17100-63-9

Usage

Synthesis Reference(s)

Tetrahedron Letters, 10, p. 1623, 1969 DOI: 10.1017/S0009838800024678

InChI:InChI=1/C9H9BrO3/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 106291-80-9 methyl 4-bromo-3-hydroxybenzoate 
• 77-78-1 dimethyl sulfate 
• 14348-38-0 4-bromo-3-hydroxybenzoic acid 
• 99-06-9 3-Carboxyphenol 
• 74-88-4 methyl iodide 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 67-56-1 methanol 
• 56256-14-5 4-bromo-3-methoxy-benzoic acid 
• 3556-83-0 methyl 4-methyl-3-methoxybenzoate 

Downstream Products

• 20105-30-0 Bis-(2-methoxy-4-methoxycarbonylphenyl)-aether 
• 2556-05-0 4,5,3'-trimethoxy-3,4'-oxy-di-benzoic acid dimethyl ester 
• 5368-81-0 methyl 3-methoxybenzoate 
• 859140-23-1 methyl 3-methoxy-4-(pyridin-4-yl)benzoate 
• 52045-79-1 C₂₈H₂₆N₄O₈S₂ 
• 20105-32-2 1,1'-oxybis[4-(chloromethyl)-2-methoxybenzene] 
• 20105-31-1 [oxybis(3-methoxy-4,1-phenylene)]dimethanol 
• 20457-50-5 Bis-(4-carboxymethyl-2-hydroxy-phenyl)-aether 
• 20105-33-3 2,2'-[oxybis(3-methoxy-4,1-phenylene)]diacetonitrile 
• 20127-64-4 Bis-(2-hydroxy-4-methoxycarbonyl-methyl-phenyl)-aether 
• 20105-34-4 2,2'-[oxybis(3-methoxy-4,1-phenylene)]diacetic acid 
• 20457-51-6 Bis-(2-benzyloxy-4-methoxycarbonyl-methyl-phenyl)-aether 
• 20127-65-5 Bis-<2-benzyloxy-4-(N-(4-benzyloxy-3-methoxy-phenaethyl)-aminocarbonyl-methyl)-phenyl>-aether 
• 56256-14-5 4-bromo-3-methoxy-benzoic acid 

Relevant academic research and scientific papers

TYK2 INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.

CANCER TREATMENTS TARGETING CANCER STEM CELLS

Disclosed are compounds, methods, compositions, and kits that allow for treating cancer by, e.g., targeting cancer stem cells. In some embodiments, the cancer is colorectal cancer, gastric cancer, gastrointestinal stromal tumor, ovarian cancer, lung cancer, breast cancer, pancreatic cancer, prostate cancer, testicular cancer, or lymphoma. In some embodiments, the cancer is liver cancer, endometrial cancer, leukemia, or multiple myeloma. The compounds utilized in the disclosure are of Formula (0), (O'), and (I):

A facile color-tuning strategy for constructing a library of Ir(III) complexes with fine-tuned phosphorescence from bluish green to red using a synergetic substituent effect of -OCH3 and -CN at only the C-ring of C∧N ligand

By simply grafting a -CN group and/or a -OCH3 group onto the meta- and/or para-site of the C-ring, a series of Ir(iii) complexes bearing a similar molecular platform of bis(1,2-diphenyl-1H-benzimidazolato-N,C2′)iridium(iii)(acetylacetonate), but showing fine-tuned phosphorescence covering nearly the whole window of the visible spectrum with a wide color-tuning range of 109 nm was acquired. With the help of DFT calculations, it was revealed that if the C-related arene moiety of the C∧N ligand (C-ring) contributes substantially to both the HOMO and LUMO of an Ir(iii) complex, the concurrent introduction of an electron-donating -OCH3 and an electron-withdrawing -CN groups on the C-ring at the meta- and para-sites relative to the Ir atom may lead to a favorable synergetic substituent effect on the color-tuning direction. This may represent a facile yet effective molecular design strategy for Ir(iii) complexes with a desirous emission color. A bluish green organic light-emitting diode (OLED) based on one of the objective complexes displayed a maximum current efficiency of 62.1 cd A-1, an external quantum efficiency of 19.8%, and a brightness of 48-040 cd m-2, implying that high-performance red and blue OLED phosphors as well as libraries of Ir(iii) complexes bearing similar molecular platforms may be developed through this -OCH3 and -CN synergetic substitution strategy.

Elongated and substituted triazine-based tricarboxylic acid linkers for MOFs

New triazine-based tricarboxylic acid linkers were prepared as elongated relatives of triazinetribenzoic acid (TATB). Additionally, functional groups (NO2, NH2, OMe, OH) were introduced for potential post-synthetic modification (PSM) of MOFs. Functionalized tris(4-bromoaryl)triazine "cores" (3a,3b) were obtained by unsymmetric trimerization mixing one equivalent of an acid chloride (OMe or NO2 substituted) with two equivalents of an unsubstituted nitrile. Triple Suzuki coupling of the cores 3 with suitable phenyl- and biphenylboronic acid derivatives provided elongated tricarboxylic acid linkers as carboxylic acids 17 and 20 or their esters 16 and 19. Reduction of the nitro group and cleavage of the methoxy group gave the respective amino and hydroxy-substituted triazine linkers.

Extended structure-activity study of thienopyrimidine-based EGFR inhibitors with evaluation of drug-like properties

Thieno[2,3-d]pyrimidines are attractive derivatives for cancer treatment, among others through regulation of the epidermal growth factor receptor tyrosine kinase (EGFR-TK). In an extended SAR study, 44 new compounds of this class have been evaluated as inhibitors, while simultaneously focussing on ADME properties. Through the application of bioisosters, hybrid structures, solubilizing tails, and a combination approach several successful alterations in terms of activity and physiochemical properties were accomplished. Compounds based on benzylamines were found superior to aniline hybrid structures with respect to activity and ADME profile. Exploration of the former class revealed meta-and para amides as favourable 6-aryl substituents, contributing to an increase in activity and acting as a linker for solubilizing tails. Next, combinations of activity-inducing groups on the same scaffold resulted in new drug candidates. Compounds containing 6-aryls with the (2-(dimethylamino)ethyl)carbamoyl substituent were found equipotent to Erlotinib. Compared to this commercial drug, improved solubility and metabolic stability were observed. However, the thieno[2,3-d]pyrimidines with a solubilizing tail was by Caco-2 experiments found to have permeability issues, making further drug development difficult. Selected compounds were further analysed for toxicity and teratogenicity in zebrafish embryos. Two thienopyrimidines were both found to be less lethal than Erlotinib and to perform as well in terms of teratogenicity. Finally, the most promising thienopyrimidine drug was evaluated in a panel of human cancer cell lines, showing a clear potential for thienopyrimidines as anti-cancer agents.

TBK/IKK INHIBITOR COMPOUNDS AND USES THEREOF

The present invention relates to compounds of Formula I and pharmaceutically acceptable compositions thereof, useful as TBK/IKKε inhibitors.

METHOD FOR PREPARING SUBSTITUTED TRIAZOLOPYRIDINES

The present invention relates to methods of preparing substituted triazolopyridine compounds of general formula (I) as described and defined herein, as well as to intermediate compounds useful in the preparation of said compounds.

METHOD FOR PREPARING SUBSTITUTED TRIAZOLOPYRIDINES

The present invention relates to methods o f preparing substituted triazolopyridine compounds of general formula (I) as described and defined herein, as well as to intermediate compounds useful in the preparation of said compounds.

SUBSTITUTED TRIAZOLOPYRIDINES HAVING ACTIVITY AS MPS-1 INHIBITORS

The present invention relates to substituted triazolopyridine compounds of general formula (I), in which R1, R2, R3, R4, and R5 are as given in the description and in the claims, to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, as well as to intermediate compounds useful in the preparation of said compounds.

NOVEL COMPOUNDS FOR THE TREATMENT OF CANCER

The present invention relates to novel compounds showing an inhibitory effect on Mps-1 kinase, to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, as well as to intermediate compounds useful in the preparation of said compounds.