14191-22-1Relevant academic research and scientific papers
Lithiation of pivaloylamino derivatives of dibenzofuran and 9-methylcarbazole
Deady,Sette
, p. 177 - 180 (2001)
2-, 3- and 4-Pivaloylamino derivatives of dibenzofuran [compounds (5), (4) and (6), respectively] and analogous 3-, 2- and 1-substituted derivatives of 9-methylcarbazole [compounds (8), (7) and (9), respectively] were subjected to lithiation at 0°C and subsequent reaction with dimethylformamide. Aldehyde formation took place at positions α to δ to the heteroatom as follows: α for (4) and (7); δ for (5); δ and β (3 : 1) for (8); and α′ (6). No formylation occurred with (9).
Triazoloazine-Diazomethylazine Valence Isomerization. [1,2,3]Triazolo[1,5-a]pyridines and 2-Diazomethylpyridines
Aylward, Nigel,Winter, Hans-Wilhelm,Eckhardt, Ulrich,Wentrup, Curt
, p. 667 - 672 (2016)
2-Diazomethylpyridines 1D and 6D, the valence isomers of [1,2,3]triazolo[1,5-a]pyridines 1T and 6T, have been observed directly at ～2080 cm-1 by a combination of mild flash vacuum pyrolysis (FVP) at 200-600°C with low temperature IR spectroscopy. Calculations confirm a ca. 17 kcal/mol barrier for the formation of 2-diazomethylpyridine 1D from [1,2,3]triazolo[1,5-a]pyridine 1T, the diazo compound lying ca. 5 kcal/mol above the triazole. In the higher temperature range (400-600°C) 2-diazomethylpyridine 1D eliminates N2 with formation of 2-pyridylcarbene 2 and rearrangement to 1-cyanocyclopentadiene 4. 2-Diazomethylpyridine 1D undergoes 1,3-dipolar cycloaddition with tetracyanoethylene (TCNE) at 20-90°C to yield 3-(2-pyridyl)cyclopropanetetracarbonitrile 11 and 3-(tricyanovinyl)-[1,2,3]triazolo[1,5-a]pyridine 13T via unobserved pyrazolines 10 and 12. FVP of triazole 13T affords an IR absorption at 2080 cm-1 ascribed to the corresponding diazo compound 13D.
COMPOSITIONS AND METHODS OF MAKING EXPANDED HEMATOPOIETIC STEM CELLS USING DERIVATIVES OF CARBAZOLE
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, (2020/11/12)
This invention is directed to, inter alia, compounds, methods, systems, and compositions for the maintenance, enhancement, and expansion of hematopoietic stem cells derived from one or more sources of CD34+ cells. Sources of CDS 4+ cells include bone marrow, cord blood, mobilized peripheral blood, and non-mobilized peripheral blood. Also provided herein are compounds of Formula I which are useful in maintaining, enhancing, and expanding of hematopoietic stem cells.
7-aminocarbazolesulfonamide derivatives as well as preparation method and application thereof
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Paragraph 0099; 0101; 0102; 0106, (2019/07/04)
The invention provides 7-aminocarbazolesulfonamide derivatives as well as a preparation method and application thereof, and relates to the technical field of medicine. The 7-aminocarbazolesulfonamidederivatives have a general formula (I) shown in the description, wherein R1 is one or more groups located on a benzene ring and at least one independently selected from the group consisting of a C1-C6lower alkoxy group, a C1-C6 lower alkyl group, an amino group and a halogen; and R2 is hydrogen or a C1-C6 lower alkyl group. The 7-aminocarbazolesulfonamide derivatives provided by the invention exhibit good inhibitory activity against various tumor cells, so that the derivatives can be well used for preparing antitumor drugs.
Novel carbazole sulfonamide derivatives of antitumor agent: Synthesis, antiproliferative activity and aqueous solubility
Sun, Lianqi,Wu, Yanbin,Liu, Yonghua,Chen, Xiaofang,Hu, Laixing
, p. 261 - 265 (2016/12/27)
The current optimization of IG-105 (3) on the carbazole-ring provided a series of new carbazole sulfonamides derivatives 13a–13m. All of the compounds have been evaluated against HepG2 cells (hepatoma cancer) for antiproliferative activity. Compounds that showed activity better or comparable to that of 3 versus HepG2 were evaluated against MCF-7 (breast cancer), MIA PaCa-2 (pancreatic cancer), and Bel-7402 (hepatoma/liver cancer) for antiproliferative activity. Of the seven compounds selected for further study five (13b, 13g, 13j, 13k and 13l) were found to give IC50values against the four cell lines comparable to those for 3. Two compounds (13f and 13i) were more active than 3 and their activity against HepG2 and MCF-7 (IC50:0.01–0.07?μM) approached that of the positive controls podophyllotoxin (podo) and CA-4. Most of compounds showed aqueous solubility (0.11–19.60?μg/mL at pH 7.4 and 2.0) better than 3. These promising results warrant further development of new compounds 13f and 13i as potential potent antitumor drug candidates.
Palladium on Carbon-Catalyzed C?H Amination for Synthesis of Carbazoles and its Mechanistic Study
Monguchi, Yasunari,Okami, Hiroki,Ichikawa, Tomohiro,Nozaki, Kei,Maejima, Toshihide,Oumi, Yasunori,Sawama, Yoshinari,Sajiki, Hironao
, p. 3145 - 3151 (2016/10/09)
10% Palladium on carbon (10% Pd/C) successfully catalyzed the intramolecular C?H amination of various N-mesylated 2-aminobiphenyls in the presence of a catalytic amount of pyridine N-oxide in heated dimethyl sulfoxide (DMSO) under an oxygen atmosphere to afford the corresponding N-mesylcarbazoles. The reaction would proceed via a single-electron transfer process based on its significant suppression by the addition of a single-electron scavenger, tetracyanoquinodimethane (TCNQ), and the substituents on the aromatic rings of the substrate have an insignificant effect on the reaction progress. (Figure presented.).
Iron-Catalyzed Intramolecular C(sp2)-H Amination
Alt, Isabel T.,Plietker, Bernd
, p. 1519 - 1522 (2016/02/14)
The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular C-H amination of α-azidobiaryls and (azidoaryl)alkenes into the corresponding carbazoles and indoles, respectively, under mild conditions and with low catalyst loadings. These features and the broad functional-group tolerance render this method a particularly attractive alternative to established noble-metal-based procedures.
Rh(I)-catalyzed decarbonylation synthesis of carbazoles via C-N cleavage
Fan, Weizheng,Jiang, Shan,Feng, Bainian
, p. 4035 - 4038 (2015/06/02)
A one-pot Rh(I)-catalyzed synthesis of 9-H carbazoles via C-N bond cleavage by activation of aldehyde C-H bonds is reported. This protocol offers good yields and tolerates a broad range of functional groups. Based on the extensive control experiments, we propose a plausible decarbonylation mechanism.
Pd-catalyzed conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics
Fors, Brett P.,Buchwald, Stephen L.
supporting information; experimental part, p. 12898 - 12899 (2009/12/07)
(Chemical Equation Presented) An efficient Pd catalyst for the transformation of aryl chlorides, triflates, and nonaflates to nitroaromatics has been developed. This reaction proceeds under weakly basic conditions and displays a broad scope and excellent
NITRATION IN THE CARBAZOLE SERIES
Kyziol, Janusz B.,Daszkiewicz, Zdzislaw
, p. 1857 - 1862 (2007/10/02)
Nitration of 9-tosylcarbazole in acetic anhydride solution gives 1-nitro (28percent), 2-nitro (19percent) and 3-nitro (53percent) derivatives.The mixture of the nitro compounds obtained from 9-acetylcarbazole contains 10percent, 48percent and 42percent of the isomers, respectively.Under similar conditions 9-nitrosocarbazole shows a different isomer distribution: 34percent of 1-nitro and 66percent of 3-nitrocarbazole.Nitration of carbazole is a two step process involving formation and rarrangement of 9-nitrocarbazole.The hypothesis was supported by the results of 1,3,6,8-tetrachlorocarbazole nitration and oxidation of 9-nitrosocarbazole and rearrengement of 9-nitrocarbazole in the nitration conditions.
