Synthesis of two 3,5-disubstituted sulfonamide catechol ligands and evaluation of their iron(III) complexes for use as MRI contrast agents

被引:30
|
作者
Schwert, DD
Richardson, N
Ji, GJ
Radüchel, B
Ebert, W
Heffner, PE
Keck, R
Davies, JA
机构
[1] Univ Toledo, Dept Chem, Toledo, OH 43606 USA
[2] Wagner Coll, Dept Chem & Phys, Staten Isl, NY 10301 USA
[3] Schering AG, Res Labs, D-13342 Berlin, Germany
[4] Med Coll Ohio, Dept Urol, Toledo, OH 43614 USA
关键词
D O I
10.1021/jm0501984
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Two 3,5-disubstituted sulfonamide catechol ligands were synthesized. Tris(ligand) iron(III) complexes were prepared and investigated as MRI contrast agents. Longitudinal relaxivity (r1) values were determined for the complexes. The rl values in water were substantially higher than those of typical six-coordinate iron(III) complexes. The rl values in plasma under the same conditions increased. The iron(III) complexes were administered to rats, and the kidney and liver signal intensities were measured by T-1-weighted MR imaging experiments.
引用
收藏
页码:7482 / 7485
页数:4
相关论文
共 50 条
  • [21] Green aqueous synthesis and antimicrobial evaluation of 3,5-disubstituted 1,2,4-triazoles
    Beyzaei, Hamid
    Malekraisi, Farideh
    Aryan, Reza
    Ghasemi, Behzad
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (04) : 482 - 487
  • [22] Green aqueous synthesis and antimicrobial evaluation of 3,5-disubstituted 1,2,4-triazoles
    Hamid Beyzaei
    Farideh Malekraisi
    Reza Aryan
    Behzad Ghasemi
    Chemistry of Heterocyclic Compounds, 2020, 56 : 482 - 487
  • [23] Baylis-Hillman reaction assisted parallel synthesis of 3,5-disubstituted isoxazoles and their in vivo bioevaluation as antithrombotic agents
    Batra, S
    Roy, AK
    Patra, A
    Bhaduri, AP
    Surin, WR
    Raghavan, SAV
    Sharma, P
    Kapoor, K
    Dikshit, M
    BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) : 2059 - 2077
  • [24] Synthesis and crystal structures of two dinuclear iron(III) complexes with tripodal ligands
    Tian, JL
    Xie, MJ
    Yan, SP
    Liao, DZ
    Jiang, ZH
    Cheng, P
    CHINESE JOURNAL OF CHEMISTRY, 2005, 23 (05) : 525 - 529
  • [25] Design, Synthesis, and Evaluation of 3,5-Disubstituted 7-Azaindoles as Trk Inhibitors with Anticancer and Antiangiogenic Activities
    Hong, Seunghee
    Kim, Jinhee
    Seo, Ju Hyeon
    Jung, Kyung Hee
    Hong, Soon-Sun
    Hong, Sungwoo
    JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (11) : 5337 - 5349
  • [26] SYNTHESIS AND EVALUATION OF A SERIES OF 3,5-DISUBSTITUTED BENZISOXAZOLE-4,7-DIONES - POTENT RADIOSENSITIZERS INVITRO
    SUTO, MJ
    STIER, MA
    WINTERS, RT
    TURNER, WR
    PINTER, CD
    ELLIOTT, WE
    SEBOLTLEOPOLD, JS
    JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (11) : 3290 - 3294
  • [27] Green synthesis and anti-biofilm activities of 3,5-disubstituted isoxazoline/isoxazole-linked secondary sulfonamide derivatives on Pseudomonas aeruginosa
    El Mahmoudi, Ayoub
    Tareau, Anne-Sophie
    Barreau, Magalie
    Chevalier, Sylvie
    Hourma, Chaimae
    Demange, Luc
    Benhida, Rachid
    Bougrin, Khalid
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2023, 96
  • [28] Synthesis, Antioxidant, and Antibacterial Activities of Two Novel Series of 3,5-Disubstituted Isoxazole Ether-Linked Isoxazolines and 3,5-Disubstituted Pyrazole Ether-Linked Isoxazolines Mediated by Chloramine-T
    Saleh, E. A. M.
    Kotian, S. Y.
    Al Dawsari, A. M.
    Hassan, I
    Husain, K.
    Abishad, P. C.
    Byrappa, K.
    Al Sharabi, R. S. S.
    Rai, K. M. L.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2022, 48 (05) : 1043 - 1052
  • [29] Synthesis, Antioxidant, and Antibacterial Activities of Two Novel Series of 3,5-Disubstituted Isoxazole Ether-Linked Isoxazolines and 3,5-Disubstituted Pyrazole Ether-Linked Isoxazolines Mediated by Chloramine-T
    E. A. M. Saleh
    S. Y. Kotian
    A. M. Al Dawsari
    I. Hassan
    K. Husain
    P. C. Abishad
    K. Byrappa
    R. S. S. AL Sharabi
    K. M. L. Rai
    Russian Journal of Bioorganic Chemistry, 2022, 48 : 1043 - 1052
  • [30] Electrochemical determination of the stability of complexes formed by proton-ionizable ligands of 3,5-disubstituted 1H-pyrazole with phenethylamine
    Doménech, A
    García-España, E
    Navarro, P
    Reviriego, F
    TALANTA, 2000, 51 (04) : 625 - 636