Flow synthesis and biological activity of aryl sulfonamides as selective carbonic anhydrase IX and XII inhibitors

被引：20
|
作者：
Rosatelli, Emiliano [1 ]
Carotti, Andrea [1 ]
Ceruso, Mariangela [2 ]
Supuran, Claudiu T. [3 ]
Gioiello, Antimo [1 ]
机构：
[1] Univ Perugia, Dept Pharmaceut Sci, Lab Med & Adv Synthet Chem Lab MASC, I-06123 Perugia, Italy
[2] Univ Florence, Lab Bioinorgan Chem, I-50019 Florence, Italy
[3] Univ Florence, Sect Pharmaceut & Nutriceut Sci, Neurofarba Dept, I-50019 Florence, Italy
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 15期
关键词：
Carbonic anhydrases; Flow synthesis; Sulfonamides; Docking;
D O I：
10.1016/j.bmcl.2014.05.086
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of secondary and tertiary aryl sulfonamides were synthesized under flow conditions and evaluated for their ability to selectively inhibit tumor-associated carbonic anhydrase isoforms IX and XII. The tested compounds revealed to be highly potent CA IX inhibitors in nanomolar range, and to inhibit CA XII activity with different ranks of potencies. Remarkably, 4-methyl-N-phenyl-benzenesulfonamide was a selective nanomolar CA IX inhibitor with an IC50 of 90 nM. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3422 / 3425
页数：4
相关论文
共 50 条
  • [1] Synthesis and biological evaluation of some coumarin hybrids as selective carbonic anhydrase IX and XII inhibitors
    Thacker, Pavitra S.
    Goud, Nerella Sridhar
    Argulwar, Omkar S.
    Soman, Jyothsna
    Angeli, Andrea
    Alvala, Mallika
    Arifuddin, Mohammed
    Supuran, Claudiu T.
    BIOORGANIC CHEMISTRY, 2020, 104
  • [2] Synthesis and biological evaluation of coumarin-thiazole hybrids as selective carbonic anhydrase IX and XII inhibitors
    Thacker, Pavitra S.
    Newaskar, Vaishnavi
    Angeli, Andrea
    Sigalapalli, Dilep Kumar
    Goud, Nerella Sridhar
    Chirra, Hepsibha
    Shaik, Afzal B.
    Arifuddin, Mohammed
    Supuran, Claudiu T.
    ARCHIV DER PHARMAZIE, 2022, 355 (12)
  • [3] Ureidobenzenesulfonamides as Selective Carbonic Anhydrase I, IX, and XII Inhibitors
    Denner, Toni C.
    Angeli, Andrea
    Ferraroni, Marta
    Supuran, Claudiu T.
    Csuk, Rene
    MOLECULES, 2023, 28 (23):
  • [4] A class of carbonic anhydrase IX/XII - selective carboxylate inhibitors
    Abd Alhameed, Rakia
    Berrino, Emanuela
    Almarhoon, Zainab
    El-Faham, Ayman
    Supuran, Claudiu T.
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2020, 35 (01) : 549 - 554
  • [5] Synthesis, characterization and biological evaluation of pyrazole-based benzene sulfonamides as inhibitors of human carbonic anhydrase II, IX and XII
    Hussain, Tajamul
    Ullah, Saif
    Alrokayan, Salman
    Alamery, Salman
    Mohammed, Arif Ahmed
    Ejaz, Syeda Abida
    Aziz, Mubashir
    Iqbal, Jamshed
    RSC ADVANCES, 2023, 13 (27) : 18461 - 18479
  • [6] Design, synthesis and biological evaluation of coumarin-3-carboxamides as selective carbonic anhydrase IX and XII inhibitors
    Thacker, Pavitra S.
    Alvala, Mallika
    Arifuddin, Mohammed
    Angeli, Andrea
    Supuran, Claudiu T.
    BIOORGANIC CHEMISTRY, 2019, 86 : 386 - 392
  • [7] Ureidosulfocoumarin Derivatives As Selective and Potent Carbonic Anhydrase IX and XII Inhibitors
    Singh, Priti
    Kumar Sigalapalli, Dilep
    Sridhar Goud, Nerella
    Swain, Baijayantimala
    Kumar Sahoo, Santosh
    Angeli, Andrea
    Shaik, Afzal B.
    Madhavi Yaddanapudi, Venkata
    Supuran, Claudiu T.
    Arifuddin, Mohammed
    CHEMMEDCHEM, 2022, 17 (05)
  • [8] Isocoumarins: a new class of selective carbonic anhydrase IX and XII inhibitors
    Onyilmaz, Mehmet
    Koca, Murat
    Bonardi, Alessandro
    Degirmenci, Mustafa
    Supuran, Claudiu T.
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2022, 37 (01) : 743 - 748
  • [9] Design, Synthesis, and In Vitro Evaluation of Aromatic Sulfonamides as Human Carbonic Anhydrase I, II, IX, and XII Inhibitors and Their Antioxidant Activity
    Mishra, K. M. Abha
    Kumari, Nutan
    Carta, Fabrizio
    Renzi, Gioele
    Supuran, Claudiu T.
    Sethi, Kalyan K.
    JOURNAL OF BIOCHEMICAL AND MOLECULAR TOXICOLOGY, 2025, 39 (01)
  • [10] Synthesis, Crystal Structure, Inhibitory Activity and Molecular Docking of Coumarins/Sulfonamides Containing Triazolyl Pyridine Moiety as Potent Selective Carbonic Anhydrase IX and XII Inhibitors
    Aimene, Yassine
    Eychenne, Romain
    Rodriguez, Frederic
    Mallet-Ladeira, Sonia
    Saffon-Merceron, Nathalie
    Winum, Jean-Yves
    Nocentini, Alessio
    Supuran, Claudiu T.
    Benoist, Eric
    Seridi, Achour
    CRYSTALS, 2021, 11 (09)
12345