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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...
March 15, 2017: Organic Letters
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 )...
March 10, 2017: Advanced Materials
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
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
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
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
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
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
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
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
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
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
Magdalena S Nel, Anél Petzer, Jacobus P Petzer, Lesetja J Legoabe
In the present study a series of fifteen 2-heteroarylidene-1-indanone derivatives were synthesised and evaluated as inhibitors of recombinant human monoamine oxidase (MAO) A and B. These compounds are structurally related to series of heterocyclic chalcone derivatives which have previously been shown to act as MAO-B specific inhibitors. The results document that the 2-heteroarylidene-1-indanones are in vitro inhibitors of MAO-B, displaying IC50 values of 0.0044-1.53μM. Although with lower potencies, the derivatives also inhibit the MAO-A isoform with IC50 values as low as 0...
September 17, 2016: Bioorganic Chemistry
Barbara V da Silva, Bianca N M Silva
BACKGROUND: Trypanosomiasis and leishmaniasis cause severe infections in humans and domestic animals in the tropics. Although typical diseases in Latin America, globalization and the migration of infected people has spread these diseases to countries in North America, Asia and Europe. Currently available drugs are not effective in the chronic phase, as well as causing side effects and the development of resistance. RESULTS: Among the chemical groups studied as potential anti-T...
September 9, 2016: Medicinal Chemistry
Magdalena S Nel, Anél Petzer, Jacobus P Petzer, Lesetja J Legoabe
In the present study, a series of twenty-two 2-benzylidene-1-indanone derivatives were synthesised and evaluated as inhibitors of recombinant human monoamine oxidase (MAO) A and B. The 2-benzylidene-1-indanone derivatives are structurally related to a series of benzylideneindanone derivatives which has previously been found to be MAO-B inhibitors. This study finds that the 2-benzylidene-1-indanones are MAO-B specific inhibitors with IC50 values <2.74μM. Among the compounds evaluated, twelve compounds exhibited IC50<0...
October 1, 2016: Bioorganic & Medicinal Chemistry Letters
Dou-Dou Nan, Chang-Sheng Gan, Chen-Wei Wang, Jin-Ping Qiao, Xin-Meng Wang, Jiang-Ning Zhou
A series of 6-methoxy indanone derivatives was synthesized and evaluated as potential probes for β-amyloid plaque imaging in Alzheimer's disease (AD). Two derivatives (5d and 5k) displayed significant binding abilities in fluorescent staining experiments using the brain sections of AD patients. Two derivatives showed high binding affinities to β-amyloid aggregates (5j, Ki = 5.82 ± 0.19 nM) and brain homogenates of AD patients (5j, Ki = 18.96 ± 0.28 nM) in in vitro binding assay. With a log P value of 3...
November 29, 2016: European Journal of Medicinal Chemistry
Aastha Singh, Kaneez Fatima, Ankita Srivastava, Sadiya Khwaja, Dev Priya, Arjun Singh, Girish Mahajan, Sarfaraz Alam, Ajit K Saxena, D M Mondhe, Suaib Luqman, Debabrata Chanda, Feroz Khan, Arvind S Negi
Benzylidene indanones have been designed and synthesized from gallic acid, a plant phenolic acid as possible anticancer agent. The best analogue of the series, that is, 3-(3',4',5'-trimethoxyphenyl)-4,5,6-trimethoxy-2-(4˝-nitrobenzylidene)-indan-1-one (8) exhibited potent cytotoxicity (IC50 =3-10 μm) against several human cancer cell lines through microtubule destabilization (IC50 =1.54 μm) after occupying colchicine-binding site of β-tubulin. In cell cycle analysis, compound 8 exerted G2/M phase arrest in both MCF-7 and MDA-MB-231 cells and induced apoptosis...
November 2016: Chemical Biology & Drug Design
Mei-Lin Tang, Peng Peng, Zheng-Yu Liu, Jian Zhang, Jian-Ming Yu, Xun Sun
The synthesis of enantiomerically pure 3-aryl substituted indanones is developed using an enantioselective sulfoxide-based Knoevenagel condensation/Nazarov cyclization procedure. After the reductive desulfonation of the methyl para-tolyl sulfoxide-containing chiral auxiliary under mild conditions, selected enantiomerically pure indanone is used for the divergent total syntheses of three resveratrol natural products (+)-isopaucifloral F, (+)-quadrangularin A, and (+)-pallidol.
October 4, 2016: Chemistry: a European Journal
Teresa A Unzner, Adriana S Grossmann, Thomas Magauer
We report the synthesis of orthogonally functionalized naphthalenes from simple, commercially available indanones in four steps. The developed method proceeds through a two-step process that features a thermally induced fragmentation of a cyclopropane indanone with simultaneous 1,2-chloride shift. Migration of the chloride substituent occurs in a regioselective manner to preferentially afford the para-chloronaphthol substitution pattern. The obtained naphthols are versatile building blocks that can be selectively modified and used for the efficient construction of biologically active molecules...
August 8, 2016: Angewandte Chemie
Jianbo Zhang, Xiuling Han, Xiyan Lu
A Pd(OAc)2-catalyzed cyclization reaction of ortho-electron-deficient alkynyl-substituted aryl aldehydes with indoles was accomplished, providing an efficient and economical way to synthesize indole-substituted indanones. The electron-withdrawing group attached to the alkyne and the nucleophilic indole play important roles in the formation of the indanone ring.
June 17, 2016: Organic Letters
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