199486-81-2

Upstream product

• 2240-25-7 5-bromocytosine 
• 98-59-9 p-toluenesulfonyl chloride 
• 1122-44-7 5-iodocytosine 
• 71-30-7 Cytosine 
• 79628-80-1 4-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-2-trimethylsilanyloxy-pyrimidine 

Downstream Products

• 1159258-17-9 Pd(1-(p-toluenesulfonyl)cytosine-N₃)2Cl₂ 
• 1193656-86-8 dichlorobis[1-(p-toluenesulfonyl)cytosine]copper(II) 
• 1193656-88-0 dichlorobis[1-(p-toluenesulfonyl)cytosine]cadmium(II) 
• 1193656-89-1 dichlorobis[1-(p-toluenesulfonyl)cytosine]cobalt(II) 
• 919524-54-2 5-(morpholin-4-ylmethyl)cytosine 
• 6339-26-0 4-tosylmorpholine 
• 1159258-18-0 Pd₂(1-(p-toluenesulfonyl)cytosine-N₃,N₄^(1-))4 
• 1159258-19-1 Pd₂(1-(p-toluenesulfonyl)cytosine-N₃,N₄^(1-))2Cl₂(DMSO)2 

Relevant academic research and scientific papers

Synthesis of the sulfonylpyrimidine derivatives as a new type of sulfonylcycloureas

The synthesis of several novel N-1 and N-1,NH-4-disulfonylpyrimidine derivatives are described.

C5-Morpholinomethylation of: N 1-sulfonylcytosines by a one-pot microwave assisted Mannich reaction

A fast and efficient route for the introduction of a methylene bridged-amine (morpholinomethyl) functionality in the C5 position of the sulfonylated cytosine nucleobase has been developed. First, novel N1-sulfonylcytosine derivatives 3-6 were prepared by the condensation of silylated cytosine with selected sulfonyl chlorides. They were subsequently transformed to 5-morpholinomethyl-N1-sulfonylcytosine derivatives (8, 12-15) using microwave irradiation. As a result of cytosine ring opening in N1-tosylcytosine, depending on the reaction conditions, peculiar tosyl-urea derivative 9 has been isolated, which provided additional insight into the reaction pathway. The influence of the C5-substituent on the antiproliferative activity has been evaluated by performing the MTT test on U251, MCF-7 and MOLT-4 tumor cell-lines.

Antiproliferative and proapoptotic activity of molecular copper(II) complex of N-1-tosylcytosine

In an attempt to enhance the previously observed antiproliferative capacity of 1-(p-toluenesulfonyl)cytosine (N-1-tosylcytosine, ligand 1), its copper(II) complex (Cu(1-TsC-N3)2Cl2, complex 2) was prepared and tested in vitro on vari

Synthesis, spectroscopic characterization and biological activity of N-1-sulfonylcytosine derivatives

Large scale preparation of N-1-sulfonylcytosine derivatives has been optimized. The best method was the condensation reaction of silylated cytosine (1) with p-toluenesulfonyl chloride in acetonitrile. Depending on the isolation procedure, 1-(p-toluenesulfonyl)cytosine 2 and 1-(p-toluenesulfonyl)cytosine hydrochloride 3 were isolated in 80 % and 75 % yields, respectively. The NMR evidence presented shows that 2 appears as a common keto-amino tautomer in DMSO-d6 solution while its hydrochloride 3 forms exclusively the rare keto-imino tautomer. N-1-Sulfonylcytosine derivatives 2 and 3 were investigated for possible cytotoxic activity on human normal fibroblasts (WI38), human pancreatic adenocarcinoma cells (MIAPaCa2), poorly differentiated cells from lymph node metastases of colon carcinoma (SW-620), and human Burkitt lymphoma cells (Raji). MTT-cytotoxicity screens in human tissue culture cell lines showed that both investigated compounds demonstrated antiproliferative activity in different histological types of tumors. In comparison with 5-fluorouracil, some of N-1-sulfonylcytosine derivatives showed 10 times stronger activity, with respect IC50. The inhibitory effect of the investigated derivatives on normal human cells was lower compared to their antitumor effects. In addition to antitumor effects, hematological findings following the parenteral administration of substances were also investigated.

5-bromo- and 5-iodo-N-1-sulfonylated cytosine derivatives. Exclusive formation of keto-imino tautomers

N-1-Sulfonylated cytosine 5 and 5-halogeno-N-1-sulfonylated cytosine derivatives 1 and 2 were synthesized by condensation of silylated cytosine or 5-halogenocytosine bases with tosylchloride in acetonitrile, or by the reaction of cytosine or 5-halogenocyt