132685-69-9Relevant academic research and scientific papers
An unprecedented intramolecular to intermolecular mechanistic switch in 1,1-diaminoazines leading to differential product formation during the I2-induced tandem oxidative transformation
Kathuria, Deepika,Gupta, Pankaj,Chourasiya, Sumit S.,Sahoo, Subash C.,Beifuss, Uwe,Chakraborti, Asit K.,Bharatam, Prasad V.
, p. 4129 - 4138 (2019/04/30)
The tautomeric preference of guanylhydrazones towards the azine form induces an unprecedented intramolecular to intermolecular mechanistic switch during the I2-catalyzed oxidative transformation leading to 4,5-disubstituted-3-amino-1,2,4-triazoles in contrast to the reaction of semicarbazones and thiosemicarbazones to form 1,3,4-oxa/thiadiazoles. This intramolecular to intermolecular cyclization shift was established through control experiments and was attributed to the high energy demand (～22 kcal mol-1) for the azine tautomer to adopt the s-cis conformation which is essential for the intramolecular reaction. An I2 induced protocol for an efficient and straightforward synthesis of 4,5-disubstituted-3-amino-1,2,4-triazoles has been developed via tandem oxidative transformation of guanylhydrazones (in its preferentially existing azine tautomeric form) with distinct advantages such as wide substrate scope, use of substoichiometric amounts of iodine, no requirement of external oxidizing agents, base free reaction conditions, short reaction time and moderate to good yields. The role of silver salt in improving the yield and shortening of reaction time was also highlighted.
Rational Design and Synthesis of 1-(Arylideneamino)-4-aryl-1H-imidazole-2-amine Derivatives as Antiplatelet Agents
Amidi, Salimeh,Esfahanizadeh, Marjan,Tabib, Kimia,Soleimani, Zohreh,Kobarfard, Farzad
, p. 962 - 971 (2017/06/27)
Based on previous studies indicating the pharmacophoric role of a hydrazone group and azole rings for antiplatelet aggregation activity, a few series of compounds with both hydrazone and an azole (imidazole) ring in their structures were synthesized, and their platelet aggregation inhibitory effects were evaluated. Two of these 1-(arylideneamino)-4-aryl-1H-imidazole-2-amine derivatives, compounds 4 a [(E)-1-(benzylideneamino)-4-phenyl-1H-imidazol-2-amine] and 4 p [(E)-4-phenyl-1-((thiophen-2-ylmethylene)amino)-1H-imidazol-2-amine], exhibited IC50 values similar to that of acetylsalicylic acid against collagen as a platelet aggregation inducer. Structural comparison of the synthesized compounds revealed that those with a para-substituted phenyl ring on the imidazole were among the most active compounds against platelet aggregation induced by arachidonic acid (AA), and the presence of a thiophene ring in these compounds maximized their antiplatelet activity.
Synthesis of aryl-hydrazones via ultrasound irradiation in aqueous medium
Leite, Ana Cristina Lima,Moreira, Diogo Rodrigo de M.,Coelho, Lucas Cunha Duarte,de Menezes, Frederico Duarte,Brondani, Dalci José
, p. 1538 - 1541 (2008/09/19)
The synthesis of aryl-hydrazones from aromatic aldehydes/ketones and hydrazides (semicarbazide, thiosemicarbazide and aminoguanidine) is described using aqueous medium (acid conditions) under ultrasound irradiation with short reaction times (20-30 min), t
Imidazolamino compounds
-
Page 13, (2008/06/13)
The invention relates to novel imidazolamino compounds. Also disclosed are methods of treating cancer by using one of these compounds and pharmaceutical compositions containing one of these compounds.
Synthesis of substituted 2-amino-1-arylidenaminoimidazoles and 1-arylidenaminoimidazo[1,2-a]imidazoles
Krimer,Makaev,Styngach,Koretskii,Pogrebnoi,Kochug
, p. 1035 - 1039 (2007/10/03)
A new method is proposed for the preparation of 2-amino-1-arylidenaminoimidazoles, which react with α-haloketones to give a series of 1-arylidenamino-3-acylmethyl-2-iminoimidazolines and 1-arylidenaminoimidazo[1,2-a]imidazoles depending on the conditions. 1997 Plenum Publishing Corporation.
