21269-61-4

Upstream product

• 1755-15-3 2-acetyldimedone 
• 126-81-8 dimedone 
• 100-63-0 phenylhydrazine 

Downstream Products

• 28795-07-5 3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-ol 
• 620545-14-4 N-(3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)benzamide 
• 1384426-50-9 N-(3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)acrylamide 
• 1384426-49-6 2,2,2-trichloro-N-(3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)acetamide 
• 620545-50-8 2-chloro-N-(3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)acetamide 
• 1384426-48-5 N-(3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)butyramide 
• 620545-34-8 N-(3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)acetamide 

Relevant academic research and scientific papers

Discovery, structure-activity relationship studies, and anti-nociceptive effects of 1-phenyl-3,6,6-trimethyl-1,5,6,7-tetrahydro-4H-indazol-4-one as novel opioid receptor agonists

The μ-opioid receptor (MOR) is the major opioid receptor targeted by most analgesics in clinical use. However, the use of all known MOR agonists is associated with severe adverse effects. We reported that the 1-phenyl-3,6,6-trimethyl-1,5,6,7-tetrahydro-4H-indazol-4-ones are novel opioid receptor agonists. Subsequent structural modification resulted in the potent MOR/KOR (κ-opioid receptor) agonists 19, 20, and 21. Testing the analgesic effect of these in WT B6 mice (tail-flick test) gave ED50 values of 8.4, 10.9, and 26.6 mg/kg, respectively. The 1-phenyl-3,6,6-trimethyl-1,5,6,7- tetrahydro-4H-indazol-4-one core could be addressed in 1 or 2 synthetic steps with moderate to high percent of yield. In the adenylyl cyclase assay, compound 19 displayed a MOR/KOR agonist profile, with IC50 values of 0.73 and 0.41 μM, respectively. Current results suggest that compound 19 is a promising lead to go further development and in vitro/in vivo adverse effects studies.

4,5,6,7-tetrahydroindazole derivatives as antitumor agents

Compounds which are 4,5,6,7-tetrahydroindazole derivative formula (1), wherein the dotted line (x) represents a single or double bond; n is 0 or 1; R1, R2 and R3 have the meanings reported in the description; Ra, R′a, Rb, R′b, Rc, R′c have the meanings reported in the description, also comprising that Ra and Rb together and/or Ra and Rc together form a N-alkylpiperydinyl ring with 1 to 6 carbon atoms in the alkyl chain or a phenyl ring; or pharmaceutically acceptable salts thereof, are useful for treating cell proliferative disorders and Alzheimer's disease.