941-90-2

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-2-imino-3-methyl-2,4a-dihydropteridin-4(3H)-one is used as a key intermediate in the synthesis of pteridine-based drugs for the treatment of various diseases, including cancer and neurological disorders. Its role in the development of pharmaceuticals is attributed to its ability to regulate one-carbon metabolism and maintain cellular integrity.
Used in Biochemical Research:
In the field of biochemical research, (2E)-2-imino-3-methyl-2,4a-dihydropteridin-4(3H)-one serves as a valuable building block for the production of folate and its derivatives. These compounds are essential for various biological processes, making this chemical a crucial component in studies related to DNA and RNA synthesis, as well as one-carbon metabolism.

Upstream product

• 445033-65-8 2-{[(dimethylamino)methylene]amino}-3-methylpteridin-4(3H)-one 
• 2236-60-4 2-aminopteridin-4(3H)-one 
• 13165-97-4 N²-acetylpterin 
• 445033-61-4 2-{[(dimethylamino)methylene]amino}pteridin-4(3H)-one 
• 522614-33-1 2-amino-3-[2-(4-nitrophenyl)ethyl]pteridin-4(3H)-one 
• 522614-23-9 4-[2-(4-nitrophenyl)ethoxy]pteridin-2-amine 
• 522614-27-3 2-{[(dimethylamino)methylene]amino}-3-[2-(4-nitrophenyl)ethyl]pteridin-4(3H)-one 
• 522614-36-4 N-{3,4-dihydro-3-[2-(4-nitrophenyl)ethyl]-4-oxopteridin-2-yl}acetamide 
• 522614-07-9 N-{4-[2-(4-nitrophenyl)ethoxy]pteridin-2-yl}acetamide 

Relevant academic research and scientific papers

Photophysical and Photochemical Properties of 3-methylpterin as a New and More Stable Pterin-type Photosensitizer

Pterin derivatives are heterocyclic compounds which are present in different biological systems. Neutral aqueous solutions of pterins present acid–base and keto–enol equilibria. These compounds, under UV-A radiation fluoresce, undergo photooxidation, generate reactive oxygen species and photoinduce the oxidation of biological substrates. As photosensitizers, they may act through different mechanisms, mainly through an electron transfer-initiated process (type-I mechanism), but they also produce singlet molecular oxygen (1O2) upon irradiation (type-II mechanism). In general, upon UV-A excitation two triplet states, corresponding to the lactim and lactam tautomers, are formed, but only the last one is the responsible for the photosensitized reactions of biomolecules. We present a study of the photochemical properties of 3-methylpterin (3-Mep) which, in contrast to most pterin derivatives, exists only in the lactam form. Also an improvement in the synthesis of 3-Mep is reported. The spectroscopic properties 3-Mep in aqueous solution were similar to those of the unsubstituted pterin derivative (Ptr) in its acid form, such as absorption, fluorescent and phosphorescent emission spectra. Experiments using 2′-deoxyguanosine 5′-monophosphate (dGMP) as oxidizable target demonstrated that methylation at C-3 position of the pterin moiety does not affect significantly the efficiency of photosensitization, but results in a more photostable sensitizer.

Pteridines. Part CXIII. Protection of Pteridines

The low solubulity of pterins can drastically be improved by N2-acylation or formation of the N2-[(dimethylamino)methylene] derivatives. Both types of compounds can be alkylated under Mitsunobu conditions to form from N2-acylpterins (see 2 and 3) and their derivatives (see 5, 6, 8, 9, 11, 13, 15, and 17) selectively the O4-alkyl derivatives 22-31, whereas the electron-donating [(dimethylamino)methyleneamino] function in 46-51 gives, in a selective reaction, the N(3)-substitution (->52-61). N2,N2-Dimethylpterins and 18 and 19 and N2-methylpterins 20 and 21 direct alkylation also to the O4-position (->32-35, 38 and 39). Deacylation can be achieved under very mild conditions by solvolysis with MeOH (22->40, 26->41), and displacement of the O4-[2-(4-nitrophenyl)ethyl] group proceeds with ammonia at room temperature to the corresponding pteridin-2,4-diamine 42-45. Cleavage of the N2-[(dimethylamino)methylene] group works well with ammonia (->62-67). The advantage of applying the 2-(4-nitrophenyl)ethyl (npe) group as blocking group is seen in its selective removal by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under aprotic conditions without harming the other substituents.