38768-08-0Relevant articles and documents
Synthesis and conformational analysis of new troponyl aromatic amino acid
Balachandra, Chenikkayala,Sharma, Nagendra K.
, p. 7464 - 7469 (2014)
Synthetic peptides are in huge demand in expansion of potential peptide mimics, which may have improved or comparable function as natural one. With these concerns, phenyl bearing aromatic amino acids and peptides has extensively explored, because phenyl r
Azulene-Derived Fluorescent Probe for Bioimaging: Detection of Reactive Oxygen and Nitrogen Species by Two-Photon Microscopy
Murfin, Lloyd C.,Weber, Maria,Park, Sang Jun,Kim, Won Tae,Lopez-Alled, Carlos M.,McMullin, Claire L.,Pradaux-Caggiano, Fabienne,Lyall, Catherine L.,Kociok-K?hn, Gabriele,Wenk, Jannis,Bull, Steven D.,Yoon, Juyoung,Kim, Hwan Myung,James, Tony D.,Lewis, Simon E.
, p. 19389 - 19396 (2019)
Two-photon fluorescence microscopy has become an indispensable technique for cellular imaging. Whereas most two-photon fluorescent probes rely on well-known fluorophores, here we report a new fluorophore for bioimaging, namely azulene. A chemodosimeter, c
Radical and Ionic Reactions of Indolizin-1-ols: Synthesis of 3-Arylsulfanyl-, 3-(Tropon-2-yl)- And 3-(Tropolon-5-ylazo)-1-hydroxyindolizines from 3,3-Difluorocyclopropenes
Cherkaev, Georgij V.,Nechaev, Ilya V.
, p. 7687 - 7700 (2021)
An aerobic multicomponent reaction between monoalkyl-3,3-difluorocyclopropenes, pyridines, and arylthiols has been discovered to afford 3-arylsulfanyl-1-hydroxyindolizines. This reaction proceeds via intermediate C3-free indolizin-1-ols, easily forming free radicals in air. In the presence of arylthiols, potent radical traps, incorporation of arylsulfanyl substituent occurs at the C3 position of indolizin-1-ols by radical recombination. On the contrary, in an inert atmosphere, intermediate 1-hydroxyindolizines react with C- and N-electrophiles in a one-pot fashion. Novel, intensively colored 3-(tropon-2-yl)-indolizin-1-ols and high absorption coefficient 3-(tropolon-5-ylazo)-indolizin-1-ol dyes were synthesized in a multicomponent manner in 50-80% yields. The presence of an O-uncapped indolizin-1-ol moiety modulates the redox properties of the whole molecule, facilitating free radical formation, which is susceptible to further transformations. Three such examples were demonstrated: oxidative recyclization of 3-(2-hydroxyphenylsulfanyl)-indolizin-1-ol, auto-oxidation of substituted 3,3′-biindolizine-1,1′-diol, and diacetoxyiodobenzene (DAIB)-mediated dehydrogenation of 3-(tropolon-5-ylazo)-indolizin-1-ol. The latter reaction affords 3-((4,5-dioxocyclohepta-2,6-dien-1-ylidene)hydrazono)-3H-indolizin-4-ium-1-olate, a mesomeric betaine, strongly absorbing light on the borders of the visible range and showing a solvatochromic effect.
Structural Biology-Guided Design, Synthesis, and Biological Evaluation of Novel Insect Nicotinic Acetylcholine Receptor Orthosteric Modulators
Benfatti, Fides,Elias, Jan,Montgomery, Mark,Pitterna, Thomas,Rendine, Stefano,Skaljac, Marisa,Zimmer, Christoph T.,Bigot, Aurélien,Schaetzer, Jürgen
, (2022/01/20)
The development of novel and safe insecticides remains an important need for a growing world population to protect crops and animal and human health. New chemotypes modulating the insect nicotinic acetylcholine receptors have been recently brought to the agricultural market, yet with limited understanding of their molecular interactions at their target receptor. Herein, we disclose the first crystal structures of these insecticides, namely, sulfoxaflor, flupyradifurone, triflumezopyrim, flupyrimin, and the experimental compound, dicloromezotiaz, in a double-mutated acetylcholine-binding protein which mimics the insect-ion-channel orthosteric site. Enabled by these findings, we discovered novel pharmacophores with a related mode of action, and we describe herein their design, synthesis, and biological evaluation.
Syntheses and properties of linear π-conjugated molecules composed of 1-azaazulene and azulene
Ohtsu, Keito,Hayami, Ryohei,Sagawa, Takuya,Tsukada, Satoru,Yamamoto, Kazuki,Gunji, Takahiro
supporting information, (2019/10/14)
Two compounds, 6-(1-azaazulen-2-yl)ethynylazulene (8) and 6-(2-azulenyl)ethynylazulene (10), were synthesized using the Sonogashira-Hagihara cross-coupling reaction followed by decarboxylation with concentrated phosphoric acid. Compounds 8 and 10 were cha