103606-72-0Relevant articles and documents
Synthesis of biaryls using nickel-catalyzed [2+2+2] cocyclization
Sato, Yoshihiro,Ohashi, Kenji,Mori, Miwako
, p. 5231 - 5234 (1999)
Methods of synthesizing biaryls using nickel-catalyzed [2+2+2] cocyclization were developed. Two ways for the synthesis of biaryl using [2+2+2] cocyclization were investigated: one method is that biaryls synthesized from alkyne having a phenyl group and 2
Identification of small molecules blocking the pseudomonas aeruginosa type iii secretion system protein pcrv
Sundin, Charlotta,Saleeb, Michael,Spjut, Sara,Qin, Liena,Elofsson, Mikael
, p. 1 - 17 (2021/01/13)
Pseudomonas aeruginosa is an opportunistic bacterial pathogen that employs its type III secretion system (T3SS) during the acute phase of infection to translocate cytotoxins into the host cell cytoplasm to evade the immune system. The PcrV protein is located at the tip of the T3SS, facilitates the integration of pore-forming proteins into the eukaryotic cell membrane, and is required for translocation of cytotoxins into the host cell. In this study, we used surface plasmon resonance screening to identify small molecule binders of PcrV. A follow-up structure-activity relationship analysis resulted in PcrV binders that protect macrophages in a P. aeruginosa cell-based infection assay. Treatment of P. aeruginosa infections is challenging due to acquired, intrinsic, and adaptive resistance in addition to a broad arsenal of virulence systems such as the T3SS. Virulence blocking molecules targeting PcrV constitute valuable starting points for development of next generation antibacterials to treat infections caused by P. aeruginosa.
Enantioselective Lactonization by π-Acid-Catalyzed Allylic Substitution: A Complement to π-Allylmetal Chemistry
Aponick, Aaron,Kizhakkayil Mangadan, Arun Raj,Liu, Ji
supporting information, p. 22224 - 22229 (2021/09/09)
Asymmetric allylic alkylation (AAA) is a powerful method for the formation of highly useful, non-racemic allylic compounds. Here we present a complementary enantioselective process that generates allylic lactones via π-acid catalysis. More specifically, a
Umpolung Strategy for Arene C?H Etherification Leading to Functionalized Chromanes Enabled by I(III) N-Ligated Hypervalent Iodine Reagents
Mikhael, Myriam,Guo, Wentao,Tantillo, Dean J.,Wengryniuk, Sarah E.
, p. 4867 - 4875 (2021/09/14)
The direct formation of aryl C?O bonds via the intramolecular dehydrogenative coupling of a C?H bond and a pendant alcohol represents a powerful synthetic transformation. Herein, we report a method for intramolecular arene C?H etherification via an umpoled alcohol cyclization mediated by an I(III) N-HVI reagent. This approach provides access to functionalized chromane scaffolds from primary, secondary and tertiary alcohols via a cascade cyclization-iodonium salt formation, the latter providing a versatile functional handle for downstream derivatization. Computational studies support initial formation of an umpoled O-intermediate via I(III) ligand exchange, followed by competitive direct and spirocyclization/1,2-shift pathways. (Figure presented.).
Metal-Free Synthesis of 4-Chloroisocoumarins by TMSCl-Catalyzed NCS-Induced Chlorinative Annulation of 2-Alkynylaryloate Esters
Norseeda, Krissada,Chaisan, Nattawadee,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
, p. 16222 - 16236 (2019/12/25)
4-Chloroisocoumarins can be conveniently prepared from 2-alkynylaryloate esters via the activation of alkynes by electrophilic chlorine, generated in situ from N-chlorosuccinimide (NCS) in the presence of 10 mol % trimethylsilyl chloride (TMSCl), which leads to 6-endo-dig-selective chlorinative annulation to give the desired products in moderate to quantitative yields. The procedure employs readily available reagents and can be conveniently carried out on a wide scope of substrates under mild conditions (0 °C to rt). Furthermore, the reaction is scalable for gram-scale preparation of 4-chloroisocoumarins. Additionally, 4-bromo- and 4-iodoisocoumarins can be prepared in moderate to good yields by replacing NCS with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS), respectively.
Metal-Free Regioselective Chloroazidation of Internal Alkynes
Huang, Bin,Liffert, Raphael,Linden, Anthony,Gademann, Karl
supporting information, p. 981 - 984 (2019/01/04)
A metal-free, room temperature protocol for the regioselective chloroazidation of internal alkynes is disclosed. The reactions of internal alkynes with trimethylsilyl azide (TMSN3) in the presence of 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) afforded the corresponding chloroazidoalkenes in good yields. This reaction has good functional group tolerance and is operationally simple.
Comparison between Conventional and Nonconventional Methods for the Synthesis of Some 2-Oxazolidinone Derivatives and Preliminary Investigation of Their Inhibitory Activity Against Certain Protein Kinases
Ziane,Mazari,Safer,Sad El Hachemi Amar,Ruchaud,Baratte,Bach
, p. 1061 - 1069 (2019/09/06)
A series of propargyl and allyl carbamates were prepared directly from propargyl and allyl alcohols and phenyl or cyclohexyl isocyanate or indirectly by generating the isocyanates in situ from the corresponding Cbz-protected amines. The obtained carbamate
Catalytic Dehydrative Lactonization of Allylic Alcohols
Liu, Ji,Miotto, Romain J.,Segard, Julien,Erb, Ashley M.,Aponick, Aaron
supporting information, p. 3034 - 3038 (2018/05/28)
A convenient strategy for the synthesis of phthalides and ?-butyrolactones is reported. The method utilizes readily prepared allylic alcohols in formal Au(I)- and Pd(II)-catalyzed SN2′ reactions. Using these catalysts, exclusive formation of the desired five-membered lactones is observed, completely avoiding the competing direct lactonization pathway that forms the undesired seven-membered ring with protic acids and alternative metal salts. This mild and operationally simple method notably tolerates exomethylene groups and should find use in both phthalide and terpene syntheses.
Design and synthesis of novel xanthine derivatives as potent and selective A2B adenosine receptor antagonists for the treatment of chronic inflammatory airway diseases
Basu, Sujay,Barawkar, Dinesh A.,Ramdas, Vidya,Patel, Meena,Waman, Yogesh,Panmand, Anil,Kumar, Santosh,Thorat, Sachin,Naykodi, Minakshi,Goswami, Arnab,Reddy, B. Srinivasa,Prasad, Vandna,Chaturvedi, Sandhya,Quraishi, Azfar,Menon, Suraj,Paliwal, Shalini,Kulkarni, Abhay,Karande, Vikas,Ghosh, Indraneel,Mustafa, Syed,De, Siddhartha,Jain, Vaibhav,Banerjee, Ena Ray,Rouduri, Sreekanth R.,Palle, Venkata P.,Chugh, Anita,Mookhtiar, Kasim A.
, p. 218 - 229 (2017/04/19)
Adenosine induces bronchial hyperresponsiveness and inflammation in asthmatics through activation of A2B adenosine receptor (A2BAdoR). Selective antagonists have been shown to attenuate airway reactivity and improve inflammatory cond
γ-Lactone Synthesis via Palladium(II)-Catalyzed Lactonization of Unactivated Methylene C(sp3)-H Bonds
Liu, Bin,Shi, Bing-Feng
supporting information, p. 2396 - 2400 (2016/09/28)
A palladium(II)-catalyzed intramolecular lactonization of unactivated methylene C(sp3)-H bonds using PIP bidentate auxiliary is described. This method provides an efficient and concise pathway to synthesize functionalized γ-lactones.