Crystal structures of pure 3-(4-bromo-2-chloro­phen­yl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one and contaminated with 3-(4-bromo­phen­yl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one

The side product of the cyclo­condensation reaction between ethyl benzimidazole-2-carboxyl­ate and the nitrile imine of the corresponding hydrazonyl chloride, C(20)H(11)BrClN(5)O, crystallized in two crystal forms. Form (1) is a co-crystal of the target compound (without any chlorine substituent) and a side product containing a Cl atom in position 2 of the bromo­phenyl group, C(20)H(12)BrN(5)O·0.143C(20)H(11)BrClN(5)O. (2) contains the pure side product. The slightly different conformation of the ring systems leads to a different packing of (1) and (2), but both crystal structures are dominated by π–π inter­actions

Crystal structures of pure 3-(4-bromo-2-chlorophenyl)-1-(pyridin-4-yl) benzo [4, 5] imidazo [1, 2-d][1, 2, 4] triazin-4 (3H)-one and contaminated with 3-(4-bromophenyl)-1 …

The side product of the cyclocondensation reaction between ethyl benzimidazole-2-carboxylate and the nitrile imine of the corresponding hydrazonyl chloride, C20H11BrClN5O, crystallized in two crystal forms. Form (1) is a co-crystal of the target compound (without any chlorine substituent) and a side product containing a Cl atom in position 2 of the bromophenyl group, C20H12BrN5O·0.143C20H11BrClN5O. (2) contains the pure side product. The slightly different conformation of the ring systems leads to a different packing of (1) and (2), but both crystal structures are dominated by π–π interactions

تفاعل امينات النيترايل مع كل من مشتقات البيريدين و البيرميدين و الترايزين

Reaction of hydrazonoyl chlorides 18a,b with picolines derivatives 86-89 The reaction of hydrazonoyl chloride 18a with picoline derivaties 86-89 in the presence of triethylamine gave the corresponding imidazo[1,2-a]pyridine 93-96. The reaction of hydrazonoyl chloride 18b with picoline derivatives 86-89 in the presence of triethylamine gave the corresponding imidazo[1,2-a]pyridine-2-one 97-100. Reaction of hydrazonoyl chlorides 18a,b with pyrimidines 90-91 The reaction of hydrazonoyl chloride 18a with 2-amino-4-methylpyrimidine 90 and 2-amino-4,6-dimethylpyrimidine 91 in the presence of triethylamine gave black gummy material at room temperature. The reaction of hydrazonoyl chloride 18b with 2-amino-4-methylpyrimidine 90 in the presence of triethylamine afforded unseparable gammy materials, while the reaction of hydrazonoyl chloride 18b with 2-amino-4,6-dimethylpyrimidine 91 in the presence of triethylamine afforded acyclic adduct 106. Reaction of hydrazonoyl chlorides 18a,b with triazine 92 The reaction of hydrazonoyl chlorides 18a,b with 3-amino-5,6-dimethyl-1,2,4-triazine 92 in the presence of triethylamine gave black gummy material

3-(2,4-Difluorophenyl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one

In the title compound, C20H11F2N5O, the central 13-membered ring system (r.m.s. deviation = 0.028 Å) makes a dihedral angle of 53.13 (7)° with the difluorophenyl ring and 79.98 (7)° with the pyridine ring. The crystal packing features aromatic π–π interactions between the 13-membered rings [shortest distance between ring centroids = 3.5682 (8) Å]

1-(Pyridin-4-yl)-3-(2,4,6-trichlorophenyl)benz[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one

In the title compound, C20H10Cl3N5O, the 13-membered ring system makes dihedral angles of 78.64 (9)° with the trichlorophenyl ring and 62.60 (10)° with the pyridine ring. The crystal packing is dominated by π–π interactions between the 13-membered ring systems [centroid–centroid distance = 3.6655 (11)°]

Crystal structures of pure 3-(4-bromo-2-chlorophenyl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one and contaminated with 3-(4-bromophenyl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one

The side product of the cyclocondensation reaction between ethyl benzimidazole-2-carboxylate and the nitrile imine of the corresponding hydrazonyl chloride, C20H11BrClN5O, crystallized in two crystal forms. Form (1) is a co-crystal of the target compound (without any chlorine substituent) and a side product containing a Cl atom in position 2 of the bromophenyl group, C20H12BrN5O·0.143C20H11BrClN5O. (2) contains the pure side product. The slightly different conformation of the ring systems leads to a different packing of (1) and (2), but both crystal structures are dominated by π–π interactions

Design, Synthesis and Biological Evaluation of Novel Pyrazolo[1,2,4]triazolopyrimidine Derivatives as Potential Anticancer Agents

Three novel pyrazolo-[4,3-e][1,2,4]triazolopyrimidine derivatives (1, 2, and 3) were designed, synthesized, and evaluated for their in vitro biological activity. All three compounds exhibited different levels of cytotoxicity against cervical and breast cancer cell lines. However, compound 1 showed the best antiproliferative activity against all tested tumor cell lines, including HCC1937 and HeLa cells, which express high levels of wild-type epidermal growth factor receptor (EGFR). Western blot analyses demonstrated that compound 1 inhibited the activation of EGFR, protein kinase B (Akt), and extracellular signal-regulated kinase (Erk)1/2 in breast and cervical cancer cells at concentrations of 7 and 11 µM, respectively. The results from docking experiments with EGFR suggested the binding of compound 1 at the ATP binding site of EGFR. Furthermore, the crystal structure of compound 3 (7-(4-bromophenyl)-9-(pyridin-4-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine) was determined by single crystal X-ray analysis. Our work represents a promising starting point for the development of a new series of compounds targeting EGFR