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Shubhandra Tripathi, Gaurava Srivastava, Aastha Singh, A P Prakasham, Arvind S Negi, Ashok Sharma
Colchicine site inhibitors are microtubule destabilizers having promising role in cancer therapeutics. In the current study, four such indanone derivatives (t1, t9, t14 and t17) with 3,4,5-trimethoxyphenyl fragment (ring A) and showing significant microtubule destabilization property have been explored. The interaction mechanism and conformational modes triggered by binding of these indanone derivatives and combretastatin at colchicine binding site (CBS) of αβ-tubulin dimer were studied using molecular dynamics (MD) simulation, principle component analysis and free energy landscape analysis...
March 7, 2018: Journal of Computer-aided Molecular Design
Hanmanth Reddy Vulupala, Yasodakrishna Sajja, Pankaj K Bagul, Raviteja Bandla, Lingaiah Nagarapu, Sanjay K Benerjee
A novel triazole derivatives(±)-2-(hydroxymethyl)-7,8-dihydro-1H-indeno[5,4-b]furan-6(2H)-one (12a-j) were designed and synthesized by the reaction between racemic azide and terminal acetylenes under click chemistry reaction conditions followed by biological evaluation as angiotensin converting enzyme (ACE) inhibitors. β-Amino alcohol derivatives of 1-indanone (15a-l) were synthesized from 5-hydroxy indanone, it was reacted with epichlorohydrin and followed by oxirane ring opening with various piperazine derivatives...
February 24, 2018: Bioorganic Chemistry
Anna Affini, Stefanie Hagenow, Aleksandra Zivkovic, Jose Marco-Contelles, Holger Stark
The design of multi-targeting ligands was developed in the last decades as an innovative therapeutic concept for Parkinson's disease (PD) and other neurodegenerative disorders. As the monoamine oxidase B (MAO B) and the histamine H3 receptor (H3 R) are promising targets for dopaminergic regulation, we synthetized dual-targeting ligands (DTLs) as non-dopaminergic receptor approach for the treatment of PD. Three series of compounds were developed by attaching the H3 R pharmacophore to indanone-related MAO B motifs, leading to development of MAO B/H3 R DTLs...
February 16, 2018: European Journal of Medicinal Chemistry
Graham R Cumming, Tao Zhang, Gaia Scalabrino, Neil Frankish, Helen Sheridan
PH46A, belonging to a class of 1,2-Indane dimers, has been developed by our research group as a potential therapeutic agent for the treatment of inflammatory and autoimmune diseases. The initial synthetic route to PH46A gave a low overall yield, due in large part to the generation of undesired diastereoisomer 5 and the unwanted enantiomer ( R , R )- 8 during the synthesis. The aim of this work was to carry out a comprehensive investigation into the stereoselective synthesis of PH46A. Significant progress was made on the ketone reduction step, where the use of triisobutylaluminum [TiBA, Al(iBu)3 ] afforded high selectivity for the target diastereoisomer ( rac )- 6 , compared to the unfavorable ratio obtained using a previous process...
December 15, 2017: Organic Process Research & Development
Timon Kurzawa, Klaus Harms, Ulrich Koert
An efficient stereoselective synthesis of the enantiomer of the benzodihydropentalene core of fijiolides A and B has been achieved. The asymmetric conjugate addition of styrylboronic acid to an indenone produced the first stereocenter. Ring C was installed by ring-closing metathesis of a cis disubstituted indanone. Regioselective epoxide opening by NaSePh and subsequent oxidative elimination produced an allylic alcohol. The final introduction of the cyclopentadiene was possible by elimination of an in situ formed triflate...
February 16, 2018: Organic Letters
Hossein Roohi, Parvaneh Alizadeh
Near-infrared (NIR) fluorescent dyes have recently gained special attention due to their applications to use as molecular probes for imaging of biological targets and sensitive determination. In this study, photophysical properties of the 7-hydroxy-1-indanone based fluorophors A1, A2, A3, B1, B2 and 3R-B2 (R=CF3, NH2, NO2and OMe) in the gas and three solution phases were probed using TD-DFT method at PBE0/6-311++G(d,p) and M06-2X/6-311++G(d,p) levels of theory. In addition to structural and photophysical properties as well as ESIPT mechanism of all mentioned molecules, the FC and relaxed potential energy surfaces of B2 and 3R-B2 (R=CF3and NH2) molecules were explored in gas phase and acetonitrile, cyclohexane and water solvents...
February 5, 2018: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
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...
February 2018: 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...
January 1, 2018: 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 19, 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 nonfullerene 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 the DTCC core provides a broad light-absorbing window and a higher-lying LUMO energy level, whereas the bulky flanked side chains reduce intermolecular interactions, making DTCCIC-C17 amorphous with excellent solution processability...
December 6, 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 chloride in good to excellent yields, which led to the first synthesis of indanone BN-analogue. The BN-aromatic ketone products have been characterized by1 H NMR spectroscopy with their molecular structures unambiguously confirmed by X-ray crystallography. The annulation reaction of BN-arenes promoted by AgBF4 occurs in a completely regioselective manner and a mechanism for this transformation is proposed.
December 1, 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
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