118-48-9Relevant articles and documents
Tryptanthrin from indigo: Synthesis, excited state deactivation routes and efficient singlet oxygen sensitization
Pinheiro, Daniela,Pineiro, Marta,Pina, Jo?o,Brand?o, Pedro,Galv?o, Adelino M.,Seixas de Melo, J. Sérgio
, (2020)
The microwave-assisted synthesis of tryptanthrin from indigo in mild oxidation conditions, and a comprehensive study of the excited state properties of this compound in a variety of solvents with different polarity and viscosity values at room and low temperatures are reported. In contrast with indigo, emission of the triplet state of tryptanthrin is observed with a very efficient singlet oxygen sensitization quantum yield, indicating that the triplet state is efficiently populated. From time-resolved fluorescence and femtosecond transient absorption data, further supported with time-dependent density functional theory (TDDFT) calculations, two species, with S1 states with locally excited (LE) of π,π* nature and a charge transfer (CT) of n,π* characteristics, originated from an initially populated Frank-Condon S2 state (π,π*), are observed. The two electronically independent species are energetically nearly degenerate and inter-conversion is predicted (and rate constants determined) to occur between LE (S1) and CT (S1) species. Due to the low value of the fluorescence quantum yield (~10?3) and high triplet state yield (?T≥?Δ), the high stability of this compound is associated to the high efficiency of the radiationless deactivation processes which involve the formation of the CT state which efficiently converts, through S1 ~~> Tn intersystem crossing, to the T1 triplet state.
Synthesis, structure, and properties of N-(nitramino)phthalimide
Klenov,Churakov,Anikin,Strelenko,Fedyanin,Lyssenko,Tartakovsky
, p. 638 - 643 (2008)
N-(Nitramino)phthalimide R2N-NHNO2 (R2NH is phthalimide) was synthesized by nitration of N-aminophthalimide with nitronium tetrafluoroborate. The structure of this compound was established by X-ray diffraction and confirmed by 1H, 13C, and 14N NMR spectroscopy. The methylation of this compound with diazomethane affords a mixture of N-methyl (R2N-NMeNO2) and O-methyl (R2N-N=N(O)OMe) isomers. The latter compound contains the previously unknown high-nitrogen-oxygen fragment. The thermal decomposition of N-(nitramino)phthalimide in vacuo at 80-100 °C gives 2H-3,1-benzoxazine- 2,4(1H)-dione (isatoic anhydride) as the major product.
Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: Preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives
Jentsch, Nicholas G.,Hume, Jared D.,Crull, Emily B.,Beauti, Samer M.,Pham, Amy H.,Pigza, Julie A.,Kessl, Jacques J.,Donahue, Matthew G.
, p. 2529 - 2536 (2018)
A convenient two-step synthesis of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate derivatives has been developed starting from commercially available 2-aminobenzoic acids. In step 1, the anthranilic acids are smoothly converted to isatoic anhydrides using solid triphosgene in THF. In step 2, the anhydride electrophiles are reacted with the sodium enolate of ethyl acetoacetate, generated from sodium hydroxide, in warm N,N-dimethylacetamide resulting in the formation of substituted quinolines. A degradation–buildup strategy of the ethyl ester at the 3-position allowed for the construction of the α-hydroxyacetic acid residue required for the synthesis of key arylquinolines involved in an HIV integrase project.
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Geckeler,Metz
, p. 842,844 (1979)
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Facile synthesis of fluoroalkylated quinolones using fluoroalk-2-ynoates as fluorinated building blocks
Wu, Jun,Zhang, Hui,Ding, Xiao,Tan, Xuefei,Shen, Hong C.,Chen, Jie,He, Weimin,Deng, Hongmei,Song, Liping,Cao, Weiguo
, p. 54 - 60 (2019)
In the presence of Na2CO3, a variety of fluoroalkylated quinolones were efficiently synthesized from isatins and fluoroalk-2-ynoates in good to excellent yields at room temperature. The reaction can proceed via two different ways with Michael adduct or isatoic anhydride as the key intermediate.
Recyclable (PhSe)2-catalyzed selective oxidation of isatin by H2O2: a practical and waste-free access to isatoic anhydride under mild and neutral conditions
Yu, Lei,Ye, Jianqing,Zhang, Xu,Ding, Yuanhua,Xu, Qing
, p. 4830 - 4838 (2015)
After a series of careful conditional optimizations and catalyst screenings, a methodology to prepare isatoic anhydrides through organoselenium-catalyzed selective oxidation of isatins by H2O2 under mild and neutral conditions was developed. The reactions were very practical because of the recyclability of the catalyst and solvent and the convenient isolation procedures of the products. This work reports the organoselenium-catalyzed oxidation of heterocycles that greatly expands the application scopes of organoselenium catalysis. It also indicates that the organoselenium catalysts are robust enough to be recycled in industrial production if suitable isolation procedures are developed.
Discovery of phthalazino[1,2-b]-quinazolinone derivatives as multi-target HDAC inhibitors for the treatment of hepatocellular carcinoma via activating the p53 signal pathway
Gou, Shaohua,Liu, Qingqing,Wang, Xinyi,Wang, Yuanjiang,Zhang, Bin
, (2021/12/30)
In view of histone deacetylases (HDACs) as a promising target for cancer therapy, a series of phthalazino[1,2-b]-quinazolinone units were hybrided with ortho-aminoanilide or hydroxamic acid to serve as multi-target HDAC inhibitors for the treatment of solid tumors. Among the target compounds, 8h possessed nano-molar IC50 values toward the tested cancer cells and HDAC subtypes, which was more potent than the HDAC inhibitor SAHA (vorinostat). Mechanism study revealed that compound 8h could suppress the HepG2 cell proliferation via prompting the acetylation of histone 3 (H3) and α-tubulin, and activating the p53 signal pathway as designed. In addition, compound 8h exhibited much stronger in vivo antitumor efficacy than SAHA in the HepG2 xenograft tumor model with negligible toxicity. As a novel multi-target HDAC inhibitor, compound 8h deserves further development as a potential anticancer agent.
Preparation method of 4(3H)-quinazolinone compound
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Paragraph 0007; 0029-0042, (2021/05/01)
The invention discloses a preparation method of a 4(3H)-quinazolinone compound, and relates to the technical field of organic synthesis, 2,3-diketone indoline is used as a raw material, sodium hypochlorite or potassium hypochlorite is used as an oxidant, an oxidation reaction is carried out in a reaction solvent, and the 4(3H)-quinazolinone compound is prepared by a one-pot method. According to the method, 2,3-diketoindoline is used as a raw material, sodium hypochlorite or potassium hypochlorite which is easily available as the raw material is used as an oxidizing agent; the target product is prepared by a one-pot method, the reaction time is short, and the yield is high. The product is high in purity and is suitable for industrial application.
