5584-15-6

Usage

Chemical Properties

OFF-WHITE CRYSTALLINE POWDER

InChI:InChI=1/C16H16ClN3/c1-10(2)7-13-8-14(15(9-18)16(19)20-13)11-3-5-12(17)6-4-11/h3-6,8,10H,7H2,1-2H3,(H2,19,20)

Upstream product

• 5202-89-1 4-chlorobenzenesulfonyl chloride 
• 635-21-2 5-chloroanthranilic acid 
• 130408-01-4 ethyl 5-chloroanthranilate hydrochloride 

Downstream Products

• 19011-98-4 2-amino-5-chloro-benzoic acid benzylidenehydrazide 
• 5584-09-8 2-amino-5-chloro-N'-(5-nitrofurfurylidene)benzohydrazide 
• 3544-03-4 5-chloro-N-(5-nitrofurfurylidene)-2-(5-nitrofurfurylideneamino)benzohydrazide 
• 104615-59-0 4-Chloro-2-(5-phenyl-1H-[1,2,4]triazol-3-yl)-phenylamine 
• 5584-16-7 3-Amino-6-chloro-4(3H)-quinazolinone 
• 104615-59-0 5-(2-amino-5-chlorophenyl)-3-phenyl-1H-1,2,4-triazole 
• 93595-52-9 5-(2-amino-5-chlorophenyl)-1,3,4-oxadiazole-2(3H)-one 
• 104615-57-8 3-(2-amino-5-chlorophenyl)-5-(2-pyridyl)-2H-1,2,4-triazole 
• 1403672-17-2 2-(9-chloro-2-pyridin-2-yl-5,6-dihydro[1,5-c]quinazolin-5-yl)phenol 
• 104615-58-9 C₁₃H₁₂ClN₅O 
• 1609006-67-8 2-amino-5-chloro-N'-(propan-2-ylidene)benzohydrazide 
• 1609006-89-4 ethyl 5-(2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamido)-5-chlorophenyl)-2,2-dimethyl-1,3,4-oxadiazole-3(2H)-carboxylate 
• 1609006-88-3 methyl 5-(2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamido)-5-chlorophenyl)-2,2-dimethyl-1,3,4-oxadiazole-3(2H)-carboxylate 
• 1609006-76-9 ethyl 5-(2-amino-5-chlorophenyl)-2,2-dimethyl-1,3,4-oxadiazole-3(2H)-carboxylate 

Relevant academic research and scientific papers

Synthesis and evaluation of adenosine antagonist activity of a series of [1,2,4]triazolo[1,5-c]quinazolines

A series of [1,2,4]triazolo[1,5-c]quinazolines were prepared in satisfactory yields by reaction of some derivatives of 2-aminobenzohydrazide with several hydrochlorides of aromatic amidines, and their binding affinities for the recombinant human adenosine A2A and A2B receptors were determined. None of the new compounds showed noteworthy affinity for these receptors, though a very high affinity for the A2A receptor and, consequently, a high level of A2A/A2B selectivity was revealed for one of the synthesized compounds.

A diversity oriented synthesis of 2,10-dioxo-10H-1,2,3,4,4a,5-hexahydropyridazino[3,2-b]quinazolines

A parallel method for the synthesis of the title compounds is described. Thus, methyl anthranilates (5) are transformed into 2-aminobenzohydrazides (3) which were treated with 4-oxo acids (4) to afford in high yields and acceptable purity of piridazino[3,2-b]quinazolines (1). Compounds (1) present four diversity centers (R1, R2, R3, and R4). The range of chemically acceptable substituents at each center has been evaluated. The isolation of a possible intermediate in the formation of 1, which presents an amino structure (10), has allowed proposing a complete mechanistic rationalization for the formation of structures (1).

Synthesis and Pharmacological Evaluation of Fenamate Analogues: 1,3,4-Oxadiazol-2-ones and 1,3,4-Oxadiazole-2-thiones

A series of fenamate pyridyl or quinolinyl analogues of 1,3,4-oxadiazol-2-ones 5a-d and 6a-r, and 1,3,4-oxadiazole-2-thiones 5e-g and 6s-v, respectively, have been synthesized and evaluated for their analgesic (hot-plate), antiinflammatory (carrageenin induced rat's paw edema) and ulcerogenic effects as well as plasma prostaglandin E2 (PGE 2) level. The highest analgesic activity was achieved with compound 5a (0.5, 0.6, 0.7 mmol/kg b.wt.) in respect with mefenamic acid (0.4 mmol/kg b.wt.). Compounds 6h, 61 and 5g showed 93, 88 and 84% inhibition, respectively on the carrageenan-induced rat's paw edema at dose level of 0.1mmol/kg, b.wt, compared with 58% inhibition of mefenamic acid (0.2mmol/kg b.wt.). Moreover, the highest inhibitory activity on plasma PGE2 level was displayed also with 6h, 61 and 5g (71, 70, 68.5% respectively, 0.1mmol/kg b.wt.) compared with indomethacin (60%, 0.01 mmol/kg b.wt.) as a reference drug. In addition 6i, 6k, 6p, 6r, 6t and 6v were devoid of any ulcerogenicity.

Synthesis and Benzodiazepine Binding Activity of a Series of Novel Triazoloquinazolin-5(6H)-ones

Investigation of tricyclic heterocycles related to the 2-arylpyrazoloquinolin-3(5H)-ones, structures with high affinity for the benzodiazepine (BZ) receptor, led to the synthesis of 2-phenyl-triazoloquinazolin-5(6H)-one, a compound wi