- Trifluoroethanol as a Unique Additive for the Chemoselective Electrooxidation of Enamines to Access Unsymmetrically Substituted NH-Pyrroles
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An electrochemical method for the synthesis of unsymmetrically substituted NH-pyrroles is described. The synthetic strategy comprises a challenging heterocoupling between two structurally diverse enamines via sequential chemoselective oxidation, addition,
- Baidya, Mrinmay,De Sarkar, Suman,Maiti, Debabrata,Roy, Lisa
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supporting information
(2021/12/23)
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- Aromaticity-Driven Access to Cycloalkyl-Fused Naphthalenes
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We report the efficient synthesis of cycloalkyl-fused naphthalenes through the [4 + 2]-cycloaddtion/decarboxylative aromatization of alkyne-tethered aryne insertion adducts. These scaffolds were difficult to synthesize using conventional reactions. The reaction proceeds via the formation of a benzopyrylium intermediate followed by intramolecular [4 + 2] cycloaddition and a subsequent decarboxylation pathway. This method is also compatible with allene-tethered substrates to afford similar products. In addition, the one-pot synthesis of polysubstituted naphthalenes via aryne insertion/benzannulation has also been developed in good yield.
- Sanjeev, Karekar,Raju, Silver,Chandrasekhar, Srivari
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supporting information
p. 4013 - 4017
(2021/05/29)
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- An efficient route for the synthesis of N-(1H-benzo[d]imidazol-2-yl)benzamide derivatives promoted by CBr4 in one pot
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A metal-free one-pot method for the synthesis of N-(1H-benzo[d]imidazol-2-yl)benzamide derivatives was proposed mediated by CBr4. The reaction went through ring formation and opening processes with only two protons leaving and the thermodynamically favorable products were selectively formed in moderate to good yields.
- Li, Songhua,Li, Yunyi,Ma, Chen,Xie, Caixia
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- CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF
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Small molecule calpain modulator compounds, including their pharmaceutically acceptable salts, can be included in pharmaceutical compositions. The compounds can be useful in inhibiting calpain, or competitive binding with calpastatin, by contacting them with CAPN1, CAPN2, and/or CAPN9 enzymes residing inside a subject. The compounds and composition can also be administered to a subject in order to treat a fibrotic disease or a secondary disease state or condition of a fibrotic disease.
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Paragraph 0431
(2019/10/23)
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- Rate Enhancement in CAN-Promoted Pd(PPh3)2Cl2-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate Esters
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Stoichiometric ceric ammonium nitrate (CAN) and a catalytic amount of Pd(PPh3)2Cl2 (5 mol %) can rapidly produce multisubstituted 2-ketofuran-4-carboxylate esters from 2-propargylic 1,3-ketoesters via oxidative O-cyclization reaction. Pd(PPh3)2Cl2 was found to be the crucial catalyst as its inclusion greatly enhanced the rate of the reaction and cleanly afforded the products within minutes. Over 30 substrates were successfully converted to the desired compounds in mostly moderate to good yields.
- Ruengsangtongkul, Sureeporn,Chaisan, Nattawadee,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
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p. 2514 - 2517
(2019/04/30)
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- Targeting tubulin polymerization by novel 7-aryl-pyrroloquinolinones: Synthesis, biological activity and SARs
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Earlier studies had confirmed that the 7-phenylpyrroloquinolinone (7-PPyQ) nucleus was an important scaffold for new chemotherapeutic drugs targeting microtubules. For wide-ranging SARs, a series of derivatives were synthesized through a robust procedure. For comparison with the reference 3-ethyl-7-PPyQ 31, the angular geometry and substituents at the 3 and 7 positions were varied to explore interactions inside the colchicine site of tubulin. Of the new compounds synthesized, potent cytotoxicity (low and sub-nanomolar GI50 values) was observed with 21 and 24, both more potent than 31, in both leukemic and solid tumor cell lines. Neither compound 21 nor 24 induced significant cell death in normal human lymphocytes, suggesting that the compounds may be selectively active against cancer cells. In particular, 24 was a potent inducer of apoptosis in the A549 and HeLa cell lines. With both compounds, induction of apoptosis was associated with dissipation of the mitochondrial transmembrane potential and production of reactive oxygen species, indicating that cells treated with the compounds followed the intrinsic pathway of apoptosis. Moreover, immunoblot analysis revealed that compound 24 even at 50 nM reduced the expression of anti-apoptotic proteins such as Bcl-2 and Mcl-1. Finally, molecular docking studies of the newly synthesized compounds demonstrate that active pyrroloquinolinone derivatives strongly bind in the colchicine site of β-tubulin.
- Bortolozzi, Roberta,Mattiuzzo, Elena,Dal Pra, Matteo,Sturlese, Mattia,Moro, Stefano,Hamel, Ernest,Carta, Davide,Viola, Giampietro,Ferlin, Maria Grazia
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p. 244 - 258
(2017/12/07)
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- SMALL MOLECULE INHIBITORS OF LACTATE DEHYDROGENASE AND METHODS OF USE THEREOF
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Provided is a compound of formula (I)[Formula (I) should be inserted here], in which Ar1, R1, U, V, W, X, and p are as described herein. Also provided are methods of using a compound of formula (I), including a method of treating cancer, a method of treating a patient with cancer cells resistant to an anti-cancer agent, and a method of inhibiting lactate dehydrogenase A (LDHA) and/ or lactate dehydrogenase B (LDHB) activity in a cell.
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Paragraph 0311; 0312
(2016/07/27)
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- 1,5-Diketones Synthesis via Three-Component Cascade Reaction
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A mild and efficient cascade synthesis of 1,5-diketones from readily available N,N-dicyclohexylmethylamine, 1,3-dicarbonyl compounds, and trifluoromethyl β-diketones has been developed. This cascade reaction occurs via an oxidation/Mannich reaction/Cope elimination/Michael addition/retro-Claisen reaction sequence, and provides multiple C-C bond formations in one pot. In addition, exquisite chemoselectivity is achieved in the reaction between 1,3-dicarbonyl compounds and trifluoromethyl β-diketones.
- Xing, Li-Juan,Lu, Tao,Fu, Wei-Li,Lou, Mei-Mei,Chen, Bo,Wang, Zhi-Shen,Jin, Yang,Li, Dan,Wang, Bin
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supporting information
p. 3076 - 3080
(2015/11/03)
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- 2-ARYLNAPHTHYRIDIN-4-ONES AS POTENT ANTITUMOR AGENTS TARGETING TUMORIGENIC CELL LINES
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In order to search for new antitumor drug candidates from 2-arylnaphthyridin-4-ones (ANs), we have designed and synthesized a series of 3 '-hydroxy or 6-hydroxy derivatives of ANs. Following the antitumor activity screening, most of these compounds were found to exhibit significant activity. Among them, 2-(3-hydroxyphenyl)-5-methyl-1,8-naphthyridin-4(1H)-one (67) was the most promising. In a preliminary action mechanism study, the treatment of Hep3B hepatoma cells with compound (67) reveals that its mechanism of action is affect on microtubule and metastasis-related proteins. Then, the corresponding phosphate prodrug (86) of compound (67) was tested against Hep3B xenograft nude mice model for antitumor activity.
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Page/Page column 9; 14; 15
(2014/11/13)
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- Copper-mediated oxidative transformation of N-allyl enamine carboxylates toward synthesis of azaheterocycles
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A method for synthesis of 3-azabicyclo[3.1.0]hex-2-enes has been developed by intramolecular cyclopropanation of readily available N-allyl enamine carboxylates. Two complementary reaction conditions, CuBr-mediated aerobic and CuBr2-catalyzed-PhIO2-mediated systems effectively induced stepwise cyclopropanation via carbocupration of alkenes. Oxidative cyclopropane ring-opening of 5-substituted 3-azabicyclo[3.1.0]hex-2-enes was also developed for synthesis of highly substituted pyridines. In addition, diastereoselective reduction of 3-azabicyclo[3.1.0]hex-2-enes to 3-azabicyclo[3.1.0]hexanes was achieved using NaBH3CN in the presence of acetic acid.
- Toh, Kah Kah,Biswas, Anup,Wang, Yi-Feng,Tan, Yun Yun,Chiba, Shunsuke
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p. 6011 - 6020
(2014/05/20)
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- Vertically π-expanded coumarin - Synthesis via the Scholl reaction and photophysical properties
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A short and efficient access to a unique type of π-expanded coumarin is achieved. The strategic placement of naphthalene at the 4-position of coumarin allowed us to fuse these two moieties via aromatic dehydrogenation under Scholl conditions. The intriguing optical properties of this π-expanded coumarin are discussed on the basis of quantum chemical calculations. The fluorescence quantum yield (~20%) is significantly higher than that obtained for the classical 7-hydroxycoumarin. The ratio of emission versus radiationless deactivation is governed by the following factors: decrease in the oscillator strength of the SS transition (vs. perylene), low yield of intersystem crossing and strong internal conversion originating from the activity of the number of vibronic states. the Partner Organisations 2014.
- Tasior, Mariusz,Deperasinska, Irena,Morawska, Karolina,Banasiewicz, Marzena,Vakuliuk, Olena,Kozankiewicz, Boleslaw,Gryko, Daniel T.
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p. 18268 - 18275
(2014/11/07)
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- Base initiated aromatization/CO bond formation: A new entry to O-pyrazole polyfluoroarylated ethers
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A base initiated intermolecular SNAr reaction of pyrazolones with polyfluoroarenes was developed. The process involved the isomerization aromatization of pyrazolone followed by the CO bond formation via the selective CF bond cleavage. With this strategy, a wide range of O-pyrazole polyfluoroarylated ethers bearing diverse functional groups were synthesized in mild to good yields. Additionally, our method was also applied to the isoxazol substrates.
- Tang, Xiangyang,Chang, Jing,Liu, Cuibo,Zhang, Bin
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supporting information
p. 6534 - 6537
(2015/01/08)
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- Ligand steric and electronic effects on β-ketiminato neutral nickel(II) olefin polymerization catalysts
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A series of novel neutral nickel complexes 3a-g and 4a-d bearing the β-ketiminato ligands [(2,6-iPr2C6H 3)N=CHCHC(R)O]Ni(R′)(L) (for 3a-g, R′ = Me, L = Py, and R = tBu (3a), Ph (3b), 1-naphthyl (3c), 9-anthryl (3d), PhNMe 2(p) (3e), PhOMe(p) (3f), PhCF3(p) (3g); for 4a-d, R′ = Ph, L = PPh3, and tBu (4a), Ph (4b), 1-naphthyl (4c), 9-anthryl (4d)) have been synthesized and characterized. The molecular structures of 3b-d,f,g and 4a,c were further confirmed by X-ray crystallographic analysis. These complexes were employed in ethylene polymerization to systematically investigate ligand steric and electronic effects on the catalytic properties, including activity, molecular weight (MW), and branching number of the polyethylene obtained. The complexes bearing more bulky ligands showed higher activities and produced more branched polyethylene. Electron-deficient ligands were found to increase the catalytic activity, decrease the MW, and enhance the branching content of the polyethylene. In addition, phosphine NiII-Ph complexes 4a-d proved to be more active than the corresponding pyridine NiII-Me complexes 3a-d, probably due to the easier dissociation of PPh3 relative to a pyridine from a nickel center.
- Song, Dong-Po,Shi, Xin-Cui,Wang, Yong-Xia,Yang, Ji-Xing,Li, Yue-Sheng
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experimental part
p. 966 - 975
(2012/04/10)
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- Fluorescent diketopyrrolopyrroles
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The present invention relates to fluorescent diketopyrrolopyrroles of the formula (I), or (III), a process for their preparation and their use for the preparation of inks, colorants, pigmented plastics for coatings, non-impact-printing material, color filters, cosmetics, polymeric ink particles, toners, as fluorescent tracers, in color changing media, in solid dye lasers, EL lasers and electroluminescent devices. A luminescent device comprising a compound, or composition according to the present invention is high in the efficiency of electrical energy utilization and high in luminance.
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Page/Page column 122
(2011/09/19)
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- Copper-mediated aerobic synthesis of 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles from N-allyl/propargyl enamine carboxylates
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Synthetic methods for 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles have been developed that use copper-mediated/catalyzed reactions of N-allyl/propargyl enamine carboxylates under an O2 atmosphere and involve intramolecular cyclopropanation and carbooxygenation, respectively. These methodologies take advantage of orthogonal modes of chemical reactivity of readily available N-allyl/propargyl enamine carboxylates; the complementary pathways can be accessed by slight modification of the reaction conditions.
- Toh, Kah Kah,Wang, Yi-Feng,Ng, Eileen Pei Jian,Chiba, Shunsuke
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supporting information; body text
p. 13942 - 13945
(2011/10/30)
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- CATALYSTS CONTAINING N-PYRROLYL SUBSTITUTED NITROGEN DONORS
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Catalyst compositions useful for the polymerization or oligomerization of olefins are disclosed. Certain of the catalyst compositions comprise N-pyrrolyl substituted nitrogen donors. Also disclosed are processes for the polymerization or oligomerization o
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- Substituted indoles and their use as integrin antagonists
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The present invention relates to novel substituted indole compounds that are antagonists of alpha V (αv) integrins, for example αvβ3 and αvβ5 integrins, their pharmaceutically acceptable salts, and pharmaceutical compositions thereof. The compounds may be used in the treatment of pathological conditions mediated by αvβ3 and αvβ5 integrins, including such conditions as tumor growth, metastasis, restenosis, osteoporosis, inflammation, macular degeneration, diabetic retinopathy, and rheumatoid arthritis. The compounds have the general formula: where R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, D, X, W, a, m, n, i, j, k and v are defined herein.
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- Antitumor agents. 178. Synthesis and biological evaluation of substituted 2-aryl-1,8-naphthyridin-4(1H)-ones as antitumor agents that inhibit tubulin polymerization
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As part of our continuing search for potential anticancer drug candidates in the 2-aryl-1,8-naphthyridin-4(1H)-one series, we have synthesized two series of 3'-substituted 2-phenyl-1,8-naphthyridin-4(1H)- ones and 2-naphthyl-1,8-naphthyridin-4(1H)-ones. A
- Chen, Ke,Kuo, Sheng-Chu,Hsieh, Ming-Chieh,Mauger, Anthony,Lin, Chii M.,Hamel, Ernest,Lee, Kuo-Hsiung
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p. 3049 - 3056
(2007/10/03)
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