3430-21-5Relevant articles and documents
Synthesis and reactions of some heterocyclic azacyanines
Huang,Haddadin,Olmstead,Kurth
, p. 1310 - 1315 (2001)
The one-step reaction of some amino-substituted heterocycles with diiodomethane to give azacyanines is reported. This useful reaction is of wider application than initially reported and includes the synthesis of new substituted pyrido-, isoquino-, benzimadazo-, and benzothiazoazacyanines 7. Furthermore, treatment of these azacyanines with base generally affects a facile opening of the dihydrotriazinium ring resulting in the formation of new heterocycles 10, 11, and 12, which would be difficult to prepare by other means. This reaction takes an additional direction in the case of halo-substituted azacyanines 7b/c/d where treatment with base gives rise to new interesting derivatives of dipyridotriazines 14b/c/d.
Preparation method of 2, 5-dibromo-3-methylpyridine
-
, (2020/03/09)
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of 2, 5-dibromo-3-methylpyridine. The preparation method comprises the following steps: (1) adding 2-amino-3-methylpyridine and acetic anhydride into a four-neck flask, heating to reflux, and carrying out thin-layer chromatography tracking reaction; (2) when the temperature of a reaction liquid obtained in the step (1) is reduced to 20-25 DEG C, dropwise adding liquid bromine, reacting for 2-3 hours at 50-60 DEG C after dropwise adding of liquid bromine, adding water until all solids are dissolved, dropwise adding a sodium hydroxide solution, continuously reacting for 30 minutes after dropwise adding, and carrying out suction filtration, drying and recrystallization to obtain 2-amino-3-methyl-5-bromopyridine; and (3) adding the obtained 2-amino-3-methyl-5-bromopyridine into a hydrogen bromide solution, dropwise adding a saturated sodium nitrite solution under the catalysis of cuprous bromide, controlling the temperature to be -5 to 10 DEG C, and reacting for 2 to 4 hours to obtain 2, 5-dibromo-3-methylpyridine. The method provided by the invention has the beneficial effects ofmild reaction conditions, high yield, low cost and short process route, and is suitable for industrial production.
Design, synthesis and biological evaluation of pyridone–aminal derivatives as MNK1/2 inhibitors
Yuan, Xinrui,Wu, Hanshu,Bu, Hong,Zheng, Peiyuan,Zhou, Jinpei,Zhang, Huibin
, p. 1211 - 1225 (2019/02/28)
Excessive phosphorylation of eukaryotic translation initiation factor 4E (eIF4E) plays a major role in the dysregulation of mRNA translation and the activation of tumor cell signaling. eIF4E is exclusively phosphorylated by mitogen-activated protein kinase interacting kinases 1 and 2 (MNK1/2) on Ser209. So, MNK1/2 inhibitors could decrease the level of p-eIF4E and regulate tumor-associated signaling pathways. A series of pyridone–aminal derivatives were synthesized and evaluated as MNK1/2 inhibitors. Several compounds exhibited great inhibitory activity against MNK1/2 and selected compounds showed moderate to excellent anti-proliferative potency against hematologic cancer cell lines. In particular, compound 42i (MNK1 IC50 = 7.0 nM; MNK2 IC50 = 6.1 nM) proved to be the most potent compound against TMD-8 cell line with IC50 value of 0.91 μM. Furthermore, 42i could block the phosphorylation level of eIF4E in CT-26 cell line, and 42i inhibited the tumor growth of CT-26 allograft model significantly. These results indicated that compound 42i was a promising MNK1/2 inhibitor for the potent treatment of colon cancer.
