82020-90-4

Usage

Classification

Triazine antifolate

Enzyme target

Dihydrofolate reductase

Synthesis involvement

DNA, RNA, and proteins

Potential use

cancer treatment

Combination therapy

with other chemotherapy drugs

Promising results

in preclinical and clinical studies

Cancer types studied

lung, breast, ovarian

Mechanism of action

inhibition of dihydrofolate reductase

Ability to overcome resistance

to other antifolate drugs

Ongoing research

for cancer therapy.

InChI:InChI=1/C7H13N5O/c1-4(2)9-6-10-5(8)11-7(12-6)13-3/h4H,1-3H3,(H3,8,9,10,11,12)

Upstream product

• 24771-25-3 dimethyl (N-cyanoimido)carbonate 

Relevant academic research and scientific papers

Preparation of 2-amino-4-alkoxy-s-triazines

2-Amino-4-alkoxy-s-triazines which are substituted by an alkyl, aryl or aralkyl moiety in the 6-position and which are useful as pharmaceutical agents and as intermediates for herbicides, dyes and optical brighteners are prepared by reacting a dialkyl (N-cyanoimido)carbonate with an amidine salt in the presence of an inert solvent and a base.

Process for the preparation of 2-amino-s-triazines

The present invention relates to a process for the preparation of 2-amino-s-triazines in three stages. In the first stage nitriles, alcohols and hydrogen chloride are reacted to form the corresponding imido-ester hydrochlorides. In the second stage, the imido-ester hydrochlorides are reacted with cyanamide in the aqueous phase to form the N-cyanimido-esters, which comprises carrying out the first stage in the presence of acetic acid esters and the second stage in an aqueous solution which has been brought to a pH value of 5-8 by addition of bases, and reacting the N-cyanimido-esters with O-alkylisourea, S-alkylisothiourea, guanidine or amidine salts in the presence of a base in the third stage. The 2-amino-s-triazines can be prepared in a high purity and with good yields in this manner.