《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. Formula: C5H11ClN2O2S And the article was included in Journal of Medicinal Chemistry on April 22 ,2004. The article conveys some information:
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 part of experimental materials, we found many familiar compounds, such as 4-Methyl-1-piperazinesulfonyl Chloride(cas: 1688-95-5Formula: C5H11ClN2O2S)
4-Methyl-1-piperazinesulfonyl Chloride(cas: 1688-95-5) is a member of sulfamide. Sulfamide was used in the synthesis of: Schiff bases of the type ArCH=NSO2NH2; 1H,3H-2,1,3-benzothiadiazin-4-one-2,2-dioxide (BTDD); sulfamide analogs of oleoylethanolamide analogs in a study of PPARα activation.Formula: C5H11ClN2O2S
Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics