- Zn2+ and Cu2+ complexes of a fluorescent scorpiand-type oxadiazole azamacrocyclic ligand: Crystal structures, solution studies and optical properties
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A ligand comprised of a macrocyclic pyridinophane core having a pendant arm containing a secondary amine group linked through a methylene spacer to a pyridyl-oxadiazole-phenyl (PyPD) fluorescent system has been prepared (L). The crystal structures of [ZnL](ClO4)2 and [CuL](ClO4)2 show that M2+ is coordinated to all the nitrogen atoms of the macrocyclic core, the secondary amine of the pendant arm and the nitrogen atom of the pyridine group of the fluorescent moiety, the latter bond being clearly weaker than the one with the pyridine of the macrocycle. Solution studies showed the formation of a highly stable Cu2+ complex with 1 : 1 stoichiometry, whereas with Zn2+ least stable complexes were formed and, given the right conditions, a [Zn3L2]6+ species was also detected, but it was not possible to isolate this species in the solid state. Following Zn2+ coordination, a strong chelation-induced enhancement of fluorescence was observed, a behaviour that was not observed with any of the other metal cations tested.
- Ambrosi, Gianluca,Formica, Mauro,Fusi, Vieri,García-Espa?a, Enrique,Inclán, Mario,Paoli, Paola,Paz Clares, M.,Pont, Isabel,Ricci, Angela,Rossi, Patrizia
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Read Online
- Two-way linkage photoisomerization of [Ru(2,2':6',2''-terpyridine)(6- {(methylsulfinyl)methyl}picolinate)]BF4
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[Ru(tpy)(picSO)]BF4 (tpy: 2,2':6',2''-terpyridine, picSO: 6- [(methylsulfinyl)methyl]picolinate) undergoes profound linkage isomerization behavior between stable S-bound and metastable O-bound isomers. S-[RuII(tpy)(picSO)]BF4 experiences photoisomerization to O-[RuII(tpy)(picSO)] BF4 upon irradiation with 436nm light, whereas the back reaction is triggered with 546nm light. Electrochemical linkage isomerization also takes place.
- Suzuki, Shoko,Sakamoto, Ryota,Nishihara, Hiroshi
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Read Online
- A deep insight into polybenzoxazole formation in the heterocycle-containing polybenzoxazine: An enlightening thought for smarter precursor design
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When artificially introducing an ortho-amide group into benzoxazine monomer, the conversion of polybenzoxazine (PBZ) into polybenzoxazole (PBO) could happen at higher temperature. However, the mechanism investigation for this reaction is far from enough,
- Liu, Jingkai,Cao, Lijun,Dai, Jinyue,Peng, Yunyan,Liu, Xiaoqing
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Read Online
- IRAK DEGRADERS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 00512; 00620-00622
(2021/06/26)
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- Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates
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Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.
- Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul
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supporting information
p. 5022 - 5037
(2021/05/04)
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- IRAK DEGRADERS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same. The compounds include an IRAK binding moiety capable of binding to IRAK4 and a degradation inducing moiety (DIM). The DIM could be DTM a ligase binding moiety (LBM) or lysine mimetic. The compounds could be useful as IRAK protein kinase inhibitors and applied to IRAK mediated disorders.
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Paragraph 00920; 001678-001680
(2021/01/23)
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- NOVEL NUCLEOSIDE OR NUCLEOTIDE DERIVATIVES, AND USES THEREOF
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The present disclosure relates to a novel nucleoside or nucleotide derivative, a racemate thereof, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof; and a pharmaceutical composition for preventing or treating viral infection-associated diseases, containing the same as an active ingredient.
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Paragraph 0062
(2020/12/10)
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- Discovery of Novel Aryl Carboxamide Derivatives as Hypoxia-Inducible Factor 1α Signaling Inhibitors with Potent Activities of Anticancer Metastasis
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In order to discover novel hypoxia-inducible factor 1 (HIF-1) inhibitors for the cancer metastasis treatment, 68 new aryl carboxamide compounds were synthesized and evaluated for their inhibitory effect by dual luciferase-reporter assay. Based on five rounds of investigation on structure-activity relationships step by step, compound 30m was discovered as the most active inhibitor (IC50 = 0.32 μM) with no obvious cytotoxicity (CC50 > 50 μM). It effectively attenuated hypoxia-induced HIF-1α protein accumulation and reduced transcription of vascular epidermal growth factor in a dose-dependent manner, which was further demonstrated by its inhibitory potency on capillary-like tube formation, angiogenesis of zebrafish as well as cellular migration and invasion. Importantly, compound 30m exhibited antimetastatic potency in breast cancer lung metastasis in the mice model, indicating its promising therapeutic potential for prevention and treatment of tumor metastasis. These results definitely merit attention for further rational design of more efficient HIF-1 inhibitors in the future.
- Liu, Mingming,Liang, Yuru,Zhu, Zhongzhen,Wang, Jin,Cheng, Xingxing,Cheng, Jiayi,Xu, Binpeng,Li, Rong,Liu, Xinhua,Wang, Yang
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p. 9299 - 9314
(2019/10/16)
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- Amide Effects in C?H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides
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A new concept for the meta-selective borylation of aromatic amides is described. It has been demonstrated that while esters gave para borylations, amides lead to meta borylations. For achieving high meta selectivity, an L-shaped bifunctional ligand has been employed and engages in an O???K noncovalent interaction with the oxygen atom of the moderately distorted amide carbonyl group. This interaction provides exceptional control for meta C?H activation/borylation.
- Bisht, Ranjana,Hoque, Md Emdadul,Chattopadhyay, Buddhadeb
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supporting information
p. 15762 - 15766
(2018/11/10)
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- Iridium(III)-Catalyzed Regioselective Intermolecular Unactivated Secondary Csp3?H Bond Amidation
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For the first time, a highly regioselective intermolecular sulfonylamidation unactivated secondary Csp3?H bond has been achieved using IrIIIcatalysts. The introduced N,N’-bichelating ligand plays a crucial role in enabling iridium–nitrene insertion into a secondary Csp3?H bond via an outer-sphere pathway. Mechanistic studies and density functional theory (DFT) calculations demonstrated that a two-electron concerted nitrene insertion was involved in this Csp3?H amidation process. This method tolerates a broad range of linear and branched-chain N-alkylamides, and provides efficient access to diverse γ-sulfonamido-substituted aliphatic amines.
- Xiao, Xinsheng,Hou, Cheng,Zhang, Zhenhui,Ke, Zhuofeng,Lan, Jianyong,Jiang, Huanfeng,Zeng, Wei
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supporting information
p. 11897 - 11901
(2016/11/16)
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- Rhodium(III)-catalyzed oxidative olefination of picolinamides: Convenient synthesis of 3-alkenylpicolinamides
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A rhodium(III)-catalyzed selective olefination of picolinamide derivatives has been developed. The reaction shows high regioselectivity, low catalyst loading (0.5 mol%), high yield and good functional group tolerance, providing a convenient strategy for the synthesis of 3-alkenylpicolinamides.
- Zhou, Jun,Li, Bo,Qian, Zhen-Chao,Shi, Bing-Feng
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supporting information
p. 1038 - 1046
(2014/04/03)
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- Rh(III)-catalyzed cascade oxidative olefination/cyclization of picolinamides and alkenes via C-H activation
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Rh(III)-catalyzed cascade oxidative alkenylation/cyclization of picolinamides and alkenes to furnish pyrido pyrrolone derivatives is described, in which three C-H bonds and one N-H bond broke, while one C-C bond and one C-N bond formed. The reaction proceeded with high yield and high regioselectivity and stereoselectivity. Moreover, copper acetate can also be used in catalytic amounts with O2 serving as the terminal oxidant.
- Cai, Shangjun,Chen, Chao,Shao, Peng,Xi, Chanjuan
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supporting information
p. 3142 - 3145
(2014/06/23)
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- PYRIDINE DERIVATIVES AS MICROBIOCIDES
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Compounds of formula (I) wherein the other substituents R1, R2, R3, and G are as defined in claim 1, and their use as microbiocides.
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Page/Page column 58
(2013/03/26)
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- 2-PYRIDIN-2-YL-QUINAZOLINE DERIVATIVES AS POTASSIUM CHANNEL MODULATING AGENTS FOR THE TREATMENT OF RESPIRATORY DISEASES
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This invention relates to novel pyridinyl-quinazoline derivatives and their use as potassium channel modulating agents. Moreover the invention is directed to pharmaceutical compositions useful for the treatment or alleviation of diseases or disorders associated with the activity of potassium channels.
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Page/Page column 8
(2009/12/24)
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- Catalytic enantioselective additions of indoles to nitroalkenes
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A new design principle that provides access to more active thiourea catalysts is described. Highly enantioselective additions of indoles to nitroalkenes are reported using a new quinolinium thioamide catalyst. Copyright
- Ganesh, Madhu,Seidel, Daniel
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supporting information; experimental part
p. 16464 - 16465
(2009/04/12)
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- Pyridine-2-carboxyamide derivatives
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The invention relates to compounds of formula I: wherein R1 to R3 are as defined in the specification, to processes for their preparation, to pharmaceutical compositions containing them, and to methods for treating CNS disorders.
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Page/Page column 17
(2008/06/13)
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- CONDENSED PYRIDINES AND PYRIMIDINES AND THEIR USE AS ALK-5 RECEPTOR LIGANDS
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Therapeutically active substituted quinoline and quinazoline compounds derivatives of formula (I) wherein X is N or CH, Y is NH, N (alkyl) or NH-CH2, and R2 and R3 are specified heterorings, the use thereof in therapy, particularly in the treatment or prophylaxis of disorders characterised by overexpression of transforming growth factor β (TGF-β), and pharmaceutical compositions for use in such therapy are disclosed.
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- High-Spin Iron(II) as a Semitransparent Partner for Tuning Europium(III) Luminescence in Heterodimetallic d - f Complexes
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The segmental ligand 2-{6-(N,N-diethylcarbamoyl)pyridin-2-yl}-1,1'-dimethyl-5,5'-methylene-2'-(6-methylpyridine-2-yl)bis[1H-benzimidazole] (L3) reacts with a stoichiometric mixture of Ln(III) (Ln = La, Eu, Gd) and M(II) (M = Zn, Fe) in acetonit
- Edder, Carine,Piguet, Claude,Buenzli, Jean-Claude G.,Hopfgartner, Gerard
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p. 3015 - 3024
(2007/10/03)
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- Lanthanide podates with predetermined structural and photophysical properties: Strongly luminescent self-assembled heterodinuclear d-f complexes with a segmental ligand containing heterocyclic imines and carboxamide binding units
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The segmental ligand 2-{6-[N,N-diethylcarbamoyl]pyridin-2-yl}-1,1'-dimethyl-5,5'-methylen e-2'-(5-methylpyridin-2-yl)bis[1H-benzimidazole] (L2) reacts with stoichiometric amounts of Ln(III) (Ln = La-Nd, Sm-Th, Tm-Lu, Y) and Zn(II) in acetonitri
- Piguet, Claude,Bünzli, Jean-Claude G.,Bernardinelli, Gérald,Hopfgartner, Gérard,Petoud, Stéphane,Schaad, Olivier
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p. 6681 - 6697
(2007/10/03)
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- Syntheses of Segmental Heteroleptic Ligands for the Self-Assembly of Heteronuclear Helical Supramolecular Complexes
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The development of a modified Phillips reaction allows the synthesis of complicated heteroleptic ligands based on pyridine and 1H-benzimidazole moieties.The key-step formation of aromatic 1H-benzimidazole rings from N-(2-nitroaryl)arenecarboxamides significantly improves the possibilities of the classical intermolecular Phillips reactions and can be applied to the synthesis of large oligo-multidentate units.Segmental heteroleptic ligands containing two different bidentate coordinating units (see 14) or bidentate and terdentate sites connected by 'diphenylmethane' (= methylenebis(phenylene)) spacers (see 15 and 16) were obtained in fair to good yield by using multistep syntheses following this strategy.Heterotrileptic ligands (bidentate-terdentate-bidentate, see 19 and 20; terdentate-terdentate-terdentate, see 23) requiring the simultaneous formation of four 1H-benzimidazole rings in one step were prepared and demonstrate the extended possibilities of this methodology.Data are presented to show that the milder conditions used for this modified Phillips reaction together with its flexibility are essential for the development of ligands adapted for the self-assembly of heteronuclear helical complexes.
- Piguet, Claude,Bocquet, Bernard,Hopfgartner, Gerard
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p. 931 - 942
(2007/10/02)
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- Antiallergic agents. III. N-(1H-tetrazol-5-yl)-2-pyridinecarboxamides
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A series of N-tetrazolylpyridinecarboxamides was prepared and evaluated for antiallergic activity by the passive cutaneous anaphylaxis assay. From the structure-activity relationships of this class of compounds, it was revealed that the N-tetrazolylcarbamoyl group as an acidic functionality is required to be at the 2-position of the pyridine nucleus and that the phenyl group as a substituent is not necessarily required for activity. 6-Methyl-N-(1H-tetrazol-5-yl)-2-pyridinecarboxamide showed good oral activity and low toxicity.
- Honma,Hanamoto,Hashiyama,et al.
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p. 125 - 128
(2007/10/02)
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