125812-44-4Relevant articles and documents
Gold-Catalyzed Aminoaromatizations of 1,2-Bis(alkynyl)benzenes with Anthranils to Yield 1-Amino-2-napthaldehyde Products
Pandit, Yashwant Bhaskar,Liu, Rai-Shung
, p. 3183 - 3189 (2020)
Gold-catalyzed aminoaromatizations of 1,n-diynes with anthranils afforded 1-amino-2-napthaldehyde derivatives efficiently. In this reaction sequence, anthranils preferably attack at gold-coordinated prop-3-yn-1-ols to generate α-imino gold carbenes that e
Substrate selectivity and its mechanistic insight of the photo-responsive non-nucleoside triphosphate for myosin and kinesin
Islam, Md. Jahirul,Matsuo, Kazuya,Menezes, Halley M.,Takahashi, Masayuki,Nakagawa, Hidehiko,Kakugo, Akira,Sada, Kazuki,Tamaoki, Nobuyuki
, p. 53 - 65 (2019)
Linear motor proteins including kinesin and myosin are promising biomaterials for developing nano-devices. Photoswitchable substrates of these biomotors can be used to optically regulate the motility of their associated cytoskeletal filaments in in vitro
Transformation of fluorinated 2-alkynylanilines by various catalytic systems
Politanskaya, Larisa,Petyuk, Maxim,Tretyakov, Evgeny
, (2019)
Simple and efficient approaches to the synthesis of fluorinated benzoazaheterocycles with good yields are reported. Firstly a series of polyfluorinated 2-alkynylanilines – the versatile building blocks – was synthesized by the Sonogashira reaction of o-iodoaniline with terminal alkynes. Then the transformations of the obtained 2,3,4-trifluo-6-alkynilanilines in the presence of KOH or PdCl2 in MeCN, and in the presence of monohydrate of p-toluenesulfonic acid (p-TSA?H2O) in MeOH, EtOH or benzene were investigated. It was found that Ph- and n-Bu-containing alkynylanilines by action of PdCl2 in MeCN underwent an intramolecular cyclization reaction to produce the corresponding indoles in high yields. The reaction of KOH with alkynes containing the tertiary alcohol function at the triple bond produced the unsubstituted on the pyrrole ring indole. It was found that fluorinated 2-alkynilanilines can be transformated into indoles, 2-arylketones and 2,3-dihydroquinolines by action of p-TSA?H2O in boiling alcohols, depending on the substituent at the triple bond. The use of benzene as a solvent in the reaction of p-TSA?H2O with polyfluorinated alkynes, bearing an alcohol group resulted in representative series of 2,3-dihydroquinolinones containing a substituents R1 and R2 in the 2nd position of their structure (R = H, H; Me, Me; H, i-Pr; H, Ph).
Metal-Free and syn-Selective Hydrohalogenation of Alkynes through a Pseudo-Intramolecular Process
Asahara, Haruyasu,Mukaijo, Yusuke,Muragishi, Kengo,Iwai, Kento,Ito, Akitaka,Nishiwaki, Nagatoshi
, p. 5747 - 5755 (2021/10/20)
A new metal-free hydrohalogenation method for alkynes has been developed, which proceeds through a pseudo-intramolecular process. In this reaction, ethynylaniline serves as a substrate to quantitatively form an anilinium salt upon treatment with hydrochloric acid. The spatial proximity facilitates the efficient electrophilic addition of HCl to the ethynyl group in syn-mode, affording the corresponding chloroalkene without overaddition. This protocol was applied to HBr and HI, and the corresponding bromo- and iodoalkenes were obtained, respectively. The obtained chloroalkene was converted to tri-substituted alkenes possessing different aryl/alkynyl groups through Pd-catalyzed cross-coupling reactions.
Bicyclobutane carboxylic amide as a cysteine-directed strained electrophile for selective targeting of proteins
Shindo, Naoya,Ojida, Akio,Tokunaga, Keisuke,Sato, Mami,Kuwata, Keiko,Miura, Chizuru,Fuchida, Hirokazu,Matsunaga, Naoya,Koyanagi, Satoru,Ohdo, Shigehiro
supporting information, p. 18522 - 18531 (2020/11/02)
Expanding the repertoire of electrophiles with unique reactivity features would facilitate the development of covalent inhibitors with desirable reactivity profiles. We herein introduce bicyclo[1.1.0]butane (BCB) carboxylic amide as a new class of thiol-reactive electrophiles for selective and irreversible inhibition of targeted proteins. We first streamlined the synthetic routes to generate a variety of BCB amides. The strain-driven nucleophilic addition to BCB amides proceeded chemoselectively with cysteine thiols under neutral aqueous conditions, the rate of which was significantly slower than that of acrylamide. This reactivity profile of BCB amide was successfully exploited to develop covalent ligands targeting Bruton's tyrosine kinase (BTK). By tuning BCB amide reactivity and optimizing its disposition on the ligand, we obtained a selective covalent inhibitor of BTK. The in-gel activitybased protein profiling and mass spectrometry-based chemical proteomics revealed that the selected BCB amide had a higher target selectivity for BTK in human cells than did a Michael acceptor probe. Further chemical proteomic study revealed that BTK probes bearing different classes of electrophiles exhibited distinct off-target profiles. This result suggests that incorporation of BCB amide as a cysteine-directed electrophile could expand the capability to develop covalent inhibitors with the desired proteome reactivity profile.
MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)
-
Page/Page column 76-77, (2020/01/08)
The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.
PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and efficient synthesis of N-acetyl-2-substituted indoles
Chaisan, Nattawadee,Kaewsri, Wilailak,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
supporting information, p. 675 - 680 (2018/01/18)
An efficient synthesis of N-acetyl-2-substituted indole derivatives via direct intramolecular hydroamination of N-acetyl-2-alkynylaniline derivatives was developed. The reaction could be applied to a wide range of substrates employing only 1–2 mol% of PtCl4 as the catalyst to furnish the desired indole products in moderate to excellent yields. The current protocol is efficient, reliable and scalable, and could serve as an important tool for convenient and rapid access to this important class of N-heterocyclic skeleton from readily available substrates.
Superacid-catalyzed tandem Meyer–Schuster rearrangement/intramolecular hydroamination of o-anilinopropargyl alcohols for the synthesis of 2,3-dihydro-4(1H)-quinolones
Sun, Guofeng,Cheng, Fengkai,Tao, Ruiheng,Sun, Yuxing,Pan, Jinpeng,Zhu, Yaohua,Wang, Zhonghua,Wu, Fanhong,Yin, Yan
supporting information, p. 1249 - 1256 (2016/08/16)
A TfOH-catalyzed synthesis of 2,3-dihydro-4(1H)-quinolones from o-anilinopropargyl alcohols was developed. Studies of N-protecting groups and substituents in phenyl rings showed that diverse groups could be applied. By controlling the catalyst loading, o-anilinopropargyl alcohols underwent the expected transformation smoothly to produce N-protected or N-deprotected 2,3-dihydro-4 (1H)-quinolones in good yields. This transformation probably involved a tandem Meyer–Schuster rearrangement/intramolecular hydroamination reaction process.
Catalytic Enantioselective Synthesis of Amino Skipped Diynes
Paioti, Paulo H. S.,Abboud, Khalil A.,Aponick, Aaron
supporting information, p. 2150 - 2153 (2016/03/05)
The Cu-catalyzed synthesis of nonracemic 3-amino skipped diynes via an enantiodetermining C-C bond formation is described using StackPhos as ligand. Despite challenging issues of reactivity and stereoselectivity inherent to these chiral skipped diynes, the reaction tolerates an extremely broad substrate scope with respect to all components and provides the title compounds in excellent enantiomeric excess. The alkyne moieties are demonstrated here to be useful synthetic handles, and 3-amino skipped diynes are convenient building blocks for enantioselective synthesis.
A robust, well-defined homogeneous silver(I) catalyst for mild intramolecular hydroamination of 2-ethynylanilines leading to indoles
McNulty, James,Keskar, Kunal
, p. 1622 - 1629 (2014/03/21)
A highly efficient, chemically stable and well-defined homogeneous silver(I) catalyst is reported for the room temperature, intramolecular hydroamination of 2-alkynylanilines leading to indole derivatives. Copyright
