36326-86-0Relevant articles and documents
A Click Synthesis, Molecular Docking, Cytotoxicity on Breast Cancer (MDA-MB 231) and Anti-HIV Activities of New 1,4-Disubstituted-1,2,3-Triazole Thymine Derivatives
Al-Hujaj, Hamsa Hussein,Al-Masoudi, Najim Aboud,Faeza, Abdul Kareem Almashal,Jassem, Ahmed Majeed
, p. 360 - 370 (2020)
Abstract: A new series of 1,4-disubstituted-1,2,3-triazolethymine derivatives (VIa–e) were synthesized and characterized by spectroscopic studies. The in vitro cytotoxic activities of selected compounds against human cancer cell line (MDA-MB 231) were eva
Inclusion of a 5-fluorouracil moiety in nitrogenous bases derivatives as human carbonic anhydrase IX and XII inhibitors produced a targeted action against MDA-MB-231 and T47D breast cancer cells
ALOthman, Zeid A.,Bonardi, Alessandro,El-Haggar, Radwan,Eldehna, Wagdy M.,Lomelino, Carrie,McKenna, Robert,Nocentini, Alessio,Osman, Sameh M.,Petreni, Andrea,Supuran, Claudiu T.
, (2020)
A new series of pyrimidine derivatives as human carbonic anhydrases (CA, EC 4.2.1.1) inhibitors is here designed by including a 5-fluorouracil (5-FU) moiety, broadly used anticancer medication, in nitrogenous base modulators of the tumor-associated CAs. Most sulfonamide derivatives efficiently inhibit the target CA IX (KIs in the range 0.47–44.7 nM) and CA XII (KIs in the range 2.9–83.1 nM), while the 5-FU coumarin derivatives showed a potent and totally selective inhibitory action against the target CA IX/XII over off-target CA I/II. The X-ray solved crystal structure of CA II in adduct with a representative uracil derivative provided insights on the binding mode to the target of such pyrimidine derivatives. On the basis of potency and selectivity inhibition profiles, coumarin 12a, the sulfonamide CAIs showing the greatest II/IX specificity (4e, 6b and 6d) and the unique subnanomolar CA IX inhibitor 10a were tested in vitro for their antiproliferative action against a panel of eight cancer cell lines. The breast cancer cell lines MDA-MB-231 and T47D were the most susceptible with IC50 values in low to medium micromolar ranges (2.45 ± 0.07–18.86 ± 0.72 μM and 6.86 ± 0.31–40.92 ± 1.59 μM, respectively). A cell cycle analysis showed that 4e and 6d arrest T-47D cells mainly in the G2/M phase. Using an annexin V-FITC apoptosis assay, 4e and 6d were shown to induce an approximately 23.6-fold and 34.8-fold total increase in apoptosis compared to the control, corroborating the concrete potential of 5-FU CAIs for the design of new effective anticancer strategies.
Synthesis of novel 4-functionalized 1,5-diaryl-1,2,3-triazoles containing benzenesulfonamide moiety as carbonic anhydrase I, II, IV and IX inhibitors
Vats, Lalit,Sharma, Vikas,Angeli, Andrea,Kumar, Rajiv,Supuran, Claudiu T.,Sharma, Pawan K.
, p. 678 - 686 (2018)
The design, synthesis and biological evaluation of a library of 1,2,3-triazole carboxylates incorporating carboxylic acid, hydroxymethyl, carboxylic acid hydrazide, carboxamide and benzenesulfonamide moieties is disclosed. All the novel compounds were inv
Discovery of novel artemisinin-sulfonamide hybrids as potential carbonic anhydrase IX inhibitors with improved antiproliferative activities
An, Ran,Lin, Bin,Zhao, Shuang,Cao, Chun,Wang, Yuanxin,Cheng, Xue,Liu, Yichuang,Guo, Mengbi,Xu, Hang,Wang, Yitong,Hou, Zhuang,Guo, Chun
, (2020)
A series of artemisinin-sulfonamide hybrids (1–16) have been designed and synthesized by using molecular hybridization approach and investigated for the inhibitory activity of four human (h) carbonic anhydrases (CAs, EC 4.2.1.1), hCA I, II, IX and XII. Th
Novel Re(I) tricarbonyl coordination compounds based on 2-pyridyl-1,2,3-triazole derivatives bearing a 4-amino-substituted benzenesulfonamide arm: synthesis, crystal structure, computational studies and inhibitory activity against carbonic anhydrase I, II
Aimene, Yassine,Seridi, Achour,Eychenne, Romain,Benoist, Eric,Mallet-Ladeira, Sonia,Saffon, Nathalie,Winum, Jean-Yves,Nocentini, Alessio,Supuran, Claudiu T.
, p. 773 - 782 (2019)
In this work, two bidentate 2-pyridyl-1,2,3-triazole ligands (3a and 3b) containing a 4-substituted benzenesulfonamide pharmacophore prepared by classical click chemistry procedures, as well as their corresponding rhenium complexes, 4a and 4b of general f
Click-tailed benzenesulfonamides as potent bacterial carbonic anhydrase inhibitors for targeting Mycobacterium tuberculosis and Vibrio cholerae
Bua, Silvia,Osman, Sameh M.,Del Prete, Sonia,Capasso, Clemente,AlOthman, Zeid,Nocentini, Alessio,Supuran, Claudiu T.
, p. 183 - 186 (2019)
A series of 1,2,3-triazole-bearing benzenesulfonamides was assessed for the inhibition of carbonic anhydrases (CA, EC 4.2.1.1) from bacteria Vibrio cholerae (VchCAα and VchCAβ) and Mycobacterium tuberculosis (β-mtCA3). Growing resistance phenomena against
Carbonic anhydrase inhibition with a series of novel benzenesulfonamide-triazole conjugates
El-Gazzar, Marwa G.,Nafie, Nessma H.,Ghorab, Mostafa M.,Heiba, Helmi I.,Nocentini, Alessio,Supuran, Claudiu T.
, p. 1565 - 1574 (2018)
We report the synthesis and characterisation of a novel series of triazole benzenesulfonamide derivatives, which incorporate the general pharmacophore associated with carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. The synthesised compounds were tested in
Novel triazole-sulfonamide bearing pyrimidine moieties with carbonic anhydrase inhibitory action: Design, synthesis, computational and enzyme inhibition studies
Hoda, Nasimul,Manzoor, Shoaib,Petreni, Andrea,Raza, Md Kausar,Supuran, Claudiu T.
, (2021)
A series of new triazole-sulfonamide bearing pyrimidine derivatives were designed and synthesized via click chemistry. All new compounds (SH-1 to SH-28) were validated by 1HNMR, 13CNMR, HRMS, and SH-3 was further structurally validated by X-Ray single diffraction study. These compounds (SH-1 to SH-28) were tested as inhibitors of human carbonic anhydrase (hCA) isoforms, such as hCA I, II, IX and XII, using a stopped flow CO2 hydrase assay. Most of the compounds exhibited significant inhibitory activity against hCA II and weak inhibitory activity against hCA I. The target compounds also displayed moderate to excellent inhibitory activity against tumor-related hCAs IX and XII. Some compounds, e.g., SH-20 (Ki = 9.4 nM), SH-26 (Ki = 1.8 nM) and SH-28 (Ki = 0.82 nM) exhibited excellent inhibitory activity and selectivity profile against hCAs XII over IX. SH-23 displayed promising inhibitory activity and selectivity profile against both tumor-related hCAs IX (Ki = 2.9 nM) as well as XII (Ki = 0.82 nM) over hCA I and II. To understand the molecular interactions, molecular docking study of compounds SH-20, SH-23, SH-26 and SH-28 with hCA XII and SH-23 also with hCA IX were performed. The computational study evidenced favorable interaction between the inhibitors and active residues of both proteins. Some of these derivatives are promising leads for the development of selective, anticancer agents based on CA inhibitors.
Design, synthesis, molecular docking, admet studies and biological evaluation of pyrazoline incorporated 1, 2, 3-triazole benzene sulphonamides
Siliveri, Sravanthi,Bashaboina, Nagaraju,Vamaraju, Harinadha Babu,Raj, Shiva
, p. 6 - 15 (2019)
Objective: The main objective of this work was to design, synthesize and evaluate the novel pyrazoline incorporated 1,2,3-triazole benzene sulphonamides for cytotoxic and anti-gout activities also to perform Insilco molecular docking studies. Methods: Des
1,5-Benzodiazepines as a platform for the design of carbonic anhydrase inhibitors
Gharbi, Rafik,Ismail, Chiraz,Nocentini, Alessio,Supuran, Claudiu T.,Winum, Jean-Yves
, (2021/12/08)
A series of novel N-triazolo-benzene sulfonamides-1,5-benzodiazepines 9a–d and 10d were designed and prepared through the copper-catalyzed azide alkyne cycloaddition click chemistry procedure, reacting the N1-propargyl-1,5-benzodiazepine 2 and
