525575-58-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-1,3-dichloro-2-(3-isopropyl-4-methoxyphenoxy)benzene is used as a pharmaceutical intermediate for the synthesis of various organic compounds. Its unique structure allows it to be a valuable building block in the development of new pharmaceuticals, potentially contributing to the creation of novel drugs with improved therapeutic properties.
Used in Agrochemical Production:
5-BROMO-1,3-DICHLORO-2-(3-ISOPROPYL-4-METHOXYPHENOXY)BENZENE may also be used in the production of agrochemicals, where its chemical properties can be harnessed to develop new pesticides or herbicides. Its potential applications in this industry could lead to the creation of more effective and environmentally friendly agricultural products.
Used in Material Science:
5-Bromo-1,3-dichloro-2-(3-isopropyl-4-methoxyphenoxy)benzene can serve as a building block in the development of new materials, particularly in the field of material science. Its unique structure and properties may contribute to the creation of innovative materials with enhanced performance characteristics, such as improved stability, reactivity, or other desirable traits.

InChI:InChI=1/C16H15BrCl2O2/c1-9(2)12-8-11(4-5-15(12)20-3)21-16-13(18)6-10(17)7-14(16)19/h4-9H,1-3H3

Upstream product

• 3217-15-0 4-bromo-2,6-dichloro-phenol 
• 13523-62-1 3-iso-propyl-4-methoxyphenol 
• 17318-08-0 5-bromo-1,3-dichloro-2-fluorobenzene 

Downstream Products

• 525575-59-1 3,5-dichloro-4-(4-hydroxy-3-isopropylphenoxy)phenyltrimethylsilylacetylene 
• 1026639-31-5 3,5-dichloro-4-(4-hydroxy-3-isopropylphenoxy)cinnamic acid 
• 525575-60-4 3,5-dichloro-4-(4-methoxy-3-isopropylphenoxy)phenylacetic acid 

Relevant academic research and scientific papers

AGONISTS OF ROR GAMMAt

The present invention is directed to compounds of the formula (I) wherein all substituents are defined herein, as well as pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

Thyroid receptor ligands. 1. Agonist ligands selective for the thyroid receptor β1

Endogenous thyroid receptor hormones 3,5,3′,5′-tetraiodo-L-thyronine (T4, 1) and 3,5,3′-triiodo-L-thyronine (T3, 2) exert a significant effects on growth, development, and homeostasis in mammals. They regulate important genes in intestinal, skeletal, and cardiac muscles, the liver, and the central nervous system, influence overall metabolic rate, cholesterol and triglyceride levels, and heart rate, and affect mood and overall sense of well being. The literature suggests many or most effects of thyroid hormones on the heart, in particular on the heart rate and rhythm, are mediated through the TRα1 isoform, while most actions of the hormones on the liver and other tissues are mediated more through the TRβ1 isoform of the receptor. Some effects of thyroid hormones may be therapeutically useful in nonthyroid disorders if adverse effects can be minimized or eliminated. These potentially useful features include weight reduction for the treatment of obesity, cholesterol lowering for treating hyperlipidemia, amelioration of depression, and stimulation of bone formation in osteoporosis. Prior attempts to utilize thyroid hormones pharmacologically to treat these disorders have been limited by manifestations of hyperthyroidism and, in particular, cardiovascular toxicity. Consequently, development of thyroid hormone receptor agonists that are selective for the β-isoform could lead to safe therapies for these common disorders while avoiding cardiotoxicity. We describe here the synthesis and evaluation of a series of novel TR ligands, which are selective for TRβ1 over TRα1. These ligands could potentially be useful for treatment of various disorders as outlined above. From a series of homologous R1-substituted carboxylic acid derivatives, increasing chain length was found to have a profound effect on affinity and selectivity in a radioreceptor binding assay for the human thyroid hormone receptors α1 and β1 (TRα1 and TRβ2) as well as a reporter cell assay employing CHOK1-cells (Chinese hamster ovary cells) stably transfected with hTRα1 or hTRβ1 and an alkaline phosphatase reporter-gene downstream thyroid response element (TRAFα1 and TRAFβ1). Affinity increases in the order formic, acetic, and propionic acid, while β-selectivity is highest when the R1 position is substituted with acetic acid. Within this series 3,5-dibromo-4-[(4-hydroxy-3-isopropylphenoxy)phenyl]acetic acid (11a) and 3,5-dichloro-4-[(4-hydroxy-3-isopropylphenoxy)phenyl]acetic acid (15) were found to reveal the most promising in vitro data based on isoform selectivity and were selected for further in vivo studies. The effect of 2, 11a, and 15 in a cholesterol-fed rat model was monitored including potencies for heart rate (ED15), cholesterol (ED50), and TSH (ED50). Potency for tachycardia was significantly reduced for the TRβ selective compounds 11a and 15 compared with 2, while both 11a and 15 retained the cholesterol-lowering potency of 2. This left an approximately 10-fold therapeutic window between heart rate and cholesterol, which is consistent with the action of ligands that are approximately 10-fold more selective for TRβ1. We also report the X-ray crystallographic structures of the ligand binding domains of TRα and TRβ in complex with 15. These structures reveal that the single amino acid difference in the ligand binding pocket (Ser277 in TRα or Asn331 in TRβ) results in a slightly different hydrogen bonding pattern that may explain the increased β-selectivity of 15.