1687-64-5Relevant academic research and scientific papers
Formation and cleavage of C-H, C-C, and C-O bonds of ortho-methyl- substituted anisoles by late transition metals
Lara, Patricia,Paneque, Margarita,Poveda, Manuel L.,Salazar, Veronica,Santos, Laura L.,Carmona, Ernesto
, p. 3512 - 3513 (2006)
2,6-Dimethyl-substituted anisoles can be converted into the corresponding 2-ethyl-6-methylphenols in a several-step reaction mediated by a TpMe2Ir(III) complex; use of the 13C-enriched anisoles, ArO13CH3/s
Synthesis of Highly Substituted Phenols and Benzenes with Complete Regiochemical Control
Zhang, Xiaojie,Beaudry, Christopher M.
supporting information, p. 6086 - 6090 (2020/08/12)
Substituted phenols are requisite molecules for human health, agriculture, and diverse synthetic materials. We report a chemical synthesis of phenols, including penta-substituted phenols, that accommodates programmable substitution at any position. This method uses a one-step conversion of readily available hydroxypyrone and nitroalkene starting materials to give phenols with complete regiochemical control and in high chemical yield. Additionally, the phenols can be converted into highly and even fully substituted benzenes.
Novel S1P1 receptor agonists - Part 3: From thiophenes to pyridines
Bolli, Martin H.,Abele, Stefan,Birker, Magdalena,Bravo, Roberto,Bur, Daniel,De Kanter, Ruben,Kohl, Christopher,Grimont, Julien,Hess, Patrick,Lescop, Cyrille,Mathys, Boris,Müller, Claus,Nayler, Oliver,Rey, Markus,Scherz, Michael,Schmidt, Gunther,Seifert, Jürgen,Steiner, Beat,Velker, J?rg,Weller, Thomas
, p. 110 - 130 (2014/02/14)
In preceding communications we summarized our medicinal chemistry efforts leading to the identification of potent, selective, and orally active S1P 1 agonists such as the thiophene derivative 1. As a continuation of these efforts, we replaced the thiophene in 1 by a 2-, 3-, or 4-pyridine and obtained less lipophilic, potent, and selective S1P1 agonists (e.g., 2) efficiently reducing blood lymphocyte count in the rat. Structural features influencing the compounds' receptor affinity profile and pharmacokinetics are discussed. In addition, the ability to penetrate brain tissue has been studied for several compounds. As a typical example for these pyridine based S1P 1 agonists, compound 53 showed EC50 values of 0.6 and 352 nM for the S1P1 and S1P3 receptor, respectively, displayed favorable PK properties, and penetrated well into brain tissue. In the rat, compound 53 maximally reduced the blood lymphocyte count for at least 24 h after oral dosing of 3 mg/kg.
PYRIDIN-4-YL DERIVATIVES
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Page/Page column 15, (2014/09/29)
The invention relates to compounds of the Formula (I), Formula (I) wherein R1 and R2 are as described in the description, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immuno
Heterogeneous copper-catalyzed hydroxylation of aryl iodides under air conditions
Ding, Guodong,Han, Hongling,Jiang, Tao,Wu, Tianbin,Han, Buxing
supporting information, p. 9072 - 9075 (2014/08/05)
In this work, the ligand-free heterogeneous copper Cu-g-C3N 4 was synthesized and used for the hydroxylation of aryl iodides to synthesize phenols using cheap bases. The catalyst was conveniently prepared, air-tolerant, reusable and scalable, and is very efficient for a wide range of substrates. The synthesis of substituted phenols can be carried out under air conditions and has great potential for practical applications. This journal is the Partner Organisations 2014.
Novel S1P1 receptor agonists - Part 1: From pyrazoles to thiophenes
Bolli, Martin H.,Müller, Claus,Mathys, Boris,Abele, Stefan,Birker, Magdalena,Bravo, Roberto,Bur, Daniel,Hess, Patrick,Kohl, Christopher,Lehmann, David,Nayler, Oliver,Rey, Markus,Meyer, Solange,Scherz, Michael,Schmidt, Gunther,Steiner, Beat,Treiber, Alexander,Velker, J?rg,Weller, Thomas
, p. 9737 - 9755 (2014/01/06)
From a high-throughput screening campaign aiming at the identification of novel S1P1 receptor agonists, the pyrazole derivative 2 emerged as a hit structure. Medicinal chemistry efforts focused not only on improving the potency of the compound but in particular also on resolving its inherent instability issue. This led to the discovery of novel bicyclo[3.1.0]hexane fused thiophene derivatives. Compounds with high affinity and selectivity for S1P1 efficiently reducing the blood lymphocyte count in the rat were identified. For instance, compound 85 showed EC50 values of 7 and 2880 nM on S1P1 and S1P3, respectively, had favorable pharmacokinetic properties in rat and dog, distributed well into brain tissue, and efficiently and dose dependently reduced the blood lymphocyte count in the rat. After oral administration to spontaneously hypertensive rats, the S1P 1 selective compound 85 showed no effect on mean arterial blood pressure and affected the heart rate during the wake phase of the animals only.
NOVEL THIOPHENE DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE-1 RECEPTOR AGONISTS
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, (2011/10/01)
The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunosuppressive agents.
Green catalysts derived from agricultural and industrial waste products: The preparation of phenols from CsOH and Aryl iodides using CuO on mesoporous silica
Chan, Chien-Ching,Chen, Yan-Wun,Su, Chi-Shen,Lin, Hong-Ping,Lee, Chin-Fa
experimental part, p. 7288 - 7293 (2012/01/06)
The synthesis of CuO catalysts supported on mesoporous silica derived from rice husks and semiconductor copper from chemical mechanical planarization (Cu-CMP) wastewater is described. These catalysts are active for the coupling reaction of CsOH with aryl iodides. Low catalyst loading (1 mol-%) without the need for ancillary ligands make these very attractive "green" catalysts. The synthesis of CuO catalysts supported on mesoporous silica derived from rice husks and semiconductor copper from chemical mechanical planarization (Cu-CMP) wastewater is described. These catalysts are active for the coupling reaction of CsOH with aryl iodides. Low catalyst loading (1 mol-%) without the need for ancillary ligands make these very attractive "green" catalysts. Copyright
Pyridin-4-yl derivatives as immunomodulating agents
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Page/Page column 23, (2010/04/23)
The invention relates to pyridine derivatives of Formula (I) wherein A, R1, R2, R3, R4, R5, and R6 are as described in the description, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.
AMINO-PYRIDINE DERIVATIVES AS S1P1 /EDG1 RECEPTOR AGONISTS
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Page/Page column 17, (2010/04/30)
The invention relates to novel amino-pyridine derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.
