- A carbazole-based turn-on fluorescent probe for the detection of hydrazine in aqueous solution
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A carbazole-based fluorescent probe, 2-(9-ethyl-9H-carbazol-3-yl) isoindoline-1,3-dione, with a low detection limit (2.673 × 10?6 M) for the detection of hydrazine is designed and synthesized based on Gabriel reaction. The probe responds selectively to hydrazine over other amino compounds with marked fluorescence enhancement. Moreover, test paper experiments indicated its great potential in the environment monitoring of hydrazine in aqueous solution.
- Wang, Wei-Dong,Hu, Yang,Li, Qiao,Hu, Sheng-Li
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Read Online
- High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates
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Commercially available Pd/C can be used as a catalyst for nitro group reductions with only 0.4 mol % Pd loading. The reaction can be performed using either silane as a transfer hydrogenating agent or simply a hydrogen balloon (μ1 atm pressure). With this technology, a series of nitro compounds was reduced to the desired amines in high chemical yields. Both the catalyst and surfactant were recycled several times without loss of reactivity.
- Gallou, Fabrice,Li, Xiaohan,Lipshutz, Bruce H.,Takale, Balaram S.,Thakore, Ruchita R.
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supporting information
p. 8114 - 8118
(2021/10/25)
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- Introduction of a luminescent sensor for tracking trace levels of hydrazine in insect pollinated cropland flowers
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In recent years the excessive use of hydazine containing chemical pesticides and insecticides in farming practices is well pronounced, which directly or indirectly impart a great threat towards the total environment. Considering the above fact we are motivated to introduce a new, efficient and simple chemodosimeter (NCD) based on a carbazole-naphthalimide framework to recognize and estimate the mutagenic hydrazine within several affected cropland flowers. ProbeNCDcan detect hydrazine in a nanomolar range (65 nM or 2 ppb) in the presence of other metal ions, anions and amines, which gives it not only great potential but also makes it selective and sensitive. The sensing mechanism is confirmed by UV-vis, emission, and mass spectroscopy, and computational studies. We have successfully characterized probeNCDby1H and13C NMR and mass spectrometry as well as by single crystal analysis.
- Chattopadhyay, Ansuman,Das, Sujoy,Rissanen, Kari,Saha, Shrabani,Sahoo, Prithidipa,Sarkar, Olivia
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supporting information
p. 17095 - 17100
(2021/10/04)
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- Copper(II)-Catalyzed Iodinations of Carbazoles: Access to Functionalized Carbazoles
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A copper-catalyzed iodination of carbazoles has been developed. Barluenga's reagent IPy2BF4 is used to generate a soft electrophilic halonium species for the iodination of the carbazoles. This report represents the first concept of copper-catalyst-promoted electrophilic halogenation of carbazoles. We demonstrated numerous applications of this methodology synthesizing diverse carbazole derivatives, i.e., both electron-rich and electron-deficient systems.
- Przypis, Lukasz,Walczak, Krzysztof Zdzislaw
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- Use for RL intermediate condensation product synthesis process (by machine translation)
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The present invention discloses a use for RL intermediate condensation product synthesis process, the process comprises the steps of: carbazole alkylation N - ethyl carbazole made, by nitration, reduction to generate a 3 - amino - N - ethyl carbazole, then in the organic solvent in the condensation reaction, use for intermediate condensate obtained RL; in this invention the condensation reaction using an alcohol as a solvent to replace the traditional O-chlorobenzene, improves the 3 - amino - N - ethyl carbazole conversion rate, and improves the use for RL crude purity and yield, and the process is stable, simple operation, high safety factor. (by machine translation)
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Paragraph 0017; 0018
(2017/08/29)
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- Substituted Carbazoles-A New Class of Anthelmintic Agent
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A series of novel carbazoles were synthesized based on structural modifications to lead carbazole 1 (EC100≤2.5M against Haemonchus contortus in vitro), which was revealed in a small molecule screening program as a potentially promising platform for the development of new anthelmintic drugs. Subsequently, analogues 19, 21, 41, 42 (EC100≤ 1.25M, all), and 39 (EC100≤0.625M) were demonstrated to exhibit enhanced in vitro anthelmintic activity over the lead structure, with compound 39 also being shown to be active in vivo against Heligmosomoides polygyrus.
- Rennison, David,Gueret, Stephanie M.,Laita, Olivia,Bland, Ross J.,Sutherland, Ian A.,Boddy, Ian K.,Brimble, Margaret A.
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p. 1268 - 1276
(2016/11/25)
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- Novel Schiff base compound taking triphenylamine as center and preparation of novel Schiff base compound
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The invention provides a novel Schiff base compound taking triphenylamine as a center and having a structural formula I, and a preparation method of the novel Schiff base compound. The preparation method comprises steps of: reacting triphenylamine with DMF and POCl3 to prepare 4,4-diformyltriphenylamine; preparing N-ethylcarbazole from carbazole and bromoethane; nitrifying N-ethylcarbazole to obtain 3-nitro-N-ethylcarbazole; further reducing nitro to obtain 3-amino-N-ethylcarbazole; and finally reacting 4,4-diformyltriphenylamine with 3-nitro-N-ethylcarbazole to obtain the Schiff base compound. The prepared Schiff base compound has carbon-nitrogen double bonds (C=N) and a relatively large pi electron delocalization skeleton, which provides the compound with a relatively large fluorescence absorption coefficient. Due to the presence of lone pair electrons of C=N, the novel Schiff base compound has a potential application to detection of metal ions.
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Paragraph 0026
(2016/10/07)
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- Turn-on trivalent cation selective chemodosimetric probe to image native cellular iron pools
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A new turn-on cell permeable chemodosimetric probe 1 has been developed and its application in the selective detection of trivalent cations (Fe 3+/Cr3+/Al3+) at a sub-nanomolar level has been demonstrated. The selectivity of 1 over a broad spectrum of mono- and divalent metal ions was established using fluorescence spectroscopy. Moreover, the changes in the absorption spectra of 1 in the presence of trivalent cations enabled the most bio-relevant metal ion Fe3+ over Cr 3+/Al3+ to be distinguished. The probe was found to be successful in the fluorescence imaging of native cellular iron pools. The fluorescence imaging of the native iron pools of banana pith further supported the high sensitivity of 1 towards Fe3+ present in living systems. To the best of our knowledge, this is the first example of a turn-on chemodosimetric probe to image native cellular Fe3+ pools. This journal is the Partner Organisations 2014.
- Venkateswarulu,Mukherjee, Trinetra,Mukherjee, Subhrakanti,Koner, Rik Rani
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supporting information
p. 5269 - 5273
(2014/04/03)
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- Carbazole N-substituent effect upon DTMA: Stabilizing and photochromic modulating
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Dithienylmaleimide derivatives 7-27 were synthesized by introducing N-substituted carbazole for photo-stabilizing purpose, and the structures were fully confirmed. The photochromism and photo-stability were recorded via UV-vis spectra. Only ortho compounds 8-17 with N-substituents on carbazole moiety showed escalated photochromic change, while compound 7 and the para counterparts 18-27 showed no appreciable photochromism. Additionally, compounds 8-18 exhibited good photo-stability except 17 under 254 nm irradiation. The unstability of 17 may probably due to overrunning hindrance. These photochromic patterns indicated that hindrance and electronic effect mutually paid a decisive influence on the photochromism and photo-stability, which potentially exploited a new way to construct novel photochromic materials with regulable and conceivable performance.
- Huo, Zhiming,Li, Zhipeng,Wang, Tingting,Zeng, Heping
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supporting information
p. 8964 - 8973
(2013/09/23)
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- Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts
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A method for the Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle precatalysts (3a, 3b, and 3c). As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.
- Cheung, Chi Wai,Surry, David S.,Buchwald, Stephen L.
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supporting information
p. 3734 - 3737
(2013/08/23)
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- One-pot three-component mild synthesis of 2-Aryl-3-(9-alkylcarbazol-3-yl) thiazolidin-4-ones
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A series of novel 2-aryl-3-(9-alkylcarbazol-3-yl)thiazolidin-4-ones were synthesized by one-pot three-component reactions of 3-amino-9-alkylcarbazoles, aromatic aldehydes, and 2-mercaptoacetic acid by using dicyclohexylcarbodiimide (DCC) as a cyclizing agent in dry diethyl ether at room temperature. This protocol has advantages of mild condition, short reaction time, high yield, and simple work-up procedure.
- Li, Zheng,Zhu, Anguo,Yang, Jingya
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p. 1458 - 1461
(2013/02/22)
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- Pharmaceutically active pyrrolidine derivatives
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The present invention is related to pyrrolidine derivatives of formula (I). Said compounds are preferably for use as pharmaceutically active compounds. Specifically, pyrrolidine derivatives of formula (I) are useful in the treatment and/or prevention of premature labor, premature birth and dysmenorrhea. In particular, the present invention is related to pyrrolidine derivatives displaying a substantial modulatory, notably an antagonist activity of the oxytocin receptor. More preferably, said compounds are useful in the treatment and/or prevention of disease states mediated by oxytocin, including premature labor, premature birth and dysmenorrhea. The present invention is furthermore related to novel pyrrolidine derivatives as well as to methods of their preparation, wherein X is selected from the group consisting of CR6R7, NOR6, NNR6R7; A is selected from the group consisting of —(C═O)—, —(C═O)—O—, —C(═NH)—, —(C═O)—NH—, —(C═S)—NH, —SO22—, —SO2NH—, —CH2—,B is either a group —(C═O)—NR8R9 or represents a heterocyclic residue having the formula (a) wherein Q is NR10, O or S; n is an integer selected of 0, 1 or 2; Y, Z and E form together with the 2 carbons to which they are attached a 5-6 membered aryl or heteroaryl ring.
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- Pharmaceutically active pyrrolidine derivatives as bax inhibitors
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The present invention is related to new substituted pyrrolidine derivatives of formula (I). Said compounds are preferably for use as pharmaceutically active compounds. Specifically, pyrrolidine derivatives of formula (I) are useful in the treatment and/or prevention of neurodegenerative disorders, diseases associated with polygultamine tracts, epilepsy, ischemia, infertility, cardiovascular disorders renal hypoxia, hepatitis and AIDS. Said pyrrolidine derivatives display a modulatory and most notably a down-regulating-up to an inhibitory-activity with respect to the cellular death agonist Bax and/or the activation pathways leading to Bax and allows therefore to block the release of cytochrome (c). The present invention is furthermore related to novel pharmaceutically activity substituted pyrrolidine derivatives as well as to methods of their preparation, wherein X is selected from the group consisting of O, S, CRR, NOR, NNRR; A is selected from the group consisting of —(C═O)—, —(C═O)—O—, —C(═NH)—, —(C═O)—NH—, —(C═S)—NH, —SO2-, —SO2NH—; —CH2-; B is either a group —(C═O)—NRR or represents a heterocyclic residue having the formula (II) wherein Q is NR, O or S; n is an integer selected of 0, 1 or 2; Y, Z and E form together with the 2 carbons to which they are attached a 5-6 membered aryl or heteroaryl ring.
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- Alkali-induced Formation of ortho-Semidines from 3-Nitro- and 3-Azocarbazoles - Synthesis of 8,16-Dialkyldiindolo[3,2-a,d]phenazines
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The ortho-semidines 9-alkyl-4-(9-alkylcarbazol-3-ylamino)-3-aminocarbazoles (2a-d) are formed either by reduction of 9-alkyl-3-nitro-carbazoles (1a-d) or of the azo-(6) or the azoxycarbazoles (7) with zinc in alkaline alcoholic solution. It could be shown by cross experiments that the semidines 2 result from an intramolecular rearrangement. The compounds 2a-d are oxidized by air or H2O2 to the 8,16-dialkyldiindolo[3,2-a,d]phenazines (3a-d). Reduction of 1a-c with Raney-alloy affords the 9-alkyl-3-azoxycarbazoles 7a-c in good yields.
- Fanghaenel,Chtcheglov
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p. 731 - 737
(2007/10/03)
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- 2-Hydrocarbyloxy-pyridine compounds
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Compounds of the formula SPC1 Wherein X is aliphatic, cycloaliphatic, aromatic, aralkyl, hetaryl, hetarylalkyl or hydrogen; Y is aliphatic, aromatic, aralkyl, --COOR1, --COR2, EQU1 --SO2 R2, EQU2 --CN, --NH2, --NO, --NO2 or hydrogen with the proviso that when Y is hydrogen, X is other than hydrogen; Z1 is cyano, EQU3 --NH--OR10, EQU4 --OR12, --SR12 or --SO2 R12 and Z2 is chlorine, bromine, cyano, hydroxy, mercapto, --OR12, --SR12, --SO2 R12, EQU5 --NH--OR10 or EQU6 R1 is aliphatic; R2 is aliphatic, cycloaliphatic, aromatic, aralkyl or heterocyclic; R3 and R4 when taken separately are hydrogen, aliphatic, cycloaliphatic, aromatic or aralkyl; R3 and R4 when taken together with the nitrogen atom to which they are attached form a heterocyclic moiety; R5 and R6 when taken separately are aliphatic, aromatic, aralkyl, heterocyclic or hydrogen; R5 and R6 when taken together with the nitrogen atom to which they are attached are heterocyclic; R7 is hydrogen, aliphatic or aromatic; R8 and R9 are aliphatic or aromatic, R10 is hydrogen, aliphatic or aralkyl, R11 is aliphatic and R12 is aliphatic, aromatic or aralkyl; R10 and R11 when taken together with the nitrogen atom to which they are attached are heterocyclic.
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