37660-22-3

Usage

Uses

Used in Oncology:
6-amino-2-(ethylthio)-1H-pyrimidin-4-one is used as an antitumor agent for the treatment of various cancers, including soft tissue sarcoma and ovarian cancer. Its unique mechanisms of action, such as binding to the minor groove of DNA and inhibiting DNA repair processes, contribute to its effectiveness in combating cancer cells.
Used in Cancer Research:
6-amino-2-(ethylthio)-1H-pyrimidin-4-one is utilized in cancer research to explore its potential applications in cancer therapy. Ongoing research and clinical trials are focused on understanding its complex structure and mechanism of action, as well as identifying ways to enhance its therapeutic efficacy and bioavailability.
Used in Drug Development:
6-amino-2-(ethylthio)-1H-pyrimidin-4-one serves as a key component in the development of novel cancer therapeutics. Its unique properties and mechanisms of action make it a promising candidate for the creation of new drugs that can target cancer cells more effectively and with fewer side effects.

InChI:InChI=1/C6H9N3OS/c1-2-11-6-8-4(7)3-5(10)9-6/h3H,2H2,1H3,(H3,7,8,9,10)

Upstream product

• 1004-40-6 6-Amino-2-thiouracil 
• 64-67-5 diethyl sulfate 
• 74-96-4 ethyl bromide 
• 1004-40-6 4-aminothiouracil 
• 75-03-6 ethyl iodide 

Relevant academic research and scientific papers

Convenient One-Pot Four-Component Synthesis of 6,8-Disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]-pyrimidin-4(3H)-ones via a Triple Mannich Reaction

An efficient and simple one-pot four-component protocol has been developed and performed for the synthesis of 6,8-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones, involving a triple Mannich reaction of 6-amino-2-(ethylthio)pyrimidin-4(3H)-one, formaldehyde, primary amines, and alcohols. Secondary amines were also utilised instead of alcohols as Mannich nucleophiles, and a variety of functional groups and electronically varied reaction partners were tolerated. This one-pot reaction facilitated the generation of a library of pyrimido[4,5-d]pyrimidin-4(3H)-ones in very good to excellent yields. The regioselectivity of this reaction was investigated using atomic charge calculations, and spectroscopic data confirmed that the triple Mannich products were 6,8-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones rather than the isomeric 3,6-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones. The structures of all compounds synthesised using the triple Mannich reaction were confirmed via spectroscopic and elemental analyses. The reaction mechanism was studied and confirmed by isolation of the intermediate.

Synthesis of 2-ethylthio-6-(3-hydroxy-1,2-O- isopropylidenepropyl)pteridin-4(3H)-one

A strategy has been described for the synthesis of 2-ethylthio-6-(3- hydroxy-1,2-O-isopropylidenepropyl)pteridin-4(3H)-one, which can be used as a useful intermediate for the conversion of neopterin to biopterin.

Chemical synthesis of some novel 6-aminouracil-2-thiones and their glycoside analogues

6-AMINOURACIL-2-THIONE (1) and its 5-bromo derivative 2 underwent alkylation yielding their respective S-alkyl products 4a-j. The reaction of compound 1 and aldehydes in the presence of chloroacetic acid afforded the respective thiazolopyrimidinyl acetamides 7a-d. The C-glycosides 8a, b and 9c-e were successfully prepared through condensing compound 1 and the appropriate sugar in the presence of chloroacetic acid. The behavior of certain S-alkyl derivative 4 towards amines and hydrazines was also studied. Structure elucidations for the new products were supported by compatible chemical and spectral measurements.

Derivatives of 4-amino-6-hydroxy-2-mercaptopyrimidine as novel, potent, and selective A3 adenosine receptor antagonists

A number of derivatives of 4-amino-6-hydroxy-2-mercaptopyrimidine (5) were synthesized and biologically evaluated as A3 adenosine receptor (A3 AR) antagonists. The new compounds were designed as open chain analogues of a triazolopyrimidinone derivative displaying submicromolar affinity for the A3 AR, which had been previously identified using a 3D database search. Substituents R, R′, and R″ attached to the parent compound 5 were chosen according to factorial design and stepwise lead optimization approaches, taking into account the essentially hydrophobic nature of the A3 AR binding site. As a result, 5m (R = n-C3H 7, R′ = 4-ClC6H4CH2, R″ = CH3) was identified among the pyrimidine derivatives as the ligand featuring the best combination of potency and selectivity for the target receptor. This compound binds to the A3 AR with a Ki of 3.5 nM and is devoid of appreciable affinity for the A1, A 2A, and A2B ARs.

Hit-to-Lead studies: The discovery of potent, orally bioavailable thiazolopyrimidine CXCR2 receptor antagonists

A Hit-to-Lead optimisation programme was carried out on a high throughput screening hit, the thiazolopyrimidine 1, resulting in the discovery of the potent, orally bioavailable CXCR2 antagonist 29.