Synthesis and evaluation of 1,2,2-tris(sulfonyl)hydrazines as antineoplastic and trypanocidal agents.

doi:10.1002/CHIN.199105149

Paper

Synthesis and evaluation of 1,2,2-tris(sulfonyl)hydrazines as antineoplastic and trypanocidal agents.

Published Aug 1, 1990 · K. Shyam, P. Penketh, A. Divo

Journal of medicinal chemistry

Q1 SJR score

38

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0

Influential Citations

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Abstract

Several 1,2,2-tris(sulfonyl)hydrazines, conceived as prodrugs of 1,2-bis(sulfonyl)hydrazines, were synthesized and evaluated for antineoplastic and trypanocidal activities in mice. 1-Methyl-1,2,2-tris(methylsulfonyl)hydrazine emerged as an extremely efficacious antitrypanosomal agent, whereas 1-(2-chloroethyl)-1,2,2-tris(methylsulfonyl)hydrazine was inactive. In contrast, 1-(2-chloroethyl)-1,2,2-tris(methylsulfonyl)hydrazine displayed potent antineoplastic activity, producing several 60-day "cures" of mice bearing leukemia L1210, leukemia P388, or Sarcoma 180. Furthermore, the fact that the tris(sulfonyl) derivatives will not generate isocyanates, which contribute to the host toxicity of nitrosoureas like 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU), makes them agents of significant promise in trypanosomal and cancer chemotherapy.

Non-RCT

Animal Study

Study Snapshot

1,2,2-tris(sulfonyl)hydrazines show potential as effective antitrypanosomal agents and potent antineoplastic agents, offering potential for both trypanosomal and cancer chemotherapy.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis and evaluation of 1,2,2-tris(sulfonyl)hydrazines as antineoplastic and trypanocidal agents.

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References

Citations

The Utility of Sulfonylhydrazines in the Study and Potential Treatment of African Sleeping Sickness

Sulfonylhydrazines show potential in studying and treating late-stage African sleeping sickness by inducing differentiation in T. brucei group trypanosomes and producing large quantities of short stumpy forms for biochemical studies.

Design Strategy for the EPR Tumor-Targeting of 1,2-Bis(sulfonyl)-1-alkylhydrazines

This design strategy for macromolecular prodrugs targeting solid tumors with short-lived cytotoxic moieties exploits the enhanced permeability and retention (EPR) effect, reducing response variability and resistance acquisition.

Sulfonamide phenylalanine (SPA) series of analogues as an antibacterial, antifungal, anticancer agents along with p53 tumor suppressor-DNA complex inhibitor – part 1

The K4 sulfonamide analogue shows better anticancer activity against PC-3 and A549 cancer cell lines, and inhibits p53 tumor suppressor-DNA complex.

Structural, Spectroscopic and Activity Calculations on Methanesulfonylhydrazone Derivative Chromium Pentacarbonyl Complexes

Optimized structures and appropriate basis sets can predict biological activities of methanesulfonylhydrazone derivative chromium pentacarbonyl complexes, potentially aiding in antibiotic development.

Antitumor sulfonylhydrazines: design, structure-activity relationships, resistance mechanisms, and strategies for improving therapeutic utility.

BSHs show potential as a more specific and versatile antitumor agent, targeting tumors deficient in MGMT activity and potentially expanding their activity by combining them with MGMT inhibitors.

Photochemical reactions of metal carbonyls with heteroaromatic methanesulfonylhydrazone-based ligands

Three new heteroaromatic methanesulfonylhydrazone derivatives synthesized by photochemical reactions with metal carbonyls show promising potential as two-electron donors in metal carbonyl complexes.

Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides.

Substituted salicylaldehyde hydrazones and hydrazides show potent inhibitory effects on fungal growth with minimal mammalian cell toxicity, making them promising targets for future therapeutic development.

Influence of Glutathione and Glutathione S-transferases on DNA Interstrand Cross-Link Formation by 1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)hydrazine, the Active Anticancer Moiety Generated by Laromustine

Glutathione and glutathione S-transferases can reduce the initial yields of DNA interstrand cross-link precursors, potentially impacting tumor cell resistance to these agents.