Indanone

A novel methodology for the synthesis of indanone derivates has been developed. The palladium-catalyzed annulation reaction of o -bromobenzaldehydes with norbornene derivatives is achieved through extremely concise reaction processes. The indanone skeleton was established directly via C-H activation of the aldehyde group under a mild reaction condition. This method is simple and practical, which simplified the traditional synthesis method for the rapid construction of indanone.

Light-induced bioorthogonal reactions offer spatiotemporal control over selective biomolecular labeling. This review covers the recent advances in the design of photo-activatable reagents for bioorthogonal conjugation reactions in living systems. These reagents are stable in the absence of light, but transformed into reactive species upon light illumination, which then undergo rapid ligation reactions. The light wavelength has been tuned from ultraviolet to near infrared to enable efficient photo-activation in reactions in deep tissues...

The triple condensation of cyclopentanone or indanone to trindane (C15 H18 ) or truxene (C27 H18 ), respectively, provides convenient access to molecular skeletons on which major fragments of the prototypical fullerene C60 can be assembled. In particular, early approaches (both organic and organometallic) towards sumanene, as well as the final successful synthesis, are described. Organometallic derivatives of trindane have been prepared in which Cr(CO)3 , Mo(CO)3 , [Mn(CO)3 ]+ or [(C5 H5 )Fe(CO)2 ]+ are η6 -bonded to the central arene ring...

Fullerenes are among the most commonly used electron-transporting materials (ETMs) in inverted perovskite solar cells (IPSCs). Although versatile functionalized fullerene derivatives have shown excellent performance in IPSCs, pristine [60]fullerene (C60 ) is still the most widely used in devices mainly because of its uniform morphology by thermal deposition. However, thermally evaporable fullerene derivatives have not yet been achieved. Herein, we developed a series of evaporable fullerene derivatives, referred to as fullerene indanones (FIDOs), affording IPSCs with high power conversion efficiency (PCE) and long-term storage stability...

The ability of guanine (G)-rich DNA to bind toxic lead (Pb2+ ) ions within a G-quadruplex (GQ) motif is a leading DNA biosensor strategy. A major analytical hurdle for GQ detection of Pb2+ is competitive GQ templating by potassium (K+ ) ions. We employ the on-strand DNA synthesis of internal fluorescent chalcone surrogates within the 15-mer thrombin binding aptamer (TBA15) to address this challenge. Replacement of thymidine at the 3-position (T3) within TBA15 with an indole-4-hydroxy-indanone (Ind4HI) chalcone strongly decreases K+ -GQ stability while enhancing Pb2+ -GQ stability to increase Pb2+ binding specificity...

A convenient synthetic protocol for regioselective and diastereoselective construction of complex dispiro-indanone-fluorenone-oxindole motifs was developed by the base-promoted annulation reaction of bindone and MBH carbonates of isatins by adjusting reaction conditions. DABCO promoted the annulation reaction of bindone and MBH carbonates of isatins in DCM at room temperature, affording dispiro[indene-2,4'-fluorene-1',3″-indoline] derivatives in good yields and with high diastereoselectivity. Triethylamine promoted the annulation reaction of two molecular 1,3-indanediones and MBH esters of isatins in ethanol at elevated temperature and selectively gave dispiro[indene-2,4'-fluorene-3',3″-indolines] in moderate yields...

Aim: Based on a multitarget design strategy, a series of novel indanone-1-benzyl-1,2,3,6-tetrahydropyridin hybrids were identified for the potential treatment of Alzheimer's disease (AD). Results: These compounds exhibited significant inhibitory activities against acetylcholinesterase (AChE) and moderate inhibitory activities toward monoamine oxidase B (MAO-B). The optimal compound A1 possessed excellent dual AChE/MAO-B inhibition both in terms of potency (AChE: IC50  = 0.054 ± 0.004 μM; MAO-B: IC50  = 3...

New-to-nature biocatalysis in organic synthesis has recently emerged as a green and powerful strategy for the preparation of valuable chiral products, among which chiral oxygen-containing benzo-fused heterocycles are important structural motifs in pharmaceutical industry. However, the asymmetric synthesis of these compounds through radical-mediated methods is challenging. Herein, a novel asymmetric radical-mediated photoenzymatic synthesis strategy is developed to realize the efficient enantioselective synthesis of oxygen-containing benzo-fused heterocycles through structure-guided engineering of a flavin-dependent 'ene'-reductase GluER...

Direct 2C-ring expansion of 1-indanones with ynones to 5H-benzo[7]annulenes has been observed, and its generality has been gauged (19 examples). Overall, this simple and convenient cascade process to 5H-benzo[7]annulenes involves engagement of 1-indanone with two ynone moieties with formation of three new C-C σ-bonds, cleavage of C-C σ-bond, and concurrent functionality amplification. The resulting seven-membered ring, laced with an opportunistic disposition of four proximal functional groups, offers avenues for their further productive interplay...

The ability of organic photovoltaics (OPVs) to be deposited on flexible substrates by roll-to-roll (R2R) processes is highly attractive for rapid mass production. Many research teams have demonstrated the great potential of flexible OPVs. However, the fabrication of R2R-coated OPVs is quite limited. There is still a performance gap between the R2R flexible OPVs and the rigid OPVs. In this study, we demonstrate the promising photovoltaic characteristics of flexible OPVs fabricated from blends of low bandgap polymer 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)] (PBDB-T) and non-fullerene 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)...

Trichloromethyl-substituted enones (1-aryl-4,4,4-trichlorobut-2-en-1-ones, ArCOCH=CHCCl3 , CCl3 -enones) undergo intramolecular transformation into 3-trichloromethylindan-1-ones (CCl3 -indanones) in Brønsted superacid CF3 SO3 H (triflic acid, TfOH) at 80 °C within 2-10 h in yields up to 92%. Protonation of the carbonyl oxygen of the starting CCl3 -enones by TfOH affords the key reactive intermediates, the O-protonated forms ArC(=OH+ )CH=CHCCl3 , which are then cyclized into the target CCl3 -indanones...

Aromatic chromophores possessing intramolecular hydrogen-bonds that can undergo excited-state intramolecular proton transfer (ESIPT) are critical tools for chemosensing/biosensing applications because they create large Stokes-shifted fluorescence with no overlap with the absorption spectrum to limit back-ground interferences. Classic ESIPT-active fluorophores, such as the 2-(2'-hydroxyphenyl) benzazole (HBX) series (X = NH, O, S), favor a ground-state (GS) enol (E) form that undergoes ESIPT to afford an excited-state (ES) keto (K) tautomer that generates red-shifted fluorescence...

Many efforts have been made to enrich the variety of BF2 complexes because of their excellent optical properties. However, the investigation on seven-membered ring N, O-chelated BF2 complexes is rare due to their instability with the removal of BF2 unit. Herein, a novel seven-membered ring N, O-chelated BF2 complexes (BOPYOs) with dual-state emission has been synthesized via a facile method. The results of optical properties showed that the fluorescence quantum yield of BOPYO-2 with donor group on 1 and 2-position of 1-indanone unit is much higher than that of BOPYO-1, 3-5 in toluene...

Here, five new acceptor-donor-acceptor (A-D-A) type small donor molecules C1-C5, have been designed based on the central D unit, dithieno[3,2- b :2',3'- d ]pyrrole (DTP). Besides, five different A units, viz. 1,1-dicyano-methylene-5,6-dimethyl-3-indanone, 1,1-dicyano-methylene-5,6-difluoro-3-indanone, 1,1-dicyano-methylene-5,6-dichloro-3-indanone, 1,1-dicyano-methylene-5-nitro-3-indanone, and 1,1-dicyano-methylene-5,6-diamino-3-indanone are selected for these designed compounds C1-C5, respectively. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods have been employed to study the influence of different A units on the geometric, electronic, optical, charge transport and photovoltaic properties of the designed donor molecules...

An SN 1-type fluorination method for monofluoroethers is developed. The key to this reaction is fluorinative C-C bond cleavage that is driven by oxygen-assisted Beckmann fragmentation. To enable this transformation, cyclic α-aryloxyoximes derived from 3-coumaranone and 1-indanones were investigated as substrates, using N , N -diethylaminosulfur trifluoride (DAST) as a dual-role reagent of an oxime activator and fluoride donor. This method features the synthesis of an underdeveloped chemical motif with simple and mild operating conditions...

Cysteine is a vital biothiols that plays an important role in numerous physiological and pathological processes. The development of simple molecule tools for detection and analysis Cys in subcellar environment is significant for further exploring their pathophysiological. In this work, a simple but activated fluorescent probe AMIA was constructed with a donor-π-accepter (D- π -A) structure, which using an indanone as the electron-withdrawing unit acting as the fluorophore, dimethylamino group attached to the position 4 of the benzene ring as the electron-donating, two double bonds as the linker group, and the acryloyl ester group as the trigger and response unit...

A series of benzocycloalkanone derivatives have been prepared and evaluated as antimalarial and antitrypanosomal agents. The compounds were obtained by direct coupling of preformed 4-substituted benzaldehyde and indanone or tetralone substitutes through aldol condensation of Claisen-Schmidt using sodium hydroxide as a catalyst in ethanol at room temperature. Although designed to inhibit the formation of β-hematin in vitro, only three compounds, 10 , 11 , and 12 , showed activities greater than 50% (75...

Glioblastoma (GBM) is the most prevalent and aggressive type of adult brain tumors with low 5-year overall survival rates. Epidemiologic data suggest that estrogen may decrease brain tumor growth, and estrogen receptor beta (ERβ) has been demonstrated to exert anti-tumor functions in GBM. The lack of potent, selective and brain permeable ERβ agonist to promote its anti-tumor action is limiting the therapeutic promise of ERβ. In this study, we discovered that Indanone and tetralone-keto or hydroxyl oximes are a new class of ER agonists...

We describe the synthesis of a triazolyl-pyridine-based aminophosphine, N -(diphenylphosphaneyl)-6-(1-phenyl)-1 H -(1,2,3-triazol-4-yl)pyridine-2-amine [2,6-{(PPh2 )-N(H)(C5 H3 N)(C2 HN3 C6 H5 )}] [ 1 , PN(H)N hereafter], and its palladium and platinum complexes and their catalytic application. The reaction of 1 with [M(COD)Cl2 ] (M = Pd or Pt) afforded the cationic complex [(MCl){PN(H)N}-κ3 -P,N,N]Cl [M = Pd ( 2 ) or Pt ( 3 )]. Alternatively, compounds 2 and 3 were also synthesized by treating [2,6-{H2 N(C5 H3 N)(C2 HN3 C6 H5 )}] ( A ) with [M(COD)Cl2 ] (M = Pd or Pt), followed by the addition of stoichiometric amounts of PPh2 Cl and Et3 N...

Over the past decades, designing of privileged structures has emerged as a useful approach to the discovery and optimisation of novel biologically active molecules, and many have been successfully exploited across and within different target families. Examples include indole, quinolone, isoquinoline, benzofuran and chromone, etc. In the current study, we focus on synthesising a novel hybrid scaffold constituting naturally occurring benzophenone (14) and indanone (22) ring systems, leading to a general structure of 2-(diphenylmethylene)-2,3-dihydro-1H-inden-1-one (23)...