170230-13-4Relevant academic research and scientific papers
Development of Scaled-Up Synthetic Method for Retinoid X Receptor Agonist NEt-3IB Contributing to Sustainable Development Goals
Kakuta, Hiroki,Kikuzawa, Shota,Morishita, Ken-Ichi,Takamura, Yuta,Watanabe, Masaki
, p. 146 - 154 (2022/02/05)
Small-molecular drugs, which are generally inexpensive compared with biopharmaceuticals and can often be taken orally, may contribute to the Sustainable Development Goals (SDGs) adopted by the United Nations. We previously reported the retinoid X receptor (RXR) agonist 4-(ethyl(3-isobutoxy-4-isopropyl-phenyl)amino)benzoic acid (NEt-3IB, 1) as a small-molecular drug candidate to replace biopharmaceuticals for the treatment of inflammatory bowel disease. The previous synthetic method to 1 required a large amount of organic solvent and extensive purification. In line with the SDGs, we aimed to develop an environmentally friendly, inexpensive method for the large-scale synthesis of 1. The developed method requires only a hydrophobic ether and EtOH as reaction and extraction solvents. The product was purified by recrystallization twice to afford 99% pure 1 at 100mmol scale in about 30% yield. The optimized process showed a 35-fold improvement of the E-factor (an index of environmental impact) compared to the original method. This work, which changes the solvent used to environmentally preferable ones based on the existing synthetic method for 1, illustrates how synthetic methods for small-molecular drugs can be adapted and improved to contribute to the SDGs.
REXINOID COMPOUND HAVING ALKOXY GROUP
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, (2009/12/05)
Disclosed is a compound represented by the general formula shown below, which can bind to a retinoid X receptor (RXR), which is one of nuclear receptors, and exhibit an agonistic or antagonistic action. [Wherein, R1 is selected from the group c
COMPOUNDS AND METHODS FOR THE TREATMENT OF VIRUSES AND CANCER
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Page/Page column 24; 25, (2010/11/26)
The present invention relates to compounds according to the formula I: Where Ra is H or an optionally OH-substituted C1-C3 alkyl; R1 is OR1, an optionally substituted C4-12 carbocyclic group which may be saturated or unsaturated (including aromatic) or an optionally substituted heterocyclic group; R1 is an optionally substituted C1-C14 hydrocarbyl group or an optionally substituted heterocyclic group;; R2 , R3 and R4 are each independently H, an optionally substituted C1-C4 alkyl group (preferably CH3, CH2CH3 or CF3), halogen (preferably F, Cl, Br), OR, CN, NO2, a C1-C6 thioether, a C1-C6 thioester group, an optionally substituted CO2R group, an optionally substituted COR group or an optionally substituted OCOR group (preferably R4 is H); R is H or an optionally substituted C1-C6 alkyl group; RHET is an optionally substituted heterocyclic group; and pharmaceutically acceptable salts, solvates or polymorphs thereof.
Optimization of diarylamines as non-nucleoside inhibitors of HIV-1 reverse transcriptase
Ruiz-Caro, Juliana,Basavapathruni, Aravind,Kim, Joseph T.,Bailey, Christopher M.,Wang, Ligong,Anderson, Karen S.,Hamilton, Andrew D.,Jorgensen, William L.
, p. 668 - 671 (2007/10/03)
Following computational analyses, potential non-nucleoside inhibitors of HIV-1 reverse transcriptase have been pursued through synthesis and assaying for anti-viral activity. The general class Het-NH-Ph-U has been considered, where Het is an aromatic heterocycle and U is an unsaturated, hydrophobic group. Results for compounds with Het = 2-thiazoyl and 2-pyrimidinyl are the focus of this report.
