1477482-53-3

Basic information

• Product Name: (E)-N-(4-chlorobenzylidene)-4,5,6,7-tetrahydro-1H-indazole-3-carbohydrazide
• Synonyms: (E)-N-(4-chlorobenzylidene)-4,5,6,7-tetrahydro-1H-indazole-3-carbohydrazide;N'-[(E)-(4-chlorophenyl)methylidene]-4,5,6,7-tetrahydro-1H-indazole-3-carbohydrazide
• CAS NO: 1477482-53-3
• Molecular Formula: C15H16ClN4O
• Molecular Weight: 303.76674
• Mol File: 1477482-53-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-N-(4-chlorobenzylidene)-4,5,6,7-tetrahydro-1H-indazole-3-carbohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-N-(4-chlorobenzylidene)-4,5,6,7-tetrahydro-1H-indazole-3-carbohydrazide(1477482-53-3)
• EPA Substance Registry System: (E)-N-(4-chlorobenzylidene)-4,5,6,7-tetrahydro-1H-indazole-3-carbohydrazide(1477482-53-3)

Safety Data

• Hazardous Substances Data: 1477482-53-3(Hazardous Substances Data)

Upstream product

• 5396-14-5 ethyl 2-oxo-2-(2-oxocyclohexyl)acetate 
• 108-94-1 cyclohexanone 
• 104-88-1 4-chlorobenzaldehyde 
• 90434-92-7 ethyl 4,5,6,7-tetrahydro-1H-indazole-3-carbohydrazide 
• 4492-02-8 ethyl 4,5,6,7-tetrahydro-1H-indazole-3-carboxylate 

Relevant articles and documents

Suprafenacine, an Indazole-hydrazide agent, target Cancer cells through microtubule destabilization

Microtubules are a highly validated target in cancer therapy. However, the clinical development of tubulin binding agents (TBA) has been hampered by toxicity and chemoresistance issues and has necessitated the search for new TBAs. Here, we report the identification of a novel cell permeable, tubulin-destabilizing molecule - 4,5,6,7-tetrahydro-1H-indazole-3- carboxylic acid [1p-tolyl-meth-(E)-ylidene]-hydrazide (termed as Suprafenacine, SRF). SRF, identified by in silico screening of annotated chemical libraries, was shown to bind microtubules at the colchicine-binding site and inhibit polymerization. This led to G2/M cell cycle arrest and cell death via a mitochondria-mediated apoptotic pathway. Cell death was preceded by loss of mitochondrial membrane potential, JNK - mediated phosphorylation of Bcl-2 and Bad, and activation of caspase-3.Intriguingly, SRF was found to selectively inhibit cancer cell proliferation and was effective against drug-resistant cancer cells by virtue of its ability to bypass the multidrug resistance transporter P-glycoprotein. Taken together, our resultssuggest that SRF has potential as a chemotherapeutic agent for cancer treatment and provides an alternate scaffold for the development of improved anti-cancer agents.

TUBULIN INHIBITORS

The present invention relates to a compound of Formula (I) for use as a medicament, wherein: m is 0, 1, 2, 3, 4, or 5; R1 and R2 together form a five-membered, six-membered, or seven-membered ring, wherein R1 and R2 together as a group is -(CH2)3-, -(CH2)4 -, or -(CH2)5-; R3 at each occurrence is independently selected from the group consisting of H, halogen, hydroxyl, alkoxy, and a substituted or unsubstituted C1-C5 alkyl; and R4 is H, halogen, or a substituted or unsubstituted C1-C5 alkyl