Synthesis of some sulfonamides, disubstituted sulfonylureas or thioureas and some structurally related variants. A class of promising antitumor agents

Medicinal Chemistry Research (Impact Factor: 1.61). 11/2007; 16(6):300-318. DOI: 10.1007/s00044-007-9033-8

ABSTRACT Some new benzenesulfonamides, disubstituted sulfonylureas, and sulfonylthioureas substituted basically with 3-(2-thienyl or
3-pyridyl)-indeno[1,2-c]pyrazol(in)e counterpart were synthesized to be evaluated for their in vitro antitumor activity. Some
of the thioureido derivatives were cyclized to the corresponding five-membered thiazolidinons, thiazolines, and the six-membered
thiazinones as interesting structure variants. According to the protocol of the National Cancer Institute (NCI) in vitro disease-oriented
human cells screening panel assay, 13 compounds showed promising broad spectrum antitumor activity. In general, compounds
containing the thienyl moiety displayed better antitumor spectra than those containing the pyridyl moiety. Compound 5, 4-(3-(2-thienyl)-3H-indeno[1,2-c]pyrazol-2-yl)-benzenesulfonamide
[GI50, TGI, and LC50 (MG-MID) values of 13.2, 33.1 and 69.2μM, respectively] proved to be the most active member in this study with variable
degrees of potencies against all the tested subpanel tumor cell lines and particular effectiveness against the leukemia and
prostate subpanels at both the GI50 (3.30 and 8.68μM, respectively) and the TGI levels (15.7 and 22.3μM, respectively).

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    ABSTRACT: We investigated the radiolabeling efficiency, in vitro stability, and biodistribution of radioactive iodine (131I)-labeled 4-benzoyl-1-(4-carboxyphenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid (P3CA). A quality-control study of the labeled substance (131I-P3CA) was conducted using electrophoresis and radio thin-layer chromatography (RTLC). Biodistribution studies were undertaken in 9 female albino Wistar rats. Rats were killed at various times (15, 60 and 180 min), their organs removed, and percentage of injected dose per gram (ID%/g) values calculated. The labeling yield of P3CA was 97.08%±0.80%. The maximum uptake of 131I-P3CA was seen in the lungs, stomach and spleen at 15 min. The uptake of labeled compound decreased over time in the lungs, whereas that in the stomach decreased. These data suggest that 131I-P3CA had high binding efficiency, high uptake in the lung, and sufficient stability to be used in diagnostic studies.
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    Medicinal Chemistry Research 11/2009; 19(8). DOI:10.1007/s00044-009-9228-2 · 1.61 Impact Factor