43191-41-9Relevant academic research and scientific papers
NOVEL CYCLIC GMP-AMP SYNTHASE (CGAS) INHIBITORS AND THEIR METHOD OF USE
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Page/Page column 60-62; 73, (2020/01/08)
Methods of treating diseases related to cGAS activation. Small molecule inhibitors of cGAS and pharmaceutical compositions and uses thereof in treating autoimmune diseases or inflammation.
Optimised synthesis of diamino-triazinylmethyl benzoates as inhibitors of Rad6B ubiquitin conjugating enzyme
Kothayer, Hend,Morelli, Matteo,Brahemi, Ghali,Elshanawani, Abdalla A.,Abu Kull, Mansour E.,El-Sabbagh, Osama I.,Shekhar, Malathy P.V.,Westwell, Andrew D.
supporting information, p. 7015 - 7018 (2015/01/09)
Recently, we have identified the first inhibitors of Rad6B, an E2 enzyme essential for post-replication DNA repair and a potential new drug target for the treatment of breast cancer. We report two newly optimised synthetic routes to our [4-amino-6-(phenylamino)-1,3,5-triazin-2-yl]methyl 4-nitrobenzoate target compounds TZ8 and TZ9 with general applicability for further structure-activity relationship studies around this pharmacophore. The key step involved the condensation/cyclisation between phenylbiguanide and either ethyl bromoacetate or dimethyloxalate in good yield.
Regioselective synthesis of pyrimido[1,2-a][1,3,5]triazin-6-ones via reaction of 1-(6-oxo-1,6-dihydropyrimidin-2-yl)guanidines with triethylorthoacetate: Observation of an unexpected rearrangement
Sachdeva, Nikhil,Dolzhenko, Anton V.,Keung Chui, Wai
scheme or table, p. 4586 - 4596 (2012/07/28)
A novel thermal rearrangement, involving pyrimidine ring opening and subsequent ring closure leading to recyclization of the system, was identified in the reaction of (6-oxo-1,6-dihydropyrimidin-2-yl)guanidines 3 (where NR 1R2 = NH2, NH alkyl, NH aralkyl, NHCH 2Ph(R)) with triethyl orthoacetate, affording 4-substituted-2-methyl- 6H-pyrimido[1,2-a][1,3,5]triazin-6-ones 6 and their ring opened products. However, no such rearrangement was observed with (6-oxo-1,6-dihydropyrimidin-2- yl)guanidines 3 bearing a tertiary amino or anilino substituent (i.e. where NR1R2 = N(CH3)2, indoline, morpholino, NHAr). As expected, 2-substituted-4-methyl-6H-pyrimido[1,2-a][1,3,5] triazin-6-ones 4 were obtained as the final products. Experimental structural determination and theoretical studies were carried out to get an understanding of the observed thermal rearrangement. In addition, an attempt to obtain similar pyrimido[1,2-a][1,3,5]triazin-6-ones using N,N-dimethylacetamide dimethyl acetal (DMA-DMA) as one carbon inserting synthon had furnished triazine ring annulated product 14 bearing N,N-dimethyl enamino substituent at position 4 as a result of further reaction with a second molecule of DMA-DMA.
