59591-84-3

Basic information

• Product Name: 1H-Indazole-3-carbohydrazide
• Synonyms: 1H-Indazole-3-carbohydrazide;1H-Indazole-3-carboxylic acid hydrazide
• CAS NO: 59591-84-3
• Molecular Formula: C₈H₈N₄O
• Molecular Weight: 176.1753
• Mol File: 59591-84-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 218-220 °C
• Appearance: /
• Density: 1.436 g/cm³
• Refractive Index: 1.734
• PKA: 11.92±0.30(Predicted)
• CAS DataBase Reference: 1H-Indazole-3-carbohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indazole-3-carbohydrazide(59591-84-3)
• EPA Substance Registry System: 1H-Indazole-3-carbohydrazide(59591-84-3)

Safety Data

• Hazardous Substances Data: 59591-84-3(Hazardous Substances Data)

Usage

General Description

1H-Indazole-3-carbohydrazide is a chemical compound with the molecular formula C8H9N5O. It is a derivative of indazole, a heterocyclic aromatic organic compound. This chemical is commonly used in the pharmaceutical industry as a building block for the synthesis of various pharmaceutical compounds. It has also been studied for its potential therapeutic properties, including antitumor and antimicrobial activities. Additionally, 1H-Indazole-3-carbohydrazide has been investigated for its potential use in materials science, such as in the development of new polymers and nanomaterials. Overall, this chemical compound has a wide range of applications in various fields, making it a versatile and important component in scientific research and drug development.

InChI:InChI=1/C8H8N4O/c9-10-8(13)7-5-3-1-2-4-6(5)11-12-7/h1-4H,9H2,(H,10,13)(H,11,12)

Upstream product

• 4498-68-4 ethyl 1H-indazole-3-carboxylate 
• 4498-67-3 1H-Indazole-3-carboxylic acid 
• 43120-28-1 methyl 1H-indazole-3-carboxylate 

Downstream Products

• 91545-21-0 dihydro-1,2 oxo-1 methyl-4 triazino-1,2,4-<4,5-b>indazole 
• 91545-17-4 N-ethoxyethylidenehydrazide de l'acide indazole-carboxylique-3 
• 93986-30-2 1⁽²⁾H-indazole-3-carboxylic acid (4-chloro-benzylidene)-hydrazide 

Relevant articles and documents

The efficient synthesis of 3-[6-(substituted)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl]-1H-indazole

This study presents an efficient synthesis of 3-[6-(substituted-phenyl)-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazol-3-yl]-1H-indazole via dehydrative condensation with cyclization of 4-amino-5-(1H-indazol-3-yl)-4H-[1,2,4]triazole-3-thiol and fluorinated or nonfluorinated carboxylic acids in presence of phosphorous oxychloride. The multistep reaction pathway proceeds through different compounds. Present synthesis has the advantages of easily accessible starting materials, convenient synthesis, simple reaction condition, wider substrate scope, and higher yield (75% to 90% isolated).

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.