256228-64-5

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indazole-7-carbonitrile is used as a synthetic intermediate for the production of pharmaceutical drugs. Its unique chemical properties and structural features contribute to the development of new compounds with biological activity, enhancing the therapeutic potential of medications.
Used in Agrochemical Industry:
1H-Indazole-7-carbonitrile is utilized as an intermediate in the synthesis of agrochemicals, specifically in the creation of compounds with biological activity relevant to agricultural applications. This includes the development of pesticides, herbicides, and other chemicals that can improve crop protection and yield.
Used in Research Chemicals:
1H-Indazole-7-carbonitrile serves as a crucial component in the synthesis of research chemicals, facilitating scientific investigations into the compound's properties and potential applications. Its role in research is vital for uncovering new uses and understanding its interactions within biological systems.

InChI:InChI=1/C8H5N3/c9-4-6-2-1-3-7-5-10-11-8(6)7/h1-3,5H,(H,10,11)

Upstream product

• 945761-94-4 7-iodo-1H-indazole 
• 557-21-1 dicyanozinc 
• 945761-97-7 C₁₀H₇O₄N₂SF₃ 
• 2942-42-9 7-Nitroindazole 
• 557-21-1 zinc(II) cyanide 
• 53857-58-2 7-bromo-1H-indazole 
• 81382-46-9 7-hydroxy-1H-indazole 
• 21443-96-9 1H-indazol-7-amine 
• 570-24-1 2-Methyl-6-nitroaniline 
• 945761-93-3 trifluoromethanesulfonic acid 1H-indazol-7-yl ester 

Downstream Products

• 945762-00-5 3-bromo-7-cyano-1H-indazole 
• 677304-69-7 1H-indazole-7-carboxylic acid 
• 1159511-51-9 2-methyl-2H-indazole-7-carbonitrile 

Relevant academic research and scientific papers

N'-hydroxyindazolecarboximidamide derivatives, optical isomer thereof, or pharmaceutically acceptable salts thereof, and, a anticancer composition containing the same as an active ingredient

A Nandprime;-hydroxyindazolecarboxyimidamide derivative compound, which is a pharmaceutical composition for anticancer medicine according to the present invention, an optical isomer thereof or a pharmaceutically acceptable salt thereof have excellent effect of inhibiting indoleamine 2,3-dioxygenase-1, and thus can be usefully used as an anticancer pharmaceutical composition.COPYRIGHT KIPO 2019

Synthesis and molecular modeling studies of N-Hydroxyindazolecarboximidamides as novel indoleamine 2,3-Dioxygenase 1 (IDO1) inhibitors

Indoleamine 2,3-dioxygenase 1 (IDO1) is an immunosuppressive enzyme that is highly overexpressed in various cancer cells and antigen-presenting cells. It has emerged as an attractive therapeutic target for cancer immunotherapy, which has prompted high interest in the development of small-molecule inhibitors. To discover novel IDO1 inhibitors, we designed and synthesized a series of N-hydroxyindazolecarboximidamides. Among the compounds synthesized, compound 8a inhibited both tryptophan depletion and kynurenine production through the IDO1 enzyme. Molecular docking studies revealed that 8a binds to IDO1 with the same binding mode as the analog, epacadostat (INCB24360). Here, we report the synthesis and biological evaluation of these hydroxyindazolecarboximidamides and present the molecular docking study of 8a with IDO1.

OXADIAZOLE DERIVATIVES AND PHARMACEUTICAL USES THEREOF

PROBLEM TO BE SOLVED: To provide therapeutic or preventive agents for various diseases or symptoms associated with a serotonin 4 receptor (particularly, neuropsychiatric diseases such as Alzheimer-type dementia). SOLUTION: The present invention provides a compound represented by formula (1) or a pharmaceutically acceptable salt thereof. In the formula (1), Het represents formula (Het-1) or the like, A represents formula (A-1) or the like, B represents (B-1) or the like, R1A represents a hydrogen atom, an alkyl group or the like, R2A, R5, R6 and R7 represent a hydrogen atom, a halogen atom, an alkyl group or the like, R8 and R9 represent a hydrogen atom, an alkyl group or the like, and l represents an integer of 0-4. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Inhibitory effects of a series of 7-substituted-indazoles toward nitric oxide synthases: Particular potency of 1H-indazole-7-carbonitrile

A series of new 7-monosubstituted and 3,7-disubstituted indazoles have been prepared and evaluated as inhibitors of nitric oxide synthases (NOS). 1H-Indazole-7-carbonitrile (6) was found equipotent to 7-nitro-1H-indazole (1) and demonstrated preference for constitutive NOS over inducible NOS. By contrast, 1H-indazole-7-carboxamide (8) was slightly less potent but demonstrated a surprising selectivity for the neuronal NOS. Further substitution of 6 by a Br-atom at carbon-3 of the heterocycle enhanced 10-fold the inhibitory effects. Inhibition of NO formation by 6 appeared to be competitive versus both substrate and the cofactor (6R)-5,6,7,8-tetrahydro-l-biopterin (H4B). In close analogies with 1, compound 6 strongly inhibited the NADPH oxidase activity of nNOS and induced a spin state transition of the heme-FeIII. Our results are explained with the help of the X-ray structures that identified key-features for binding of 1 at the active site of NOS.

Efficient synthesis of 7-substituted or 3,7-disubstituted 1H-indazoles

This work reports on the synthesis of the novel indazole scaffolds 7-OTf-1H-indazole (trifluoromethanesulfonic acid 1H-indazol-7-yl ester), 7-iodo-1H-indazole and 3-bromo-7-iodo-1H-indazole. These new compounds are potent building blocks in divergent syntheses of indazoles via palladium cross-coupling reactions. Georg Thieme Verlag Stuttgart.