- High Tg fluorene-based hole-transporting materials for organic light-emitting diodes
-
A new series of fluorene-based hole-transporting materials, 9,9-bis[4-(di-p-tolylamino)phenyl]-2,7-bis(diphenylamino)fluorene (1), 9,9-bis[4-(di-p-tolylamino)phenyl]-2,7-bis(di-p-tolylamino)fluorene (2), 9,9-bis[4-(di-p-tolylamino)phenyl]-2,7-bis(2-naphth
- Shao, Ke-Feng,Li, Ying-Feng,Yang, Lian-Ming,Xu, Xin-Jun,Yu, Gui,Liu, Yun-Qi
-
-
Read Online
- Design, synthesis and antiproliferative evaluation of fluorenone analogs with DNA topoisomerase i inhibitory properties
-
A series of 2,7-diamidofluorenones were designed, synthesized, and screened by SRB assay. Some synthesized compounds exhibited antitumor activities in submicromolar range. Ten compounds (3a, 3b, 3c, 3g, 3j, 3l, 4a, 4h, 4i, and 4j) were also selected by NCI screening system and 3c (GI50 = 1.66 μM) appeared to be the most active agent of this series. Furthermore, 3c attenuated topoisomerase I-mediated DNA relaxation at low micromolar concentrations. These results indicated that fluorenones have potential to be further developed into anticancer drugs.
- Lee, Chia-Chung,Chang, Deh-Ming,Huang, Kuo-Feng,Chen, Chun-Liang,Chen, Tsung-Chih,Lo, Yang,Guh, Jih-Hwa,Huang, Hsu-Shan
-
-
Read Online
- Tuning HOMO-LUMO levels: Trends leading to the design of 9-fluorenone scaffolds with predictable electronic and optoelectronic properties
-
Highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) tuning is an important consideration in the development of organic-based semiconducting materials. A study of the specific effects and overall trends for the HOMO-LUMO tuning of a diverse series of 9-fluorenones by means of extended conjugation and substituent effects is described. Trends were explored in a range of compounds, beginning with structures having highly electron-withdrawing substituents and progressing to structures having highly electron-donating substituents. Compounds with an incremental increase in conjugation were also examined. Electrochemical and optical measurements were used to calculate the HOMO-LUMO levels and HOMO-LUMO bandgap (HLG) for each structure. Results from both methods were compared and correlated with the differences in molecular structure. Increasing the electron-donating character of the substituents was observed to decrease the HLG and increase the energy levels of the HOMO and the LUMO, whereas an increase in the electron-withdrawing character produced the opposite results. Increasing conjugation decreased the HLG, increased the HOMO energy level, but decreased the LUMO energy level. Spectroscopic evidence of substituent influence on the carbonyl suggests that substituents directly impact the HLG by influencing the availability of nonbonding electrons within the carbonyl, which impacts the probability of an nπ* transition. The data presented not only elaborate on the HOMO-LUMO tuning of 9-fluorenone systems but also enable the consideration of 9-fluorenones as analogous models for HOMO-LUMO tuning in other more complex polyaromatic systems such as bifluorenylidenes. These trends may provide insight into developing materials with specifically tuned HLGs and HOMO-LUMO levels for a variety of applications. Copyright
- Eakins, Galen L.,Alford, Joshua S.,Tiegs, Brandon J.,Breyfogle, Bryan E.,Stearman, Chad J.
-
-
Read Online
- Synthesis, DNA affinity, and antiprotozoal activity of fused ring dicationic compounds and their prodrugs
-
Dicationic guanidine, N-alkylguanidine, and reversed amidine derivatives of fused ring systems (9a-d, 12a-c, 13a, and 13b) have been synthesized from their corresponding bis-amines. DNA binding studies suggest that the diguanidines and the N-alkyl diguanidines fluorenes bind in the minor groove in a manner similar to that of the previously reported dicationic carbazole derivatives. The diguanidines and the N-alkyl diguanidines showed promising in vitro activity against both Trypanosoma brucei rhodesiense and Plasmodium falciparum. Promising in vivo biological results were obtained for the dicationic N-isopropylguanidino-9H-fluorene (12c), giving 4/4 cures of the treated animals in the STIB900 animal model for African trypanosomiasis. The N-methyl analogue (12a) showed high activity as well. In addition, with the goal of enhancing the oral bioavailability, two novel classes of potential guanidine prodrugs were prepared. The N-alkoxyguanidine derivatives (12d) and (12e) were not effective as prodrugs. In contrast, a number of the carbamates (11a,c-e) showed promising activity. The value of the carbamate prodrugs was clearly demonstrated by the results for (11c), which gave 4/4 cures on oral administration in the STIB900 mouse model.
- Arafa, Reem K.,Brun, Reto,Wenzler, Tanja,Tanious, Farial A.,Wilson, W. David,Stephens, Chad E.,Boykin, David W.
-
-
Read Online
- 2,7-Disubstituted amidofluorenone derivatives as inhibitors of human telomerase
-
Telomerase is a major new target for the rational design of novel anticancer agents. We have previously identified anthraquinone-based molecules capable of inhibiting telomerase by stabilizing G-quadruplex structures formed by the folding of telomeric DNA
- Perry, Philip J.,Read, Martin A.,Davies, Rhian T.,Gowan, Sharon M.,Reszka, Anthony P.,Wood, Alexis A.,Kelland, Lloyd R.,Neidle, Stephen
-
-
Read Online
- An expeditious and highly efficient synthesis of substituted pyrroles using a low melting deep eutectic mixture
-
An expeditious green method for the synthesis of diverse valued substituted pyrroles through a Paal-Knorr condensation reaction, using a variety of amines and 2,5-hexanedione/2,5-dimethoxytetrahydrofuran in the presence of a low melting mixture ofN,N’-dimethylurea andL-(+)-tartaric acid (which acts as a dual catalyst/solvent system), has fruitfully been revealed. Herein, we have disclosed the applicability of this simple yet effective strategy for the generation of mono- and dipyrroles in good to excellent yields. Moreover,C3-symmetric tripyrrolo-truxene derivatives have also been assembled by means of cyclotrimerization, Paal-Knorr and Clauson-Kaas reactions as crucial steps. Interestingly, the melting mixture was recovered and reused with only a gradual decrease in the catalytic activity (over four cycles) without any significant drop in the yield of the product. This particular methodology is simple, rapid, environmental friendly, and high yielding for the generation of a variety of pyrroles. To the best of our knowledge, the present work reveals the fastest greener method reported up to this date for the construction of substituted pyrroles by utilizing the Paal-Knorr synthetic protocol, achieving impressive yields under operationally simple reaction conditions without involving any precarious/dangerous catalysts or unsafe volatile organic solvents.
- Alvi, Shakeel,Ali, Rashid
-
p. 9732 - 9745
(2021/12/01)
-
- METHODS FOR PRODUCING DIAMINOFLUORENOL
-
The present invention relates to a method for producing diaminofluorenol, and more particularly, to a 2,7-diamino-9H-fluoren-9-ol compound and a method for producing the same. According to the present invention, it is possible to provide a diaminofluorenol-based compound that can be favorably used as an intermediate important for the synthesis of diaminofluorenol compounds of various embodiments in a high yield and simple synthesis process. The compound is represented by chemical formula 1.COPYRIGHT KIPO 2020
- -
-
Paragraph 0114-0118
(2020/09/08)
-
- COMPOSITIONS AND METHODS OF MAKING EXPANDED HEMATOPOIETIC STEM CELLS USING DERIVATIVES OF FLUORENE
-
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 CD34+ 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.
- -
-
Paragraph 0400
(2019/05/15)
-
- A New Photocage Derived from Fluorene
-
Photolabile protecting groups (PPGs or photocages) are increasingly subject to molecular design to meet requirements such as absorbance in the visible spectral range, high molar absorption coefficients, and high quantum yields of leaving group release. Improvements in these properties for the promising 3-diethylaminobenzyl (DEAMb) photocage, the photoactivity of which is based on the Zimmerman meta effect, are reported. Expansion of the aromatic system with a second aromatic ring resulted in improved spectral properties. A systematic trend relating the electronic (π-donor or acceptor) properties of the new aryl substituent and its position in the DEAMb ring to changes in the spectral properties could be observed. Conclusions from the experimental results were supported by computations obtained by using time-dependent DFT. A second generation of DEAMb-based photocages was designed. A rigid linker was introduced to ensure more efficient conjugation of the aromatic ring π systems by limiting rotational freedom. The resulting fluorenol (9-hydroxyfluorene)-based photocages had superior spectral properties to those of simple biphenyl systems. The best uncaging cross section achieved was 5320 m?1 cm?1 (?Φ365).
- Reinfelds, Matiss,von Cosel, Jan,Falahati, Konstantin,Hamerla, Carsten,Slanina, Tomá?,Burghardt, Irene,Heckel, Alexander
-
supporting information
p. 13026 - 13035
(2018/09/10)
-
- BENZIDINE DERIVATIVE, METHOD FOR PREPARING SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING BENZIDINE DERIVATIVE FOR TREATING LIVER DISEASE CAUSED BY HEPATITIS C VIRUS
-
The disclosed compounds have antiviral activity against C-type virus, an optical isomer thereof, a pharmaceutically acceptable salt thereof, a method for preparing the same, and a pharmaceutical composition containing the same as an active ingredient for preventing or treating liver disease caused by hepatitis C virus. The benzidine derivative according to the present invention has excellent antiviral activity against hepatitis C virus and exhibits excellent medicinal activity in the living body, and thus the pharmaceutical composition containing the same as an active ingredient can be useful as a pharmaceutical composition for preventing or treating liver disease, such as acute hepatitis C, chronic hepatitis C, cirrhosis, or hepatocellular carcinoma, caused by C-type virus.
- -
-
Paragraph 0205; 0206; 0207; 0208; 0209
(2016/02/24)
-
- High-planarity diamine monomer containing fluorene or fluorenone structure and synthesis method and application thereof
-
The invention discloses a high-planarity diamine monomer containing a fluorene or fluorenone structure and a synthesis method and application thereof.Halogen atoms of dihalogenation fluorene or fluorenone react with amidogen to form secondary amine; or di
- -
-
Paragraph 0075; 0076; 0077
(2016/10/08)
-
- Novel benzidine and diaminofluorene prolinamide derivatives as potent hepatitis C virus NS5A inhibitors
-
Our study describes the discovery of a series of highly potent hepatitis C virus (HCV) NS5A inhibitors based on symmetrical prolinamide derivatives of benzidine and diaminofluorene. Through modification of benzidine, l-proline, and diaminofluorene derivatives, we developed novel inhibitor structures, which allowed us to establish a library of potent HCV NS5A inhibitors. After optimizing the benzidine prolinamide backbone, we identified inhibitors embedding meta-substituted benzidine core structures that exhibited the most potent anti-HCV activities. Furthermore, through a battery of studies including hERG ligand binding assay, CYP450 binding assay, rat plasma stability test, human liver microsomal stability test, and pharmacokinetic studies, the identified compounds 24, 26, 27, 42, and 43 are found to be nontoxic, and are expected to be effective therapeutic anti-HCV agents.
- Bae, Il Hak,Kim, Hee Sun,You, Youngsu,Chough, Chieyeon,Choe, Weonu,Seon, Min Kyung,Lee, Seung Gi,Keum, Gyochang,Jang, Sung Key,Moon Kim
-
p. 163 - 178
(2015/07/07)
-
- Discovery, synthesis and structure-activity analysis of symmetrical 2,7-disubstituted fluorenones as urea transporter inhibitors
-
Kidney urea transporters are targets for development of small-molecule inhibitors with action as salt-sparing diuretics. A cell-based, functional high-throughput screen identified 2,7-bisacetamido fluorenone 3 as a novel inhibitor of urea transporters UT-A1 and UT-B. Here, we synthesized twenty-two 2,7-disubstituted fluorenone analogs by acylation. Structure-activity relationship analysis revealed: (a) the carbonyl moiety at C9 is required for UT inhibition; (b) steric limitation on C2, 7-substituents; and (c) the importance of a crescent-shape structure. The most potent fluorenones inhibited UT-A1 and UT-B urea transport with IC50 ～ 1 μM. Analysis of in vitro metabolic stability in hepatic microsomes indicated metabolism of 2,7-disubstituted fluorenones by reductase and subsequent elimination. Computational docking to a homology model of UT-A1 suggested UT inhibitor binding to the UT cytoplasmic domain at a site that does not overlap with the putative urea binding site.
- Lee, Sujin,Esteva-Font, Cristina,Phuan, Puay-Wah,Anderson, Marc O.,Verkman
-
supporting information
p. 1278 - 1284
(2015/07/15)
-
- Photochromism of dihydroindolizines: Part XIV. Synthesis and photophysical behavior of photochromic dihydroindolizine-tripodal linkers toward anchoring sensitizers to semiconductor nanoparticles
-
Photochromic dihydroindolizines (DHIs) 4a,5-dihydropyrrolo[1,2-b]pyridazine based tripodal-linker systems with adamantane core and ethyl benzoate tripods as anchoring groups have been successfully synthesized. In addition, new spirocyclopropene precursors have been prepared through both chemical and photochemical processes. The photochromic properties of the newly synthesized DHIs derivatives have been optimized and fine-tuned by the incorporation of various substituents on the fluorene (region A) and pyridazine (region C) moieties. Several alternative routes for the synthesis of the DHIs under investigation have been established. The Sonogashira crosscoupling reaction was utilized for fragment coupling between DHIs and the phenylacetylene tether of the adamantane core. Several reaction conditions of this key reaction were surveyed to obtain optimal yields of a new series of coupling products targeted for anchoring to semiconductor nanoparticles. The chemical structures of the newly synthesized materials were elucidated by both analytical and spectroscopic tools. Irradiation of the photochromic DHIs with polychromatic light resulted in ring opened colored betaines which underwent cycloreversion reactions via thermal 1,5-electrocyclization processes. The kinetic of the thermal 1,5-electrocyclization was studied by using a UV/VIS/NIR spectrophotometer. The kinetic measurements showed the half-lives of the colored betaines to be in the second domain. A pronounced increase in the half-lives of betaines bearing dimethyl-substituted pyridazine was noted compared with non-substituted pyridazine betaines. A strong effect of solvent polarity on the λmax and half-lives of the betaines was observed. The further adjustment of the absorption maxima and the kinetic properties via the manipulation of substituents on the fluorene (region A) and pyridazine moieties (region C) should yield more refined systems for application as supports onto metal-oxide surfaces which remains an active area of our ongoing research. Copyright
- Ahmed, Saleh Abdel-Mgeed,Al-Raqa, Shaya Y.
-
scheme or table
p. 173 - 184
(2011/10/02)
-
- Facile and selective aerobic oxidation of arylalkanes to aryl ketones using cesium carbonate
-
Various arylalkanes such as fluorenes, xanthene, anthrone, 9,10-dihydroanthracene, and diphenylmethane are effectively transformed into the corresponding aryl ketones, while amino and aldehyde functionalities remain intact, under air in the presence of cesium carbonate. Georg Thieme Verlag Stuttgart.
- Park, Kwanghee Koh,Tsou, Lun K.,Hamilton, Andrew D.
-
p. 3617 - 3620
(2008/03/13)
-
- Synthesis of conjugated 2,7-bis(trimethylsilylethynyl)-(phenylethynyl) nfluoren-9-one and 9-(p-methoxyphenyl)-9-methyl derivatives: Optical properties
-
2,7-Substituted 9-fluorenones and 9,9-disubstituted fluorene have been synthesized and their fluorescence properties analyzed. The synthesis of conjugated 2,7-bis(trimethylsilylethynyl)-(phenylethynyl)nfluoren-9- one (or the 9-(p-methoxyphenyl)
- Rodríguez, J. Gonzalo,Tejedor, J. Luis,La Parra, Teresa,Díaz, Cristina
-
p. 3355 - 3361
(2007/10/03)
-
- FLUORENES AND ANTHRACENES THAT INHIBIT P2X3 AND P2X2/3 CONTAINING RECEPTORS
-
Compounds of formula (I) are novel P2X3 and P2X2/P2X3 containing receptor antagonists and are useful in treating pain, urinary incontinence, and bladder overactivity.
- -
-
Page/Page column 11
(2008/06/13)
-
- Azine-based dimeric charge transport materials
-
Improved organophotoreceptor comprises an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising: (a) a charge transport material having the formula 1 where R1, R2, R3, and R4 comprise, each independently, an alkyl group, an alkenyl group, an aromatic group, a heterocyclic group, or a part of a ring group; X and X′ comprise, each independently, an aromatic group; Y and Y′ comprise, each independently, a (disubstituted)methylene group; and Z is a linking group; (b) a charge generating compound; and (c) an electrically conductive substrate on which said charge transport material and said charge generating compound are located. Corresponding electrophotographic apparatuses and imaging methods are also described.
- -
-
-
- Effects of additional linkers in biphenyl-4,4′-dinitrene on the low-lying singlet-triplet energy gap and zero-field splitting
-
Perturbation effects of additional linkers on the spin-spin coupling in biphenyl-4,4′-dinitrene (1) were examined by introducing a linking group between 2- and 2′-positions of 1. Five different doubly linked systems showed triplet ESR spectra corresponding to quinonoid dinitrenes. Curie law analyses suggested that all those triplet states were thermally excited triplet states. In addition, the singlet-triplet energy gaps, which were determined by the Curie law analyses, were well correlated with their corresponding zero-field-splitting (zfs) D values. The result could be explained by the stability of dinitrene character which is estimated from the resonance energy of the intervening π-system. Our semiempirical molecular orbital calculations supported the experimental correlation between the singlet-triplet energy gap and the zfs D value.
- Nimura,Kikuchi,Ohana,Yabe,Kondo,Kaise
-
p. 2083 - 2088
(2007/10/03)
-
