- Electron Push-Pull Effects on Intramolecular Charge Transfer in Perylene-Based Donor-Acceptor Compounds
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A series of asymmetric donor-acceptor (D-A) perylene-based compounds, 3-(N,N-bis(4′-(R)-phenyl)amino)perylene (Peri-DPA(R)), were successfully prepared to explore their intramolecular charge transfer (ICT) properties. To induce ICT between the donor and acceptor, diphenylamine (DPA) derivatives (electron donor units) with the same functional groups (R = CN, F, H, Me, or OMe) at both para positions were linked to the C-3 position of perylene to produce five Peri-DPA derivatives. A steady-state spectroscopy study on Peri-DPA(R)s exhibited a progressively regulated ICT trend consistent with the substituent effect as it progressed from the electron-withdrawing group to the electron-donating group. In particular, a comparative study using a D-A-D (donor-acceptor-donor) system demonstrated that not only the electron push-pull substituent effect but also subunit combinations influence photophysical and electrochemical properties. The different ICT characters observed in Lippert-Mataga plots of D-A(CN) and D-A-D(CN) (CN-substituted D-A and D-A-D) led to the investigation on whether ICT emission of two systems with differences in subunit combinations is of the same type or of a different type. The femtosecond transient absorption (fs-TA) spectroscopic results provided direct evidence of ICT origin and confirmed that D-A(CN) and D-A-D(CN) exhibited the same transition mix of ICT (from donor to acceptor) and reverse ICT (rICT, from arylamine to CN unit). Density functional theory (DFT)/TD-DFT calculations support the presence of ICT for all five compounds, and the experimental observations of rICT presented only for CN-substituted compounds.
- Ahn, Mina,Kim, Min-Ji,Cho, Dae Won,Wee, Kyung-Ryang
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p. 403 - 413
(2020/12/23)
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- Design, synthesis and structure-activity relationship study of novel urea compounds as FGFR1 inhibitors to treat metastatic triple-negative breast cancer
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Triple-negative breast cancer (TNBC) is an aggressive type of cancer characterized by higher metastatic and reoccurrence rates, where approximately one-third of TNBC patients suffer from the metastasis in the brain. At the same time, TNBC shows good responses to chemotherapy, a feature that fuels the search for novel compounds with therapeutic potential in this area. Recently, we have identified novel urea-based compounds with cytotoxicity against selected cell lines and with the ability to cross the blood-brain barrier in vivo. We have synthesized and analyzed a library of more than 40 compounds to elucidate the key features responsible for the observed activity. We have also identified FGFR1 as a molecular target that is affected by the presence of these compounds, confirming our data using in silico model. Overall, we envision that these compounds can be further developed for the potential treatment of metastatic breast cancer.
- Akwii, Racheal,Alvina, Karina,Ashraf-Uz-Zaman, Md,Farshbaf, Mohammad Jodeiri,German, Nadezhda A.,Kallem, Raja Reddy,Mikelis, Constantinos M.,Putnam, William,Sajib, Md Sanaullah,Shahi, Sadisna,Trippier, Paul C.,Wang, Wei,Zhang, Ruiwen
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supporting information
(2020/10/12)
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- ORGANIC COMPOUNDS, LIGHT EMITTING DIODE AND LIGHT EMITTING DEVICE HAVING THE COMPOUNDS
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The present invention relates to an organic compound having a condensed aromatic core with a fluorene moiety and substituted with one or more functional groups having excellent hole transport properties, and a light emitting diode and a light emitting device using the same. According to the present invention, the organic compound can be introduced into a light emitting diode by using a solution process, and has a very deep HOMO energy level. When the organic compound of the present invention is applied to a hole transport layer, a band gap of the HOMO energy level between the hole transport layer and a light emitting material layer can be reduced, and thus holes and electrons can be injected into the light emitting material layer in a balanced manner. Accordingly, the light emitting diode and the light emitting device capable of low-voltage driving with higher light emitting efficiency can be implemented.COPYRIGHT KIPO 2020
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Paragraph 0214; 0219-0222
(2020/08/07)
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- Electron Push-Pull Effects in 3,9-Bis(p-(R)-diphenylamino)perylene and Constraint on Emission Color Tuning
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A series of perylene-based donor-acceptor-donor (D-A-D) compounds, 3,9-bis(p-(R)-diphenylamino)perylene (R: CN (2a), F (2b), H (2c), Me (2d), and OMe (2e)), was synthesized using 3,9-dibromoperylene with p-(R)-diphenylamine, and the intramolecular charge transfer (ICT) on the D-A-D system with regard to the electron push-pull substituent effect was investigated. By introducing various p-(R)-diphenylamine derivatives with electron-donating or electron-withdrawing R groups, the energy band gaps of the D-A-D compounds were systematically controlled and the emission colors were efficiently tuned from green to red. As expected, the steady state emission spectra of all D-A-D compounds were observed, as well as the emission color controlled, depending on the Hammett substituent constants (σp). In the Lippert-Mataga plots, a different charge-transfer character was observed depending on the electron push-pull substitution, which showed gradually increased ICT characters from the electron-withdrawing to donating substitution. However, exceptionally, the strong electron-withdrawing group of CN-substituted 2a did not correlate with the other R group compounds. From the experimental data and density functional theory calculations, we assume that there is a constraint on emission color tuning to generate higher energy of blue emission in the D-A-D molecular system, due to the reverse charge-transfer property caused by the strong electron-withdrawing group.
- Ahn, Mina,Kim, Min-Ji,Wee, Kyung-Ryang
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p. 12050 - 12057
(2019/10/11)
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- Tuning the Photophysical Properties of Symmetric Squarylium Dyes: Investigation on the Halogen Modulation Effects
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A series of symmetric squarylium dyes (SQDPA-X) with different halogen (X=F, Cl, Br, I) substituents have been developed. The photophysical properties could be facilely tuned by the halogen modulation effects. The strategy of incorporating different halogen substitutions into AIE active luminogens enables a facile approach for exploring new intriguing organic fluorescent dyes.
- Chen, Weiben,Zhang, Simeng,Dai, Gaole,Chen, Ying,Li, Miao,Zhao, Xiaoyu,Chen, Yulan,Chen, Long
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supporting information
p. 469 - 473
(2019/01/04)
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- Analogs of penfluridol as chemotherapeutic agents with reduced central nervous system activity
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Several recent reports have highlighted the feasibility of the use of penfluridol, a well-known antipsychotic agent, as a chemotherapeutic agent. In vivo experiments have confirmed the cytotoxic activity of penfluridol in triple-negative breast cancer model, lung cancer model, and further studies have been proposed to assess its anticancer activity and viability for the treatment of glioblastomas. However, penfluridol anticancer activity was observed at a dosage significantly higher than that administered in antipsychotic therapy, thus raising the concern for the potential onset of CNS side effects in patients undergoing intensive pharmacological treatment. In this study, we evaluate the potential CNS toxicity of penfluridol side by side with a set of analogs.
- Ashraf-Uz-Zaman, Md,Sajib, Md Sanaullah,Cucullo, Luca,Mikelis, Constantinos M.,German, Nadezhda A.
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supporting information
p. 3652 - 3657
(2018/11/03)
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- An electroluminescent compound and an electroluminescent device comprising the same
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The present invention relates to an organic light emitting compound adopted to an organic electroluminescent device. The organic light emitting compound is represented by chemical formula 1. In the case of adopting the same as a dopant compound or a hole transfer compound in a luminous layer, an organic electroluminescent device having excellent luminous characteristics such as driving voltage, brightness, long lifespan, and the like, can be embodied.COPYRIGHT KIPO 2016
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Paragraph 0088-0091; 0109-0112; 0154-0157
(2016/10/20)
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- Synthesis of benzo-γ-sultams via the Rh-catalyzed aromatic C-H functionalization of diazosulfonamides
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An efficient synthesis of 1-aryl-benzo-γ-sultams, 1-aryl-1,3-dihydrobenzo[c]isothiazole-2,2-dioxides, was achieved in 65-99% yields via the Rh-catalyzed intramolecular aromatic C-H functionalization of N,N-diaryl diazosulfonamides with 0.5 mol% Rh2(oct)4 as the catalyst. This journal is the Partner Organisations 2014.
- Yang, Zhanhui,Xu, Jiaxi
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supporting information
p. 3616 - 3618
(2014/04/03)
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- O-iodoxybenzoic acid mediated N-arylation of aromatic amines by using arylhydrazines as the arylating counterpart
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Through free-radical trapping experiments we have established, for the first time, the combination of arylhydrazines with o-iodoxybenzoic acid (IBX) for the generation of aryl free radicals. On the basis of this finding, a method was developed for the N-arylation of aromatic amines under mild conditions (base-free, -5 °C) by using arylhydrazines as the arylating counterpart and arylamines. The scope of this method was demonstrated by using a number of arylhydrazines and arylamines, which gave the N-arylated amines in good yields. Through free-radical trapping experiments, the present work describes the combination of arylhydrazines with o-iodoxybenzoic acid (IBX) for the generation aryl free radicals. This finding is exploited in the development of a mild method for the N-arylation of arylamines by using arylhydrazines as the arylating agents. The scope of this method is demonstrated through a number of examples. Copyright
- Jadhav, Ravindra R.,Huddar, Sameerana N.,Akamanchi, Krishnacharya G.
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supporting information
p. 6779 - 6783
(2013/11/06)
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- Selective one-pot synthesis of symmetrical and unsymmetrical di- and triarylamines with a ligandless copper catalytic system
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The one-pot synthesis of symmetrical or unsymmetrical di- or triarylamines using aryl iodides or bromides and LiNH2 as ammonia source is reported. This highly selective method is based, for the first time, on a copper-catalyzed system, which does not require the presence of any additional ligand.
- Tlili, Anis,Monnier, Florian,Taillefer, Marc
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supporting information; experimental part
p. 6408 - 6410
(2012/07/27)
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- A simple access to symmetric diarylamines via copper(II)-catalyzed coupling of aqueous ammonia with arylboronie acids
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A simple and efficient CuII-catalyzed coupling reaction of arylboronic acids with aqueous ammonia under air is described. The reaction was conducted under atmospheric pressure and no additional ligand was required. Benzoic acid was added to tune the basicity of the reaction system. Copyright
- Zhou, Changfeng,Chen, Fan,Yang, Dongpeng,Jia, Xiaofei,Zhang, Lixue,Cheng, Jiang
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supporting information; experimental part
p. 708 - 709
(2011/04/22)
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- The use of hydroxylamine hydrochloride in the Chan-Lam reaction: A simple access to symmetric diarylamines
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A CuBr-catalyzed coupling reaction of hydroxylamine hydrochloride and arylboronic acids is described, providing a simple and efficient methodology for the synthesis of symmetric diaryl amines. The reaction shows good functional group tolerance. Georg Thie
- Zhou, Changfeng,Yang, Dongpeng,Jia, Xiaofei,Zhang, Lixue,Cheng, Jiang
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scheme or table
p. 3198 - 3200
(2010/03/31)
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- Synthesis of diarylamines catalyzed by iron salts
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A study was conducted to demonstrate the synthesis of diarylamines catalyzed by iron salts. The study evaluated the influence acetyl as an N-protecting group. The coupling of acetanilide and iodobenzene was selected as a model reaction, to optimize the reaction conditions. It was observed that a considerable amount of the N-deprotected compound was obtained along with the desired N-acetyl diarylamine. It was also observed that diphenylamine was isolated in a significant yield, by performing a basic hydrolysis with NaOMe after the iron-catalyzed arylation. A one-pot synthesis of diphenylamine was performed by adding NaOMe to the N-arylation reaction mixture, after the acetanilide was consumed completely. It was demonstrated that the strategy overcomes the synthetic limitations associated with poor reactivity of aromatic amines under iron catalysis and serves as an alternative approach for the preparation of diarylamines.
- Correa, Arkaitz,Carril, Monica,Bolm, Carsten
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supporting information; experimental part
p. 10919 - 10922
(2009/11/30)
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- AMINO-SUBSTITUTED AZO-HETEROCYCLIC COMPOUNDS FOR TREATING INFLAMMATORY CONDITIONS
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Compounds of formula (I) are CRTH2 antagonists, useful in the treatment of inflammatory, autoimmune, respiratory or allergy disease: wherein X1 is -S-, -O-, -N=N-. -NR5-, -CR5=CR6-, -CR5=N-, wherein R5 and R6 are independently hydrogen or C1-C3 alkyl; R1 is hydrogen or C1-C3 alkyl or cyclopropyl; R2 is an optionally substituted phenyl or 5- or 6-membered monocyclic heteroaryl ring; R3 is an optionally substituted carbocyclic ring of 3 to 7 ring atoms, or an optionally substituted 4-, 5- or 6-membered monocyclic heterocyclic ring; R4 is a group other than hydrogen, methyl or ethyl of formula Q-[Alk1]m-[X]n-[Alk2]p-[Z}s- wherein m, n p, and s are independently 0 or 1 ; Q is hydrogen or an optionally substituted 4-, 5- or 6-membered monocyclic heterocyclic ring; Alk1 and Alk2 are independently optionally substituted C1-C3 alkylene radicals; X is -O-, -S-, -C(=O)-, - S(=O)-, -S(=O)2-, -CH(R7)-, -N(R7)-, or, in either orientation -SO2N(R7)- or - C(=O)N(R7)-, wherein R7 is hydrogen, or R7 represents a C2-C4 bridge between the C or N atom of X to which it is attached and a carbon atom of Alk2 and Z is -CH2, - C(=O) or -S(=O)2.
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Page/Page column 20-21
(2008/06/13)
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- FUSED AND SPIROCYCLE COMPOUNDS AND THE USE THEREOF
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The invention relates to fused and spirocycle compounds of Formula (I), or a pharmaceutically acceptable salt, prodrug, or solvate thereof, wherein R1, R2, Q1-Q3, and Z are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula (I) to treat, prevent or ameliorate a disorder responsive to the blockade of calcium channels, and particularly N-type calcium channels. Compounds of the present invention are especially useful for treating pain.
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Page/Page column 98
(2008/06/13)
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- BENZENESULFONAMIDE COMPOUNDS AND THEIR USE AS BLOCKERS OF CALCIUM CHANNELS
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The invention relates to piperidinyl and hexahydroazepinyl compounds of Formula (I): and pharmaceutically acceptable salts, prodrugs, or solvates thereof, wherein R1-R3, Z and q are defined as set forth in the specification. The inve
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Page/Page column 151-152
(2010/11/28)
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- BENZENESULFONAMIDE COMPOUNDS AND THEIR USE
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The invention relates to azetidinyl, pyrrolidinyl, piperidinyl, and hexahydroazepinyl compounds of Formula I and pharmaceutically acceptable salts, prodrugs, or solvates thereof, wherein R1-R3 and Z are defined as set forth in the sp
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Page/Page column 118-119
(2008/06/13)
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- Metabolism investigation leading to novel drug design 2: Orally active prostacyclin mimetics. Part 5
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A metabolism study of FK788 (2) led to the discovery of new diphenylcarbamoyl derivatives as prostacyclin mimetics without the PG skeleton. We designed and evaluated PGI2 mimetics based on blocking the main metabolic pathway of FK788. The new compound 7c was found to be equipotent to FK788 towards PGI2 agonist activity and metabolically more stable than FK788.
- Takamura, Fujiko,Tanaka, Akira,Takasugi, Hisashi,Taniguchi, Kiyoshi,Nishio, Mie,Seki, Jiro,Hattori, Kouji
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p. 4475 - 4478
(2007/10/03)
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- HETEROCYCLIC MCHr1 ANTAGONISTS AND THEIR USE IN THERAPY
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Compounds of formula I depicted below, pharmaceutical compositions containing them, processes for preparing the compounds, and their use in the treatment of obesity, type II diabetes, metabolic syndrome, psychiatric disorders, cognitive disorders, memory disorders, schizophrenia, epilepsy and related conditions, neurological disorders such as dementia, multiple sclerosis, Parkinson's disease, Huntington's chorea and Alzheimer's disease, and pain related disorders. The compounds are melanin concentrating hormone receptor 1 (MCHr1) antagonists.
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Page/Page column 52
(2008/06/13)
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- Novel azido and isothiocyanato analogues of [3-(4-phenylalkylpiperazin-1- yl)propyl]bis(4-fluorophenyl)amines as potential irreversible ligands for the dopamine transporter
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Potential irreversible ligands were prepared, based on a series of 3-(1-piperazinyl)propyl-N/N-bis(4-fluorophenyl)amines, as molecular probes for the dopamine transporter (DAT). Both azidoand isothiocyanato-substituted phenylalkyl analogues were synthesiz
- Cao, Jianjing,Lever, John R.,Kopajtic, Theresa,Katz, Jonathan L.,Pham, Anh T.,Holmes, Muhsinah L.,Justice, Joseph B.,Newman, Amy Hauck
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p. 6128 - 6136
(2007/10/03)
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- [3-cis-3,5-dimethyl-(1-piperazinyl)alkyl]-bis-(4′-fluorophenyl)amine analogues as novel probes for the dopamine transporter
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In a continuing effort to identify novel probes with which to study the dopamine transporter (DAT), we discovered that the σ receptor antagonist, rimcazole, binds with moderate affinity (Ki=224 nM) to the DAT. The results from previous SAR stud
- Cao, Jianjing,Husbands, Stephen M.,Kopajtic, Theresa,Katz, Jonathan L.,Newman, Amy Hauck
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p. 3169 - 3173
(2007/10/03)
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- 1-piperidines and Related Compounds, Potential Antipsychotic Agents with Low Cataleptogenic Profiles
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On the basis of a structural model of the postsynaptic dopaminergic antagonist pharmacophore, a series of 1-piperidines and related compounds was synthesized and evaluated for potential antipsychotic activity.For a rapid measure of activity, the target compounds were initially screened in vitro for inhibition of haloperidol binding and in vivo in a test of locomotor activity.Behavioral efficacy of compounds identified from the initial screens was more accurately measured in rats by using a suppression of high base-line medial forebrain bundle self-stimulation test model.The propensity of these compounds for causing extrapyramidal side effects was evaluated by using a rat catalepsy method.On the basis of these test models, we have shown that the methine carbon of the 1-(4,4-diarylbutyl)piperidines can be advantageously replaced with a nitrogen atom.The 1-piperidines were less cataleptic than the corresponding 1-(4,4-diarylbutyl)piperidines.The compounds with the widest separation between efficacious dose and cataleptic dose are 8-propyl>-1-phenyl-1,3,8-triazaspirodecan-4-one (6), 1-propyl>-4-piperidinyl>-1,3-dihydro-2H-benzimidazol-2-one (11), 1-propyl>-1,2,3,6-tetrahydro-4-pyridinyl>-1,3-dihydro-2H-benzimidazol-2-one (22), and 1-propyl>-4-(2-methoxyphenyl)piperazine (26).
- Wise, Lawrence D.,Pattison, Ian C.,Butler, Donald E.,DeWald, Horace A.,Lewis, Edward P.,et al.
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p. 606 - 612
(2007/10/02)
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- Heteroylidene indolone compounds
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Certain substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones are highly potent gabaergic agents, valuable in the treatment of individuals suffering from schizophrenia or reversing the side effects of a previously or concurrently administered neuroleptic agent; or in the treatment of epilepsy. A wider class of substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones, together with 1-phenyl-3-(2-pyrrolidinylidene)-2(1H,3H)-indolones, and homologs thereof, are valuable in the treatment of anxiety.
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- Dynamics at the Active Site of Bis(4-fluorophenyl)carbamoyl-α-chymotripsin
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Treatment of α-chimotripsin with bis(4-fluorophenyl)carbamoyl chloride produces an inactive enzyme that has been stoichiometrically carbamoylated, presumably at the active site.Fluorine NMR spectra of this enzyme derivative show two broad signals separate
- Cairi, M.,Gerig J. T.
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p. 4793 - 4800
(2007/10/02)
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