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Rabah Azzouz, Ludovic Peauger, Vincent Gembus, Mihaela-Liliana Ţînţaş, Jana Sopková-de Oliveira Santos, Cyril Papamicaël, Vincent Levacher
As an extension of our previous work on donepezil-based "bio-oxidizable" prodrug approach, two new classes of N-benzylpyridinium donepezil analogues in tetralone B2 and acetophenone B3 series and a new set of indanone derivatives B1 were investigated along with the corresponding dihydropyridine prodrugs A1-3. A total of fifty one N-benzylpyridinium quaternary donepezil analogues B1-3 and twenty two prodrugs A1-3 were synthesized and evaluated for their inhibitory activities against hAChE and eqBuChE. While most prodrugs A1-3 were demonstrated to be inactive against AChE (IC50 > 10 μM), a large number of the corresponding N-benzylpyridinium salt B1-3 exhibited appealing three-to-one-digit nanomolar hAChE inhibitory activities and even reaching subnanomolar activity (IC50 = 0...
December 27, 2017: European Journal of Medicinal Chemistry
Dileep K Singh, Ikyon Kim
Described herein is a novel synthetic approach to diptoindonesin G, a highly potent anticancer oligostilbenoid natural product, from pauciflorol F pentamethyl ether through a skeletal reorganization strategy where oxidative cleavage of the indanone ring system of pauciflorol F and sequential cyclization of the key intermediate allowed direct access to the target skeleton.
January 11, 2018: Journal of Organic Chemistry
Deyu Liu, Junyi Wang, Chunyang Gu, Yonghai Li, Xichang Bao, Renqiang Yang
Two series of new polymers with medium and wide bandgaps to match fullerene (PC71 BM) and fullerene-free 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) acceptors are designed and synthesized, respectively. For constructing the key donor building blocks, the effective symmetry-breaking strategy is employed. Two common aromatic rings (thiophene and benzene) are chosen as one side substituted groups in the asymmetric benzodithiophene (BDT) monomers...
January 8, 2018: Advanced Materials
Han Yan, Shuyang Ye, Dwight S Seferos
Post processing is widely used to improve the photovoltaic performance of organic solar cells. However, high-temperature and long-time release of halogenated solvents are incompatible with future printing manufacturing. Inspired by the dependence of donor/acceptor optical properties on "ink" temperature, we designed a study to test its effect on photovoltaic performance. We utilize the newly reported nonfullerene ink, poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-benzo[1,2-b:4,5-b']dithiophene))-alt-(5,5-(1',3'-di-2-thienyl-5',7'-bis(2-ethylhexyl)benzo[1',2'-c:4',5'-c']dithiophene-4,8-dione))]/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 as a model system, and find that device performance can be improved by heating and then cooling the ink in a specific temperature range...
December 20, 2017: ACS Applied Materials & Interfaces
Kyle A Windisch, Cristine L Czachowski
Previous studies suggest that group II metabotropic glutamate receptors (mGluR2/3) are involved in regulating ethanol-seeking and consumption. The mGluR2/3 agonist LY379268 (LY37) and selective mGluR2 positive allosteric modulator biphenyl‑indanone A (BINA) were used to investigate the relative contribution of mGlu2 and mGlu3 receptors on ethanol- and sucrose-seeking and consumption. A microinjection study was then performed to examine the role of nucleus accumbens (NAc) core mGluR2/3 on ethanol-seeking. For the systemic experiments, separate groups of male Wistar rats [LY37 (0-2...
September 23, 2017: Alcohol
Ahmet Ozdemir, Sevtem Gokbulut, Belgin Sever, Gulsen Akalın Ciftci, Mehlika Dilek Altıntop
BACKGROUND: Arylidene indanones have attracted a great deal of interest due to their outstanding therapeutic applications. In particular, considerable research has pointed out the importance of arylidene indanones in the field of cancer research. OBJECTIVE: The aim of the current work was to design and synthesize arylidene indanone-based anticancer agents. METHOD: New arylidene indanones were obtained via the Claisen-Schmidt condensation of 5-chloro-6-methoxy-2,3-dihydro-1H-inden-1-one with p-substituted benzaldehyde derivatives...
December 5, 2017: Anti-cancer Agents in Medicinal Chemistry
Poonam Piplani, Ankit Jain, Dhiksha Devi, Anjali, Anuradha Sharma, Pragati Silakari
The present study reports the effect of indanone derivatives on scopolamine induced deficit cholinergic neurotransmission serving as promising leads for the therapeutics of cognitive dysfunction. Eleven compounds 54-64 have been designed, synthesised and evaluated against behavioural alterations using step down passive avoidance protocol at a dose of 0.5 mg/kg with Donepezil (1) as the reference standard. All the synthesised compounds were evaluated for their in vitro acetylcholinesterase (AChE) inhibition at five different concentrations using mice brain homogenate as the source of the enzyme...
November 22, 2017: Bioorganic & Medicinal Chemistry
Jinwoo Kim, Ikyon Kim
A chemical backbone of tetracyclic homoisoflavanoid natural products such as brazilin inspired us to design a new chemical scaffold, 6a,11b-dihydroindeno[2,1-c]chromen-7(6H)-one, which is a hybrid structure of indanone and chromane. Pd-catalyzed Suzuki-Miyaura cross-coupling of 4-chloro-2H-chromene-3-carbaldehydes with (hetero)aryl boronic acids was employed as a means to introduce a wide variety of (hetero)aryl groups as the D ring and intramolecular Friedel-Crafts acylation was utilized to construct the C ring of this skeleton...
December 1, 2017: Organic & Biomolecular Chemistry
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
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