955127-80-7

Basic information

• Product Name: 1H-Indazole-5-carboxaldehyde, 3-methyl-
• Synonyms: 1H-Indazole-5-carboxaldehyde, 3-methyl-;3-methyl-1H-indazole-5-carbaldehyde
• CAS NO: 955127-80-7
• Molecular Formula: C₉H₈N₂O
• Molecular Weight: 160.17
• Mol File: 955127-80-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Indazole-5-carboxaldehyde, 3-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indazole-5-carboxaldehyde, 3-methyl-(955127-80-7)
• EPA Substance Registry System: 1H-Indazole-5-carboxaldehyde, 3-methyl-(955127-80-7)

Safety Data

• Hazardous Substances Data: 955127-80-7(Hazardous Substances Data)

Usage

Structure

A derivative of indazole with a carboxaldehyde group and a 3-methyl substitution

Type of compound

Heterocyclic compound with a five-membered ring and two nitrogen atoms

Biological activities

Anti-inflammatory, antimicrobial, and anticancer properties

Interest in research

Value in organic synthesis and pharmaceutical research, potential for further study and development in medicinal chemistry.

Upstream product

• 552331-16-5 5-bromo-3-methyl-1H-indazole 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1240786-25-7 2-(4-fluorophenyl)-4-(3-methyl-1H-indazol-5-yl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carbonitrile 
• 1240786-28-0 2-(4-chlorophenyl)-4-(3-methyl-1H-indazol-5-yl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carbonitrile 
• 1240786-29-1 2-(4-chloro-3-fluorophenyl)-4-(3-methyl-1H-indazol-5-yl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carbonitrile 
• 1240786-30-4 2-(3,5-difluorophenyl)-4-(3-methyl-1H-indazol-5-yl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carbonitrile 
• 1240786-31-5 2-(2,4-difluorophenyl)-4-(3-methyl-1H-indazol-5-yl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carbonitrile 
• 1311135-39-3 2-(4-methoxyphenyl)-6-methyl-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydropyridine-3,5-dicarbonitrile 
• 1311135-15-5 2-(difluoromethyl)-4-(3-methyl-1H-indazol-5-yl)-6-phenyl-1,4-dihydropyridine-3,5-dicarbonitrile 
• 1311135-25-7 4-(3-methyl-1H-indazol-5-yl)-2-phenyl-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile 
• 1311135-40-6 2-(4-fluorophenyl)-6-methyl-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydropyridine-3,5-dicarbonitrile 

Relevant articles and documents

Design, synthesis and anticancer evaluation of 3-methyl-1H-indazole derivatives as novel selective bromodomain-containing protein 4 inhibitors

Bromodomain-containing Protein 4 (BRD4), an ‘epigenetic reader’, regulates chromatin structure and gene expression via recognizing and binding acetylated lysine in histones. BRD4 has become a therapeutic target for cancers because it promotes the expression of the tumor genes, such as c-Myc, NF-κB, and Bcl-2. In this study, a new series of 3-methyl-1H-indazole derivatives were designed via virtual screening and structure-based optimization. All compounds were synthesized and evaluated for their inhibitory activities to BRD4-BD1 and their antiproliferative effects in cancer cell lines. Among them, several compounds (such as 9d, 9u and 9w) exhibited strong BRD4-BD1 affinities and inhibition activities, and potently suppressed MV4;11 cancer cell line proliferation. Among them, compound 9d showed excellent selectivity for BRD4 and effectively suppressed c-Myc, the downstream protein of BRD4. This study provided new lead compounds for further biological evaluation on BRD4.

Bromodomain protein 4 small-molecule inhibitor, and preparation method and application thereof

The invention discloses a bromodomain protein 4 small-molecule inhibitor, and a preparation method and application thereof. Belongs to the field of chemical medicines, and relates to a compound which has antitumor activity and is shown in a general formul

MAP4K4 (HGK) Inhibitors

The invention provides mitogen-activated protein kinase kinase kinase kinase 4 (MAP4K4) inhibitors, and pharmaceutically acceptable salts, hydrides and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof with an effective amount of the compound or composition, and detecting a resultant diminution of tumor cell growth, cancer or metastasis.

SUBSTITUTED AMINOTHIAZOLONE INDAZOLES AS ESTROGEN RELATED RECEPTOR-ALPHA MODULATORS

The present invention relates to compounds of Formula (I), methods for preparing these compounds, compositions, intermediates and derivatives thereof and for treating a condition including but not limited to ankylosing spondylitis, artherosclerosis, arthritis (such as rheumatoid arthritis, infectious arthritis, childhood arthritis, psoriatic arthritis, reactive arthritis), bone-related diseases (including those related to bone formation), breast cancer (including those unresponsive to anti-estrogen therapy), cardiovascular disorders, cartilage-related disease (such as cartilage injury/loss, cartilage degeneration, and those related to cartilage formation), chondrodysplasia, chondrosarcoma, chronic back injury, chronic bronchitis, chronic inflammatory airway disease, chronic obstructive pulmonary disease, diabetes, disorders of energy homeostasis, gout, pseudogout, lipid disorders, metabolic syndrome, multiple myeloma, obesity, osteoarthritis, osteogenesis imperfecta, osteolytic bone metastasis, osteomalacia, osteoporosis, Paget's disease, periodontal disease, polymyalgia rheumatica, Reiter's syndrome, repetitive stress injury, hyperglycemia, elevated blood glucose level, and insulin resistance.

INDAZOLYL-SUBSTITUTED DIHYDROISOXA-ZOLOPYRIDINES AND METHODS OF USE THEREOF

This invention relates to novel 4-(indazol-5-yl)-4,7-dihydroisoxazolo[5,4-b]pyridine derivatives having protein tyrosine kinase inhibitory activity, to a process for the manufacture thereof and to the use thereof for the treatment of c-Met-mediated diseas

FLUORINATED 2,6-DIALKYL-3,5-DICYANO-4-(1H-INDAZOL-5-YL)-1,4-DIHYDROPYRIDINES AND METHODS OF USE THEREOF

The present invention relates to novel fluorinated 2,6-dialkyl-3,5-dicyano-4-(1H-indazol-5-yl)-1,4- dihydropyridine derivatives having protein tyrosine kinase inhibitory activity, to a process for the manufacture thereof and to the use thereof for the tre

FLUORO-SUBSTITUTED 3,5-DICYANO-4-(1H-INDAZOL-5-YL)-2,6-DIMETHYL-1,4-DIHYDROPYRIDINE DERIVATIVES AND METHODS OF USE THEREOF

The present invention relates to novel fluoro-substituted 3,5-dicyano-4-(1H-indazol-5-yl)-2,6-dimethyl-1,4-dihydropyridine derivatives having protein tyrosine kinase inhibitory activity, to a process for the manufacture thereof and to the use thereof for

FLUORO-SUBSTITUTED 2-ARYL-3,5-DICYANO-4-INDAZOLYL-6-METHYL-1,4-DIHYDROPYRIDINES AND USES THEREOF

The present invention relates to novel, fluoro-substituted 2-aryl-3,5-dicyano-4-(1H-indazol-5-yl)-6- methyl-l,4-dihydropyridine derivatives having protein tyrosine kinase inhibitory activity, to a process for the manufacture thereof and to the use thereof

BI- AND TRICYCLIC INDAZOLE-SUBSTITUTED 1,4-DIHYDROPYRIDINE DERIVATIVES AND USES THEREOF

This invention relates to novel bi- and tricyclic indazole-substituted 1,4-dihydropyridine derivatives having protein tyrosine kinase inhibitory activity, to a process for the manufacture thereof and to the use thereof for the treatment of c-Met-mediated

ANNELLATED 4- (INDAZOLYL) -1,4-DIHYDROPYRIDINE DERIVATIVES AND METHODS OF USE THEREOF

This invention relates to novel annellated 4-(indazolyl)-l,4-dihydropyridine derivatives having protein tyrosine kinase inhibitory activity, to a process for the manufacture thereof and to the use thereof for the treatment of c-Met-mediated diseases or c-