110570-27-9

Upstream product

• 1448308-26-6 C₁₈H₁₆N₂O₃ 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 2555-37-5 3-acetyl-4-hydroxychromen-2-one 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 110570-14-4 4-Hydroxy-3-{1-[(4-methoxy-phenyl)-hydrazono]-ethyl}-chromen-2-one 

Relevant 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

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.

Copper-catalyzed cyclization of 3-acylcoumarin hydrazone using air as the oxidant: Efficient synthesis of pyrazole-fused coumarin derivatives

An efficient, convenient Cu-catalyzed formation of chromeno[4,3-c]pyrazol-4(1H)-ones is reported. In this atom economic process, readily available 3-acylcoumarin hydrazone is oxidative cyclized by direct C-N bond formation. Air has been successfully used

Synthesis, anticancer activity and photophysical properties of novel substituted 2-oxo-2H-chromenylpyrazolecarboxylates

2-Oxo-2H-chromenylpyrazolecarboxylates (8a-h and 12a-zb) have been synthesized by [3 + 2] cycloaddition of 2H-chromenophenylhydrazones (7a-h and 11a-w) with diethyl/dimethylbut-2-ynedioates. Phenylchromeno[4,3-c]pyrazol-4(1H) -ones (13i-n) were prepared from corresponding phenylhydrazones (7a-h) with catalytic amount of piperidine in presence of pyridine as a solvent at 100°C. All the synthesized compounds (8a-h, 12a-zb and 13a-n) were screened for anticancer activity against three human cancer cell lines such as prostate (DU-145), lung adenocarcinoma (A549), and cervical (HeLa) by standard MTT assay method. Further, photophysical properties (UV and fluorescence) for these compounds were discussed.

Microwave-assisted synthesis of 3-methyl-1-phenyl-chromeno[4,3-c]pyrazol- 4(1H)-ones under solvent-free conditions

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