133632-88-9Relevant academic research and scientific papers
Structural investigations on coumarins leading to chromeno[4,3-c]pyrazol-4-ones and pyrano[4,3-c]pyrazol-4-ones: New scaffolds for the design of the tumor-associated carbonic anhydrase isoforms IX and XII
Bonardi, Alessandro,Falsini, Matteo,Catarzi, Daniela,Varano, Flavia,Di Cesare Mannelli, Lorenzo,Tenci, Barbara,Ghelardini, Carla,Angeli, Andrea,Supuran, Claudiu T.,Colotta, Vittoria
, p. 47 - 59 (2018/02/09)
Human carbonic anhydrases (hCAs, EC 4.2.1.1) IX and XII are overexpressed in a wide variety of cancers and are considered available drug targets for anti-tumor therapy since their inhibition has been shown to reduce tumor growth and metastasis. A set of coumarin derivatives (1–10) and several 1-aryl and 2-aryl-substituted chromeno[4,3-c]pyrazol-4-ones (11–37) and pyrano[4,3-c]pyrazol-4-ones (38–39) were synthesized and tested against the tumor-associated hCAs IX and XII and the cytosolic isoforms hCAs I and II. Several compounds were potent (Ki i = 5.6–9.6 nM), while none were effective against the off-target cytosolic hCAs I and II. Some selected inhibitors (6, 11, 13, 19, 21, 25, 31 and 39) showed activity as antiproliferative agents on HT-29 colon cancer cell lines both in normoxic and hypoxic conditions. This finding led us to hypothesize for these derivatives more than one mechanism of action, involving hCAs IX and XII inhibition in hypoxia and other not identified target(s) in normoxia.
Microwave-assisted synthesis of 3-methyl-1-phenyl-chromeno[4,3-c]pyrazol- 4(1H)-ones under solvent-free conditions
Yang, Guo-Yu,Yang, Jing-Tian,Wang, Cai-Xia,Fan, Su-Fang,Xie, Pu-Hui,Xu, Cui-Lian
, p. 1327 - 1336 (2013/07/19)
A novel microwave-assisted method for the synthesis of 3-methyl-1- phenylchromeno[4,3-c]pyrazol-4(1H)-ones by the cyclization of 3-[1-(phenylhydrazono)ethyl]chromen-2-ones with CuO/SBA-15 under solvent-free conditions is described. The reaction gave the c
X-ray supramolecular structure, NMR spectroscopy and synthesis of 3-methyl-1-phenyl-1H-chromeno[4,3-c]pyrazol-4-ones formed by the unexpected cyclization of 3-[1-(phenylhydrazono)ethyl]-chromen-2-ones
Padilla-Martinez, Itzia I.,Flores-Larios, Irma Y.,Garcia-Baez, Efren V.,Gonzalez, Jorge,Cruz, Alejandro,Martinez-Martinez, Francisco J.
, p. 915 - 932 (2011/04/18)
The molecular structures of nine 3-methyl-1-phenyl-1H-chromeno[4,3-c] pyrazol-4-one isomers, obtained by the oxidative cyclization of the corresponding 1-phenylhydrazono chromen-2-ones with copper acetate as catalyst, are reported. The molecular and supra
Tricyclic heteroaromatic systems: [1]benzopyrano-pyrazol-4-ones as benzodiazepine receptor ligands
Colotta,Cecchi,Melani,Filacchioni,Martini,Gelli,Lucacchini
, p. 276 - 279 (2007/10/02)
The synthesis of a series of 8-substituted 1,4-dihydro-1-aryl-3-methyl-[1]benzopyrano[3,4-d]pyrazol-4-ones (series 7) and 2,4-dihydro-2-aryl-3-methyl[1]benzopyrano[4,3-c] pyrazol-4-ones (series 8) is reported. Compounds of series 7 and 8 were tested for their ability to displace [3H]flunitrazepam from bovine brain membranes and for their in vitro biological activity. The results allowed some conclusions to be drawn about the structural requirements of the benzodiazepine recognition site within this class of unusual ligands.
