1484-12-4Relevant articles and documents
Synthesis and reactions of 2-bis(methylthio)methylene-1-methyl-3- oxoindole: A facile access to benzo- and heterocyclo- fused carbazoles and indoles
Basaveswara Rao,Syam Kumar,Ila,Junjappa
, p. 11563 - 11578 (1999)
The synthesis and reactions of 2-bis(methylthio)methylene-1-methyl-3- oxoindole 5 as a novel 3-carbon 1,3-bielectrophilic component are described. Thus cycloaromatization of 5 with allyl, methallyl and crotyl Grignard reagents affords substituted carbazoles 12a-c in good yields. Cycloaromatization of 5 with various anions derived from aryl/heteroaryl acetonitriles and antipyrine gives novel benzo[c]- (16), naphtho[1,2-c]- (19), indolo[3,2-a]- (21), thieno[2,3-c]- (23), pyrrolo[2,3c]- (25) and pyrazolo[4,3-b]- (29) carbazole ring systems in good yields. Similarly heterocyclo[b]fused indoles like pyrido[3,4-b]- (36), pyrido[3,2-b]- (39) indoles and indolo[3,2-b]quinolizinium salt 42 were synthesized by cyclization of 5 with lithioacetonitrile, lithioaminocrotonitrile, and 2- picolyl lithium respectively via our heteroaromatic annelation protocol.
Synthesis and biological evaluation of novel carbazolyl glyoxamides as anticancer and antibacterial agents
Venkataramana Reddy,Tantak, Mukund P.,Valdez, Reyna,Singh, Rajnish Prakash,Singh, Okram Mukherjee,Sadana, Rachna,Kumar, Dalip
, p. 9379 - 9386 (2016)
A new library of 24 carbazolyl glyoxamides 14a-x were designed and synthesized from glyoxalic acids and arylamines in the presence of HATU as a coupling reagent under MW irradiation. The synthesized carbazolyl glyoxamides were evaluated for their in vitro anticancer and antibacterial activities. Of the synthesized carbazolyl glyoxamides, compounds 14l and 14q exhibited the most potent cytotoxicity towards a breast cancer cell line with IC50 values of 9.3 and 9.8 μM, respectively. Further, caspase-3 assay for carbazolyl glyoxamides indicated that these compounds induced apoptotic cell death in Jurkat cells. Furthermore, some of the synthesized carbazolyl glyoxamides 14g, 14k, 14l and 14n exhibited comparable or even better antibacterial activity (MIC = 8-16 μg mL-1) than chloramphenicol against the selected bacterial strains.
Enhanced photochemical [6π] electrocyclization within the lipophilic protein binding site
Marin, Mireia,Lhiaubet-Vallet, Virginie,Miranda, Miguel A.
, p. 1788 - 1791 (2012)
Photocyclization of N-methyldiphenylamine to N-methylcarbazole is achieved within the microenvironment provided by site I of serum albumins. Quantum yield determinations, combined with transient absorption spectroscopic detection of the dihydrocarbazole intermediate, demonstrate that protein encapsulation provides a subtle control of the kinetic parameters, leading to optimized efficiencies.
9,10-Bis(N-methylcarbazol-3-yl-vinyl-2)anthracene: High contrast piezofluoro-chromism and remarkably doping-improved electroluminescence performance
Liu, Wei,Ying, Shian,Sun, Qikun,Qiu, Xu,Zhang, Haichang,Xue, Shanfeng,Yang, Wenjun
, p. 8 - 14 (2016)
This paper reported the synthesis, optical and electroluminescent properties of 9,10-bis(N-methylcarbazol-3-yl-vinyl-2)anthracene (MCA). MCA could be facilely prepared by the Wittig-Horner reaction of N-methyl-3-formylcarbazole and 9,10-bis(diethoxyphosphorylmethyl)anthracene and exhibited strong aggregation-induced and crystallization-enhanced emission (AIE/CEE) effect. Simple mechanical force could change MCA solid from initial green to final red emission, affording high contrast piezofluorochromism with large spectral shift of up to 90 nm. When MCA was used as the emissive material in light-emitting diodes, the doped devices showed remarkably improved electroluminescence (EL) performance whose EL efficiency was 8 times higher than that of the non-doped device. Moreover, the dopant concentrations did not affect significantly the fluorescence properties of doped films and EL performances of doped devices, demonstrating the potential advantage of AIE/CEE luminogens applicable for EL dopants.
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Fischer et al.
, p. 6267 (1974)
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Gilman,Spatz
, p. 860,864 (1952)
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PHOTOCHEMICAL REACTION OF CARBAZOLE AND SOME DERIVATIVES IN DICHLOROMETHANE
Balsells, R. Erra,Frasca, A. R.
, p. 5363 - 5366 (1984)
By irradiation of carbazole and some derivatives in CH2Cl2 soln two different reaction pathways were observed depending on the substitution of the heterocyclic compound.
Aromatic and heteroaromatic annelation studies on 3-[bis(methylthio)methylene]-1-methyloxindole: Synthesis of carbazoles and an efficient route to pyrido[2,3-b]indoles
Suresh,Syam Kumar,Ila,Junjappa
, p. 781 - 789 (2001)
The 3-[bis(methylthio)methylene]-1-methyloxindole (2) is shown to undergo cycloaromatization with allyl and methallyl magnesium chlorides to afford substituted carbazoles. A novel route to 2-substituted-3-cyano-4-methylthio/aminopyrido[2,3-b]indoles has been developed via heteroaromatic annelation of 2 with in situ generated 2-lithioamino-2-substituted acrylonitriles.
1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) and microwave-accelerated green chemistry in methylation of phenols, indoles, and benzimidazoles with dimethyl carbonate
Shieh, Wen-Chung,Dell, Steven,Repic, Oljan
, p. 4279 - 4281 (2001)
(Equation Presented) 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) is a novel and active catalyst in promoting the methylation reaction of phenols, indoles and benzimidazoles with dimethyl carbonate under mild condition. Additional rate enhancement is accomplished by applying microwave irradiation. By incorporating tetrabutylammonium iodide, the same microwave reactions can be further accelerated. By combining these acceleration strategies, very low chemical transformations that take up to several days can be performed efficiently in high yield within minutes.
REGIOSPECIFIC C-9 SUBSTITUTION OF ELLIPTICINE DERIVATIVES
Langendoen, Albert,Plug, Johannes P. M.,Koomen, Gerrit-Jan,Pandit, Upendra K.
, p. 1759 - 1762 (1989)
6-Methylellipticine (6) undergoes acylation at the C(9)-position, under Friedel Crafts reaction conditions.The C(9)-formyl compound (8) rearranges to the corresponding hydroxy derivative (9) upon treatment with hydrogen peroxide, in methanol, in the presence of sulphuric acid.The two steps provide a convenient procedure for the specific C(9)-hydroxylation of the ellipticine template.
Dual-site fluorescent probe for highly selective and sensitive detection of sulfite and biothiols
Li, Mengyang,Cui, Pengcheng,Li, Kun,Feng, Jiahui,Zou, Mingming,Yu, Xiaoqi
, p. 992 - 994 (2018)
A dual-site fluorescent probe with double bond and aldehyde as reactive sites, was designed for the selective detection of sulfite and biothiols. Sulfite reacts with conjugate bond selectively, while Cys responses with aldehyde and GSH occurs substitution reaction. Different interactions cause different absorption and fluorescence responses. Moreover, it could be further applied in imaging in living cells.
A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination
Tang, Yu,Yu, Biao
, (2022/03/27)
A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.
Novel yellow- to red-emitting fluorophores: Facile synthesis, aggregation-induced emission, two-photon absorption properties, and application in living cell imaging
Dong, Qi-Ji,Cai, Zhi-Bin,Ding, Ling,Luo, Pei-Hua,He, Qiao-Jun,Li, Sheng-Li,Chen, Li-Jun,Ye, Qing,Tian, Yu-Peng
, (2020/10/29)
Four novel yellow-to red-emitting fluorophores with a 1-(2-hydroxyethyl) pyridinium core and different electron-donating terminal moieties (N-methylcarbazole, N,N-dibutylbenzenamine, N-methylpyrrole, and 2-methylfuran) were designed and facilely synthesized via the one-step Knoevenagel condensation. All these compounds (HPs) were characterized by 1H NMR, 13C NMR, and HRMS. Their photophysical properties including linear absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence, were systematically investigated in various solvents. And the density functional theory calculations were conducted to analyze the electronic structures of HPs. The two-photon absorption cross-sections (δ) values of HPs measured by the Z-scan technique were determined to be as large as 1354 (1HP-CZ), 4462 (2HP-BA), 836 (3HP-PR), and 2944 GM (4HP-FU) in DMSO. The two-photon action cross-sections (Φ × δ) values of 1HP-CZ and 2HP-BA in H2O measured by the two-photon induced fluorescence method were about 50 GM. 1HP-CZ, 3HP-PR, and 4HP-FU also exhibited good water solubility. Meanwhile, it was found that 2HP-BA exhibited notable aggregation-induced emission characteristic in DMSO/H2O mixture. The aggregate particle size distribution of 2HP-BA was measured by the dynamic light scattering method, and the aggregation characteristic of 2HP-BA was observed by the transmission electron microscopy. Besides, 2HP-BA also exhibited red emission. Then, HPs with relatively low cytotoxicity were used for one- and two-photon excited fluorescence imaging in living HepG2 cells. The results indicate that HPs are potential candidates in the bioimaging field due to their photophysical properties and biocompatibility.
Design and synthesis of aryl-functionalized carbazole-based porous coordination cages
Rowland, Casey A.,Lorzing, Gregory R.,Bhattacharjee, Rameswar,Caratzoulas, Stavros,Yap, Glenn P. A.,Bloch, Eric D.
supporting information, p. 9352 - 9355 (2020/10/02)
A subset of coordination cages have garnered considerable recent attention for their potential permanent porosity in the solid state. Herein, we report a series of functionalized carbazole-based cages of the structure type M12(R-cdc)12 (M = Cr, Cu, Mo) where the functional groups include a range of aromatic substituents. Single-crystal X-ray structure determinations reveal a variety of intercage interactions in these materials, largely governed by pi-pi stacking. Density functional theory for a subset of these cages was used to confirm that the nature of the increased stability of aryl-functionalized cages is a result of inter-cage ligand interactions. This journal is
