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https://www.readbyqxmd.com/read/28526475/identification-and-preliminary-structure-activity-relationships-of-1-indanone-derivatives-as-novel-indoleamine-2-3-dioxygenase-1-ido1-inhibitors
#1
Dingding Gao, Yingxia Li
Indoleamine 2,3-dioxygenase 1 (IDO1) plays a vital role in the catabolism of tryptophan along with the kynurenine pathway which is involved in many human diseases including cancer, Alzheimer's disease, etc. In this study, compound 1 bearing a 1-Indanone scaffold was identified as a novel IDO1 inhibitor by structure-based virtual screening, with moderate to good enzymatic and cellular inhibitory activities. Also, surface plasmon resonance analysis validated the direct interaction between compound 1 and IDO1 protein...
May 10, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28504882/visible-light-induced-tandem-radical-addition-cyclization-of-alkenyl-aldehydes-leading-to-indanones-and-related-compounds
#2
Danyang Lu, Yimei Wan, Lichun Kong, Gangguo Zhu
Herein we describe a novel, visible light-induced tandem radical addition-cyclization of alkenyl aldehydes with α-bromocarbonyl compounds. A set of cyclic ketones, including indanones, cyclopentenones, 3,4-dihydronaphthalen-1(2H)-ones, and chroman-4-ones, are synthesized at room temperature with high efficiency and good functional group compatibility. It represents the first report on the catalytic 1,2-acylalkylation of unactivated alkenes.
May 15, 2017: Organic Letters
https://www.readbyqxmd.com/read/28481313/two-new-metabolites-from-the-endophytic-fungus-alternaria-sp-a744-derived-from-morinda-officinalis
#3
Ying Wang, Hong-Xin Liu, Yu-Chan Chen, Zhang-Hua Sun, Hao-Hua Li, Sai-Ni Li, Ming-Li Yan, Wei-Min Zhang
Two new compounds isobenzofuranone A (1) and indandione B (2), together with eleven known compounds (3-13) were isolated from liquid cultures of an endophytic fungus Alternaria sp., which was obtained from the medicinal plant Morinda officinalis. Among them, the indandione (2) showed a rarely occurring indanone skeleton in natural products. Their structures were elucidated mainly on the basis of extensive spectroscopic data analysis. All of the compounds were evaluated with cytotoxic and α-glucosidase inhibitory activity assays...
May 8, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28384544/design-synthesis-and-structure-activity-relationship-study-of-halogen-containing-2-benzylidene-1-indanone-derivatives-for-inhibition-of-lps-stimulated-ros-production-in-raw-264-7-macrophages
#4
Aarajana Shrestha, Hye Jin Oh, Mi Jin Kim, Nirmala Tilija Pun, Til Bahadur Thapa Magar, Ganesh Bist, Hongseok Choi, Pil-Hoon Park, Eung-Seok Lee
As a continuous effort to discover new potential anti-inflammatory agents, we systematically designed and synthesized sixty-one 2-benzylidene-1-indanone derivatives with structural modification of chalcone, and evaluated their inhibitory activity on LPS-stimulated ROS production in RAW 264.7 macrophages. Systematic structure-activity relationship study revealed that hydroxyl group in C-5, C-6, or C-7 position of indanone moiety, and ortho-, meta-, or para-fluorine, trifluoromethyl, trifluoromethoxy, and bromine functionalities in phenyl ring are important for inhibition of ROS production in LPS-stimulated RAW 264...
March 27, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28382183/synthesis-of-1-indanones-with-a-broad-range-of-biological-activity
#5
REVIEW
Marika Turek, Dorota Szczęsna, Marek Koprowski, Piotr Bałczewski
This comprehensive review describes methods for the preparation of 1-indanones published in original and patent literature from 1926 to 2017. More than 100 synthetic methods utilizing carboxylic acids, esters, diesters, acid chlorides, ketones, alkynes, alcohols etc. as starting materials, have been performed. This review also covers the most important studies on the biological activity of 1-indanones and their derivatives which are potent antiviral, anti-inflammatory, analgesic, antimalarial, antibacterial and anticancer compounds...
2017: Beilstein Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28377529/catabolism-of-the-last-two-steroid-rings-in-mycobacterium-tuberculosis-and-other-bacteria
#6
Adam M Crowe, Israël Casabon, Kirstin L Brown, Jie Liu, Jennifer Lian, Jason C Rogalski, Timothy E Hurst, Victor Snieckus, Leonard J Foster, Lindsay D Eltis
Most mycolic acid-containing actinobacteria and some proteobacteria use steroids as growth substrates, but the catabolism of the last two steroid rings has yet to be elucidated. In Mycobacterium tuberculosis, this pathway includes virulence determinants and has been proposed to be encoded by the KstR2-regulated genes, which include a predicted coenzyme A (CoA) transferase gene (ipdAB) and an acyl-CoA reductase gene (ipdC). In the presence of cholesterol, ΔipdC and ΔipdAB mutants of either M. tuberculosis or Rhodococcus jostii strain RHA1 accumulated previously undescribed metabolites: 3aα-H-4α(carboxyl-CoA)-5-hydroxy-7aβ-methylhexahydro-1-indanone (5-OH HIC-CoA) and (R)-2-(2-carboxyethyl)-3-methyl-6-oxocyclohex-1-ene-1-carboxyl-CoA (COCHEA-CoA), respectively...
April 4, 2017: MBio
https://www.readbyqxmd.com/read/28345917/enantiodivergent-synthesis-of-tertiary-%C3%AE-aryl-1-indanones-evidence-toward-disparate-mechanisms-in-the-palladium-catalyzed-decarboxylative-asymmetric-protonation
#7
Cian Kingston, Patrick J Guiry
Herein, we describe a study into the scope and origin of an enantiodivergent effect in the palladium-catalyzed decarboxylative asymmetric protonation. By switching the achiral proton source, both enantiomers of a series of tertiary α-aryl-1-indanones are readily accessed from the corresponding α-aryl-β-keto allyl esters. In this example of dual stereocontrol, enantioselectivities up to 94% (S) and 92% (R) were achieved using Meldrum's acid and formic acid, respectively. In an attempt to rationalize this switch in absolute configuration an investigation of the ambiguous mechanism of the decarboxylative asymmetric protonation was conducted...
March 27, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28333391/high-performance-nonfullerene-polymer-solar-cells-based-on-imide-functionalized-wide-bandgap-polymers
#8
Baobing Fan, Kai Zhang, Xiao-Fang Jiang, Lei Ying, Fei Huang, Yong Cao
High-performance nonfullerene polymer solar cells (PSCs) are developed by integrating the nonfullerene electron-accepting material 3,9-bis(2-methylene-(3-(1,1-dicyanomethylene)-indanone))-5,5,11,11-tetrakis(4-hexylphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophne) (ITIC) with a wide-bandgap electron-donating polymer PTzBI or PTzBI-DT, which consists of an imide functionalized benzotriazole (TzBI) building block. Detailed investigations reveal that the extension of conjugation can affect the optical and electronic properties, molecular aggregation properties, charge separation in the bulk-heterojunction films, and thus the overall photovoltaic performances...
March 23, 2017: Advanced Materials
https://www.readbyqxmd.com/read/28296421/silver-catalyzed-regioselective-fluorination-of-carbonyl-directed-alkynes-synthesis-of-%C3%AE-fluoroketones
#9
Fang-Hui Li, Zhong-Jian Cai, Ling Yin, Jian Li, Shun-Yi Wang, Shun-Jun Ji
A novel silver-catalyzed fluorination reaction of carbonyl directed alkynes in the presence of N-fluorobenzenesulfonimide and water with high regioselectivities has been developed. The established protocol provides an alternative method for rapid assembly of α-fluoroketone derivatives under simple and mild reaction conditions. The reaction pathway involves a ring closure and opening process for the construction of new C-O and C-F bonds. In addition, a fluorine-containing indanone was observed through further N-heterocyclic carbene catalyzed intramolecular crossed-benzoin reaction of α-fluoroketone...
April 7, 2017: Organic Letters
https://www.readbyqxmd.com/read/28295734/single-junction-binary-blend-nonfullerene-polymer-solar-cells-with-12-1-efficiency
#10
Fuwen Zhao, Shuixing Dai, Yang Wu, Qianqian Zhang, Jiayu Wang, Li Jiang, Qidan Ling, Zhixiang Wei, Wei Ma, Wei You, Chunru Wang, Xiaowei Zhan
A new fluorinated nonfullerene acceptor, ITIC-Th1, has been designed and synthesized by introducing fluorine (F) atoms onto the end-capping group 1,1-dicyanomethylene-3-indanone (IC). On the one hand, incorporation of F would improve intramolecular interaction, enhance the push-pull effect between the donor unit indacenodithieno[3,2-b]thiophene and the acceptor unit IC due to electron-withdrawing effect of F, and finally adjust energy levels and reduce bandgap, which is beneficial to light harvesting and enhancing short-circuit current density (JSC )...
May 2017: Advanced Materials
https://www.readbyqxmd.com/read/28157151/dft-study-of-the-structure-reactivity-natural-bond-orbital-and-hyperpolarizability-of-thiazole-azo-dyes
#11
Osman I Osman
The structure, reactivity, natural bond orbital (NBO), linear and nonlinear optical (NLO) properties of three thiazole azo dyes (A, B and C) were monitored by applying B3LYP, CAM-B3LYP and ωB97XD functionals with 6-311++G** and aug-cc-pvdz basis sets. The geometrical parameters,dipolemoments,HOMO-LUMO(highest occupied molecular orbital,lowest unoccupied molecular orbital) energy gaps, absorption wavelengths and total hyperpolarizabilities were investigated in carbon tetrachloride (CCl4) chloroform (CHCl3), dichloromethane (CH2Cl2) and dimethlysulphoxide (DMSO)...
February 1, 2017: International Journal of Molecular Sciences
https://www.readbyqxmd.com/read/28116791/cobalt-catalyzed-enantio-and-diastereoselective-intramolecular-hydroacylation-of-trisubstituted-alkenes
#12
Junfeng Yang, Alice Rérat, Yang Jie Lim, Corinne Gosmini, Naohiko Yoshikai
Enantio- and diastereoselective synthesis of trans-2,3-disubstituted indanones is achieved by intramolecular hydroacylation of 2-alkenylbenzaldehydes bearing trisubstituted alkenyl groups under cobalt-chiral diphosphine catalysis. Notably, a high level of enantioselectivity is induced regardless of the stereochemistry (E/Z ratio) of the alkenyl group of the starting material. Deuterium-labeling experiments shed light on the productive reaction pathways of the E- and Z-isomers.
January 24, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28059503/fused-nonacyclic-electron-acceptors-for-efficient-polymer-solar-cells
#13
Shuixing Dai, Fuwen Zhao, Qianqian Zhang, Tsz-Ki Lau, Tengfei Li, Kuan Liu, Qidan Ling, Chunru Wang, Xinhui Lu, Wei You, Xiaowei Zhan
We design and synthesize four fused-ring electron acceptors based on 6,6,12,12-tetrakis(4-hexylphenyl)-indacenobis(dithieno[3,2-b;2',3'-d]thiophene) as the electron-rich unit and 1,1-dicyanomethylene-3-indanones with 0-2 fluorine substituents as the electron-deficient units. These four molecules exhibit broad (550-850 nm) and strong absorption with high extinction coefficients of (2.1-2.5) × 10(5) M(-1) cm(-1). Fluorine substitution downshifts the LUMO energy level, red-shifts the absorption spectrum, and enhances electron mobility...
January 13, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/27992080/enantioseparation-of-nine-indanone-and-tetralone-derivatives-by-hplc-using-carboxymethyl-%C3%AE-cyclodextrin-as-the-mobile-phase-additive
#14
Xiaoyu Hu, Xin Guo, Shuo Sun, Bolin Zhu, Jia Yu, Xingjie Guo
High-performance liquid chromatography (HPLC) is a powerful method in the area of chiral separation. In this study, a method of HPLC using carboxymethyl-β-cyclodextrin (CM-β-CD) as chiral selector was developed for enantioseparation of nine indanone and tetralone derivatives. The separation was performed on a conventional C18 column. The optimal mobile phase was a mixture of methanol and 0.05 mol/L phosphate buffer at pH 1.8 (55:45, v/v) containing 22.9 mmol/L CM-β-CD. Under such conditions, the resolutions of all analytes were over 1...
December 19, 2016: Chirality
https://www.readbyqxmd.com/read/27978729/silver-catalyzed-domino-reaction-of-ortho-carbonylated-alkynyl-substituted-arylaldehydes-with-conjugated-dienes-stereoselective-access-to-indanone-fused-cyclohexenes
#15
Ziping Cao, Hongbo Zhu, Xin Meng, Laijin Tian, Guang Chen, Xuejun Sun, Jinmao You
A silver-catalyzed domino reaction of ortho-carbonylated alkynyl-substituted arylaldehydes with conjugated dienes is described here. Through this reaction, the synthesis of a variety of indanone-fused cyclohexene derivatives can be achieved efficiently. The formation of these tricyclic products could involve a key Diels-Alder reaction of in situ generated indanenone dienophiles with conjugated dienes. Particularly, the products can be accomplished in a high endo/exo selective way.
December 16, 2016: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/27936694/chiral-n-n-dioxide-organocatalyzed-asymmetric-electrophilic-%C3%AE-cyanation-of-%C3%AE-keto-esters-and-%C3%AE-keto-amides
#16
Baiwei Ma, Xiaobin Lin, Lili Lin, Xiaoming Feng, Xiaohua Liu
An enantioselective electrophilic α-cyanation of 1-indanone-derived β-keto esters and β-keto amides using a hypervalent iodine as the cyanide-transfer reagent was realized. A chiral N,N'-dioxide was used as the efficient bifunctional organocatalyst in the presence of inorganic base, which gave the corresponding α-cyano dicarbonyl compounds in yields of 50-99% with good enantioselectivities (87-97% ee).
December 22, 2016: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/27922737/%C3%AF-conjugated-lewis-base-efficient-trap-passivation-and-charge-extraction-for-hybrid-perovskite-solar-cells
#17
Yuze Lin, Liang Shen, Jun Dai, Yehao Deng, Yang Wu, Yang Bai, Xiaopeng Zheng, Jiayu Wang, Yanjun Fang, Haotong Wei, Wei Ma, Xiao Cheng Zeng, Xiaowei Zhan, Jinsong Huang
A π-conjugated Lewis base is introduced into perovskite solar cells, namely, indacenodithiophene end-capped with 1.1-dicyanomethylene-3-indanone (IDIC), as a multifunctional interlayer which combines efficient trap-passivation and electron-extraction. Perovskite solar cells with IDIC layers yield higher photovoltages and photocurrents, and 45% enhanced efficiency compared with control devices without IDIC.
December 6, 2016: Advanced Materials
https://www.readbyqxmd.com/read/27892638/a-new-nonfullerene-electron-acceptor-with-a-ladder-type-backbone-for-high-performance-organic-solar-cells
#18
Nailiang Qiu, Huijing Zhang, Xiangjian Wan, Chenxi Li, Xin Ke, Huanran Feng, Bin Kan, Hongtao Zhang, Qiang Zhang, Yan Lu, Yongsheng Chen
Nonfullerene acceptor FDICTF (2,9-bis(2methylene-(3-(1,1-dicyanomethylene)indanone))-7,​12-​dihydro-​4,​4,​7,​7,​12,​12-​hexaoctyl-​4H-​cyclopenta[2″,​1″:5,​6;3″,​4″:5',​6']​diindeno[1,​2-​b:1',​2'-​b']dithiophene) modified by fusing the fluorene core in a precursor, yields 10.06% high power conversion efficiency, and demonstrates that the ladder and fused core backbone in A-D-A structure molecules is an effective design strategy for high-performance nonfullerene acceptors...
November 28, 2016: Advanced Materials
https://www.readbyqxmd.com/read/27823887/targeting-alzheimer-s-disease-by-investigating-previously-unexplored-chemical-space-surrounding-the-cholinesterase-inhibitor-donepezil
#19
Divan G van Greunen, Werner Cordier, Margo Nell, Chris van der Westhuyzen, Vanessa Steenkamp, Jenny-Lee Panayides, Darren L Riley
A series of twenty seven acetylcholinesterase inhibitors, as potential agents for the treatment of Alzheimer's disease, were designed and synthesised based upon previously unexplored chemical space surrounding the molecular skeleton of the drug donepezil, which is currently used for the management of mild to severe Alzheimer's disease. Two series of analogues were prepared, the first looking at the replacement of the piperidine ring in donepezil with different sized saturated N-containing ring systems and the second looking at the introduction of different linkers between the indanone and piperidine rings in donepezil...
February 15, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/27731646/total-synthesis-of-coprinol
#20
Muthiah Suresh, Navin Kumar, Gorre Veeraraghavaiah, Sunit Hazra, Raj Bahadur Singh
The first synthesis of coprinol has been achieved from 2-methoxy-3,5-dimethylbenzaldehyde via the intermediacy of an indanone derivative where dialkylation, Friedel-Crafts acylation, demethylation, and regioselective formation of a primary -OH group from a chloroacetyl group are the key steps.
October 12, 2016: Journal of Natural Products
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