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Yu-Tang Hsiao, Chia-Hua Li, Shao-Ling Chang, Soowon Heo, Keisuke Tajima, Yen-Ju Cheng, Chain-Shu Hsu
In this research, a haptacyclic carbazole-based dithienocyclopentacarbazole (DTCC) ladder-type structure was formylated to couple with two 1,1-dicyanomethylene-3-indanone (IC) moieties, forming a new non-fullerene acceptor DTCCIC-C17 using a bulky branched 1-octylnonayl side chain at the nitrogen of the embedded carbazole and four 4-octylphenyl groups at the sp3-carbon bridges. The rigid and coplanar main-chain backbone of DTCC core provides a broad light-absorbing window and a higher-lying LUMO energy level, while the bulky flanked side chains to reduce intermolecular interactions make DTCCIC-C17 amorphous with excellent solution processability...
November 10, 2017: ACS Applied Materials & Interfaces
A Sólimo, M C Soraires Santacruz, A I Loaiza Perez, E Bal de Kier Joffé, L M Finkielsztein, M A Callero
Breast cancer is the first cause of cancer death in women. Many patients are resistant to current therapies, and even those were sensitive at first may eventually become resistant later. Thiosemicarbazones (TSCs) are synthetic compounds that exhibit several pharmacological activities. In this study, we investigated the potential anti-tumor activity of a set of N(4) -arylsubstituted TSCs (N(4) -TSCs) on human breast cancer cell lines. Studies on the effect of N(4) -TSCs (T1, T2 and T3) were carried on MCF-7, MDA-MB 231 and BT 474 cell lines which differ in their expression of ER, PR and Her2/neu...
November 7, 2017: Journal of Cellular Physiology
Ying Zhang, Feiye Sun, Wenyan Dan, Xiangdong Fang
The acylation reaction of BN-arenes has been studied using BN-arene and acyl choride in good to excellent yields, which led to the first synthesis of indanone BN-analogue. The BN-aromatic ketone products have been characterized by 1H NMR spectroscopy with their molecular structures unambiguously confirmed by X-ray crystallography. The annulation of BN-arenes promoted by AgBF4 occurs in a completely regioselective manner and a mechanism for this transformation is proposed.
October 30, 2017: Journal of Organic Chemistry
Yiwen Wang, Bo Wu, Zhenghui Wu, Zhaojue Lan, Yongfang Li, Maojie Zhang, Furong Zhu
We report our effort to unravel the origin of efficient operation of nonfullerene organic solar cells (OSCs), based on a poly[4,8-bis(5-(2-ethylhexyl) thiophen-2-yl)benzo[1,2-b;4,5-b']dithiophene-2,6-diyl-alt-(4-(2-ethylhexyl)-3-fluorothieno[3,4-b]thiophene-)-2-carboxylate-2-6-diyl)](PTB7-Th):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']dithiophene (ITIC) blend system. The effects of buildup of space charges, charge extraction, and bimolecular recombination processes on the performance and the stability of PTB7-Th:ITIC-based regular and reverse configuration OSCs are analyzed...
October 13, 2017: Journal of Physical Chemistry Letters
Rui He, Penglin Liu, Xiaohong Huo, Wanbin Zhang
A one-step enantioselective and diastereodivergent α-allylation of unprotected α-hydroxy indanones has been developed using an Ir/Zn dual catalyst system; no additional base is required. The cyclic tertiary α-hydroxyketones containing vicinal stereocenters can be synthesized with excellent enantioselectivity (up to >99% ee) and good diastereoselectivity (up to 12:1 dr). By a simple choice of the appropriate chiral metal catalyst combination, all four product stereoisomers could be obtained from the same starting materials and under identical conditions...
October 6, 2017: Organic Letters
Talita P C Chierrito, Susimaire Pedersoli-Mantoani, Carlos Roca, Carlos Requena, Victor Sebastian-Perez, Willian O Castillo, Natalia C S Moreira, Concepción Pérez, Elza T Sakamoto-Hojo, Catarina S Takahashi, Jesús Jiménez-Barbero, F Javier Cañada, Nuria E Campillo, Ana Martinez, Ivone Carvalho
The lack of an effective treatment for Alzheimer' disease (AD), an increasing prevalence and severe neurodegenerative pathology boost medicinal chemists to look for new drugs. Currently, only acethylcholinesterase (AChE) inhibitors and glutamate antagonist have been approved to the palliative treatment of AD. Although they have a short-term symptomatic benefits, their clinical use have revealed important non-cholinergic functions for AChE such its chaperone role in beta-amyloid toxicity. We propose here the design, synthesis and evaluation of non-toxic dual binding site AChEIs by hybridization of indanone and quinoline heterocyclic scaffolds...
October 20, 2017: European Journal of Medicinal Chemistry
Lingwei Xue, Yankang Yang, Jianqiu Xu, Chunfeng Zhang, Haijun Bin, Zhi-Guo Zhang, Beibei Qiu, Xiaojun Li, Chenkai Sun, Liang Gao, Jia Yao, Xiaofeng Chen, Yunxu Yang, Min Xiao, Yongfang Li
Suppression of carrier recombination is critically important in realizing high-efficiency polymer solar cells. Herein, it is demonstrated difluoro-substitution of thiophene conjugated side chain on donor polymer can suppress triplet formation for reducing carrier recombination. A new medium bandgap 2D-conjugated D-A copolymer J91 is designed and synthesized with bi(alkyl-difluorothienyl)-benzodithiophene as donor unit and fluorobenzotriazole as acceptor unit, for taking the advantages of the synergistic fluorination on the backbone and thiophene side chain...
August 31, 2017: Advanced Materials
Liuliu Feng, Jun Yuan, Zhenzhen Zhang, Hongjian Peng, Zhi-Guo Zhang, Shutao Xu, Ye Liu, Yongfang Li, Yingping Zou
A novel nonfullerene small molecular acceptor (BZIC) based on a ladder-type thieno[3,2-b]pyrrolo-fused pentacyclic benzotriazole core (dithieno[3,2-b]pyrrolobenzotriazole, BZTP) and end-capped with 1,1-dicyanomethylene-3-indanone (INCN) has been first reported in this work. Through introducing multifused benzotriazole and INCN, BZIC could maintain a high-lying lowest unoccupied molecular orbital (LUMO) energy level of -3.88 eV. Moreover, BZIC shows a low optical bandgap of 1.45 eV with broad and efficient absorption band from 600 to 850 nm due to increased π-π interactions by the covalently locking thiophene and benzotriazole units...
September 20, 2017: ACS Applied Materials & Interfaces
Ang Gao, Xiu-Yan Liu, Hao Li, Chang-Hua Ding, Xue-Long Hou
Under Pd catalysis with a newly synthesized electron-deficient heterocycle, 2-(4,5-dihydroimidazol-2-yl)pyrimidine (as the ligand), the reaction of α,β-unsaturated esters with arylboronic acids afforded a wide range of 3,3-disubstituted indan-1-ones bearing a quaternary carbon in high yields. Mechanistic studies revealed that the reaction involves a tandem conjugate addition/1,4-Pd shift followed by a cyclization.
September 13, 2017: Journal of Organic Chemistry
Hahk-Soo Kang, So-Ae Ji, So-Hyun Park, Jong-Pyung Kim
Three new chlorinated sesquiterpenes, named lepistatins A-C, were isolated from the culture broth of Basidiomycete Lepista sordida. The structures were determined by the analysis of spectroscopic data including HREIMS and 1D and 2D NMR. The absolute configuration of lepistatin B was determined by comparing the specific rotation and circular dichroism spectrum with those of known structurally related compounds bearing the same chiral carbon. The structures of lepistatins A-C feature the indanone core structure, but differ from other indanone-containing sesquiterpenes of fungal origin by the alkyl substitution pattern...
November 2017: Phytochemistry
Hao Yuan, Jianxian Gong, Zhen Yang
An efficient strategy for the synthesis of structurally diverse indole-substituted indanones via a rhodium(ii)-catalyzed tandem reaction of N-sulfonyltriazoles with indoles was developed. The reaction involves rhodium(ii)-catalyzed denitrogenation of the N-sulfonyltriazoles to form an oxonium ylide, followed by nucleophilic addition of the indoles and subsequent skeletal rearrangement. This strategy provides straightforward access to indanone frameworks bearing quaternary carbon centers.
July 31, 2017: Chemical Communications: Chem Comm
Jiayu Wang, Wei Wang, Xiaohui Wang, Yang Wu, Qianqian Zhang, Cenqi Yan, Wei Ma, Wei You, Xiaowei Zhan
A side-chain conjugation strategy in the design of nonfullerene electron acceptors is proposed, with the design and synthesis of a side-chain-conjugated acceptor (ITIC2) based on a 4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b']di(cyclopenta-dithiophene) electron-donating core and 1,1-dicyanomethylene-3-indanone electron-withdrawing end groups. ITIC2 with the conjugated side chains exhibits an absorption peak at 714 nm, which redshifts 12 nm relative to ITIC1. The absorption extinction coefficient of ITIC2 is 2...
July 17, 2017: Advanced Materials
Shaowei Shi, Xiaofeng Chen, Xubo Liu, Xuefei Wu, Feng Liu, Zhi-Guo Zhang, Yongfang Li, Thomas P Russell, Dong Wang
Rapid improvements in nonfullerene polymer solar cells (PSCs) have brought power conversion efficiencies to greater than 12%. To further improve device performance, a fundamental understanding of the correlations between structure and performance is essential. In this paper, based on a typical high-performance system consisting of J61(one donor-acceptor (D-A) copolymer of benzodithiophene and fluorine substituted benzotriazole) and ITIC (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']-dithiophene), a 3D structural model is directly imaged by employing high-resolution atomic force microscopy (AFM)...
July 17, 2017: ACS Applied Materials & Interfaces
Siddappa A Patil, Renukadevi Patil, Shivaputra A Patil
Indanone is one of the privileged structures in medicinal chemistry and it's commonly associated with various pharmacologically active compounds. The indanone moiety is found in several natural compounds and also, it can be used as intermediate in the synthesis of many different types of medicinally important molecules. Among the medicinally important indanones, the most significant drug probably is donepezil (IV), an acetylcholinesterase (AChE) inhibitor, which has been approved by the US Food and Drug Administration for the treatment of Alzheimer's disease (AD)...
September 29, 2017: European Journal of Medicinal Chemistry
Shao-Ling Chang, Fong-Yi Cao, Wen-Chia Huang, Po-Kai Huang, Chain-Shu Hsu, Yen-Ju Cheng
A formylated benzodi(cyclopentadithiophene) (BDCPDT) ladder-type structure with forced coplanarity is coupled with two 1,1-dicyanomethylene-3-indanone (IC) moieties via olefination to form a non-fullerene acceptor, BDCPDT-IC. The BDCPDT-IC, as an acceptor (A1) with broad light-absorbing ability and excellent solution processability, is combined with a second PC71BM acceptor (A2) and a medium band gap polymer, PBDB-T, as the donor (D) to form a ternary blend with gradient HOMO/LUMO energy alignments and panchromatic absorption...
July 13, 2017: ACS Applied Materials & Interfaces
Ludovic Peauger, Rabah Azzouz, Vincent Gembus, Mihaela-Liliana Ţînţaş, Jana Sopková-de Oliveira Santos, Pierre Bohn, Cyril Papamicaël, Vincent Levacher
With the aim of reducing side effects of acetylcholinesterase inhibitors (AChEIs) during symptomatic treatment of Alzheimer's disease, we report herein a new class of donepezil-based "bio-oxidizable" prodrugs 1 designed to be converted into dual binding site AChEIs 2. While most of indanone-derived N-benzylpyridinium salts 2 revealed to be highly potent dual binding site hAChEIs (IC50 up to 3 nM), outperforming the standard drug donepezil (IC50 = 11 nM), most of the corresponding 1,4-dihydropyridines 1 were found to be inactive...
July 13, 2017: Journal of Medicinal Chemistry
Wei Wang, Cenqi Yan, Tsz-Ki Lau, Jiayu Wang, Kuan Liu, Yan Fan, Xinhui Lu, Xiaowei Zhan
A fused hexacyclic electron acceptor, IHIC, based on strong electron-donating group dithienocyclopentathieno[3,2-b]thiophene flanked by strong electron-withdrawing group 1,1-dicyanomethylene-3-indanone, is designed, synthesized, and applied in semitransparent organic solar cells (ST-OSCs). IHIC exhibits strong near-infrared absorption with extinction coefficients of up to 1.6 × 10(5) m(-1) cm(-1) , a narrow optical bandgap of 1.38 eV, and a high electron mobility of 2.4 × 10(-3) cm(2) V(-1) s(-1) . The ST-OSCs based on blends of a narrow-bandgap polymer donor PTB7-Th and narrow-bandgap IHIC acceptor exhibit a champion power conversion efficiency of 9...
June 13, 2017: Advanced Materials
María C Soraires Santacruz, Matías Fabiani, Eliana F Castro, Lucía V Cavallaro, Liliana M Finkielsztein
A series of N(4)-arylsubstituted thiosemicarbazones derived from 1-indanones and a set of compounds lacking such substitution in the N(4) position of the thiosemicarbazone moiety were synthesized and evaluated for their anti-bovine viral diarrhea virus (BVDV) activity. Among these, derivatives 2 and 15 displayed high activity (EC50=2.7±0.4 and 0.7±0.1µM, respectively) as inhibitors of BVDV replication. Novel key structural features related to the anti-BVDV activity were identified by structure-activity relationship (SAR) analysis...
May 27, 2017: Bioorganic & Medicinal Chemistry
Yan Zhang, Shangyi Ye, Mingming Ji, Lisha Li, Dongmei Guo, Gangguo Zhu
A novel copper-catalyzed cascade difluoromethylation/cyclization of 2-(3-arylpropioloyl)benzaldehydes has been developed. This method affords an efficient and straightforward access to structurally diverse difluoromethylated naphthoquinones in one pot, starting from readily available starting materials. The reaction represents the first trans-acyldifluoromethylation of internal alkynes, which features aldehydes as acceptors for the addition of alkenyl radicals. Furthermore, this protocol can also access to monofluoromethylated naphthoquinone and difluoromethylated indanones in the same reaction condition...
June 12, 2017: Journal of Organic Chemistry
Jialin Wang, Jiajun Peng, Xiaoyu Liu, Ziqi Liang
Planar perylene diimides (PDIs), when used as nonfullerene acceptors for organic photovoltaics, are constrained by their large π-aggregation in solid state. To tackle this issue, another planar nonfullerene acceptor 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']dithiophene (ITIC) with weak crystallinity and near-infrared light absorption is introduced into the PTB7-Th:PDI binary blend to fabricate efficient and stable ternary solar cells...
June 21, 2017: ACS Applied Materials & Interfaces
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