- Caged glutamates with π-extended 1,2-dihydronaphthalene chromophore: Design, synthesis, two-photon absorption property, and photochemical reactivity
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Caging and photochemical uncaging of the excitatory neurotransmitter l-glutamate (glu) offers a potentially valuable tool for understanding the mechanisms of neuronal processes. Designing water-soluble caged glutamates with the appropriate two-photon absorption property is an attractive strategy to achieve this. This paper describes the design, synthesis, and photochemical reactivity of caged glutamates with π-extended 1,2-dihydronaphthalene structures, which possess a two-photon cross-section of ~120 GM and an excellent buffer solubility (up to 115 mM). High yields up to 99% glutamate were observed in the photolysis of two caged glutamates. Suzuki-Miyaura cross-coupling and Buchwald-Hartwig amination were used as the key reactions to synthesize the caged compounds.
- Boinapally, Srikanth,Huang, Bo,Abe, Manabu,Katan, Claudine,Noguchi, Jun,Watanabe, Satoshi,Kasai, Haruo,Xue, Bing,Kobayashi, Takayoshi
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Read Online
- Conformational Change of Self-Assembled DNA Nanotubes Induced by Two-Photon Excitation
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Two-photon-regulated, shape-changing DNA nanostructures are demonstrated by integrating a DNA nanotube with a two-photon photocleavable module that enables the opening of the cavities of tube, and becomes partially single-stranded in response to two-photo
- Dai, Ziwen,Tam, Dick Yan,Xu, Hailiang,Chan, Miu Shan,Liu, Ling Sum,Bolze, Frédéric,Sun, Xiao Hua,Lo, Pik Kwan
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Read Online
- Palladium-Catalyzed Regioselective Syn-Chloropalladation-Olefin Insertion-Oxidative Chlorination Cascade: Synthesis of Dichlorinated Tetrahydroquinolines
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A palladium catalyzed cascade process involving syn-chloropalladation, intramolecular olefin insertion, and oxidative C-Cl bond formation reactions was demonstrated for the synthesis of dichlorinated tetrahydroquinolines in high yields (up to 93%). The N-propargyl arylamines having a tethered α,β-unsaturated carbonyl moiety underwent a regioselective syn-chloropalladation followed by a Heck-type reaction to deliver the tetrahydroquinoline scaffold. The rare insertion of the second chlorine atom was rationalized comprising a PdII/IV catalytic cycle and oxidative cleavage of the C-PdII bond.
- Vinoth, Perumal,Karuppasamy, Muthu,Vachan,Muthukrishnan, Isravel,Maheswari, C. Uma,Nagarajan, Subbiah,Pace, Vittorio,Roller, Alexander,Bhuvanesh, Nattamai,Sridharan, Vellaisamy
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supporting information
(2019/05/08)
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- Direct Access to 9-Chloro-1 H-benzo[ b]furo[3,4- e]azepin-1-ones via Palladium(II)-Catalyzed Intramolecular syn-Oxypalladation/Olefin Insertion/sp2-C-H Bond Activation Cascade
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An efficient Pd(II)-catalyzed cascade approach was established for the synthesis of 9-chloro-1H-benzo[b]furo[3,4-e]azepin-1-ones starting from N-propargyl arylamines having a pendant α,β-unsaturated ester scaffold. The mechanism of this sequential process involved intramolecular syn-oxypalladation followed by olefin insertion and ortho sp2-C-Cl bond formation reactions. This high atom- and step-economical cascade sequence generated two heterocycle rings and three new bonds in a single synthetic operation.
- Karuppasamy, Muthu,Vachan,Vinoth, Perumal,Muthukrishnan, Isravel,Nagarajan, Subbiah,Ielo, Laura,Pace, Vittorio,Banik, Subrata,Maheswari, C. Uma,Sridharan, Vellaisamy
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supporting information
p. 5784 - 5788
(2019/08/26)
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- HETEROCYCLIC COMPOUNDS AS INHIBITORS OF RAS AND METHODS OF USE THEREOF
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Compounds having activity as inhibitors of G12C mutant KRAS protein are provided. The compounds have the following structure (I): or a pharmaceutically acceptable salt, stereoisomer or prodrug thereof, wherein A, B, R", Q, W, X, Y, Z, n1, n2and '--" are as defined herein. Methods associated with preparation and use of such compounds, pharmaceutical compositions comprising such compounds and methods to modulate the activity of G12C mutant KRAS protein for treatment of disorders, such as cancer, are also disclosed.
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Page/Page column 154; 156; 157
(2018/04/21)
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- FUSED QUADRACYCLIC COMPOUNDS, COMPOSITIONS AND USES THEREOF
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Provided herein are substituted fused quadracyclic compounds useful as inhibitors of MK2. The invention further provides pharmaceutical compositions of the compounds of the invention. The invention also provides medical uses of substituted fused quadracyclic compounds.
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- Co-delivery system of photo-responsive chemotherapeutic drug and preparation method thereof
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The invention discloses a co-delivery system of a photo-responsive chemotherapeutic drug and a preparation method thereof. A prodrug is prepared through covalent linkage of a double branched type photosensitive carrier with o-nitrobenzyl as a structural u
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- A double branched photosensitive prodrug: Synthesis and characterization of light triggered drug release
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A novel oNB based, double branched photosensitive prodrug 1, and a biphenyl counterpart 2 were designed and synthesized. Their photo-triggered drug release properties were studied by HPLC and UV-vis spectra. The isobestic points in UV-vis spectra of prodr
- Liu, Wei,Liang, Li,Lo, Pik Kwan,Gou, Xiao Jun,Sun, Xiao Hua
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p. 959 - 963
(2016/02/05)
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- Decoupling fluorescence and photochromism in bifunctional azo derivatives for bulk emissive structures
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Bifunctional molecules that combine independent push-pull fluorophores and azo photochromes have been synthesized to create fluorescent structures upon light-induced migration in neat thin films. Their photochromic and emissive properties have been systematically investigated and interpreted in light of those of the corresponding model compounds. Fluorescence lifetimes and photoisomerization and fluorescence quantum yields have been determined in toluene solution. Kinetic analyses of the femtosecond transient absorption spectra reveal that the fluorophores evolve in a few picoseconds into a distorted intramolecular charge-transfer excited state, strongly stabilized in energy. Radiative relaxation to the ground state occurred competitively with the energy-transfer process to the azo moiety. Introduction of a 10 A-long rigid and nonconjugated bridge between the photoactive units efficiently inhibits the energy transfer while it imparts enhanced free volume, which favors photoactivated molecular migration in the solid state. Copyright
- Jacquart, Aurelie,Williams, Rene M.,Brouwer, Albert M.,Ishow, Elena
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scheme or table
p. 3706 - 3720
(2012/05/04)
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- Tunable emissive thin films through ICT photodisruption of nitro-substituted triarylamines
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UV-assisted photocleavage in the solid state of orange emitting nitro-substituted triarylamines leads to the appearance of blue emission following photodisruption of the ICT state.
- Jacquart, Aurelie,Tauc, Patrick,Pansu, Robert B.,Ishow, Elena
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supporting information; experimental part
p. 4360 - 4362
(2010/08/22)
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