Diaminopyrimidines

Diaminopyrimidines are basic organic compounds with two amino groups on one pyrimidine ring . Four isomers can arise depending on the arrangement of the amino groups on the ring.

Representative

Diaminopyrimidines
Surname	2,4-diaminopyrimidine	2,5-diaminopyrimidine	4,5-diaminopyrimidine	4,6-diaminopyrimidine
other names	Pyrimidine-2,4-diamine	Pyrimidine-2,5-diamine	Pyrimidine-4,5-diamine	Pyrimidine-4,6-diamine
Structural formula
CAS number	156-81-0	22715-27-1	13754-19-3	2434-56-2
PubChem	67431	229075	83703	79608
Molecular formula	C 4 H 6 N 4
Molar mass	110.12 g mol −1
Physical state	firmly
Brief description	light yellow solid	orange to brown solids
Melting point	143-147 ° C		204-206 ° C
solubility	soluble in water
GHS labeling	Caution	no classification available	no GHS pictograms	Caution
H and P phrases	315-319-335	see above	no H-phrases	315-319
	no EUH phrases	see above	no EUH phrases	no EUH phrases
	261-305 + 351 + 338	see above	no P-phrases	264-280-305 + 351 + 338-337 + 313- 302 + 352-332 + 313-362 + 364

use

Derivatives of diaminopyrimidines are used as pharmacological agents. They often act as folic acid antagonists and inhibit the bacterial dihydrofolate reductase . Since folic acid is an important growth substance for many bacteria and the diaminopyrimidines block the synthesis of folic acid within a bacterium, they act as an antibiotic .

Representatives of this group are for example:

• Aminopterin
• Iclaprim
• Kopexil (used as "Aminexil" to treat hair loss)
• Methotrexate
• Pyrimethamine
• Minoxidil (used to treat hair loss)
• Trimethoprim (most important representative of the group)
• 2,5-diaminopyrimidine nucleoside triphosphate (occurs in the biosynthesis of biopterin from GTP )

The structurally similar diaminopyridine derivatives, e.g. B. 3,4-diaminopyridine are used in neurological diseases such as Lambert-Eaton syndrome . Their influence on presynaptic potassium channels and the increased release of transmitters mediated by them is used.

Related links

• Aminopyrimidines Pyrimidines with an amino group
• Triaminopyrimidines Pyrimidines with three amino groups
• Diaminopyridines Pyridines with two amino groups

Web links

• Freepatentsonline: 2,4-Diaminopyrimidines
• Freepatentsonline: Diaminopyrimidines as modulators for an EP2 receptor

Individual evidence

1. ↑ ^{a b c} data sheet 2,4-diaminopyrimidine from Sigma-Aldrich , accessed on November 13, 2017 ( PDF ).
2. ↑ ^{a b} data sheet 4,5-diaminopyrimidine from Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).
3. ↑ Entry on 4,6-diaminopyrimidines at TCI Europe, accessed on November 13, 2017.
4. ↑ Entry on diaminopyrimidine in Flexikon , a wiki from DocCheck , accessed on November 26, 2015.