1346702-52-0

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl 6-bromo-1-(1-methylethyl)-1H-indazole-4-carboxylate is used as a key intermediate in the synthesis of various pharmaceuticals for its potential therapeutic effects, including anti-inflammatory and analgesic properties. Its unique structure and functional groups contribute to the development of new drugs for treating a range of diseases and conditions.
Used in Organic Chemistry Reactions:
In the field of organic chemistry, Methyl 6-bromo-1-(1-methylethyl)-1H-indazole-4-carboxylate is utilized as a reagent due to its distinctive structural features. It facilitates a variety of chemical reactions, aiding in the creation of new organic compounds and contributing to the advancement of chemical research and development.
Used in Medicinal Chemistry and Drug Development:
Methyl 6-broMo-l-(lMethylethyl)-lH-indazole-4-carboxylate plays a significant role in medicinal chemistry, where it is employed for the exploration of new drug candidates. Its potential applications in the treatment of various diseases and conditions make it a valuable asset in drug development, driving the discovery of innovative therapeutic agents.

Upstream product

• 885518-49-0 methyl 6-bromo-1H-indazole-4-carboxylate 
• 75-26-3 isopropyl bromide 
• 75-30-9 2-iodo-propane 
• 1346597-55-4 methyl 1-acetyl-6-bromo-1H-indazole-4-carboxylate 
• 1000342-11-9 2-methyl-3-amino-5-bromobenzoic acid methyl ester 
• 1975-50-4 2-methyl-3-nitrobenzic acid 
• 220514-28-3 5-bromo-2-methyl-3-nitrobenzoic acid methyl ester 
• 107650-20-4 5-bromo-2-methyl-3-nitro-benzoic acid 

Downstream Products

• 1346704-33-3 GSK343 
• 1396772-45-4 N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(4-(morpholinomethyl)phenyl)-1H-indazole-4-carboxamide 
• 1346703-10-3 N-((4-cyclohexyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-cyclopropyl-1-isopropyl-1H-indazole-4-carboxamide 
• 1346703-11-4 6-bromo-N-((4-cyclohexyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide 
• 1346702-88-2 6-{4-[(dimethylamino)methyl]phenyl}-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide hydrochloride 
• 1347232-05-6 6-{4-[(dimethylamino)methyl]phenyl}-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide 
• 1346702-68-8 6-(4-((dimethylamino)methyl)phenyl)-N-((4-ethyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide 
• 1346702-54-2 6-bromo-1-(1-methylethyl)-1H-indazole-4-carboxylic acid 
• 1346704-12-8 N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-{4-[(methylamino)sulfonyl]phenyl}-1-(methylethyl)-1H-indazole-4-carboxamide 
• 1346702-59-7 N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(4-(2-(dimethylamino)ethoxy)phenyl)-1-isopropyl-1H-indazole-4-carboxamide 
• 1346704-23-1 N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(2-methylphenyl)-1H-indazole-4-carboxamide 
• 1346704-21-9 6-{4-[(dimethylamino)sulfonyl]phenyl}-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide 
• 1346704-20-8 N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[2-(trifluoromethyl)phenyl]-1H-indazole-4-carboxamide 
• 1346704-10-6 N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-phenyl-1H-indazole-4-carboxamide 

Relevant academic research and scientific papers

Discovery of First-in-Class Dual PARP and EZH2 Inhibitors for Triple-Negative Breast Cancer with Wild-Type BRCA

PARP inhibitors have highly significant effects on BRCA mutant cells, allowing targeted therapy of triple-negative breast cancer (TNBC). However, some TBNC patients lack BRCA mutations. Recent studies have shown that EZH2 inhibitors can increase the sensitivity of wild-type BRCA cells to PARP inhibitors. We designed a series of dual PARP and EZH2 inhibitors, and the most promising compound, 5a, showed good inhibitory activity against PARP-1 and EZH2 and good inhibitory effects on MDA-MB-231 (IC50 = 2.63 μM) and MDA-MB-468 (IC50 = 0.41 μM) cells with wild-type BRCA. Compared with that of olaparib, the growth inhibitory activities against these two cell types increased by approximately 15- and 80-fold, respectively, which was even more effective than the combination of olaparib and tazemetostat/GSK126. 5a can induce autophagy death of tumor cells and cause less damage to normal cells. Therefore, 5a, as a first-in-class dual PARP and EZH2 inhibitor, is a potential anticancer drug candidate for the treatment of TNBC.

18F-Labeled PET Probe Targeting Enhancer of Zeste Homologue 2 (EZH2) for Cancer Imaging

The enzyme enhancer of zeste homologue 2 (EZH2) plays a catalytic role in histone methylation (H3K27me3), one of the epigenetic modifications that is dysregulated in cancer. The development of a positron emission tomography (PET) imaging agent targeting E

SUBSTITUTED INDOLE MCL-1 INHIBITORS

The present disclosure provides for compounds that inhibit the activity of an anti- apoptotic Bcl-2 family member Myeloid cell leukemia-1 (Mcl-1) protein. The present disclosure also provides for pharmaceutical compositions as well as methods for using co

Structure-activity relationship studies for enhancer of zeste homologue 2 (EZH2) and enhancer of zeste homologue 1 (EZH1) inhibitors

EZH2 or EZH1 (enhancer of zeste homologue 2 or 1) is the catalytic subunit of polycomb repressive complex 2 (PRC2) that catalyzes methylation of histone H3 lysine 27 (H3K27). PRC2 hyperactivity and/or hypertrimethylation of H3K27 are associated with numerous human cancers, therefore inhibition of PRC2 complex has emerged as a promising therapeutic approach. Recent studies have shown that EZH2 and EZH1 are not functionally redundant and inhibition of both EZH2 and EZH1 is necessary to block the progression of certain cancers such as mixed-lineage leukemia (MLL)-rearranged leukemias. Despite the significant advances in discovery of EZH2 inhibitors, there has not been a systematic structure-activity relationship (SAR) study to investigate the selectivity between EZH2 and EZH1 inhibition. Here, we report our SAR studies that focus on modifications to various regions of the EZH2/1 inhibitor UNC1999 (5) to investigate the impact of the structural changes on EZH2 and EZH1 inhibition and selectivity.

SUBSTITUTED 6,5-FUSED BICYCLIC HETEROARYL COMPOUNDS

The present invention relates to substituted 6,5 -fused bicyclic heteroaryl compounds. The present invention also relates to pharmaceutical compositions containing these compounds and methods of treating cancer by administering these compounds and pharmaceutical compositions to subjects in need thereof.

Identification of potent, selective, cell-Active inhibitors of the histone lysine methyltransferase EZH2

The histone H3-lysine 27 (H3K27) methyltransferase EZH2 plays a critical role in regulating gene expression, and its aberrant activity is linked to the onset and progression of cancer. As part of a drug discovery program targeting EZH2, we have identified highly potent, selective, SAM-competitive, and cell-Active EZH2 inhibitors, including GSK926 (3) and GSK343 (6). These compounds are small molecule chemical tools that would be useful to further explore the biology of EZH2.