Citation
Żołnowska, Beata, et al. "Carbonic Anhydrase Inhibitors. Synthesis, and Molecular Structure of Novel Series N-substituted N'-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines and Their Inhibition of Human Cytosolic Isozymes I and II and the Transmembrane Tumor-associated Isozymes IX and XII." European Journal of Medicinal Chemistry, vol. 71, 2014, pp. 135-47.
Żołnowska B, Sławiński J, Pogorzelska A, et al. Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N'-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII. Eur J Med Chem. 2014;71:135-47.
Żołnowska, B., Sławiński, J., Pogorzelska, A., Chojnacki, J., Vullo, D., & Supuran, C. T. (2014). Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N'-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII. European Journal of Medicinal Chemistry, 71, 135-47. https://doi.org/10.1016/j.ejmech.2013.10.081
Żołnowska B, et al. Carbonic Anhydrase Inhibitors. Synthesis, and Molecular Structure of Novel Series N-substituted N'-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines and Their Inhibition of Human Cytosolic Isozymes I and II and the Transmembrane Tumor-associated Isozymes IX and XII. Eur J Med Chem. 2014;71:135-47. PubMed PMID: 24291567.
TY - JOUR
T1 - Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N'-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII.
AU - Żołnowska,Beata,
AU - Sławiński,Jarosław,
AU - Pogorzelska,Aneta,
AU - Chojnacki,Jarosław,
AU - Vullo,Daniela,
AU - Supuran,Claudiu T,
Y1 - 2013/11/10/
PY - 2013/07/12/received
PY - 2013/10/21/revised
PY - 2013/10/31/accepted
PY - 2013/12/3/entrez
PY - 2013/12/3/pubmed
PY - 2014/9/19/medline
KW - Anticancer activity
KW - Carbonic anhydrase isozymes I, II, IX and XII inhibitors
KW - Sulfonamide
KW - Sulfonylguanidine
KW - Synthesis
SP - 135
EP - 47
JF - European journal of medicinal chemistry
JO - Eur J Med Chem
VL - 71
N2 - A series of novel N-substituted N'-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines 9-41 have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA.EC 4.2.1.1), that is the cytosolic CA I and II, and cancer-associated isozymes CA IX and XII. Against the human CA I investigated compounds showed KI in the range of 87-6506 nM, toward hCA II ranging from 7.8 to 4500 nM, against hCA IX in the range of 4.7-416 nM and against hCA XII at range of 0.96-540 nM. Compounds 10, 12-14, 16, 18-20, 24-26, 31 and 32 exhibited a powerful inhibitory potency toward hCA IX (K(I) = 4.7-21 nM) in comparison to the reference sulfonamides AAZ, MZA, EZA, DCP and IND (K(I) = 24-50 nM). Compound 14 was the most potent inhibitor of hCA I (K(I) = 87 nM), hCA IX (K(I) = 4.7 nM) and hCA XII (K(I) = 0.96 nM), while 26 was the most effective inhibitor of hCA II (K(I) = 7.8 nM). The most promising compound 32 exerted the highest selectivity ratios toward hCA IX versus hCA I (hCA I/hCA IX = 261) and hCA II (hCA II/hCA IX = 26). The in vitro antitumor activity of compounds 10, 13, 14, 21, 22, 25, 32, 38 and 41 was evaluated at the US National Cancer Institute (NCI) against a panel of 60 human tumor cell lines. The most active antitumor agents 21 and 25, inhibiting 32-35 human tumor cell lines with GI₅₀ in the range of 2.1-5.0 μM also showed relatively high inhibitory activity toward hCA IX and XII with KI from 18 to 40 nM.
SN - 1768-3254
UR - https://www.unboundmedicine.com/medline/citation/24291567/Carbonic_anhydrase_inhibitors__Synthesis_and_molecular_structure_of_novel_series_N_substituted_N'__2_arylmethylthio_4_chloro_5_methylbenzenesulfonyl_guanidines_and_their_inhibition_of_human_cytosolic_isozymes_I_and_II_and_the_transmembrane_tumor_associated_isozymes_IX_and_XII_
L2 - https://linkinghub.elsevier.com/retrieve/pii/S0223-5234(13)00738-1
DB - PRIME
DP - Unbound Medicine
ER -