229174-43-0Relevant articles and documents
Acetylenic Replacement of Albicidin's Methacrylamide Residue Circumvents Detrimental E/Z Photoisomerization and Preserves Antibacterial Activity
Behroz, Iraj,Kleebauer, Leonardo,Hommernick, Kay,Seidel, Maria,Gr?tz, Stefan,Mainz, Andi,Weston, John B.,Süssmuth, Roderich D.
, p. 9077 - 9086 (2021/05/27)
The natural product albicidin is a highly potent inhibitor of bacterial DNA gyrase. Its outstanding activity, particularly against Gram-negative pathogens, qualifies it as a promising lead structure in the search for new antibacterial drugs. However, as we show here, the N-terminal cinnamoyl moiety of albicidin is susceptible to photochemical E/Z isomerization. Moreover, the newly formed Z isomer exhibits significantly reduced antibacterial activity, which hampers the development and biological evaluation of albicidin and potent derivatives thereof. Hence, we synthesized 13 different variants of albicidin in which the vulnerable para-coumaric acid moiety was replaced; this yielded photostable analogues. Biological activity assays revealed that diaryl alkyne analogues exhibited virtually undiminished antibacterial efficacy. This promising scaffold will therefore serve as a blueprint for the design of a potent albicidin-based drug.
Unsymmetric bifunctional carborane derivatives, and preparation method and application thereof
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Paragraph 0016; 0054-0060, (2019/03/24)
The invention relates to the fields of anti-tumor and polymer materials, in particular to unsymmetric bifunctional carborane derivatives, and a preparation method and application thereof. The carborane derivatives are a series of carborane derivatives con
The Direct Conversion of α-Hydroxyketones to Alkynes
Ghiringhelli, Francesca,Nattmann, Lukas,Bognar, Sabine,Van Gemmeren, Manuel
, p. 983 - 993 (2019/01/24)
Alkynes are highly important functional groups in organic chemistry, both as part of target structures and as versatile synthetic intermediates. In this study, a protocol for the direct conversion of α-hydroxyketones to alkynes is reported. In combination with the variety of synthetic methods that generate the required starting materials by forming the central C-C bond, it enables a highly versatile fragment coupling approach toward alkynes. A broad scope for this novel transformation is shown alongside mechanistic insights. Furthermore, the utility of our protocol is demonstrated through its application in concert with varied α-hydroxyketone syntheses, giving access to a broad spectrum of alkynes.
Synthesis of Internal Alkynes through an Effective Tandem Elimination-Hydrodebromination-Cross-Coupling of gem-Dibromoalkenes with Halobenzenes
Ji, Yuan,Zhong, Ning,Kang, Zinan,Yan, Guobing,Zhao, Ming
supporting information, p. 209 - 214 (2018/03/26)
Carbon-carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C-C cross-coupling reaction of two kinds of organic halide, a gem -dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination-hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction proceeded under simple, facile, and classic copper-free Sonogashira coupling reaction conditions in good to excellent yields.
Intermolecular Desymmetrizing Gold-Catalyzed Yne–Yne Reaction of Push–Pull Diarylalkynes
Weingand, Vanessa,Wurm, Thomas,Vethacke, Vanessa,Dietl, Martin C.,Ehjeij, Daniel,Rudolph, Matthias,Rominger, Frank,Xie, Jin,Hashmi, A. Stephen K.
supporting information, p. 3725 - 3728 (2018/02/23)
Push–pull diaryl alkynes are dimerized in the presence of a cationic gold catalyst. The polarized structure of the applied starting materials enables the generation of a highly reactive vinyl cation intermediate in an intermolecular reaction. Trapping of the vinyl cation by a nucleophilic attack of the electron-poor aryl unit then leads to the selective formation of highly substituted naphthalenes in a single step and in complete atom economy.
Immobilization of copper complexes with (1,10-phenanthrolinyl)phosphonates on titania supports for sustainable catalysis
Mitrofanov, Alexander,Brandès, Stéphane,Herbst, Frédéric,Rigolet, Séverinne,Bessmertnykh-Lemeune, Alla,Beletskaya, Irina
, p. 12216 - 12235 (2017/07/11)
Different strategies for the immobilization of copper complexes with 1,10-phenanthroline (phen) using the phosphonate anchoring group were investigated to prepare robust and porous heterogeneous catalysts. Homoleptic and heteroleptic copper(i) complexes with phen bearing the bis(trimethylsiloxy)phosphoryl anchoring group (Pphen-Si) at different positions of the phen backbone were prepared and covalently incorporated into titania (TiO2) xerogels by using the sol-gel process or grafted onto the surface of mesoporous TiO2 (SBET = 650 m2 g-1). Copper(i) bis(Pphen-Si) complexes were the only complexes that were successfully anchored onto the TiO2 surface because the heterogenization was often accompanied by the undesirable dissociation of copper complexes. Hybrid materials based on copper(i) chelates with one phen ligand were obtained following a two-step procedure involving the immobilization of Pphen-Si chelators and their successive complexation with copper(i) ions. Porous material, Cu/6b/SM/A, displaying a BET surface area of 243 m2 g-1 and bearing 0.57 mmol g-1 of the complex was synthesized according to this approach. Excellent catalytic performance of the reusable Cu/6b/SM/A material in the Sonogashira-type coupling and the Huisgen 1,3-dipolar cycloaddition was also demonstrated. This solid represents the first example of mesoporous TiO2-supported transition metal catalysts.
Method for synthesizing interior alkyne from 1,1-dibromo-1-olefin compounds and halogenated benzene derivative
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Paragraph 0061; 0062; 0063, (2017/08/24)
The invention discloses a method for synthesizing an interior alkyne compound by taking 1,1-dibromo-1-olefin compounds and a halogenated benzene derivative as raw materials, and performing elimination-crossed coupling reaction under action of alkali and a palladium catalyst. The interior alkyne compound is a very important chemical raw material and an intermediate, and widely exists in natural compounds, medicine molecules, biological active substances and organic functional materials. The method has the advantages of being low in raw material cost, high in reaction yield, simple to operate, capable of recycling the catalyst and the like, and has a very good application prospect.
One-pot synthesis of unsymmetrical diarylacetylenes via Sonogashira/deacetonation/Sonogashira cross-coupling of two different aryl chlorides with 2-methyl-3-butyn-2-ol
Xu, Kai,Sun, Suyan,Zhang, Guodong,Yang, Fan,Wu, Yangjie
, p. 32643 - 32646 (2014/08/18)
With the assistance of PdCl2/X-Phos as the catalyst system, a green and efficient protocol for one-pot Sonogashira/Deacetonation/Sonogashira coupling reaction of two different aryl chlorides with 2-methyl-3-butyn-2-ol was developed, affording various unsymmetrical diarylacetylenes in mostly moderate to excellent yields. Note that the cheap and economically available aryl chlorides and 2-methyl-3-butyn-2-ol as the starting materials could be added to the catalyst system directly and simultaneously. Moreover, this tandem reaction could tolerate substrates bearing one or even two ortho-sterically hindered groups and was also applicable to the synthesis of symmetrical diarylacetylenes. In addition, the competitive reaction was performed and a possible mechanism was also proposed. This journal is the Partner Organisations 2014.
Iron-catalyzed oxidative coupling of terminal alkynes with arylboronic acids
You, Xiu L.,Xu, Lai,Hu, Tao
experimental part, p. 300 - 304 (2012/07/14)
Abstract: Iron-catalyzed cross-coupling of terminal alkynes with arylboronic acids under mild conditions has been developed. Although the reaction gave only moderate yields, the advantage of this method was its use of convenient and inexpensive iron catal
