E. A.
    Petkevich, S. K.
    Kletskov, A. V.
    Semenova, E. A.
    Potkin, V. I.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (01) : 61 - 68
  • [46] Methyl 3-aryl(pyridyl)-5-oxopyrrolidine-2-carboxylates: synthesis and structure
    Natal’ya V. Gorodnicheva
    Olga S. Vasil’eva
    Evgeny S. Ostroglyadov
    Ruslan I. Baichurin
    Igor A. Litvinov
    Sergey V. Makarenko
    Chemistry of Heterocyclic Compounds, 2023, 59 : 48 - 53
  • [47] Synthesis of functional derivatives of isothiazole and isoxazole basing on (5-arylizoxazol-3-yl)- and (4,5-dichloroisothiazol-3-yl)arylmethanol
    V. I. Potkin
    N. A. Bumagin
    A. V. Kletskov
    S. K. Petkevich
    P. V. Kurman
    Russian Journal of Organic Chemistry, 2016, 52 : 1661 - 1669
  • [48] Synthesis and structure of cobalt(II) 1-aryl-3-aryl(alkyl)-5-(benzothiazol-2-yl)formazanates
    Z. G. Rezinskikh
    P. A. Slepukhin
    I. G. Pervova
    G. N. Lipunova
    T. I. Maslakova
    I. N. Lipunov
    G. I. Sigeikin
    Russian Journal of Inorganic Chemistry, 2009, 54 : 396 - 402
  • [49] Synthesis and Structure of Cobalt(II) 1-Aryl-3-aryl(alkyl)-5-(benzothiazol-2-yl)formazanates
    Rezinskikh, Z. G.
    Slepukhin, P. A.
    Pervova, I. G.
    Lipunova, G. N.
    Maslakova, T. I.
    Lipunov, I. N.
    Sigeikin, G. I.
    RUSSIAN JOURNAL OF INORGANIC CHEMISTRY, 2009, 54 (03) : 396 - 402
  • [50] Synthesis and Antifungal Screening of 2-(2-Aryl-4-methyl-thiazol-5-yl)-5-((2-aryl/benzylthiazol-4-yl)methyl)-1,3,4-oxadiazole Derivatives
    Mhaske, Pravin C.
    Shelke, Shivaji H.
    Gadge, Kisan
    Shinde, Abhijit
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (01) : 129 - 134
12345