765-50-4Relevant articles and documents
Enhanced cytotoxicity of indenyl molybdenum(ii) compounds bearing a thiophene function
Mrózek, Ond?ej,Melounková, Lucie,Dostál, Libor,Císa?ová, Ivana,Eisner, Ale?,Havelek, Radim,Peterová, Eva,Honzí?ek, Jan,Vinklárek, Jaromír
, p. 11361 - 11373 (2019)
A series of six indenyl molybdenum compounds bearing a thiophenyl function in the side chain were prepared and characterized by analytical and spectroscopic methods. The structures of [(η5-C9H6CH2C4H3S)(η3-C3H5)Mo(CO)2] and [(η5-C9H6CH2C4H3S)Mo(CO)2(bpy)][BF4] were determined by single-crystal X-ray diffraction. The compounds bearing N,N-chelating ligands exhibit increased cytotoxic activity against human leukemia cell lines MOLT-4; up to two orders of magnitude lower IC50 values were observed compared to analogues with unsubstituted indenyl, which clearly demonstrates the strong effect of the indenyl ligand modification on the biological activity of the molybdenum(ii) compounds. The highest cytostatic potential was observed for the complex bearing 4,7-diphenyl-1,10-phenanthtoline [(η5-C9H6CH2C4H3S)Mo(CO)2(Ph2phen)][BF4] with IC50 (MOLT-4) = 0.19 ± 0.02 μM. Detailed regulation of the molecular and cellular mechanism by this derivative was investigated on the lung carcinoma cell line A549 and compared with the lung fibroblast cell line MRC-5. Rather unusual differences in the effects on tumor and non-tumor cell lines provide a unique insight into the cytostatic action of molybdenum(ii) complexes.
Convenient preparation of diethyl (2-thienyl)methanephosphonate
Davis, Matthew C.
, p. 2079 - 2083 (2005)
This article describes a convenient preparation of diethyl (2-thienyl)methanephosphonate in 88% overall yield. Copyright Taylor & Francis, Inc.
Structure–Activity Studies of 3,9-Diazaspiro[5.5]undecane-Based γ-Aminobutyric Acid Type A Receptor Antagonists with Immunomodulatory Effect
Bavo, Francesco,de-Jong, Heleen,Petersen, Jonas,Falk-Petersen, Christina Birkedahl,L?ffler, Rebekka,Sparrow, Emma,Rostrup, Frederik,Eliasen, Jannik Nicklas,Wilhelmsen, Kristine S.,Barslund, Kasper,Bundgaard, Christoffer,Nielsen, Birgitte,Kristiansen, Uffe,Wellendorph, Petrine,Bogdanov, Yury,Fr?lund, Bente
, p. 17795 - 17812 (2022/01/03)
The 3,9-diazaspiro[5.5]undecane-based compounds 2027 and 018 have previously been reported to be potent competitive γ-aminobutyric acid type A receptor (GABAAR) antagonists showing low cellular membrane permeability. Given the emerging peripheral application of GABAAR ligands, we hypothesize 2027 analogs as promising lead structures for peripheral GABAAR inhibition. We herein report a study on the structural determinants of 2027 in order to suggest a potential binding mode as a basis for rational design. The study identified the importance of the spirocyclic benzamide, compensating for the conventional acidic moiety, for GABAAR ligands. The structurally simplified m-methylphenyl analog 1e displayed binding affinity in the high-nanomolar range (Ki = 180 nM) and was superior to 2027 and 018 regarding selectivity for the extrasynaptic α4βδ subtype versus the α1- and α2- containing subtypes. Importantly, 1e was shown to efficiently rescue inhibition of T cell proliferation, providing a platform to explore the immunomodulatory potential for this class of compounds.
Method for continuously synthesizing 2-chloromethylthiophene by using micro-channel reactor
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Paragraph 0034; 0037-0052, (2021/07/08)
The invention discloses a method for continuously synthesizing 2-chloromethylthiophene by using a micro-channel reactor. The micro-channel reactor comprises a premixing temperature control module and a reaction module, the premixing temperature control module and the reaction module are connected in series, and each of the premixing temperature control module and the reaction module is formed by connecting more than two units in series through reaction. The invention relates to the technical field of organic compound preparation. According to the method for continuously synthesizing 2-chloromethylthiophene by using a micro-channel reactor, one-step synthesis can be realized, the operation is simple, the production process is simplified, and the reaction time is about 60 seconds. The reaction time of a traditional kettle type reactor is more than 4 hours, the reaction temperature is about 20 DEG C, and the traditional kettle type reactor needs a low-temperature reaction (about -10 DEG C). The yield of the produced 2-chloromethylthiophene reaches about 80%, the selectivity reaches about 90%, by-products are reduced, the amount of three wastes is small, and the mass transfer and heat transfer performances of the reaction are enhanced.
