6331-61-9Relevant articles and documents
(Trifluoromethylselenyl)methylchalcogenyl as Emerging Fluorinated Groups: Synthesis under Photoredox Catalysis and Determination of the Lipophilicity
Grollier, Kevin,De Zordo-Banliat, Arnaud,Bourdreux, Flavien,Pegot, Bruce,Dagousset, Guillaume,Magnier, Emmanuel,Billard, Thierry
supporting information, p. 6028 - 6033 (2021/03/15)
The synthesis of molecules bearing (trifluoromethylselenyl)methylchalcogenyl groups is described via an efficient two-step strategy based on a metal-free photoredox catalyzed decarboxylative trifluoromethylselenolation with good yields up to 88 %, which raised to 98 % in flow chemistry conditions. The flow methods allowed also to scale up the reaction. The mechanism of this key reaction was studied. The physicochemical characterization of these emerging groups was performed by determining their Hansch–Leo lipophilicity parameters with high values up to 2.24. This reaction was also extended to perfluoroalkylselenolation with yields up to 95 %. Finally, this method was successfully applied to the functionalization of relevant bioactive molecules such as tocopherol or estrone derivatives.
Novel coupled molecules from active structural motifs of synthetic and natural origin as immunosuppressants
Minhas, Richa,Bansal, Gulshan,Bansal, Yogita
, p. 544 - 554 (2020/06/21)
Introduction: Nitric oxide (NO) is an important mediator in the pathogenesis and control of immune system-related disorders and its levels are modulated by inducible NO synthase (iNOS). Oxidative stress is another pathological indication in majority of autoimmune disorders. The present study aims at the development of coupled molecules via selection of pharmacophores for both immunomodulatory and antioxidant activities through iNOS inhibition. Methods: Variedly substituted coumarin moieties are coupled with naturally occurring phenols through an amide linkage and were predicted for activities using computer-based program PASS. The compounds predicted to have dual activities were synthesized. Docking studies were carried out against iNOS (PDB 1R35) and compounds having good docking score were evaluated for immunomodulatory and antioxidant activities. Results: The synthesized compounds were found to be pure and were obtained in good yields. Compounds with maximum docking score (YR1a, YR2e, YR2c and YR4e) were selected for evaluation by in vitro models. Compounds YR2e and YR2c markedly inhibited the reduction of NBT dye and showed maximum percent iNOS inhibition. In DPPH assay, compound YR4e was observed as the most potent antioxidant (EC50 0.33 μM/mL). Based on these studies, compounds YR2e and YR2c were selected for haemagglutination test. Compound YR2e was observed as the most active immunosuppressant with maximal inhibitory ability of iNOS and NBT reduction and lower HAT value of 3.5. Conclusion: Compound YR2e can be utilized as a pharmacological agent in the prevention or treatment of immunomodulatory diseases such as tumors, rheumatoid arthritis, ulcerative colitis, organ transplant and other autoimmune disorders.
Microwave (MW), ultrasound (US) and combined synergic MW-US strategies for rapid functionalization of pharmaceutical use phenols
Pawe?czyk, Anna,Sowa-Kasprzak, Katarzyna,Olender, Dorota,Zaprutko, Lucjusz
, (2018/09/26)
Increasingly stringent regulations aimed at protection of the natural environment have stimulated the search for new synthetic methodologies in organic and medicinal chemistry having no or minimum harmful effect. An interesting approach is the use of alternative activation factors, microwaves (MW) or ultrasounds (US) and also their cross-combination, which has been tested in the fast and efficient creation of new structures. At present, an easy and green hybrid strategy (“Lego” chemistry) is generally recommended for the design of new substances from different chemistry building blocks. Often, selected biologically active components with specific chemical reactivities are integrated by a suitably designed homo- or heterodifunctional linker that modifies the functionality of the starting structure, allowing easy covalent linkage to another molecule. In this study, a fast introduction of heterodifunctional halogenoacidic linker to selected mono-, di- and triphenolic active substances, allowing their functionalization, was investigated. Nucleophilic substitution reaction was chosen to produce final ethers with the reactive carboxylic group from phenols. The functionalization was performed using various green factors initiating and supporting the chemical reactions (MW, US, MW-US). The benefits of the three green supporting methods and different conditions of reactions were analyzed and compared with the results of the reaction performed by conventional methods.
With herbicidal activity of 4 - benzoyl pyrazoles
-
Paragraph 0060; 0061; 0062, (2017/08/14)
The invention relates to a 4-benzoyl pyrazole compound with herbicidal activity. The structural formula of the 4-benzoyl pyrazole compound with the herbicidal activity is as shown in specifications, wherein R1 in the structural formula is selected from hy
Synthesis and hypolipidaemic evaluation of a series of α-asarone analogues related to clofibrate in mice
Labarrios, Fernando,Garduno, Leticia,Vidal, Maria Del Rosario,Garcia, Raul,Salazar, Maria,Martinez, Elizdath,Diaz, Francisco,Chamorro, German,Tamariz, Joaquin
, p. 1 - 7 (2007/10/03)
A series of α-asarone analogues related to clofibrate, containing an acetic acid group at C-2 of the aromatic ring, has been prepared as the acids or as the ethyl and methyl esters. The corresponding alcohols were also synthesized by reduction of the ethy
Probing the scope of the asymmetric dihydroxylation of polymer-bound olefins. Monitoring of HRMAS NMR allows for reaction control and on-bead measurement of enantiomeric excess
Riedl, Rainer,Tappe, Robert,Berkessel, Albrecht
, p. 8994 - 9000 (2007/10/03)
The aim of this study was (I) to define the scope and limitations of the Sharpless asymmetric dihydroxylation (AD) for polymer-bound olefins of different structural types and (II) to elaborate HRMAS NMR methods for the direct on-bead monitoring of the asymmetric dihydroxylation, including the on-bead determination of enantiomeric excess (ee). (I) 2-Methoxy-4-(2- propenyl)phenol (eugenol, E), 10-undecenoic acid (U), and (E)-4- hydroxystilbene (S) were bound to Wang-resin or TentaGel S-OH. These olefins gave low (E, 32%), intermediate (U, 88%), and very high enantiomeric excesses (S, > 99%) when treated with AD mix β in solution. When bound to the polymers, the trend of the enantioselectivities remained the same [S (97%) > U (20-45%) > E (0-3%)]. However, the absolute ee values demonstrate that only the most selective types of substrates in homogeneous solution have practical potential for enantioselective AD on solid phase. (II) HRMAS NMR was successfully used for on-bead monitoring and for the first time for the ee measurement of the polymer-bound dihydroxylation product. As an example, the full assignment of all resonances of polymer-bound 10-undecenoic acid (U) and its dihydroxylation product is presented. For the ee measurement, the polymer-bound dihydroxylation product was derivatized with Mosher's acid. The integration of seven different pairs of resonances in the 13C HRMAS NMR of the diastereomeric Mosher esters gave (in each case) an ee value that agreed within 1% with that determined by chiral HPLC after cleavage of the AD product.
Synthesis of monocyclic &β-lactams incorporating an essential oil constituent in the ring
Varma, Luxmi R,Narayanan, C S
, p. 676 - 680 (2007/10/02)
A series of new monocyclic β-lactams has been prepared using acyl chlorides derived from 1-menthol, thymol and eugenol and Schiff bases derived from aromatic aldehydes and amines, and their antibacterial activity determined.The compounds have been charact
Synthesis of Monocyclic β-Lactams with a Terpenoid Moiety
Varma, R. Luxmi,Narayanan, C. S.
, p. 302 - 304 (2007/10/02)
A series of new monocyclic β-lactams with a terpenoid moiety have been prepared by reaction of schiff bases with appropriate terpenyl acid chlorides in the presence of triethylamine.Their structural assignments are based on elemental analyses and spectral
Design, Synthesis, and Testing of Potential Antisickling Agents. 4. Structure-Activity Relationships of Benzyloxy and Phenoxy Acids
Abraham, D. J.,Kennedy, P. E.,Mehanna, A. S.,Patwa, D. C.,Williams, F. L.
, p. 967 - 978 (2007/10/02)
In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation.Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains.We have also found a halogenated aromatic malonic acid derivative to be quite active.Compounds reported in this paper are compared with other antigelling agents studied in our laboratory.Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function.
