A new family of potential oncostatics: 2-chloroethylnitrososulfamides (CENS)—I. Synthesis, structure, and pharmacological evaluation (preliminary results)
A new series of alkylating agents, 2-chloroethylnitrososulfamides (CENS), were developed on the model of 2-chloroethylnitrosoureas. Starting from chlorosulfonyl isocyanate, a four-step synthesis (carbamoylation-sulfamoylation, Mitsunobu alkylation, deprotection and nitrosation) gives the title compounds. The pharmacological evaluation shows a significant oncostatic activity.
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The relationship between solvatochromic properties and in silico ADME parameters of new chloroethylnitrosourea derivatives with potential anticancer activity and their β-Cyclodextrin complexes
2021, Spectrochimica Acta - Part A: Molecular and Biomolecular SpectroscopyCitation Excerpt :The subsequent nitrosation reaction was carried out with sodium nitrite, which is not regiospecific and gives the N’-aryl-N-nitrosoureas as major and the N’-aryl-N’-nitrosoureas as a minor product (Fig. S2) as revealed by thin layer chromatography. Separation of the two isomers by column chromatography on silica gel was, however, straightforward and the structure of the CENUs was confirmed by 1H NMR spectroscopy and ESI-MS. In ESI-MS, all CENUs gave [M−NO + H]+ ion peaks corresponding to the loss of NO due to the instability of the N-nitroso group under ESI-MS conditions [27]. In 1H NMR, successful nitrosation was confirmed by disappearance of the exchangeable N-H protons and by appearance of an A2X2 system with a triplet between 3.10 and 3.75 ppm corresponding to the chloromethylene group and a triplet between 3.65 and 4.32 ppm corresponding to the CH2NNO group.
Pathways for N-Nitroso Compound Formation: Secondary Amines and beyond
2020, Organic Process Research and DevelopmentHost-guest complex of N-(2-chloroethyl), N-nitroso, N′, N′ -dicyclohexylsulfamid with β-cyclodextrin: Fluorescence, QTAIM analysis and structure-chemical reactivity
2017, Journal of Molecular StructureCitation Excerpt :Finally, for better understanding of biological molecule behavior before and after complexation, a detailed analysis of structure–chemical reactivity of the interesting drug, in free and in complexed state was undertaken at the end of this work. N-(2-chloroethyl), N-nitroso, N′, N′-dicyclohexylsulfamid derived from di-cyclohexylamin (DCY/CENS) molecule has been synthesized following the procedure described in Ref. [15]. The used chemicals are of high purity (analytical grade).
Inclusion complex of N-nitroso, N-(2-chloroethyl), N′, N′-dibenzylsulfamid with β-Cyclodextrin: Fluorescence and molecular modeling
2012, Comptes Rendus ChimieCitation Excerpt :Bidistilled water was used in all of the experiments. The investigated compound was synthesised according to the procedure described in the literature [12]. All chemicals used were of high purity (analytical grade).
Structure-activity relationships of bioisosteric replacement of the carboxylic acid in novel androgen receptor pure antagonists
2010, Bioorganic and Medicinal Chemistry
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Permanent address: Department of Chemistry, University of Annaba, BP 12, El Hadjar, Algeria.