115377-83-8Relevant academic research and scientific papers
Ligand-based drug design: Synthesis and biological evaluation of substituted benzoin derivatives as potential antitumor agents
Al-Shalabi, Eveen,Alqaisi, Khalid M.,Bardaweel, Sanaa K.,Ibrahim, Ameerah H.,Khalaf, Reema A.,Mubarak, Mohammad S.,Sabbah, Dima A.,Sheikha, Ghassan A.,Sweidan, Kamal,Talib, Wamidh H.,Zhong, Haizhen A.
, p. 417 - 429 (2019/07/12)
Background: Phosphoinositide 3-kinase α (PI3Kα) has emerged as a promising target for anticancer drug design. Objectives: Target compounds were designed to investigate the effect of the p-OCH3 motifs on ligand/PI3Ka complex interaction and anti
Purines. VIII. Reactions of 1-Benzoyl-1,6-dihydro-9-phenyl-9H-purine-6-carbonitrile (9-Phenylpurine Reissert Compound) with Acid, Bases, and Electrophiles
Tanji, Ken-ichi,Sato, Susumu,Miyashita, Akira,Oishi, Etsuo,Higashino, Takeo
, p. 187 - 189 (2007/10/02)
1-Benzoyl-1,6-dihydro-9-phenyl-9H-purine-6-carbonitrile (1, 9-phenylpurine Reissert compound) was hydrolyzed in an acid medium to give the ring fission product of the pyrimidine ring (3, 4).Alkaline hydrolysis of 1 gave 9-phenyl-9H-purine (2) and benzoic acid (5).The anion of 1 generated from 1 and sodium hydride in tetrahydrofuran underwent aromatization, resulting in the formation of 9-phenyl-9H-purine-6-carbonitrile (6) together with 2.The reaction of 1 with aromatic aldehydes in the presence of sodium hydride proceeded to give the 6-purinylmethyl benzoates (8a-c), together with 2 and 9.On the other hand, the reaction of 1 with 2,4-dinitrochlorobenzene in the presence of sodium hydride failed to give the corresponding 6-arylpurine, and the aromatization product 6 was obtained.Keywords - 9H-purine; Reissert compound anion; 9H-purin-6-ylmethyl benzoate
Studies on Pyrazolopyrimidine Derivatives. XV. Reactions Involving the Formation of the Anion of the Reissert Compound Derived form 1H-Pyrazolopyrimidine
Hagishino, Takeo,Sato, Susumu,Miyashita, Akira,Katori, Tatsuhiko
, p. 4078 - 4086 (2007/10/02)
The anion (A) of the Reissert compound (1, 5-benzoyl-4,5-dihydro-1-phenyl-1H-pyrazolopyrimidine-4-carbonitrile) was found to react with electrophiles in two ways.One is nucleophilic attack of the anion A.The other is self-decomposition of the anion A.Thus, A underwent nucleophilic attack with aromatic and aliphatic aldehydes (4a-j), resulting in the formation of the corresponding α-aryl (or alkyl)-1-phenyl-1H-pyrazolopyrimidin-4-ylmethyl benzoates (6a-j) together with 1-phenyl-1H-pyrazolopyrimidine (2), the 4,4'-dimer (7) of 2, O-benzoylaroins (8a-d), and O-benzoylcyanohydrins (9e-j).Nucleophilic substitution took place in the reaction of A with 2,4-dinitrochlorobenzene (14a) and methyl iodide (14d), giving the 4-(2,4-dinitrophenyl) derivative (17a) of 2 and 5,7-dibenzoyl-4-methyl-1-phenyl-4-(1-phenyl-1H-pyrazolopyrimidin-4-yl)-4,5,6,7-tetrahydro-1H-pyrazolopyrimidine-6-carbonitrile (19), respectively.However, the anion A did not react with other aryl (or alkyl) halides (14b, c, e), ketones (11a, b), 2-alkenonitriles (21a, b), and dimethylacetylenedicarboxylate (22), and underwent the known self-decomposition, resulting in the formation of products such as 2, 7, the cyano derivative (18) of 2, and the ester 6a.Keywords - pyrazolopyrimidine; Reissert compound; aldehyde; aryl halide; nucleophilic attack; self-decomposition; pyrazolopyrimidinemethanol
