133642-20-3Relevant articles and documents
Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs
Barrow, Andrew S.,Cheng, Yunfei,Gialelis, Timothy L.,Giel, Marie-Claire,Kitamura, Seiya,Li, Gencheng,Moses, John E.,Ottonello, Alessandra,Sharpless, K. Barry,Smedley, Christopher J.,Wolan, Dennis W.
supporting information, p. 12460 - 12469 (2020/06/10)
Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease”, by combining classic C?C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels–Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates—demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.
Thieme Chemistry Journals Awardees - Where Are They Now? Bis(2-pyridyl)amides as Readily Cleavable Amides under Catalytic, Neutral, and Room-Temperature Conditions
Adachi, Shinya,Kumagai, Naoya,Shibasaki, Masakatsu
supporting information, p. 301 - 305 (2018/02/10)
Mild solvolytic cleavage of bis(2-pyridyl)amide under neutral and room-temperature conditions is described. The inherently stable amide was readily activated by catalytic amounts of metal cations to react with alcohols. Based on X-ray crystallographic analysis, the primary driving force was considered to be amide distortion induced by the metal coordination of two pyridyl groups in a bidentate fashion without affecting the amide functionality. The compatibility of the acid/base-sensitive functionalities and the absence of racemization during solvolysis highlight the mildness of the present protocol.
NOVEL COMPOUND HAVING ISOXAZOLE CORE AND PHARMACEUTICAL COMPOSITION FOR DIABETES CONTAINING THE SAME MOLECULAR SKELETONS
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Paragraph 0120-0123, (2017/08/02)
The purpose of the present invention is to provide novel compounds having isoxazole by central structure as a PPAR gamma selective ligand, a manufacturing method thereof, and a pharmaceutical composition for treating PPAR gamma-related diseases containing the novel compounds or pharmaceutically acceptable salt thereof. The compounds can be applied to treatment of PPAR gamma-related diseases, especially, diabetes as an effective medicine without side effects which an existing TZD-series diabetes medicine has.
Indazole-oxadiazole derivative, medicinal composition containing derivative, and application of derivative in tumor prevention
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Paragraph 0245; 0246; 0247; 0248, (2017/07/25)
The invention discloses an indazole-oxadiazole derivative with the structure represented by general formula a shown in the description, or a pharmaceutically acceptable salt or solvate thereof. In the formula, X is O or N, Y is N, Z is N or O, and all groups are as defined in the description. The invention also discloses a medicinal composition adopting the derivative as an active component, and a use of the derivative. Compounds synthesized in the invention have an HIF-1 inhibition effect, and most of the compounds have a substantial HIF-1 inhibition effect, have strong in-vivo and in-vitro anti-HIF-1 effect on human colorectal carcinoma cell strains (HCT116) and other tumor cell strains, and can be used for treating tumor diseases.
Synthesis, electrochemistry and anticancer activity of novel ferrocenyl phenols prepared via azide-alkyne 1,3-cycloaddition reaction
Plazuk, Damian,Rychlik, B?azej,B?auz, Andrzej,Domaga?a, S?awomir
scheme or table, p. 102 - 112 (2012/09/07)
A series of monophenols and diphenols containing the ferrocene-C triazolyl and ferrocene-Ntriazolyl bond were prepared in a cycloaddition reaction of ethynylferrocene with aryl and benzyl azides and in a reaction of azidoferrocene with phenylacetylenes, respectively. The anticancer activity of the prepared compounds against hormone-dependent (MCF-7) and hormone-independent (HCC38) breast cancer cell lines was studied. The investigated compounds exhibited moderate anticancer activity against hormone-independent (IC50 ～ 15-48 μM) cancer cell line and low activity against hormone-dependent cancer cell line (IC50 ～ 84-98 μM).
Microwave-assisted protection of phenols as tert-butyldimethylsilyl (TBDMS) ethers under solvent-free conditions
Bastos, Erick L.,Ciscato, Luiz F. M. L.,Baader, Wilhelm J.
, p. 1501 - 1509 (2007/10/03)
A facile, time-saving procedure to protect phenols with tert-butyldimethylsilyl chloride using imidazole as catalyst under solvent-free conditions is described. Several phenolic compounds with different substitution patterns can be silylated in high yield
Mercury(II)-Catalyzed Synthesis of Spiro[4.5]decatrienediones from Allenyl Ketones and Comparison with Silver(I)-, Palladium(II)- and Bronsted Acid-Catalyzed Reactions
Hashmi, A. Stephen K.,Schwarz, Lothar,Bats
, p. 40 - 51 (2007/10/03)
The allenyl p-methoxybenzyl ketone 3a and allenyl p-siloxybenzyl ketones 6b selectively delivered three different products with three different transition metal-catalysts. With Hg(II)-catalysts a spiro[4.5]decene 9, with Ag(I)-catalysts a 2-substituted furan (10/11) and with Pd(II)-catalysts a 2,4-disubstituted furan (8/12) was formed. Only with perchloric acid the intermolecular addition of water to the allene, leading to 1,3-dicarbonyl compounds 7, was observed. While with the corresponding allenyl o-methoxybenzyl ketone 3b the Ag(I)- and Pd(II)-catalysts provided the expected products, the mercury-catalyst led to a new and interesting side-product rac-17 which combined both the furan moiety and the spiro[4.5]decene moiety. Efforts to prepare allenyl hydroxybenzyl ketones failed, in one case a small amount of a 5H-benzo[b]oxepin-4-one 21 was isolated. It also was not possible to extend the spirocyclization to allenyl p-siloxyphenyl ketone 6a or allenyl 2-(p-siloxyphenyl)ethyl ketone 6c.
A Short and Facile Synthetic Route to Hydroxylated Flavones. New Syntheses of Apigenin, Tricin, and Luteolin
Nagarathnam, Dhanapalan,Cushman, Mark
, p. 4884 - 4887 (2007/10/02)
Reaction of lithium polyanions generated from o-hydroxyacetophenones 3a-f with O-silyloxylated benzoates 2a-d gave 1-aryl-3-(2-hydroxyphenyl)-1,3-propanediones 4a-n, which on treatment with acetic acid containing 0.5percent H2SO4 at 95 - 100 deg C afforded hydroxylated flavones 5-18 in high yields (76 - 92percent).
