Synthesis and Biological Activity of Sulfonamide Derivatives of Epipodophyllotoxin was written by Guianvarc’h, Dominique;Duca, Maria;Boukarim, Chawki;Kraus-Berthier, Laurence;Leonce, Stephane;Pierre, Alain;Pfeiffer, Bruno;Renard, Pierre;Arimondo, Paola B.;Monneret, Claude;Dauzonne, Daniel. And the article was included in Journal of Medicinal Chemistry in 2004.Electric Literature of C6H7ClN2O3S2 This article mentions the following:
A series of novel 4β-substituted sulfonamide derivatives of 4′-O-demethyl-4-desoxypodophyllotoxin, I [R1 = SO2R, R = Me, n-Pr, (CH2)3NH2, 2-thienyl, piperidino, etc.] (II), has been synthesized. II were synthesized by silylating the alc. I (R1 = H), followed by reaction with RSO2Cl, and desilylation. Their effects on human DNA topoisomerase II and, in some cases, on tubulin polymerization were evaluated. Several of the compounds, e.g. II (R = Me), and the synthetic precursor, the 4β-azido compound, are potent topoisomerase II poisons that induce double-stranded breaks in DNA, with either improved or similar activity compared to etoposide. Only the amino precursor, compound I (R1 = H), was slightly active in tubulin polymerization inhibition assays. We observed that the derivatives bearing an aromatic ring on the 4β-sulfonamide substituent were either less cytotoxic or equivalent to the parent drug, while the sulfonamides containing an aliphatic side chain and the amino-sulfonamide derivatives, except II [R = (CH2)15Me, (CH2)3NH2], exhibited increased cytotoxicity compared to etoposide. In vivo, against the P388 leukemia and the A-549 orthotopic model of lung carcinoma, the most promising compounds were the morpholino- and the piperazino-containing sulfonamides derivatives II (R = morpholino, 4-methylpiperazino). In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Electric Literature of C6H7ClN2O3S2).
2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Electric Literature of C6H7ClN2O3S2
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica