78155-75-6

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 5-NITRO-1H-INDAZOLE-3-CARBOXYLATE is used as a key intermediate in the synthesis of various pharmaceutical drugs. Its unique chemical structure allows for the development of new drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, METHYL 5-NITRO-1H-INDAZOLE-3-CARBOXYLATE is utilized as a vital component in the creation of agrochemicals. Its properties enable the production of effective compounds for crop protection and other agricultural applications.
Used in Organic Synthesis:
METHYL 5-NITRO-1H-INDAZOLE-3-CARBOXYLATE is employed as a versatile building block in organic synthesis. Its reactivity and functional groups make it suitable for the preparation of a wide range of organic compounds for various applications, including the development of new materials and the synthesis of complex organic molecules.

InChI:InChI=1/C9H7N3O4/c1-16-9(13)8-6-4-5(12(14)15)2-3-7(6)10-11-8/h2-4H,1H3,(H,10,11)

Upstream product

• 677702-36-2 5-nitro-1H-indazole-3-carboxaldehyde 
• 5401-94-5 5-nitroindazole 
• 4498-67-3 1H-Indazole-3-carboxylic acid 
• 43120-28-1 methyl 1H-indazole-3-carboxylate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 70315-69-4 3-iodo-5-nitro-1H-indazole 
• 78155-76-7 5-nitro-1H-indazole-3-carboxylic acid 
• 660823-32-5 7-nitro-1⁽²⁾H-indazole-3-carboxylic acid 

Downstream Products

• 1448314-37-1 1-(3-methoxybenzoyl)-5-nitro-1H-indazole-3-carboxylic acid methyl ester 
• 1448314-36-0 1-(3-methylbenzoyl)-5-nitro-1H-indazole-3-carboxylic acid methyl ester 
• 1448314-35-9 1-benzoyl-5-nitro-1H-indazole-3-carboxylic acid methyl ester 
• 1093064-20-0 C₃₁H₂₃N₅O₂ 
• 1093066-24-0 C₃₁H₂₅N₅ 
• 1093064-69-7 3-(1-methyl-1H-pyrazol-3-yl)-5-nitro-1-trityl-1H-indazole 
• 1093064-19-7 1-(5-nitro-1-trityl-1H-indazol-3-yl)-propynone 
• 1093064-18-6 5-nitro-1-trityl-1H-indazole-3-carboxylic acid methoxy-methyl-amide 
• 1093064-17-5 5-nitro-1-trityl-1H-indazole-3-carboxylic acid 
• 1093064-16-4 5-nitro-1-trityl-1H-indazole-3-carboxylic acid methyl ester 
• 660411-95-0 methyl 5-amino-1H-indazole-3-carboxylate 
• 660823-37-0 7-amino-1H-indazole-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and anticancer evaluation of indazole-aryl hydrazide-hydrazone derivatives

A new series of hydrazide-hydrazones linked between indazole and substituted benzaldehydes were designed, synthesized and evaluated for their cytotoxicity against four human cancer cell lines (HeLa, MDA-MB-231, MCF-7 and A549). Among the synthesized compo

Synthesis, antitumor evaluation, and molecular docking studies of indole–indazolyl hydrazide–hydrazone derivatives

Abstract: A series of ten novel hydrazide–hydrazones linked indole and indazole moieties were designed and synthesized. All the synthesized compounds were evaluated for their cytotoxicity against four human cancer cell lines (HeLa, MDA-MB-231, MCF-7, and A549). Three of the synthesized compounds showed promising cytotoxicity specifically on some of the tested cell lines with IC50 values ranging between 1.93 and 25.6?μM. Further, one compound was identified as a promising drug lead which showed promising cytotoxicity with IC50 value of 1.93?μM towards MCF-7 breast cancer cell line as compared to the standard drug doxorubicin (IC50 value 0.98?μM). While, all these new compounds showed no cytotoxicity on the normal human embryonic kidney cell line, HEK-293. Graphical abstract: [Figure not available: see fulltext.]

Optimization of N-benzoylindazole derivatives as inhibitors of human neutrophil elastase

Human neutrophil elastase (HNE) is an important therapeutic target for treatment of pulmonary diseases. Previously, we identified novel N-benzoylindazole derivatives as potent, competitive, and pseudoirreversible HNE inhibitors. Here, we report further development of these inhibitors with improved potency, protease selectivity, and stability compared to our previous leads. Introduction of a variety of substituents at position 5 of the indazole resulted in the potent inhibitor 20f (IC50 ～10 nM) and modifications at position 3 resulted the most potent compound in this series, the 3-CN derivative 5b (IC50 = 7 nM); both derivatives demonstrated good stability and specificity for HNE versus other serine proteases. Molecular docking of selected N-benzoylindazoles into the HNE binding domain suggested that inhibitory activity depended on geometry of the ligand-enzyme complexes. Indeed, the ability of a ligand to form a Michaelis complex and favorable conditions for proton transfer between Hys57, Asp102, and Ser195 both affected activity.

Synthesis of 3-indazolecarboxylic esters and amides via Pd-catalyzed carbonylation of 3-iodoindazoles

A straightforward and effective procedure for the preparation of 1H-indazole-3-carboxylic acid esters and amides was developed. A series of functionalized 3-iodoindazoles were subjected to Pd-catalyzed carbonylations in the presence of methanol or amines,

POLYCYCLIC INDAZOLE DERIVATIVES AND THEIR USE AS ERK INHIBITORS FOR THE TREATMENT OF CANCER

Disclosed are the ERK inhibitors of formula 1.0: (Chemical formula should be inserted here as it appears on abstract in paper form) and the pharmaceutically acceptable salts, esters and solvates thereof. Q is a piperidine or piperazine ring that can have a bridge or a fused ring. The piperidine ring can have a double bond in the ring. All other substitutents are as defined herein. Also disclosed are methods of treating cancer using the compounds of formula 1.0.

1H-INDAZOLE-3-CARBOXAMIDE COMPOUNDS AS MAPKAP KINASE MODULATORS

The invention provides compounds of the formula: (I) for use in the prophylaxis or treatment of a disease state or condition mediated by a MAPKAP kinase: wherein A is a bond or a group CH2; R1 is a carbocyclic or heterocyclic group having from 3 to 12 ring members; R3, R4, R5 and R6 are the same or different and are each selected from hydrogen, halogen, hydroxy, trifluoromethyl, cyano, nitro, carboxy, amino, carbocyclic and heterocyclic groups having from 3 to 12 ring members; a group Ra -Rbwherein Ra is a bond, 0, CO, X1C(X2), C(X2)Xl, X1C(X2)X1, S, SO, S02, NRc, SO2NRc or NRcS02; and Rb is selected from hydrogen, carbocyclic and heterocyclic groups having from 3 to 12 ring members, and a C1-8 hydrocarbyl group optionally substituted by one or more substituents selected from hydroxy, oxo, halogen, cyano, nitro, amino, mono or di-C1-4 hydrocarbylamino, carbocyclic and heterocyclic groups having from 3 to 12 ring members and wherein one or more carbon atoms of the C1-8 hydrocarbyl group may optionally be replaced by 0, S, SO, SO2, NRc, X1C(X2), C(X2)X1 or X1C(X2)X1; Rc is hydrogen or C1-4hydrocarbyl; and X1 is O, S or NRc and X2 is =O, =S or =NRc.