65764-56-9Relevant academic research and scientific papers
Rational Design, Synthesis and Evaluation of Indole Nitrogen Hybrids as Photosystem II Inhibitors
de Souza, Jéssica Maria,Fazolo, Bruno Rodrigues,Lacerda, Jhully Wellen Ferreira,Moura, Mariana de Souza,dos Santos, Arielly Celestino Rodrigues,de Vasconcelos, Leonardo Gomes,de Sousa Junior, Paulo Teixeira,Dall’Oglio, Evandro Luiz,Ali, Akbar,Sampaio, Olívia Moreira,Vieira, Lucas Campos Curcino
, p. 1233 - 1242 (2020/07/06)
We report the synthesis of twelve indole derivatives bearing nitro or amide groups via Fischer indole methodology followed by reduction/acetylation and amidation reactions. After thorough characterization, these indoles were subjected to a number of studies in order to evaluate their bioactive potential as photosynthesis and plant growth inhibitors. Firstly, these molecular hybrids were evaluated as photosystem II (PSII) inhibitors through chlorophyll a (Chl a) fluorescence measurement. In this study, 6-chloro-8-nitro-2,3,4,9-tetrahydro-1H-carbazole (15a) and 5-chloro-2,3-dimethyl-7-nitro-1H-indole (15b) showed the best results by reducing the phenomenological parameters of reaction centers ABS/RC, TR0/RC and ET0/RC of PSII. Electron chain blockage by these compounds may lead to diminished ATP synthesis and CO2 fixation which interrupt the plant development. The compounds 15a and 15b both act as postemergent herbicides, reducing the dry biomass of Ipomoea grandifolia and Senna alata weeds by an average of 40% and 37%, respectively, corroborating the fluorescence results. Additionally, the molecular docking study revealed that the presence of strong electron-withdrawing groups at the indole phenyl ring is important for the ligand’s interaction with the binding pocket of protein D1 on PSII. The optimization of these molecular features is the goal of our research group in further understanding and development of new potent herbicides.
Synthesis and evaluation of indole derivatives as photosynthesis and plant growth inhibitors
Mendes, Mylla Cristie Da Silva,Fazolo, Bruno Rodrigues,De Souza, Jéssica Maria,De Vasconcelos, Leonardo Gomes,De Sousa Junior, Paulo Teixeira,Dall'Oglio, Evandro Luiz,Soares, Marcos Ant?nio,Sampaio, Olívia Moreira,Vieira, Lucas Campos Curcino
, p. 1350 - 1358 (2019/06/19)
Indole derivatives were synthetized based on the Fischer indole methodology using different phenyl hydrazine hydrochlorides and either cyclohexanone or 2-butanone. The pre- and post-emergent herbicidal activities were evaluated against Ipomoea grandifolia. A carbazole, 6-chloro-2,3,4,9-tetrahydro-1H-carbazole (3b), decreased the PIabs parameter by 32% and increased the cross-section related parameters, indicating the inactivation of the reaction center on photosystem II. Compound 3b acts as a post-emergent herbicide prototype since dry biomass was reduced by 50%, corroborating the fluorescence results. Comparing instead with a germination experiment, 2,3,4,9-tetrahydro-1H-carbazole (3a) was found to be the most effective agent, inhibiting seed germination by 22% and decreasing root length by 50%. The tetrahydrocarbazoles showed better results than indole derivatives potentially due to the presence of methylene groups at structures, which increase the compounds' lipophilicity and may facilitate their access to the plant. In addition, electron withdrawing groups on the aromatic ring were found to correlate with increased herbicide activity. Further optimization of this series towards the development of herbicides is ongoing.
N-Benzyl-indolo carboxylic acids: Design and synthesis of potent and selective adipocyte fatty-acid binding protein (A-FABP) inhibitors
Barf, Tjeerd,Lehmann, Fredrik,Hammer, Kristin,Haile, Saba,Axen, Eva,Medina, Carmen,Uppenberg, Jonas,Svensson, Stefan,Rondahl, Lena,Lundbaeck, Thomas
scheme or table, p. 1745 - 1748 (2010/02/28)
Small molecule inhibitors of adipocyte fatty-acid binding protein (A-FABP) have gained renewed interest following the recent publication of pharmacologically beneficial effects of such inhibitors. Despite the potential utility of selective A-FABP inhibito
NOVEL INDOLE DERIVATES AS FABP-4 INHIBITORS
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Page 40, (2010/02/07)
The present invention relates to novel compounds (I) wherein R0, R1, R2, R3, R4, R5, R6, R7, R8, A, B, n, X, and Y are as defined in the description and claims; and also to pharmaceutical compositions comprising the compounds, as well as to the use of the compounds in medicine and for the preparation of a medicament, which acts on the fatty acid binding protein FABP-4. The present invention relates to novel compounds (I) wherein R0, R1, R2, R3, R4, R5, R6, R7, R8, A, B, n, X, and Y are as defined in the description and claims; and also to pharmaceutical compositions comprising the compounds, as well as to the use of the compounds in medicine and for the preparation of a medicament, which acts on the fatty acid binding protein FABP-4.
Synthesis and evaluation of novel pyrimido-acridone, -phenoxadine, and -carbazole as topoisomerase II inhibitors
Kamata, Junichi,Okada, Toshimi,Kotake, Yoshihiko,Niijima, Jun,Nakamura, Katsuji,Uenaka, Toshimitsu,Yamaguchi, Atsumi,Tsukahara, Kappei,Nagasu, Takeshi,Koyanagi, Nozomu,Kitoh, Kyosuke,Yoshimatsu, Kentaro,Yoshino, Hiroshi,Sugumi, Hiroyuki
, p. 1071 - 1081 (2007/10/03)
As part of a series of studies to discover new topoisomerase II inhibitors, novel pyrimidoacridones, pyrimidophenoxadines, and pyrimidocarbazoles were synthesized, and in vitro and in vivo antitumor activities and DNA-protein and/or DNA-topoisomerase II c
Improved Syntheses of Substituted Carbazoles and Benzocarbazoles via Lithiation of the (Dialkylamino)methyl (Aminal)Derivatives
Katritzky, Alan R.,Rewcastle, Gordon W.,Vazquez de Miguel, Luis M.
, p. 794 - 799 (2007/10/02)
The lithiation of N-carbazoles occurs readily and exclusively at the protonated carbon adjacent to the nitrogen atom.Reaction with a variety of electrophiles produces good to excellent yields of monosubstituted derivatives.Removal of the lithio-directing and nitrogen-protecting function is readily achieved by mild acid-catalyzed hydrolysis during workup of the reaction.Thus, carbazole undergoes lithiation at the 1-position, dibenzocarbazole at the analogous 6-position, and benzocarbazole at both the 6-and 8-positions, with the former predominating. 1,2,3,4-Tetrahydrocarbazole undergoes lithiation at the 8-position, but with 2,3-dimethylindole reaction occurs at the 2-methyl group.Benzocarbazole fails to form an aminal derivative, but on direct lithiation in ether it can be substituted exclusively at the 1-position of the fused benzene ring.
