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Use of benzothiophene ring to improve the photovoltaic efficacy of cyanopyridinone-based organic chromophores: a DFT study

RSC Adv., 2024, 14,12841-12852
DOI: 10.1039/D3RA06817J, Paper
Open Access
Iqra Shafiq, Muhammad Khalid, Gul Maria, Nadeem Raza, Ataualpa A. C. Braga, Saifullah Bullo, Mohamed Khairy
The benzothiophene based chromophores (A1D1–A1D5) with A–π–A configuration were designed via end-capped tailoring with benzothiophene type acceptors using reference compound (A1R).
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A surface-independent bioglue using photo-crosslinkable benzophenone moiety

RSC Adv., 2024, 14,12966-12976
DOI: 10.1039/D4RA01866D, Paper
Open Access
Yue Shi, Xuelian Tao, Ping Du, Paul Pasic, Lars Esser, Hsien-Yeh Chen, Helmut Thissen, Peng-Yuan Wang
The UV-crosslinkable benzophenone (BP) “bio-glue” efficiently crosslinks with various surfaces and biomolecules. The beauty of this bio-glue lies in its simplicity and broad applicability, requiring no sophisticated equipment or reaction conditions.
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The CF3TMS adduct of anthraquinone as a monomer for making polymers with potential as separation membranes

Polym. Chem., 2024, 15,4312-4318
DOI: 10.1039/D4PY01002G, Communication
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Kim Jiayi Wu, John M. Tobin, Anli Ji, Yang Shi, Chunchun Ye, Gary S. Nichol, Alessio Fuoco, Mariagiulia Longo, Johannes C. Jansen, Neil B. McKeown
The CF3TMS adduct of anthraquinone reacts with diphenyl ether via a superacid-catalysed step-growth polymerisation to give a polymer (BTFMA-DPE) with promise for making gas separation membranes.
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Reducing Agent Triggered Templated Synthesis of Dynamic Covalent Poly(disulfide)s Nanonetwork: Remarkable Tuning in Noncovalent Encapsulation Stabilities and Cargo Release

Polym. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4PY01109K, Paper
Arun Mondal, S. K. Sujauddin, Dhiman Mondal, Soumya Kolay, Shuvajyoti Sarkar, Mijanur Rahaman Molla
Here, we demonstrated a new methodology for the templated synthesis of cross-linked poly(disulfide)s based dynamic covalent nanonetwork as highly stable potential delivery vehicle in the field of chemotherapeutic applications. The...
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DFT rationalization of the mechanism and selectivity in a gold-catalyzed oxidative cyclization of diynones with alcohols

Phys. Chem. Chem. Phys., 2024, Advance Article
DOI: 10.1039/D4CP01700E, Paper
Guowei Yan, Ji Ma, Simeng Qi, Alexander M. Kirillov, Lizi Yang, Ran Fang
The mechanism, regioselectivity, and chemoselectivity in a gold-catalyzed oxidative cyclization of diynones with alcohols to give furan-3-carboxylate derivatives were explored by density functional theory (DFT).
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Radiolytic degradation of selective actinide extractants from the bis-1,2,4-triazine family in cyclohexanone solutions

Phys. Chem. Chem. Phys., 2024, Advance Article
DOI: 10.1039/D4CP02623C, Paper
Adrian Sulich, Jan Grodkowski, Krzysztof Bobrowski
Absorption spectra of transients derived from bis-1,2,4-triazine ligands in cyclohexanone solutions mimicking the extraction system studied by pulse radiolysis. The addition of benzophenone and saturation by O2 protect ligands from radiation damage.
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The structural, electronic and thermodynamic properties of the designed p-benzoquinone based dicationic ionic liquids: insight from DFT–GD3 and QTAIM

Mol. Syst. Des. Eng., 2024, Advance Article
DOI: 10.1039/D4ME00119B, Paper
Hossein Roohi, Sajedeh Habibipour, Khatereh Ghauri
In this work, physicochemical properties of the dicationic ionic liquids [BTAD][A1–8]2 ([BTAD]2+ = [p-C6O2(N3H2)2]2+ and A1–8 = [CH3CO2], [CF3CO2], [N(CN)2], [CF3SO3], [ClO4], [BF4], [NTf2] and [PF6]) were theoretically investigated.
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Design of Fe and N co-decorated biomass-derived hierarchical porous carbon frameworks with boosted oxidase-like activity for hydroquinone detection

New J. Chem., 2024, 48,7197-7204
DOI: 10.1039/D4NJ00509K, Paper
Han Zhang, Xiaodan Qi, Zhifei Wang, Lihua Jin, Yehua Shen
An Fe and N co-decorated biomass-derived porous carbon framework with boosted oxidase-like activity was prepared and applied to sensitive hydroquinone detection.
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Hydroquinone colorimetric sensing based on core–shell structured CoFe2O4@N-GQDs@CeO2 nanocomposites as oxidase mimics

New J. Chem., 2024, 48,7323-7333
DOI: 10.1039/D4NJ00284A, Paper
Xuefang Lei, Yujin Li, Peiqing Guo, Mingzhu Qiu, Rang Meng, Shaohui Li, Dongxia Zhang, Nali Chen, Xibin Zhou
The core–shell structured CoFe2O4@N-GQDs@CeO2 nanocomposites were successfully synthesized by co-precipitation method, and CeO2 was uniformly dispersed on the shell layer with the help of nitrogen-doped graphene quantum dots (N-GQDs).
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Synthesis of 3,5-disubstituted isoxazoles by domino reductive Nef reaction/cyclization of β-nitroenones

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00232F, Paper
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Muhammad Ehtisham Ibraheem Khan, Tomas Lighuen Cassini, Marino Petrini, Alessandro Palmieri
β-Nitroenones were converted into 3,5-disubstituted isoxazoles via a domino reaction promoted by tin(II) dichloride. The protocol efficiently works under both microwave and flow conditions.
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Dehydrative alkynylation of 3-hydroxyisoindolinones with terminal alkynes for the synthesis of 3-alkynylated 3,3-disubstituted isoindolinones

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00190G, Paper
Kai-Cheng Yang, Shi-Lu Zheng, Zhong Wen, Yu-Shan Zhang, Hai-Liang Ni, Long Chen
A HOTf or Fe(OTf)3-catalyzed dehydrative alkynylation of 3-hydroxyisoindolinones with terminal alkynes was developed, which represents a brand-new procedure for the synthesis of 3-alkynylated 3,3-disubstituted isoindolinones.
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Diastereoselective synthesis of functionalized spiroindolines via intramolecular ipso-iodocyclization/nucleophile addition cascade reactions of indole-tethered ynones

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00112E, Paper
Debojyoti Bag, Sanghapal D. Sawant
Herein, we describe a highly diastereoselective approach for synthesizing polyfunctionalized spiroindolines from indolyl-ynones involving an ipso-iodocyclization/nucleophile addition cascade.
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Copper catalyzed dehydrogenative cyclization, alkenylation towards dihydroquinolinones

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00134F, Paper
Pari Keerthana, Fazlur-Rahman Nawaz Khan
An efficient copper-catalysized one-pot sequential synthesis of alkenylated quinolinyldihydroquinolinones is reported utilizing ketones, 1,3-cyclohexanediones, and benzyl alcohols via dehydrogenative cyclisation, followed by alkenylation. This highly straightforward method provides a mild...
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Total synthesis of diplofuranone A and diapolic acid A

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00433G, Communication
Dattatraya H. Dethe, Vimlesh Kumar, Nagabhushana C. Beeralingappa
The first and concise syntheses of the anticancer agent diplofuranone A and the fatty acid-derived metabolite diapolic acid A have been demonstrated using easily accessible and commercially available starting materials.
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Photogenerated chlorine radicals activate C(sp3)–H bonds of alkylbenzenes to access quinazolinones

Org. Biomol. Chem., 2024, 22,2968-2973
DOI: 10.1039/D4OB00129J, Communication
Xin-Yao Pan, Gui-Xia Sun, Fang-Ping Huang, Wen-Jian Qin, Qing-Hu Teng, Kai Wang
An Fe-catalyzed visible-light induced condensation of alkylbenzenes with anthranilamides has been developed.
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BBr3-mediated dearomative spirocyclization of biaryl ynones: facile access to spiro[5.5]dienones

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00274A, Communication
Gaurav Jaiswal, Subhas Chandra Pan
BBr3 mediated dearomative spirocyclization of biaryl ynones has been reported for the direct synthesis of spiro[5.5]dienones with a tri-substituted double bond.
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Exploring the mechanism of the reductive amination of acetophenones via Borch approach: the role of the acid catalyst

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00160E, Paper
João Pedro Albuquerque Souza, Amanda Krauskopf Jacobs, Leandro Piovan, Renan Borsoi Campos
The energetic viability of several mechanistic variations of the reductive amination of acetophenones via the Borch approach was reexamined through density functional theory calculations. The crucial involvement of the acid...
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Regioselective synthesis of 4-arylamino-1,2-naphthoquinones in eutectogel as a confined reaction medium using LED light

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00140K, Communication
R. Vara Prasad, Yogendra Kumar, R. Arun Kumar, Tohira Banoo, Subbiah Nagarajan
The use of a simple carbohydrate-derived eutectogel facilitating a LED-light-induced regioselective synthesis of 4-arylamino-1,2-naphthoquinones in good yields is reported.
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Efficient synthesis of SCF3-containing 3-alkenylquinoxalinones via three-component radical cascade reaction

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00363B, Paper
Si-Yu Wang, Chu Liu, Wei Yang, Zhong-Ying Tian, Lin Yuan, Long-Yong Xie
A three-component cascade reaction of quinoxalinones, alkynes and AgSCF3 toward complete E-selective SCF3-containing 3-alkenylquinoxalinones was developed.
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60fps scrolling using pointer-events: none

Paul Lewis did an interesting article a while back about avoiding unnecessary paints through disabling hover effects as the user scrolls, which is a great approach. The down side being managing all your hover states through a parent class. UPDATE: I’ve done a follow up article which demonstrates a more robust technique. .hover .element:hover { … Continue reading "60fps scrolling using pointer-events: none"




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Wages and the Value of Nonemployment [electronic journal].

National Bureau of Economic Research




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JanOne Inc. MarketLine Company Profile [electronic journal].

Marketline




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A facile self-saturation process enabling the stable cycling of a small molecule menaquinone cathode in aqueous zinc batteries

Chem. Sci., 2024, 15,17971-17978
DOI: 10.1039/D4SC04685D, Edge Article
Open Access
Shuo Li, Guoli Zhang, Qianrui Li, Tianshun He, Xiaoqi Sun
A facile self-saturation strategy, realized by the introduction of a hydrophobic methyl group on naphthoquinone, is demonstrated to suppress the dissolution of small molecule cathode materials and achieve stable cycling in aqueous zinc cells.
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Regioselectivity switches between anthraquinone precursor fissions involved in bioactive xanthone biosynthesis

Chem. Sci., 2024, Advance Article
DOI: 10.1039/D4SC06369D, Edge Article
Open Access
Xiao Jing Lv, Chun Zhi Ai, Li Rong Zhang, Xiu Xiu Ma, Juan Juan Zhang, Jia Peng Zhu, Ren Xiang Tan
BruN and BTG13 cleave chrysophanol hydroquinone into monodictyphenone and cephalanone F, respectively, with the regioselectivities found tunable via the key amino acid (AA) substitution strategy.
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Diphosphaenones: Beyond the Phosphorus Analogue of Enones

Chem. Sci., 2024, Accepted Manuscript
DOI: 10.1039/D4SC06462C, Edge Article
Open Access
Jieli Lin, Shihua Liu, Shunlin Zheng, Hansjörg Grützmacher, Cheng-Yong Su, Zhongshu Li
Phosphaenones, like their carbon analogue enones (C=C–C=O), are promising building blocks for synthetic chemistry and materials science. However, in contrast to the α- and β-phosphaenones, structurally and spectroscopically well-defined diphosphaenones...
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Pyridazinone-based derivatives as anticancer agents endowed with anti-microbial activity: molecular design, synthesis, and biological investigation

RSC Med. Chem., 2024, 15,3529-3557
DOI: 10.1039/D4MD00481G, Research Article
Mohamed K. S. El-Nagar, Mai I. Shahin, Mohammed F. El-Behairy, Ehab S. Taher, Mohamed F. El-Badawy, Marwa Sharaky, Dalal A. Abou El Ella, Khaled A. M. Abouzid, Mai Adel
Discovery of novel pyridazinone derivatives with dual antimicrobial and anticancer activities.
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Inhibition of monoamine oxidases by heterocyclic derived conjugated dienones: synthesis and in vitro and in silico investigations

RSC Med. Chem., 2024, Advance Article
DOI: 10.1039/D4MD00608A, Research Article
Sunil Kumar, Bishnu Prasad Pandey, Mohamed A. Abdelgawad, Mohammed M. Ghoneim, Rania B. Bakr, Hoon Kim, Bijo Mathew
A total of 18 heterocyclic derived conjugated dienones (CD1–CD18) were evaluated for their potential monoamine oxidase (MAO)-A/-B inhibitory activity.
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Generation and capture of naphthoquinonynes: a new frontier in the development of trypanocidal quinones via aryne chemistry

RSC Med. Chem., 2024, Advance Article
DOI: 10.1039/D4MD00558A, Research Article
Laura P. R. Figueroa, Renato L. de Carvalho, Renata G. Almeida, Esther R. S. Paz, Emilay B. T. Diogo, Maria H. Araujo, Warley S. Borges, Victor F. S. Ramos, Rubem F. S. Menna-Barreto, James M. Wood, John F. Bower, Eufrânio N. da Silva Júnior
This article presents A-ring functionalized quinones via a modern and efficient new strategy involving the generation and capture of benzyne quinones and their evaluation against Trypanosoma cruzi.
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Asymmetric synthesis of (aza)flavanones by the evolution of CarOx ligands

Org. Chem. Front., 2024, 11,6444-6449
DOI: 10.1039/D4QO01345J, Research Article
Juan Yang, Wenlong Kong, Mingxin Chang, Jixing Lai, Shengkun Li
Amino-pyridine-oxazoline (NHPyOx) is conceived as an unprecedented model via the core-emulating optimization of CarOx ligands.
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Well-defined chiral dinuclear copper-catalyzed tandem asymmetric propargylic amination–carboxylative cyclization sequence toward chiral 2-oxazolidinone derivatives

Org. Chem. Front., 2024, 11,6319-6326
DOI: 10.1039/D4QO01368A, Research Article
Yu Lan, Peng Liu, Zekai Fang, Lili Shao, Qilong Cai, Xiaoming Wang
A variety of chiral 2-oxazolidinones was obtained via a dinuclear copper-catalyzed asymmetric propargylic amination–carboxylative cyclization sequence of propargylic esters with alkyl amine hydrochlorides and CO2.
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Sulfenylation of bioactive maleimides, acrylates and cyclohexenones under ambient organophotocatalysis

Org. Chem. Front., 2024, 11,6503-6509
DOI: 10.1039/D4QO01342E, Research Article
Debanjana Bag, Rajjakfur Rahaman, Anindya S. Manna, Subhasis Pal, Rajesh Nandi, Shobhon Aich, Narendra Nath Ghosh, Dilip K. Maiti
A novel visible light-induced sulfenylation of biologically important maleimides, acrylates and cyclohexenones has been developed using cheap and easily available organophotoredox catalyst Eosin Y with thiols under ambient conditions.
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Copper(II)-catalyzed synthesis of sulfonyl-functionalized quinone-fused cyclopenta[b]indoles via four-component cascade annulation

Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01560F, Research Article
Hong Xu, Jie Liao, Fei Ren, Chuan-Rong Zhou, Xiao-Zhuo Liu, Yao Xiao, Dong-Wei Hang, Fuyu Li, Bei Wang, Ji-Yu Wang
Through crucial selective radical tandem process and intramolecular nucleophilic addition, a facile copper-catalyzed four-component cascade has been realized to selectively construct novel sulfonyl-functionalized quinone-fused cyclopenta[b]indole.
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Iridium-catalyzed asymmetric cascade allylation/lactonization of methyl salicylates: enantioselective construction of chiral benzodioxepinones

Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01771D, Research Article
Bendu Pan, Yunru Wu, Yaqi Zhang, Xiaobo He, Long Jiang, Liqin Qiu
An efficient asymmetric cascade allylation/lactonization of methyl salicylates is achieved. The utilization of chiral-bridged biphenyl phosphoramidite ligand resulted in good results for the construction of a wide range of chiral benzodioxepinones.
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Palladium-catalyzed cascade decarboxylative cyclization of alkyne-tethered aryl iodides with o-bromobenzoic acids for the synthesis of fused isoquinolinones

Org. Chem. Front., 2024, Advance Article
DOI: 10.1039/D4QO01573H, Research Article
Zhaolin Quan, Yubo Duan, Zhengkai Chen
A straightforward approach for the preparation of fused isoquinolinone derivatives via palladium-catalyzed cascade decarboxylative cyclization of alkyne-tethered aryl iodides with o-bromobenzoic acids is described.
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Rhodium-catalyzed synthesis of N-substituted 3-acylpyrroles from enaminones and vinylene carbonate

Org. Chem. Front., 2025, Accepted Manuscript
DOI: 10.1039/D4QO01816H, Research Article
Sheng-Jiao Yan, Jian-Bo Ma, Yi-Mai Yin, Xing-Mei Hu, Bi-Na Shao, Kun Huang, Qing-Sheng Zhao
Skeletal editing is a highly efficient strategy for modifying the core scaffolds of drug molecules, with multi-atomic editing as an emergent approach. Herein, we present a protocol for constructing N-substituted...
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I drank soup, sniffed some wine, and took a walk in the woods at MWC 2024. And none of it was real!

Here’s a firsthand account of ‘Feel Tech Bar’ in World Mobile Congress 2024, Barcelona





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Light-induced isomerization of quinoline-N-oxide derivatives through Zn-catalysis: a photochemical approach for synthesizing 2-quinolinone derivatives

Green Chem., 2024, 26,10818-10823
DOI: 10.1039/D4GC03226H, Communication
Xiaoqiang Yu, Sana Yang, Ning Yan, Yukang Fu, Yang Li, Wanhui Wang, Ming Bao
The light-induced Zn-catalyzed isomerization of quinoline-N-oxides proceeded smoothly to afford 2-quinolinone derivatives via intramolecular hydrogen and oxygen transfer.
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Modular access to multi-substituted allenones via environmentally friendly organocatalytic C–H allenylation of aldehydes

Green Chem., 2024, Advance Article
DOI: 10.1039/D4GC04550E, Paper
Xinying Hu, Ayisenbati Jialingbieke, Yuzhi Ren, Yifan Yang, Donghui Wei, Jian Gao, Ding Du
Organocatalytic direct C–H allenylation of aldehydes with propargyl bromides has provided a straightforward and step-economical strategy for allenone modular synthesis.
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Single cobalt atom catalysis for the construction of quinazolines and quinazolinones via the aerobic dehydrocyclization of ethanol

Green Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4GC04928D, Paper
Xueping Zhang, Kai Xu, Yi Zhuang, Shihao Yuan, Yamei Lin, Guo-Ping Lu
It is still a significant and challenging for the synthesis of N-heterocycles through the aerobic dehydrocyclization of ethanol since ethanol is the largest renewable small molecule feedstock but with high...
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Mike Rowe says many Americans workers feel labeled 'nonessential' by coronavirus lockdowns

The U.S. response to the coronavirus outbreak has led to "unintended consequences" -- including lost pride for many American workers, TV host Mike Rowe said Saturday night.




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OECD, BSR and Danone launch 3-year initiative to strengthen inclusive growth through public-private collaboration

Business and government should work more closely together to reduce inequality and foster inclusive growth. To help achieve this, at the Paris Peace Forum, Gabriela Ramos, OECD Chief of Staff, G7/G20 Sherpa and leader of the OECD’s Inclusive Growth Initiative, and Emmanuel Faber, Chairman & CEO of Danone, launched the Business for Inclusive Growth (B4IG) Platform.




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Structural and thermodynamic analysis of interactions between death-associated protein kinase 1 and anthraquinones

Death-associated protein kinase 1 (DAPK1) was found to form a complex with purpurin and the crystal structure of the complex was determined. Purpurin may be a good lead compound for for the discovery of inhibitors of DAPK1.




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2,4-Di­chloro-6-[(2-hy­droxy-5-methyl­anilino)methyl­idene]cyclo­hexa-2,4-dienone

The title compound, C14H11Cl2NO2, has been prepared by the condensation of 3,5-di­chloro­salicyl­aldehyde and 2-amino-4-methyl­phenol. The asymmetric unit consists of two independent mol­ecules, both of which are almost planar; the dihedral angle between the two benzene rings is 10.61 (8)° for one mol­ecule and 2.46 (8)° for the other. There is an intra­molecular N—H⋯O hydrogen bond that generates S(6) ring motifs in each mol­ecule. In the crystal, the two independent mol­ecules are linked by O—H⋯O and C—H⋯Cl hydrogen bonds, forming a pseudo-inversion dimer. A π–π inter­action, with a centroid–centroid distance of 3.6065 (12) Å, is also observed.




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Crystal structure and Hirshfeld surface analysis of 2,2'-{(1E,1'E)-[ethane-1,2-diylbis(aza­nylyl­idene)]bis­(methanylyl­idene)}bis­[4-(tri­fluoro­meth­oxy)phenol]copper(II) hydro­quinone hemisolvate

In the title com­plex, [Cu(C18H12F6N2O4)]·0.5C6H6O2, the CuII ion has a square-planar coordination geometry, being ligated by two N and two O atoms of the tetra­dentate open-chain Schiff base ligand 6,6'-{(1E,1'E)-[ethane-1,2-diylbis(aza­nylyl­idene)]bis­(methanylyl­idene)}bis­[2-(tri­fluoro­meth­oxy)phenol]. The crystal packing is stabilized by intra­molecular O—H⋯O and inter­molecular C—H⋯F, C—H⋯O and C—H⋯π hydrogen bonds. In addition, weak π–π inter­actions form a three-dimensional structure. Hirshfeld surface analysis and two-dimensional fingerprint plots were performed and created to analyze the inter­molecular inter­actions present in the crystal, indicating that the most important contributions for the crystal packing are from F⋯H/H⋯F (25.7%), H⋯H (23.5%) and C⋯H/H⋯C (12.6%) inter­actions.




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Crystal structure, Hirshfeld surface analysis and contact enrichment ratios of 1-(2,7-di­methyl­imidazo[1,2-a]pyridin-3-yl)-2-(1,3-di­thio­lan-2-yl­idene)ethanone monohydrate

In the title hydrated hybrid compound C14H14N2OS2·H2O, the planar imidazo[1,2-a]pyridine ring system is linked to the 1,3-di­thiol­ane moiety by an enone bridge. The atoms of the C—C bond in the 1,3-di­thiol­ane ring are disordered over two positions with occupancies of 0.579 (14) and 0.421 (14) and both disordered rings adopt a half-chair conformation. The oxygen atom of the enone bridge is involved in a weak intra­molecular C—H⋯O hydrogen bond, which generates an S(6) graph-set motif. In the crystal, the hybrid mol­ecules are associated in R22(14) dimeric units by weak C—H⋯O inter­actions. O—H⋯O hydrogen bonds link the water mol­ecules, forming infinite self-assembled chains along the b-axis direction to which the dimers are connected via O—H⋯N hydrogen bonding. Analysis of inter­molecular contacts using Hirshfeld surface analysis and contact enrichment ratio descriptors indicate that hydrogen bonds induced by water mol­ecules are the main driving force in the crystal packing formation.




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Crystal structures of (E)-5-(4-methyl­phen­yl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis(phenyl­ethyn­yl)cyclo­butane-1,2-di­yl]bis­(pyridin-2-yl­methanone)

Recrystallization of (E)-5-phenyl-1-(pyridin-2-yl)pent-2-en-4-yn-1-one at room temperature from ethyl­ene glycol in daylight afforded [3,4-bis­(phenyl­ethyn­yl)cyclo­butane-1,2-di­yl)bis­(pyridin-2-yl­methanone], C32H22N2O2 (3), while (E)-5-(4-methyl­phen­yl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one, C17H13NO (2), remained photoinert. This is the first experimental evidence that pentenynones can be photoreactive when fixed in nearly coplanar parallel positions. During the photoreaction, the bond lengths and angles along the pentenyne chain changed significantly, while the disposition of the pyridyl ring towards the keto group was almost unchanged. The cyclo­butane ring adopts an rctt conformation.




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Crystal structure of (4-chloro­phen­yl)(4-methyl­piperidin-1-yl)methanone

The title compound, C13H16ClNO, contains a methyl­piperidine ring in the stable chair conformation. The mean plane of the twisted piperidine ring subtends a dihedral angle of 39.89 (7)° with that of the benzene ring. In the crystal, weak C—H⋯O inter­actions link the mol­ecules along the a-axis direction to form infinite mol­ecular chains. H⋯H inter­atomic inter­actions, C—H⋯O inter­molecular inter­actions and weak dispersive forces stabilize mol­ecular packing and form a supra­molecular network, as established by Hirshfeld surface analysis.




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Crystal structure of (R)-5-[(R)-3-(4-chloro­phen­yl)-5-methyl-4,5-di­hydro­isoxazol-5-yl]-2-methyl­cyclo­hex-2-enone

The title compound, C17H18ClNO2, was prepared and isolated as a pure diastereoisomer, using column chromatography followed by a succession of fractional crystallizations. Its exact structure was fully identified via 1H NMR and confirmed by X-ray diffraction. It is built up from a central five-membered di­hydro­isoxazole ring to which a p-chloro­phenyl group and a cyclo­hex-2-enone ring are attached in the 3 and 5 positions. The cyclo­hex-2-one and isoxazoline rings each exhibit an envelope conformation. The crystal packing features C—H⋯O, C—H⋯N and C—H⋯π inter­actions, which generate a three-dimensional network.




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Structural and thermodynamic analyses of interactions between death-associated protein kinase 1 and anthraquinones

Death-associated protein kinase 1 (DAPK1) is a serine/threonine protein kinase that regulates apoptosis and autophagy. DAPK1 is considered to be a therapeutic target for amyloid-β deposition, endometrial adenocarcinomas and acute ischemic stroke. Here, the potent inhibitory activity of the natural anthraquinone purpurin against DAPK1 phosphorylation is shown. Thermodynamic analysis revealed that while the binding affinity of purpurin is similar to that of CPR005231, which is a DAPK1 inhibitor with an imidazopyridazine moiety, the binding of purpurin was more enthalpically favorable. In addition, the inhibition potencies were correlated with the enthalpic changes but not with the binding affinities. Crystallographic analysis of the DAPK1–purpurin complex revealed that the formation of a hydrogen-bond network is likely to contribute to the favorable enthalpic changes and that stabilization of the glycine-rich loop may cause less favorable entropic changes. The present findings indicate that purpurin may be a good lead compound for the discovery of inhibitors of DAPK1, and the observation of enthalpic changes could provide important clues for drug development.