- Regioselective aromatic substitution reactions of cyclometalated Ir(III) complexes: Synthesis and photochemical properties of substituted Ir(III) complexes that exhibit blue, green, and red color luminescence emission
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In this manuscript, the regioselective halogenation, nitration, formylation, and acylation of Ir(tpy)3 and Ir(ppy)3 (tpy = 2-(4/-tolyl)pyridine and ppy = 2-phenylpyridine) and the subsequent conversions are described. During attempte
- Aoki, Shin,Matsuo, Yasuki,Ogura, Shiori,Ohwada, Hiroki,Hisamatsu, Yosuke,Moromizato, Shinsuke,Shiro, Motoo,Kitamura, Masanori
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Read Online
- UV Light Generation and Challenging Photoreactions Enabled by Upconversion in Water
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Sensitized triplet-triplet annihilation (sTTA) is the most promising mechanism for pooling the energy of two visible photons, but its applications in solution were so far limited to organic solvents, with a current maximum of the excited-singlet state energy of 3.6 eV. By combining tailor-made iridium complexes with naphthalenes, we demonstrate blue-light driven upconversion in water with unprecedented singlet-state energies approaching 4 eV. The annihilators have outstanding excited-state reactivities enabling challenging photoreductions driven by sTTA. Specifically, we found that an aryl-bromide bond activation can be achieved with blue photons, and we obtained full conversion for the very energy-demanding decomposition of a persistent ammonium compound as typical water pollutant, not only with a cw laser but also with an LED light source. These results provide the first proof-of-concept for the usage of low-power light sources for challenging reactions employing blue-to-UV upconversion in water and pave the way for the further development of sustainable light-harvesting applications.
- Pfund, Bj?rn,Steffen, Debora M.,Schreier, Mirjam R.,Bertrams, Maria-Sophie,Ye, Chen,B?rjesson, Karl,Wenger, Oliver S.,Kerzig, Christoph
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supporting information
p. 10468 - 10476
(2020/07/27)
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- Ionic type iridium complex with double phosphorescence emission properties as well as preparation method and application of ionic type iridium complex
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The invention belongs to the technical field of organic photoelectric functional materials, and particularly relates to an ionic type iridium complex with double phosphorescence emission properties as well as a preparation method and an application of the ionic type iridium complex. The complex comprises a metal center and cyclometalated ligands. The preparation method comprises steps as follows: dichloro bridge is prepared from a phenylpyridine derivative and iridium(III) chloride trihydrate through a coordination reaction, and the ionic type iridium complex with the double phosphorescence emission properties is prepared from dichloro bridge and a dipyridyl derivative or sodium carbonate through coordination reaction. The ionic type iridium complex with the double phosphorescence emission properties can be applied to the fields of biological detection and biological imaging for hypoxic oxygen-enriched conditions; a diagnosis and treatment integrated multifunctional probe based on the ionic type iridium complex with the double phosphorescence emission properties has great potential in further biomedicine application.
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Paragraph 0036; 0042; 0043
(2018/01/11)
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- Discovery and structural optimization of 4-(4-(benzyloxy)phenyl)-3,4-dihydropyrimidin-2(1H)-ones as RORc inverse agonists
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Aim: Retinoic acid receptor-related orphan nuclear receptors (RORs) are orphan nuclear receptors that show constitutive activity in the absence of ligands. Among 3 subtypes of RORs, RORc is a promising therapeutic target for the treatment of Th17-mediated autoimmune diseases. Here, we report novel RORc inverse agonists discovered through structure-based drug design. Methods: Based on the structure of compound 8, a previously described agonist of RORa, a series of 4-(4-(benzyloxy)phenyl)-3,4-dihydropyrimidin-2(1H)-one derivatives were designed and synthesized. The interaction between the compounds and RORc was detected at molecular level using AlphaScreen assay. The compounds were further examined in 293T cells transfected with RORc and luciferase reporter gene. Thermal stability shift assay was used to evaluate the effects of the compounds on protein stability. Results: A total of 27 derivatives were designed and synthesized. Among them, the compound 22b was identified as the most potent RORc inverse agonist. Its IC50 values were 2.39 μmol/L in AlphaScreen assay, and 0.82 μmol/L in inhibition of the cell-based luciferase reporter activity. Furthermore, the compound 22b displayed a 120-fold selectivity for RORc over other nuclear receptors. Moreover, a molecular docking study showed that the structure-activity relationship was consistent with the binding mode of compound 22b in RORc. Conclusion: 4-(4-(Benzyloxy)phenyl)-3,4-dihydropyrimidin-2(1H)-one derivatives are promising candidates for the treatment of Th17-mediated autoimmune diseases, such as rheumatoid arthritis, psoriasis, and multiple sclerosis.
- Wu, Xi-Shan,Wang, Rui,Xing, Yan-Li,Xue, Xiao-Qian,Zhang, Yan,Lu, Yong-Zhi,Song, Yu,Luo, Xiao-Yu,Wu, Chun,Zhou, Yu-Lai,Jiang, Jian-Qin,Xu, Yong
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p. 1516 - 1524
(2016/11/11)
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- Calix[6]arene derivatives selectively functionalized at alternate sites on the smaller rim with 2-phenylpyridine and 2-fluorenylpyridine substituents to provide deep cavities
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The synthesis is described of calix[6]arene derivatives 4, 9, and 14 functionalized at alternate sites on the smaller rim with 4′-(pyrid- 2″-yl)phenylmethoxy, (6′-phenylpyrid-3′-ylmethoxy), and {6′-[2-(9,9-di-n-hexylfluorenyl)]pyrid-3′-ylmethoxy} substitu
- Zeng, Xianshun,Batsanov, Andrei S.,Bryce, Martin R.
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p. 9589 - 9594
(2007/10/03)
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- Tripeptide and tetrapeptide sulfones
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Tripeptide and tetrapeptide sulfones, pharmaceutical compositions containing them, their pharmaceutical use, and their preparation. The compounds are useful in potentiating the cytotoxic effects of chemotherapeutic agents in tumor cells, selectively exerting toxicity in tumor cells, elevating the production of GM progenitors in bone marrow cells, stimulating the differentiation of bone marrow, mitigating the myelosuppressive effects of chemotherapeutic agents, and modulating hematopoiesis in bone marrow.
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Page/Page column 8
(2008/06/13)
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- 2-phenylpyridine derivative and production method thereof
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A series of compounds capable of deriving an intermediate for the production of a compound (A) of the following formula, which is an anti-HIV drug, and a production method thereof. To be specific, 4-(pyridin-2-yl)benzaldehyde hydrazone, a production metho
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- N-AROYLAMINO ACID AMIDES AS ENDOTHELIN INHIBITORS
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The present invention relates to the compounds of formula (I) STR1 wherein R is carboxy, esterified carboxy, carbamoyl, N-(alkyl or aryl)-carbamoyl, cyano, 5-tetrazolyl or CONH--SO 2--R 4 ; R. sub.1 is hydrogen, lower alkyl, aryl-lower alkyl or cycloalkyl-lower alkyl; R 2 is hydrogen or lower alkyl, or R 1 and R 2 represent lower alkylene to form together with the carbon and nitrogen atoms to which they are attached an azacycloalkane ring; R 3 is heterocyclic or carbocyclic (aryl or biaryl)-lower alkyl; Y is lower alkylidenyl, 3-to 10-membered cycloalkylidenyl which may be substituted by oxo, alkylenedioxy, hydroxy, acyloxy, lower alkoxy; or Y is 5-to 10-membered cycloalkylidenyl fused to a saturated or unsaturated carbocyclic 5-or 6-membered ring; or Y is 5-to 8-membered oxacycloalkylidenyl, 5-to 8-membered (thia-, oxothia-or dioxothia-) cycloalkylidenyl, or 5-to 8-membered azacycloalkylidenyl optionally N-substituted by lower alkyl or aryl-lower alkyl; R 4 represents hydrogen, lower alkyl, carbocyclic aryl, heterocyclic aryl, cycloalkyl, (carbocyclic aryl, heterocyclic aryl, cycloalkyl, hydroxy, acyloxy, or lower alkoxy)-lower alkyl, lower alkyl substituted by carboxyl, by esterified carboxyl or by amidated carboxyl; Ar represents carbocyclic or heterocyclic aryl; and pharmaceutically acceptable salts thereof; which are useful as endothelin inhibitors in mammals.
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- Inhibitors of acyl-coA:cholesterol O-acyltransferase. 2. Identification and structure-activity relationships of a novel series of N-alkyl-N- (heteroaryl-substituted benzyl)-N'-arylureas
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A series of N-alkyl-N-(heteroaryl-substituted benzyl)-N'-arylurea and related derivatives represented by 2 and 3 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Among these novel compounds, the type 3 series was superior. A pyrazol-3-yl group on the N-benzyl group of this trisubstituted urea (i.e. 3, Ar1 = pyrazol-3- yl) was identified as a heteroaromatic ring providing a good profile of biological activity. As a result of optimization of the combination with the N-alkyl group (R) and N-aryl group (At3), compound 3aq (FR186054) was identified as a new, orally efficacious ACAT inhibitor, which exhibited potent in vitro ACAT inhibitory activity (rabbit intestinal microsomes IC50 = 99 nM) and excellent hypocholesterolemic effects in cholesterol-fed rats, irrespective of administration mode (ED50 = 0.046 mg/kg dosed via the diet, ED50 = 0.44 mg/kg administered by gavage in PEG400 vehicle). Moreover, a toxicological study revealed compound 3aq to be nontoxic to the adrenal glands of dogs when tested at a single dose of 10 mg/kg po.
- Tanaka, Akira,Terasawa, Takeshi,Hagihara, Hiroyuki,Sakuma, Yuri,Ishibe, Noriko,Sawada, Masae,Takasugi, Hisashi,Tanaka, Hirokazu
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p. 2390 - 2410
(2007/10/03)
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- Aromatic hydrazides as specific inhibitors of bovine serum amine oxidase
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New hydrazides were synthesized in search for specific inhibitors of bovine serum amine oxidase: a series of benzoic and phenylacetic acid hydrazides containing the 1H-imidazol-1-yl or the 1H-imidazol-1-ylmethyl group as (o,m,p)-substituent in the phenyl ring; an analogous series of p-substituted phenylhydrazides with 5 or 6-membered heterocyclic ring as substituent, and a series of similar phenylpropionic hydrazides. The longer and more flexible phenylacetic hydrazides, and to a somewhat lesser extent the phenylpropionic ones, were better specific inhibitors of bovine serum amine oxidase than the benzoic hydrazides, which were also bound by the enzyme with high affinity, but at a slow rate. Derivatives with p- and m-substituents were more reactive than the o-substituted ones. The chemical nature of the substituent was less important than its position in the phenyl ring and the presence of methylene spacers. These data point to the presence of a hydrophobic site at short distance from the protein carbonyl cofactor, so that simultaneous interaction of the 2 ends of the inhibitor molecule can occur at the 2 sites. The presence of the hydrophobic site was confirmed by the capability of some molecule deprived of the hydrazidic group to act as mild inhibitors. All hydrazides were less reactive by 2-3 orders of magnitude towards pig kidney diamine oxidase and FAD-dependent monoamine oxidase from rat brain mitochondria, while the other compounds showed similar inhibition power against all proteins. The specificity for the bovine enzyme seems therefore to be related to the concerted action of the 2 moieties of the inhibitor molecule.
- Artico,Silvestri,Stefancich,Avigliano,Di Giulio,Maccarrone,Agostinelli,Mondovi,Morpurgo
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p. 219 - 228
(2007/10/02)
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