Category: 1062608-42-7

Younis, Yassir published the artcileStructure-Activity-Relationship Studies around the 2 Amino Group and Pyridine Core of Antimalarial 3,5-Diarylaminopyridines Lead to a Novel Series of Pyrazine Analogues with Oral in Vivo Activity, Name: 5-Bromo-3-iodopyrazin-2-amine, the main research area is antimalarial diarylaminopyridine pyrazine analog preparation antimalarial SAR.

Replacement of the pyridine core of antimalarial 3,5-diaryl-2-aminopyridines led to the identification of a novel series of pyrazine analogs with potent oral antimalarial activity. However, other changes to the pyridine core and replacement or substitution of the 2-amino group led to loss of antimalarial activity. The 3,5-diaryl-2-aminopyrazine series showed impressive in vitro antiplasmodial activity against the K1 (multidrug resistant) and NF54 (sensitive) strains of Plasmodium falciparum in the nanomolar IC50 range of 6-94 nM while also demonstrating good in vitro metabolic stability in human liver microsomes. In the Plasmodium berghei mouse model, this series generally exhibited good efficacy at low oral doses. One of the frontrunner compounds, (I), displayed potent in vitro antiplasmodial activity with IC50 values of 8.4 and 10 nM against the K1 and NF54 strains, resp. When evaluated in P. berghei-infected mice, compound I was completely curative at an oral dose of 4×10 mg/kg.

Journal of Medicinal Chemistry published new progress about Antimalarials. 1062608-42-7 belongs to class pyrazines, name is 5-Bromo-3-iodopyrazin-2-amine, and the molecular formula is C4H3BrIN3, Name: 5-Bromo-3-iodopyrazin-2-amine.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 1062608-42-7, name is 5-Bromo-3-iodopyrazin-2-amine, molecular formula is C4H3BrIN3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 5-Bromo-3-iodopyrazin-2-amine

To the solution of compound (iii) (355 mg, 1.18 mmol) in 1,4-dioxane (5 ml) was added a boronic acid of formula (iv) such as 6-methoxypyridin-3-yl boronic acid (CombiB locks 190 mg, 1.24 mmol) at RT and the reaction mixture was purged with N2 gas for 30 minutes. Bis(triphenylphosphine)palladium(II)chloride (58 mg, 0.08 mmol) and 1 M aqueous solution of potassium carbonate (1.42 ml, pre-purged with N2 gas) were added to the reaction mixture. The solution was heated to reflux for 16 h and then cooled to RT, added Brine solution (5 ml) and extracted with ethyl acetate (10 ml X 4). Combined organic layers were dried over anhydrous Na2S04 and concentrated. Crude material was purified by column chromatography over silica gel 230-400 mesh by using 1-2% MeOH in DCM as an eluent to yield compound (v) (150 mg, 45.18%) as solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1062608-42-7, its application will become more common.

Reference:
Patent; UNIVERSITY OF CAPE TOWN; MMV MEDICINES FOR MALARIA VENTURE; YOUNIS, Yassir; CHIBALE, Kelly; WITTY, Michael, John; WATERSON, David; WO2013/121387; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 1062608-42-7, name is 5-Bromo-3-iodopyrazin-2-amine, molecular formula is C4H3BrIN3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 5-Bromo-3-iodopyrazin-2-amine

To a solution of 2b (4.0 g, 13.33 mmol) in 1,4-dioxane (55 mL) was added 3- (trifluoromethyl)phenyl boronic acid (6) (2.79 g, 14.67 mmol) followed by 1M aqueous solution of potassium carbonate (26.6 mL, 26.67 mmol) at RT. Reaction mixture was purged with N2 gas for 30 minutes. Bis(triphenylphosphine)palladium(II)chloride (0.65 g, 0.93 mmol) was added to the reaction mixture and was heated to reflux for 4 h, cooled to RT, filtered through celite. Filtrate was concentrated under vacuum to remove dioxane. 50 mL of water was added and extracted with dichloromethane. Organic layer combined and washed with water, dried over sodium sulfate and concentrated under vacuum. Crude product purified by flash chromatography using 30% ethyl acetate in petroleum ether to afford compound 3b (3.5 g, 83.3%) as pale yellow solid. 1H NMR (400 MHz, DMSO-d6): delta 8.14 (s, 1H), 7.90 (d, J = 8.40 Hz, 2H), 7.84 (d, J = 8.40 Hz, 2H), 6.63 (s, 2H). LC-MS APCI: Calculated for C11H7BrF3N3: 318.10; Observed m/z [M+H]+: 318.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1062608-42-7, its application will become more common.

Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; UNIVERSITY OF CAPE TOWN; WATERSON, David; WITTY, Michael John; CHIBALE, Kelly; STREET, Leslie; GONZALEZ CABRERA, Diego; PAQUET, Tanya; (36 pag.)WO2017/9773; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem