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Klaudia T Amakali, Lesetja J Legoabe, Anél Petzer, Jacobus P Petzer
The present study investigates the human monoamine oxidase (MAO) inhibition properties of a series of twelve 2-heteroarylidene-1-tetralone derivatives. Also included are related cyclohexylmethylidene, cyclopentylmethylidene and benzylidene substituted 1-tetralones. These compounds are related to the 2-benzylidene-1-indanone class of compounds which has previously been shown to inhibit the MAOs, with specificity for the MAO-B isoform. The target compounds were synthesised by the Claisen-Schmidt condensation between 7-methoxy-1-tetralone or 1-tetralone, and various aldehydes, under acid (hydrochloric acid) or base (potassium hydroxide) catalysis...
May 14, 2018: Drug Research
Yongtao Chen, Chenyun Shu, Fang Luo, Xiaohui Xiao, Gangguo Zhu
A novel photocatalytic acylarylation of unactivated alkenes using diaryliodonium salts as the arylation reagent is described. The reaction produces a variety of 2-benzyl indanones, 3,4-dihydronaphthalen-1(2H)-ones, and 2,3-dihydroquinolin-4(1H)-ones in promising yields with excellent diastereoselectivity under very mild conditions, which may be appealing for the synthesis of biologically active molecules.
May 14, 2018: Chemical Communications: Chem Comm
Andrej Emanuel Cotman, Barbara Modec, Barbara Mohar
Activated racemic 2,3-disubstituted 1-indanones 1 possessing two stereolabile centers were stereoselectively reduced to the corresponding chiral 2,3-disubstituted-1-indanols 2 by ruthenium(II)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation. In particular, this route offers a practical access to a new class of conformationally rigid enantiopure 1,4-diols 2k-m having four contiguous chiral centers. Transformation of ent-2k into a Pallidol analogue via a highly diastereo- and regioselective Friedel-Crafts benzylation of o-chloroanisole is presented...
May 10, 2018: Organic Letters
Siyang Xiao, Wenxin Zhang, Hongjin Chen, Bo Fang, Yinda Qiu, Xianxin Chen, Lingfeng Chen, Sheng Shu, Yali Zhang, Yunjie Zhao, Zhiguo Liu, Guang Liang
Purpose: The purpose of this study was to design and synthesize novel 2-benzylidene-1-indanone derivatives for treatment of acute lung injury. Methods: A series of 39 novel 2-benzylidene-indanone structural derivatives were synthesized and evaluated for anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated murine primary macrophages. Results: Most of the obtained compounds effectively inhibited the LPS-induced expression of IL-6 and TNF-α...
2018: Drug Design, Development and Therapy
Klaudia T Amakali, Lesetja Jan Legoabe, Anel Petzer, Jacobus P Petzer
Chalcone has been identified as a promising lead for the design of monoamine oxidase (MAO) inhibitors. This study attempted to discover potent and selective chalcone-derived MAO inhibitors by synthesising a series consisting of various cyclic chalcone derivatives. The cyclic chalcones were selected based on the possibility that their restricted structures would confer a higher degree of MAO isoform selectivity, and included the following chemical classes: 1-indanone, 1-tetralone, 1-benzosuberone, chromone, thiochromone, 4-chromanone and 4-thiochromanone...
May 1, 2018: Central Nervous System Agents in Medicinal Chemistry
Shengli Niu, Zhiyong Liu, Ning Wang
A dihydronaphthyl-based C60 bisadduct (NCBA) acceptor was introduced as a third component to typical poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-benzo[1,2-b:4,5-b0]dithiophene))-alt-(5,5-(10,30-di-2-thienyl-50,70-bis(2-ethylhexyl)benzo[10,20-c:40,50-c0]dithiophene-4,8-dione))] (PBDB-T): 3,9-bis(2-methylene-(3-(1,1-dicyanomethylene)-indanone))-5,5,11,11-tetrakis(4-hexylphenyl)-dithieno[2,3-d:20,30-d0]-s-indaceno[1,2-b:5,6-b0]-dithiophene (ITIC) binary polymer solar cells (PSCs). NCBA plays a bridging role between the lowest unoccupied molecular orbital (LUMO) of PBDB-T and ITIC and provides more routes for charge carrier transfer at the interface between PBDB-T and ITIC, whereupon a higher open-circuit voltage (VOC) could be realized upon the addition of NCBA relative to the neat ITIC as an electron acceptor...
April 25, 2018: Nanoscale
Pulla Reddy Boggu, Jungsuk Cho, Youngsoo Kim, Sang-Hun Jung
A novel series of 2-benzyl-1-indanone analogs were investigated as IL-5 inhibitory activity. Among the synthesized compounds, 7-(cyclohexylmethoxy)-2-(4-hydroxybenzyl)-2,3-dihydro-1H-inden-1-one (7s, 100.0% inhibition at 30 μM, IC50  = 4.0 μM), and 7-(cyclohexylmethoxy)-2-(3-hydroxybenzyl)-2,3-dihydro-1H-inden-1-one (7t, 95.0% inhibition at 30 μM, IC50  = 6.0 μM) showed the best inhibitory activity against IL-5. The 2-benzyl-1-indanone analogs showed moderate to strong IL-5 inhibitory activity...
April 16, 2018: European Journal of Medicinal Chemistry
Ying Xia, Jianchun Wang, Guangbin Dong
Here, we describe that simple ketones can be efficiently employed as electrophiles in Suzuki-Miyaura coupling reactions via catalytic activation of unstrained C-C bonds. A range of common ketones, such as cyclopentanones, acetophenones, acetone and 1-indanones, could be directly coupled with various arylboronates in high site-selectivity, which offers a distinct entry to more functionalized aromatic ketones. Preliminary mechanistic study suggests that the ketone α-C-C bond was cleaved via oxidative addition...
April 13, 2018: Journal of the American Chemical Society
Rajib Saha, Dhanarajan Arunprasath, Govindasamy Sekar
The carbene migratory insertion involving domino reaction by highly stable, reusable and binaphthyl stabilized Pd-nanoparticles (Pd-BNP) is disclosed. The reaction was catalyzed by 2 mol% of heterogeneous Pd-BNP catalyst under external ligand-free conditions and afforded 3-aryl-substituted indanone derivatives in up to 90% yield with exclusive E-selectivity. Furthermore, a one-pot reaction and derivatization of indanone derivatives were also successfully demonstrated.
April 2, 2018: Journal of Organic Chemistry
Johannes Teske, Bernd Plietker
A cycloisomerization of aryl allenyl ketones to 3-arylidene-indan-1-ones using a cationic Fe-complex as a catalyst is reported. The catalyst opens a synthetically interesting reaction pathway to this surprisingly underrepresented class of indanones that are not accessible using alternative catalytic systems.
March 27, 2018: Organic Letters
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...
April 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...
April 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...
March 25, 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...
March 2, 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 , NO2 and 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=CF3 and NH2 ) molecules were explored in gas phase and acetonitrile, cyclohexane and water solvents...
May 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...
February 10, 2018: European Journal of Medicinal Chemistry
Dileep Kumar 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.
February 2, 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...
February 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...
January 10, 2018: ACS Applied Materials & Interfaces
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