Derivatives Bearing Research Articles

Organic Thin‐film Solar Cells Using Benzotrithiophene Derivatives Bearing Acceptor Units as Non‐Fullerene Acceptors

AbstractNew star‐shaped non‐fullerene acceptors (5Z,5′Z,5′′Z)‐5,5′,5′′‐((benzo[1,2‐b : 3,4‐b′ : 5,6‐b′′]trithiophene‐2,5,8‐triyltris(4‐octylthiophene‐5,2‐diyl))tris(methaneylylidene))tris(3‐octyl‐2‐thioxothiazolidin‐4‐one) (1: BTT‐OT‐ORD) and 2,2′,2′′‐((5Z,5′Z,5′′Z)‐((benzo[1,2‐b : 3,4‐b′ : 5,6‐b′′]trithiophene‐2,5,8‐triyltris(4‐octylthiophene‐5,2‐diyl))tris(methaneylylidene))tris(3‐octyl‐4‐oxothiazolidine‐5,2‐diylidene))trimalononitrile (2: BTT‐OT‐OTZDM) with a benzotrithiophene core, alkyl‐thiophen units, and acceptor units were designed and synthesized. The HOMO‐LUMO levels of 1 and 2 were determined by photoemission spectroscopy and UV‐Vis absorption spectroscopy. Binary blend and ternary blend bulk heterojunction (BHJ) organic solar cells with non‐fullerene acceptors 1 and 2 were fabricated with the inverted device structures of glass/ITO/ZnO/active_layer/MoO3/Ag. Both binary blend BHJ solar cells with 1 and 2 show lower JSC and larger VOC values than P3HT : PCBM solar cells. On the other hand, ternary blend BHJ organic solar cells, including 10 % of 1, exhibited a larger power conversion efficiency than P3HT : PCBM solar cells because the JSC value was largely improved.

Synthesis and Biological Evaluation of Honokiol Derivatives Bearing 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)oxazol-2(3H)-ones as Potential Viral Entry Inhibitors against SARS-CoV-2.

The 2019 coronavirus disease (COVID-19) caused by SARS-CoV-2 virus infection has posed a serious danger to global health and the economy. However, SARS-CoV-2 medications that are specific and effective are still being developed. Honokiol is a bioactive component from Magnoliae officinalis Cortex with damp-drying effect. To develop new potent antiviral molecules, a series of novel honokiol analogues were synthesized by introducing various 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)oxazol-2(3H)-ones to its molecule. In a SARS-CoV-2 pseudovirus model, all honokiol derivatives were examined for their antiviral entry activities. As a result, 6a and 6p demonstrated antiviral entry effect with IC50 values of 29.23 and 9.82 µM, respectively. However, the parental honokiol had a very weak antiviral activity with an IC50 value more than 50 µM. A biolayer interfero-metry (BLI) binding assay and molecular docking study revealed that 6p binds to human ACE2 protein with higher binding affinity and lower binding energy than the parental honokiol. A competitive ELISA assay confirmed the inhibitory effect of 6p on SARS-CoV-2 spike RBD’s binding with ACE2. Importantly, 6a and 6p (TC50 > 100 μM) also had higher biological safety for host cells than honokiol (TC50 of 48.23 μM). This research may contribute to the discovery of potential viral entrance inhibitors for the SARS-CoV-2 virus, although 6p’s antiviral efficacy needs to be validated on SARS-CoV-2 viral strains in a biosafety level 3 facility.

Fluorene Derivatives Bearing Two to Seven Phthalimidomethyl Groups: Syntheses, Crystal Structures and Conversion to Amines

AbstractFluorene derivatives containing four to seven phthalimidomethyl groups (1,3‐dioxo‐1,3‐dihydro‐2H‐isoindol‐2‐yl‐methyl groups) were prepared from 9H‐fluorene, 9,9‐diethyl‐9H‐fluorene as well as from 2,7‐ and 2,4,7‐functionalized 9,9‐diethyl‐9H‐fluorenes by using the conditions of the Tscherniac‐Einhorn reaction. By reacting the 9,9‐diethyl substituted fluorenes with N‐(hydroxymethyl)phthalimide the 2,4,6,7‐ and 2,3,4,6,7‐substituted derivatives were obtained. In the absence of the ethyl groups, as in the case of 9H‐fluorene, the formation of the sixfold and sevenfold substituted compounds was observed (1,2,3,5,7,8‐ and 1,2,3,4,6,7,8‐substituted fluorenes). It should be noted that one position in the bay region of the fluorene skeleton (position 4 or 5) remains unsubstituted in each of the prepared four‐ to sevenfold substituted 9H‐fluorenes. The conversion of the phthalimidomethyl substituted 9,9‐diethyl‐9H‐fluorenes into the corresponding amines takes place with excellent yields. The solid‐state structures of the compounds bearing phthalimidomethyl groups were determined by single‐crystal X‐ray diffraction analysis. The crystal structures are characterized by the presence of C−H⋅⋅⋅O, C−H⋅⋅⋅π and π⋅⋅⋅π interactions as well as C=O⋅⋅⋅π contacts. In the case of the chloroform and dichloromethane solvates the Cl⋅⋅⋅O=C, Cl⋅⋅⋅Cl, and Cl⋅⋅⋅π halogen bonds as well as the C−H⋅⋅⋅Cl hydrogen bonds influence furthermore the crystal packing. Ten‐membered supramolecular motifs of the graph set (10), which are created by the C−H⋅⋅⋅O bonds, can be recognized in some crystal structures. The manuscript provides information about the synthetic routes to new fluorene derivatives and their molecular structures as well as the patterns of noncovalent interactions in the crystalline state.

Synthesis and Antiproliferative Activity of Novel Hydrazono Thiazolidene and Thiazole Derivatives Bearing Rhodanine Moiety

Synthesis and Antiproliferative Activity of Novel Hydrazono Thiazolidene and Thiazole Derivatives Bearing Rhodanine Moiety

A Triad Fluorenone Derivative Bearing Two Imidazole Groups That Switches between Three States by Base and Acid Stimuli

2,7-Bis(2-phenyl-1H-imidazol-4-yl)fluorenone (BPIFO) was synthesized as a new fluorenone derivative bearing two imidazole moieties, and it exhibited remarkable and reversible changes in photo physi...

Competition of Lamellar Crystal and Smectic Liquid Crystal in Precise Polyethylene Derivative Bearing Mesogenic Side-Chains

For side-chain liquid-crystalline polymers (SCLCPs) bearing calamitic mesogens, nematic and typical smectic (Sm) phases are expected. Here, using a precise polyethylene derivative with the biphenyl...

Synthesis of Hydroxylated Biphenyl Derivatives Bearing an α,β-Unsaturated Ketone as a Lead Structure for the Development of Drug Candidates against Malignant Melanoma.

A small collection of C2 -symmetric hydroxylated biphenyl derivatives featuring an α,β-unsaturated ketone as a lead structure was prepared, and the capacity of these compounds to act as antiproliferative agents against four human malignant melanoma cell lines was assayed. The prodrug approach was applied in order to improve the delivery of compounds into the cell by modulation of the phenolic hydroxy protecting group. The hydroxylated biphenyl structure bearing an α,β-unsaturated ketone and a phenolic-O-prenylated chain was found to facilitate the delivery of the molecule and interactions with biological targets. Four compounds showed antiproliferative activity resulting in IC50 values in the range of 1.2 to 2.8 μM.

Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide

Synthesis and Biological Activity of <i>N</i>-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide

Synthesis, Antibacterial and Antifungal Evaluation of Rhodanine Derivatives Bearing Quinoxalinyl Imidazole Moiety as ALK5 Inhibitors

Synthesis, Antibacterial and Antifungal Evaluation of Rhodanine Derivatives Bearing Quinoxalinyl Imidazole Moiety as ALK5 Inhibitors

Synthesis of Novel Coumarin Derivatives Bearing Phosphor Ester Motifs and Evaluation of their Antioxidant Activities

phosphoramidate, phosphoranylidenetriazene, and azaphosphole derivatives can be respectively formed when the substituted azidocoumarin 1 reacted with trialkylphosphites (TAP), dialkylphosphonates (DAP), and tris(dialkylamino)phosphines. The known triazinedione was revealed to be a side product in the reactions of carbaldehyde 1 with TAP and tris(dialkylamino)-phosphines. In the same context, when the starting coumarin 16 was allowed to react with P (III) reagents, chromen phosphoramidates and chromen phosphoric triamide derivatives were obtained via Staudinger reaction. Contrary to that pathway, phosphoranylidenetriazen chromen derivative could be isolated and identified when coumarin 16 was allowed to react with tris(diethylamino)-phosphine. The antioxidant activities of 6-newly products were evaluated. The results showed that two from the six screened compounds exhibited good antioxidant activities.

Design, Synthesis, and Anti-ToCV Activity of Novel 4(3H)-Quinazolinone Derivatives Bearing Dithioacetal Moiety.

Tomato chlorosis virus (ToCV) has caused great harm to the production of tomato worldwide. To develop efficient anti-ToCV agents, some novel 4(3H)-quinazolinone derivatives containing dithioacetal were designed and synthesized, and their anti-ToCV activities were evaluated by microscale thermophoresis (MST) using ToCV coat protein (ToCV-CP) as a new target. The results showed that some compounds had a strong binding capacity to ToCV-CP. In particular, compounds C5 and C22 have an excellent binding capacity to ToCV-CP, with binding constant values of 0.24 and 0.25 μM, respectively. Additionally, reduced ToCV-CP gene expression levels of 81.05 and 87.59% could be achieved when tomato was treated with compounds C5 and C22, respectively, which were obviously higher than the levels after ningnanmycin (NNM) treatment (43.88%) and lead compound Xiangcaoliusuobingmi (XCLSBM) treatment (63.56%). Therefore, this work indicates that 4(3H)-quinazolinone derivatives containing dithioacetal moiety can be used as novel anti-ToCV agents.

Naked Eye Detection of Anions by 2,2′-Bianthracene Derivative Bearing Urea Groups in Various Organic Solvents

A highly fluorescent 2,2′-bianthryl derivative bearing urea groups (2) was prepared as an anion receptor. The UV-vis and fluorescence titrations of 2 in various organic solvents revealed that the a...

Synthesis and Antiproliferative Evaluation of Novel Longifolene-Derived Tetralone Derivatives Bearing 1,2,4-Triazole Moiety.

Seventeen novel 2-(5-amino-1-(substituted sulfonyl)-1H-1,2,4-triazol-3-ylthio)-6- isopropyl-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one compounds were synthesized from the abundant and naturally renewable longifolene and their structures were confirmed by FT-IR, NMR, and ESI-MS. The in vitro cytotoxicity of the synthesized compounds was evaluated by standard MTT assay against five human cancer cell lines, i.e., T-24, MCF-7, HepG2, A549, and HT-29. As a result, compounds 6d, 6g, and 6h exhibited better and more broad-spectrum anticancer activity against almost all the tested cancer cell lines than that of the positive control, 5-FU. Some intriguing structure–activity relationships were found and are discussed herein by theoretical calculation.

Selective Synthesis and Molecular Structure of Novel Aminooxyglycosyl Derivatives Bearing Hydroxyphenyl Moieties

AbstractWe present the selective synthesis of novel aminooxy glycosyl derivatives bearing hydroxy phenyl moieties. A strict control over the anomeric and E/Z configurations has been achieved. The products obtained are α‐glycosides and the aromatic moiety substitute the Schiff's base trans to the O‐glycosidic bond. Single crystal X‐ray diffraction and NMR spectral data are reported and analysed.

Electrochemical Properties and Fluorination of Cyclopropane Derivatives Bearing Arylthio Groups

Electrochemical analyses of phenylthiocyclopropane derivatives and bis(arylthio)cyclopropanes were comparatively studied by cyclic voltammetric measurements. Based on the substituent effects on their oxidation potentials, a cyclopropane ring was confirmed to have a double bond system as reported. Anodic fluorination of phenylthiocyclopropanes resulted in the formation of sulfoxide and/or ring opening fluorinated products while 1,1-bis(arylthio)cyclopropanes afforded mainly desulfurizative monofluorinated cyclopropanes and sulfoxides together with ring opening fluorinated products. This is the first successful electrochemical fluorination of a cyclopropane ring.

Improved Antioxidant and Antifungal Activity of Chitosan Derivatives Bearing Urea Groups

AbstractEight novel chitosan derivatives bearing urea groups are designed and synthesized. Fourier transform infrared spectroscopy, 1H nuclear magnetic resonance spectrometer, and elemental analysis are performed to confirm the structural characteristics of chitosan derivatives. The antioxidant activities, including superoxide radicals’ scavenging activity, 1,1‐diphenyl‐2‐picrylhydrazyl radicals’ scavenging activity, and hydroxyl radical’ scavenging activity, of the derivatives are explored within different concentrations in the reaction system. In vitro fungicidal activity of these compounds is further tested against Fusarium oxysporum f. sp. niveum, Phomopsis asparagus, F. oxysporum f. sp. cucumebrium Owen, and Botrytis cinerea, respectively, particularly compounds exhibit significant control effect at 1.0 mg mL−1. The experimental results indicate that the products bearing urea groups show enhanced antifungal property and antioxidant activity compared with pristine chitosan. Meanwhile, their bioactivities follow some regularity on the whole, that is, they are related to the electron‐withdrawing property of the different substituted groups of urea. Derivatives with stronger electron‐withdrawing property will have higher biological activities. L929 cells are used to carry out cytotoxicity test of chitosan and chitosan derivatives by Cell Counting Kit‐8 assay. The results indicate that some of the samples show low cytotoxicity. This research will be helpful to broaden the application of chitosan in materials.

Design, Synthesis and Antiproliferative Activity of Chrysin Derivatives Bearing Triazole Moieties

Design, Synthesis and Antiproliferative Activity of Chrysin Derivatives Bearing Triazole Moieties

Synthesis and Antibacterial Activity of Thienyl Chalcone Derivatives Bearing Piperazine Moiety

Synthesis and Antibacterial Activity of Thienyl Chalcone Derivatives Bearing Piperazine Moiety

Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Bearing an Oxazole Moiety

Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Bearing an Oxazole Moiety

Design, Synthesis, Antimicrobial, and Antioxidant Activity of Dimers of Chromene Containing 1,2,3-Triazole Derivatives Bearing an Alkyl Spacer

A new series of chromene based 1,2,3-triazole derivatives has been synthesized by incorporating biologically active heterocyclic rings containing chromene and triazole moieties in one molecular structure. All newly synthesized compounds are characterized by 1H and 13C NMR, mass, and IR spectra. The title compounds are tested for their activity against different bacterial and fungal strains, and antioxidant activity. Several compounds are determined to be potent antimicrobial and antioxidant agents.