cas 539-47-9, Furylacrylic acid | Articles data

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Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation
A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.
Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei
supporting information
p. 5905 - 5908
(2021/06/18)

Amino Group Functionalized Hf-Based Metal-Organic Framework for Knoevenagel-Doebner Condensation
A Hf(IV) metal-organic framework (MOF) with di-amino functionalized linker was obtained as a crystalline solid with UiO-67 topology under solvothermal reaction conditions. The guest free form of Hf(IV) MOF (1′) was efficiently employed as a heterogeneous catalyst to synthesize cinnamic acid derivatives via Knoevenagel-Doebner reaction for the first time. The catalyst (1′) was efficiently active to directly achieve cinnamic acid from benzaldehyde and malonic acid. The solid retained its activity up to 6th cycle with no decay in its activity. The noticeable advantages of the catalyst are its milder reaction conditions, high yield, high stability, recyclable nature towards catalysis and wide substrate scope as well as shape-selective behaviour. The possible mechanism of the reaction was also studied thoroughly with suitable control experiments.
Das, Aniruddha,Anbu, Nagaraj,Gogoi, Chiranjib,Dhakshinamoorthy, Amarajothi,Biswas, Shyam
p. 3396 - 3403
(2021/08/20)

Biomass-derived rctt-3,4-di-2-furanyl-1,2-cyclobutanedicarboxylic acid: a polytopic ligand for synthesizing green metal-organic materials
Biomass is an abundant and environmentally friendly source for materials that can be used in a multitude of applications in the effort to replace petrochemicals. Furfural and malonic acid are biomass-sourced platforms that can be utilized in the synthesis of biobased compounds; rctt-3,4-di-2-furanyl-1,2-cyclobutanedicarboxylic acid (CBDA-2) is one such compound. In this study, CBDA-2 has been introduced into metal-organic materials chemistry as a semi-rigid polytopic ligand. This compound has been utilized as a polytopic ligand in the formation of two different 2D coordination polymers with Cu2+ and Co2+ as the metal centers via a conventional solution method. Both complexes have been characterized by X-ray crystal structure determination and showed visual thermochromic behaviors. This study demonstrates that CBDA-2 is a promising green building block in coordination chemistry.
Shahni, Rahul K.,Amjaour, Houssein,Krupinsky, Briana,Reagen, Sarah,Wang, Zijun D.,Wu, Xu,Nkemngong, Dominic,Zhao, Julia X.,Ugrinov, Angel,Robertson, Joseph,Chu, Qianli Rick
p. 226 - 240
(2021/02/26)

Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand
Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.
Liu, Feng,Wu, Na,Cheng, Xu
supporting information
p. 3015 - 3020
(2021/05/05)

Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters
Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.
Gao, Ang,Jiang, Run-Chuang,Liu, Chuang-Chuang,Liu, Qi-Le,Lu, Xiao-Yu,Xia, Ze-Jie
supporting information
p. 8829 - 8842
(2021/06/30)

Synthesis, biological evaluation and computational studies of acrylohydrazide derivatives as potential Staphylococcus aureus NorA efflux pump inhibitors
The NorA efflux pump decreases the intracellular concentration of fluoroquinolones (ciprofloxacin, norfloxacin) by effluxing them from Staphylococcus aureus cells. The synthesis of novel acrylohydrazide derivatives was achieved using well-known reactions and were characterized by various spectroscopy techniques. The synthesized 50 compounds were evaluated for the NorA efflux pump inhibition activity against S. aureus SA-1199B (norA++) and K1758 (norA-) strains. The study provided two most active compounds viz. 19 and 52. Compound 19 was found to be most active in potentiating effect of norfloxacin and also it showed enhanced uptake, efflux inhibition in ethidium bromide assay. Further compound 19 also enhanced post antibiotic effect and reduced mutation prevention concentration of norfloxacin. The homology modeling study was performed to elucidate three-dimensional structure of NorA. Docking studies of potent molecules were done to find the binding affinity and interaction with active site residues. Further, all the tested compounds exhibited good ADME and drug-likeness properties in- silico. Based on the in-silico studies and detailed in vitro studies, acrylohydrazides derivatives may be considered as potential NorA EPI candidates.
Kumar, Gautam,Goutami Godavari, Ambati,Tambat, Rushikesh,Kumar, Siva,Nandanwar, Hemraj,Elizabeth Sobhia,Jachak, Sanjay M.
(2020/10/02)

Enantioselective Synthesis of 3,4-Dihydropyran-2-ones via Phase-Transfer-Catalyzed Addition-Cyclization of Acetylacetone to Cinnamic Thioesters
Herein, we present the first example of synthesis of 3,4-dihydropyran-2-ones from cinnamic thioesters via a stereoselective phase-transfer-catalyzed domino Michael-cyclization reaction with acetylacetone. The reaction proceeded under the catalysis of Cinchona-derived quaternary ammonium phenoxide that, in combination with inorganic bases, provided 3,4-dihydropyran-2-ones in yields of up to 93% and enantioselectivities of up to 88% enantiomeric excess.
Destro, Dario,Bottinelli, Carlo,Ferrari, Ludovica,Albanese, Domenico C. M.,Bencivenni, Grazia,Gillick-Healy, Malachi W.,Kelly, Brian G.,Adamo, Mauro F. A.
supporting information
p. 5183 - 5192
(2020/04/10)

Process for the preparation of fatty acids
The invention discloses a method for preparing fatty acid. The method comprises the following steps: providing a first reactant which is a furan compound containing an carbonyl group; providing a second reactant which is a compound containing a carboxyl group, an ester group or an anhydride group and can participate in a condensation reaction with the carbonyl group of the first reactant; allowingthe first reactant and the second reactant to participate in a first condensation reaction, and allowing a C=O bond of the carbonyl group of the first reactant to be connected with alpha carbon of the carbonyl group of the second reactant and to be converted into a C=C bond so as to form a condensation product; and carrying out a second-step reaction under hydrogen pressure in the presence of a co-catalytic system of a hydrogenation catalyst and Lewis acid, opening a furan ring of the condensation product, carrying out hydrodeoxygenation at the same time, removing all oxygen except for oxygenin the carboxyl group, and allowing a carbon chain to be saturated so as to obtain the fatty acid.
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Paragraph 0134-0137

(2020/09/04)

Polyfunctional furan acrylate derivative and application thereof in preparation of polyester containing furan ring
The invention discloses a polyfunctional furan acrylate derivative and application thereof in preparation of polyester containing a furan ring. The general structural formula of the polyfunctional furan acrylate derivative is as shown in the specification. In the general formula, R1 and R2 independently represent a methylene group, an ethylene group, a dimethylene group, a 1,2-propylene group or an alkoxy group respectively; and R3 is an ether bond, or n1 and n2 are independently 1 or 2. The polyfunctional furan acrylate derivative disclosed by the invention can quickly undergo solid-state photopolymerization under ultraviolet irradiation without a photoinitiator; double bonds form a cyclobutane structure with good chemical and thermal stability; and the polyester formed after polymerization has a rigid chain segment and a flexible chain segment, is excellent in thermal stability and can be applied to the fields of coating, packaging, photoetching, 3D printing and the like.
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Paragraph 0036-0040

(2020/10/30)

Knoevenagel-Doebner condensation promoted by chitosan as a reusable solid base catalyst
The development of green and sustainable processes using naturally occurring biopolymers is becoming one of the suitable remedies to replace the conventional catalytic systems that generate large amount of byproducts with high risk factors. In this context, although Knoevenagel-Doebner condensation reaction has been reported with many organocatalysts including proline, no attempts were made to develop heterogeneous catalysts with environmental concerns. Considering these factors in mind, the title reaction is studied with chitosan as a heterogeneous solid base catalyst for the synthesis of α,β-unsaturated carboxylic acids through the condensation followed by decarboxylation reactions. Chitosan offers many advantages including high stability as evidenced by leaching, reusability tests, wide substrate scope and providing higher yields of the desired products with high purity. Powder X-ray diffraction (XRD), Fourier transform infrared (FT-IR), scanning electron microscope (SEM) and elemental analysis revealed that there are no major changes in the structural integrity and morphology of chitosan before and after catalysis under the optimized reaction conditions.
Anbu, Nagaraj,Hariharan, Surendran,Dhakshinamoorthy, Amarajothi
(2019/12/27)

Organic metal compound and organic light-emitting device
Organic metal compounds and organic light-emitting devices employing the same are provided. The organic metal compound has a chemical structure of Formula (I) or Formula (II): In particular, one of the following two conditions (1) and (2) is met: (1) R1 is deuterium or C1-6 deuterated alkyl group, when R3 and R4 are independently hydrogen, halogen, C1-6 alkyl group, C1-6 fluoroalkyl or C3-12 heteroaryl group; and (2) R1 is hydrogen, deuterium, C1-6 alkyl group, C1-6 deuterated alkyl group, C3-12 heteroaryl group, or C6-12 aryl group, when at least one of R3 and R4 is C6-12 aryl group or C6-12 fluoroaryl group.
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Paragraph 0041-0043

(2020/02/10)

Radical-Cation Vinylcyclopropane Rearrangements by TiO2Photocatalysis
Radical cation vinylcyclopropane rearrangements by TiO2 photocatalysis in lithium perchlorate/nitromethane solution are described. The reactions are triggered by oxidative single electron transfer, which is followed by immediate ring-opening of the cyclopropanes to generate distonic radical cations as unique reactive intermediates. This approach can also be applied to vinylcyclobutane, leading to the construction of six-membered rings. A stepwise mechanism via distonic radical cations is proposed based on preliminary mechanistic studies, which is supported by density functional theory calculations.
Maeta, Naoya,Kamiya, Hidehiro,Okada, Yohei
supporting information
p. 6551 - 6566
(2020/07/14)

Toward a Scalable Synthesis and Process for EMA401, Part II: Development and Scale-Up of a Pyridine- A nd Piperidine-Free Knoevenagel-Doebner Condensation
During route scouting for EMA401 (1), an angiotensin II type 2 antagonist, we identified the synthesis of key amino acid intermediate 2 via its cinnamic acid derivative 3 as a streamlined option. In general, cinnamic acids can be synthesized from the corresponding aldehydes by a Knoevenagel-Doebner condensation in pyridine with piperidine as an organocatalyst. We aimed to replace both of these reagents and found novel conditions involving toluene as the solvent and morpholine as the organocatalyst. Scale-up of the process allowed the production of 25 kg of cinnamic acid 3 that was of the quality required for process development of the subsequent phenylalanine ammonia lyase-catalyzed step. The modified conditions were found to be widely applicable to alternative aldehydes and thus are of relevance to practitioners of chemical scale-up.
Hardegger, Leo A.,Humair, Roger,Sidler, Eric
p. 1756 - 1762
(2020/10/26)

ATF6 INHIBITORS AND USES THEREOF
Compounds as inhibitors of Activating Transcription Factor 6 (ATF6) are provided. The compounds may find use as therapeutic agents for the treatment of diseases or disorders mediated by ATF6 and may find particular use in the treatment of viral infections, neurodegenerative diseases, vascular diseases, or cancer.
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(2019/10/29)

Synthesis and biological evaluation of 2,2-dimethylbenzopyran derivatives as potent neuroprotection agents
The development of novel neuroprotection agents is of great significance for the treatment of ischemic stroke. In this study, a series of compounds comprising 2,2-dimethylbenzopyran groups and cinnamic acid groups have been synthesized. Preferential combination principles and bioisostere that improved the neuroprotective effect of the compounds were identified for this series via biological activity assay in vitro. Meanwhile, a functional reversal group of the acrylamide amide resulted in the most active compounds. Among them, BN-07 significantly improved the morphology of neurons and obviously increased cell survival rate of primary neurons induced by oxygen glucose deprivation (OGD), superior to clinically used anti-ischemic stroke drug edaravone (Eda). Overall, our findings may provide an alternative strategy for the design of novel anti-ischemic stroke agents with more potency than Eda.
Du, Fangyu,Zhou, Qifan,Fu, Xiaoxiao,Shi, Yajie,Chen, Yuanguang,Fang, Wuhong,Yang, Jingyu,Chen, Guoliang
p. 2498 - 2508
(2019/02/01)

CYCLOBUTANE-1, 3-DIACID BUILDING BLOCKS
A method of making polymers utilizes cyclobutane-1,3-diacid (CBDA) molecules as polymer building blocks includes and linker molecules with a non-reactive R group and at least two reactive X groups used to create chemically stable polymers of CBDA. The resulting polymers are thermally, photochemically, and chemically stable.
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Paragraph 0048; 0115; 0127; 0128

(2019/01/16)

Pyridazinone derivative, and preparation method and medical application thereof
The invention provides a pyridazinone derivative, and a preparation method and a medical application thereof. O-formylbenzoic acid used as a raw material reacts with dimethyl phosphite to obtain dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate, the dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate reacts with 3-cyano-4-fluorobenzaldehyde in the presence of triethylamine to prepare (Z,E)-2-fluoro-5-[(3-oxoisobenzofuran-1(3H)-ylidene)methyl]benzonitrile, and the (Z,E)-2-fluoro-5-[(3-oxoisobenzofuran-1(3H)-ylidene)methyl]benzonitrile is reduced by hydrazine hydrate to prepare 2-fluoro-5-[(4-oxo-3,4-dihydropyridazin-1-yl)methyl]benzoic acid; and benzaldehyde or substituted aromatic formaldehyde or furfural used as a raw material and malonic acid undergo a Knoevenagel reaction to obtain cinnamic acid or substituted cinnamic acid or furan-2-acrylic acid, the cinnamic acid or substituted cinnamic acid or furan-2-acrylic acid and 1-tert-butoxycarbonylpiperazine undergo an amidation reaction, a tert-butoxycarbonyl group is removed from the obtained amidation product in the presence of trifluoroacetic acid, and the obtained product and the 2-fluoro-5-[(4-oxo-3,4-dihydropyridazin-1-yl)methyl]benzoic acid undergo the amidation reaction to obtain a series of (E)-4-{3-[4-[(3-substituted aryl)acryloyl]piperazin-1-carbonyl]-4-fluorobenzyl}-2H-pyridazin-1-one derivatives. Results of preliminary pharmacological activity screening show that the compound represented by a general formula shown in the present invention has a certain in-vitro PARP-1 inhibition ability and a certain in-vitro tumor cell proliferation resisting activity. The structural general formula of compound is shown in the description; and in the general formula, Ar is selected from two formulas also shown in the description, and R1, R2, R3, R3, R4 and R5 can be the hydrogen atom, the fluorine atom, the chlorine atom, the bromine atom, a methyl group, a methoxy group, a tetrafluoromethyl group and a nitro group.
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Paragraph 0026; 0033

(2019/10/07)

Synthesis, preliminarily biological evaluation and molecular docking study of new Olaparib analogues as multifunctional PARP-1 and cholinesterase inhibitors
A series of new Olaparib derivatives was designed and synthesized, and their inhibitory activities against poly (ADP-ribose) polymerases-1 (PARP-1) enzyme and cancer cell line MDA-MB-436 in vitro were evaluated. The results showed that compound 5l exhibited the most potent inhibitory effects on PARP-1 enzyme (16.10 ± 1.25 nM) and MDA-MB-436 cancer cell (11.62 ± 2.15 μM), which was close to that of Olaparib. As a PARP-1 inhibitor had been reported to be viable to neuroprotection, in order to search for new multitarget-directed ligands (MTDLs) for the treatment of Alzheimer’s disease (AD), the inhibitory activities of the synthesized compounds against the enzymes AChE (from electric eel) and BChE (from equine serum) were also tested. Compound 5l displayed moderate BChE inhibitory activity (9.16 ± 0.91 μM) which was stronger than neostigmine (12.01 ± 0.45 μM) and exhibited selectivity for BChE over AChE to some degree. Molecular docking studies indicated that 5l could bind simultaneously to the catalytic active of PARP-1, but it could not interact well with huBChE. For pursuit of PARP-1 and BChE dual-targeted inhibitors against AD, small and flexible non-polar groups introduced to the compound seemed to be conducive to improving its inhibitory potency on huBChE, while keeping phthalazine-1-one moiety unchanged which was mainly responsible for PARP-1 inhibitory activity. Our research gave a clue to search for new agents based on AChE and PARP-1 dual-inhibited activities to treat Alzheimer’s disease.
Gao, Cheng-Zhi,Dong, Wei,Cui, Zhi-Wen,Yuan, Qiong,Hu, Xia-Min,Wu, Qing-Ming,Han, Xianlin,Xu, Yao,Min, Zhen-Li
p. 150 - 162
(2018/11/30)

Synthesizing method of 2-furanacrylic acid medicine intermediate
The invention discloses a synthesizing method of a 2-furanacrylic acid medicine intermediate. The synthesizing method comprises the following steps of adding furan allyl alcohol and a sodium nitrate solution into a reaction container, raising temperature and adding an aqueous solution and aluminium isopropylate to continue the reaction; adding columbium oxytrichloride powder in batches, then adding a potassium chloride solution, controlling stirring speed, continuing the reaction, lowering the temperature, adding an oxalic acid solution to be adjusted, washing through an undecanol solution, recrystallizing in a cyclobutane solution and dehydrating through dehydrant to obtain a finished product 2-furanacrylic acid.
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Paragraph 0012; 0017; 0018; 0021-0026

(2018/07/30)

Synthesis of heteroleptic pentavalent antimonials bearing heterocyclic cinnamate moieties and their biological studies
In the search of new drugs with high therapeutic efficacy, antimony (V) dicarboxylates bearing cinnamate moieties with general formula [SbR3(O2CR′)2] have been synthesized and characterized by spectroscopic techniques like FTIR, multinuclear (1H and 13C) NMR and single crystal X-ray diffraction. The organic moieties (R) in the complexes are phenyl and p-tolyl while the carboxylates are heterocyclic acrylates. In the crystal structure of [Sb(phenyl)3(O2CC2H2C4H3O)2] (1), [Sb(phenyl)3(O2CC2H2C4H3S)2] (3), [Sb(p-tolyl)3(O2CC2H2C4H3S)2] (5) and [Sb(p-tolyl)3(O2CC2H2C4H2O(CH3))2] (6), antimony was found to adopt a distorted trigonal bipyramidal geometry and was monomeric with phenyl or p-tolyl groups at equatorial and carboxylate ligands at axial positions. Furthermore, biological activities of carboxylates and their corresponding complexes were conducted including antileishmanial activity (against Leishmania tropica KWH23 parasite), anticancer (against HepG2 cell line), antibacterial (against Staphylococcus aureus, E. coli, P. aeruginosa and K. pneumoniae) and α-amylase inhibition potentials. Results show that compounds (4), (5) and (6) are significantly cytotoxic against cancer cells (median inhibitory concentration (IC50): 7.44, 4.61, 5.0 μg/mL respectively) and leishmania parasite (IC50: 1.75, 0.03 and 0.02 μg/mL respectively). Results of biological activities suggest these complexes as attractive therapeutic agents for further in vivo studies except α-amylase inhibition.
Sarwar, Sidra,Iftikhar, Tuba,Rauf, Muhammad Khawar,Badshah, Amin,Waseem, Durdana,Tahir, Muhammad Nawaz,Khan, Khalid Mohammed,Khan, Gul Majid
p. 12 - 19
(2018/02/23)

One-pot synthesis of fused 2-pyridones from heteroarylacrylic acid via curtius rearrangement & microwave-assisted thermal electrocyclization
We investigated the one-pot synthesis of several fused 2-pyridone ring systems based on a Curtius rearrangement, followed by a microwave-assisted thermal electrocyclization of a 2-aza-6?-electron system including isocyanate. We synthesized seven heterocyclic compounds containing a fused 2-pyridone ring. In these results, the one-pot synthesis of fused 2-pyridone ring system 5 from (E)-acrylic acids 1 under microwave irradiation conditions was more effective than the conventional reaction conditions in terms of the yield and the reaction time.
Nishiyama, Takashi,Hatae, Noriyuki,Hayashi, Kaori,Obata, Manami,Taninaka, Kimiko,Yamane, Masahiro,Oda, Shota,Abe, Takumi,Ishikura, Minoru,Hibino, Satoshi,Choshi, Tominari
p. 251 - 267
(2017/07/28)

Cinnamoylated chloroquine analogues: A new structural class of antimalarial agents
A novel series of cinnamoylated chloroquine hybrid analogues were synthesized and evaluated as antimalarial agents. The trans cinnamic acid derivatives (3–8) were synthesized by utilizing substituted aldehydes and malanoic acid in DMF catalysed by DABCO. The final cinnamoylated chloroquine analogues (9–14) were synthesized by utilizing DCC coupling reagent. The amido chloroquine (17) was prepared from acid (16) and compound 2 in benzene using SOCl2 as chlorinating agent. The corresponding ester (15) was prepared from 2-hydroxy acetophenone and 2-bromoacetates in actonitrile in presence of K2CO3?as?base followed by basic hydrolysis. The preparation of amide based chloroquine-chalcone analogues (18–22), were obtained by the combination of amido chloroquine (17) and aldehydes in 10% aq. KOH in methanol at room temperature. Further we prepared epichlorohydrin based chloroquine-chalcone analogues (25–28), by reacting the epoxide (24a, 24b and 24c) with 2 and methelenedioxy aniline. In?vitro antimalarial activity against chloroquine sensitive strain 3D7, chloroquine resistant strain K1 of P.?falciparum and in?vitro cytotoxicity of compounds using VERO cell line was carried out. The synthesized molecules showed significant in?vitro antimalarial activity especially against CQ resistant strain (K1). Among tested compounds, 13, 9 and 10 were found to be the most potent compounds of the series with IC50 value of 44.06, 48.04 and 59.37?nM against chloroquine resistant K1 strain.
Gayam, Venkatareddy,Ravi, Subban
p. 382 - 391
(2017/05/04)

Sulfuric acid and Amberlyst-H+ catalyzed condensation reactions of renewable keto acids with paraformaldehyde: Synthesis of a new dispiro bis-lactone ring system 2,9,13-trioxadispiro[4.1.4.3]tetradecane-3,6,10-trione
The sulfuric acid and Amberlyst-H+ catalyzed condensation reactions of renewable feedstock levulinic acid with paraformaldehyde under neat conditions at 80 °C gives 2,9,11,14-tetraoxadispiro[4.1.5.3]pentadecane-3,6-dione in 91-93% yield, in which the structure was confirmed by single crystal X-ray crystallography. A similar condensation reaction between 4-ketopimelic acid and paraformaldehyde at 80 °C gives 2,9,13-trioxadispiro[4.1.4.3]tetradecane-3,6,10-trione. This new dispiro bis-lactone was found to composed of a 1.6 : 1 mixture of isomers with planes of symmetry bisecting the tetrahydro-2H-pyran-4-one rings through the carbonyl groups.
Amarasekara, Ananda S.,Ha, Uyen,Fonari, Marina S.,Bejagam, Shabari Nath,Margeti?, Davor
p. 23917 - 23923
(2017/07/10)

A Simple and straightforward synthesis of cinnamic acids and ylidene malononitriles via knoevenagel condensation employing dabco as catalyst
An efficient method for the synthesis of substituted cinnamic acid and ylidene malanonitriles is developed via Knoevenagel condensation of aromatic aldehydes with malonic acid and malononitrile in the presence of catalytic amounts of DABCO. This method has many advantages, such as mild reaction conditions, excellent yields, short reaction times and no furthur purification required.
Nagalakshmi,Diwakar,Govindh,Gopal Reddy,Venu,Bhargavi,Prasanna Devi,Murthy,Siddaiah
p. 1561 - 1564
(2017/05/29)

A novel furo[3,2-: C] pyridine-based iridium complex for high-performance organic light-emitting diodes with over 30% external quantum efficiency
A novel furo[3,2-c]pyridine based Ir complex, namely (pfupy)2Ir(acac), has been developed by replacing sulfur with oxygen in the C^N ligand. Compared with the thiophene-containing (pthpy)2Ir(acac), the LUMO level is elevated while the HOMO level remains almost unchanged for the resultant furan-containing (pfupy)2Ir(acac). As a consequence, the emissive maximum is blue-shifted from 556 nm of (pthpy)2Ir(acac) to 538 nm of (pfupy)2Ir(acac) together with an improved photoluminescence quantum yield of 0.80. The corresponding device based on (pfupy)2Ir(acac) realizes a record-high external quantum efficiency (EQE) of 30.5% (110.5 cd A-1) without any out-coupling technology. Even at a luminance of 1000 and 5000 cd m-2, the EQE still remains at 26.6% (96.4 cd A-1) and 25.6% (92.7 cd A-1), respectively, indicative of the gentle efficiency roll-off. The results clearly demonstrate the great potential of furan-based functional materials applied in OLEDs.
Yan, Zhimin,Wang, Yanping,Wang, Jiaxiu,Wang, Yue,Ding, Junqiao,Wang, Lixiang
supporting information
p. 10122 - 10125
(2017/10/19)

Enantioselective Synthesis of N?H-Free 1,5-Benzothiazepines
An enantioselective sulfa-Michael-cyclization reaction was developed for the synthesis of 1,5-benzothiazepines with versatile pharmacological activities. The reaction between 2-aminothiophenol and α,β-unsaturated pyrazoleamides gave direct access to N?H-free 1,5-benzothiazepines in the presence of a chiral N,N′-dioxide/Yb(OTf)3complex. Excellent enantioselectivities (up to 96 % ee) and high yields (up to 99 %) were obtained for a broad range of substrates under mild reaction conditions. This method provided a facile approach to the antidepressant drug (R)-(?)-Thiazesim.
Wang, Guojin,Tang, Yu,Zhang, Yu,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
supporting information
p. 554 - 557
(2017/01/18)

Synthesis and antibacterial evaluation of novel 11-O-carbamoyl clarithromycin ketolides
A series of novel 11-O-carbamoyl clarithromycin ketolides were designed, synthesized and evaluated for their in vitro antibacterial activity. The results showed that the majority of the target compounds displayed improved activity compared with references against erythromycin-resistant S. pneumoniae A22072 expressing the mef gene, S. pneumoniae B1 expressing the erm gene and S. pneumoniae AB11 expressing the mef and erm genes. In particular, compounds 9, 18, 19 and 22 showed the most potent activity against erythromycin-resistant S. pneumoniae A22072 with the MIC values of 0.5?μg/mL. Furthermore, compounds 11, 18, 19, 24 and 29 were also found to exhibit favorable antibacterial activity against erythromycin-susceptible S. pyogenes with the MIC values of 0.125–1?μg/mL, and moderate activity against erythromycin-susceptible S. aureus ATCC25923 and B. subtilis ATCC9372.
Jia, Li,Yan, Mi,Shen, Yan,Qin, Yinhui,Qiang, Shengsheng,Ma, Shutao
supporting information
p. 3693 - 3697
(2017/07/27)

Synthesis and biological evaluation of (E)-cinnamic acid, (E)-2-styrylthiazole and (E)-2-[2-(naphthalen-1-yl)vinyl]thiazole derivatives
Cinnamyl- and thiazole-based compounds have been shown to exhibit diverse medicinal properties and a series of twelve (E)-2-styrylthiazole and (E)-2-[(naphthalen-1-yl)vinyl]thiazole derivatives, which are conjugates of both systems and which satisfy the "Lipinski rule of 5", have been synthesised and subjected to in vitro biological screening. While insignificant inhibition (60-98% viability at 10 μM) of HeLa (cervical cancer) cells was noted, all five of the (E)-2-[naphthalen-1- yl)vinyl]thiazole derivatives proved remarkably active against SH-SY5Y (neuroblastoma) cells with IC50 values ranging from 2.09 to 8.64 μM. Two of the seven (E)-2-styrylthiazoles were found to be moderately active (with IC50 values of 10.8 and 11.7 mM), whereas the remaining five analogues exhibit significant proliferation of SH-SY5Y cells (with IC50 values of 180-1000 mM). The results warrant further studies on the effects of styrylthiazoles on the differentiation and extension of SH-SY5Y cells in order to assess their activity in neurological degenerative diseases.
Olawode, Emmanuel O.,Tandlich, Roman,Prinsloo, Earl,Isaacs, Michelle,Hoppe, Heinrich,Seldon, Ronnett,Warner, Digby F.,Steenkamp, Vanessa,Kaye, Perry T.
p. 284 - 296
(2018/03/09)

Synthesis and biological evaluation of (E)-cinnamic acid, (E)-2-styrylthiazole and (E)-2-[2-(naphthalen-1-yl)vinyl]thiazole derivatives
Cinnamyl- and thiazole-based compounds have been shown to exhibit diverse medicinal properties and a series of twelve (E)-2-styrylthiazole and (E)-2-[(naphthalen-1-yl)vinyl]thiazole derivatives, which are conjugates of both systems and which satisfy the “Lipinski rule of 5”, have been synthesised and subjected to in vitro biological screening. While insignificant inhibition (60-98% viability at 10 μM) of HeLa (cervical cancer) cells was noted, all five of the (E)-2-[naphthalen-1-yl)vinyl]thiazole derivatives proved remarkably active against SH-SY5Y (neuroblastoma) cells with IC50 values ranging from 2.09 to 8.64 μM. Two of the seven (E)-2-styrylthiazoles were found to be moderately active (with IC50 values of 10.8 and 11.7 mM), whereas the remaining five analogues exhibit significant proliferation of SH-SY5Y cells (with IC50 values of 180-1000 mM). The results warrant further studies on the effects of styrylthiazoles on the differentiation and extension of SH-SY5Y cells in order to assess their activity in neurological degenerative diseases.
Olawode, Emmanuel O.,Tandlich, Roman,Prinsloo, Earl,Isaacs, Michelle,Hoppe, Heinrich,Seldon, Ronnett,Warner, Digby F.,Steenkamp, Vanessa,Kaye, Perry T.
p. 284 - 296
(2018/05/09)

NOVEL COMPOUNDS AS REARRANGED DURING TRANSFECTION (RET) INHIBITORS
This invention relates to novel compounds which are inhibitors of the Rearranged during Transfection (RET) kinase, to pharmaceutical compositions containing them, to processes for their preparation, and to their use in therapy, alone or in combination, for the normalization of gastrointestinal sensitivity, motility and/or secretion and/or abdominal disorders or diseases and/or treatment related to diseases related to RET dysfunction or where modulation of RET activity may have therapeutic benefit including but not limited to all classifications of irritable bowel syndrome (IBS) including diarrhea-predominant, constipation-predominant or alternating stool pattern, functional bloating, functional constipation, functional diarrhea, unspecified functional bowel disorder, functional abdominal pain syndrome, chronic idiopathic constipation, functional esophageal disorders, functional gastroduodenal disorders, functional anorectal pain, inflammatory bowel disease, proliferative diseases such as non-small cell lung cancer, hepatocellular carcinoma, colorectal cancer, medullary thyroid cancer, follicular thyroid cancer, anaplastic thyroid cancer, papillary thyroid cancer, brain tumors, peritoneal cavity cancer, solid tumors, other lung cancer, head and neck cancer, gliomas, neuroblastomas, Von Hippel-Lindau Syndrome and kidney tumors, breast cancer, fallopian tube cancer, ovarian cancer, transitional cell cancer, prostate cancer, cancer of the esophagus and gastroesophageal junction, biliary cancer, adenocarcinoma, and any malignancy with increased RET kinase activity.
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Page/Page column 145; 146

(2016/04/20)

3-aryl acrylic acid and its derivatives viral anti-plant
The invention relates to an application of 3-aryl acrylic acid represented by a general formula (I) and a derivative thereof in pesticides, wherein the 3-aryl acrylic acid and the derivative thereof can be adopted as novel anti-plant virus agents, can be provided for well inhibiting tobacco mosaic virus, pepper virus, tomato virus, sweet potato virus, potato virus, melon virus, maize dwarf mosaic virus and the like, and can be provided for effectively preventing and controlling virus diseases of a plurality of crops such as tobacco, pepper, tomato, melon vegetables, grains, vegetables, beans and the like, especially tobacco mosaic diseases. (Wherein Ar and R are defined in an instruction).
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Paragraph 0022; 0023; 0024; 0025; 0026

(2016/11/21)

Synthesis, biological evaluation and molecular docking studies of some novel cyclopropane carbohydrazide derivatives as potential anticancer agents
The synthesis of novel series of cyclopropane carbohydrazides is described viaKnoevenagel condensation of 2-furfuraldehyde with malonic acid in five steps. Condensation of the key intermediate 2-(furan-2-yl)cyclopropanecarbohydrazide (4)with heteroaryl/aryl aldehydes (a-t) in presence of ZnO NP in ethanol resulted in substituted N- hetero/arylidene-2-(furan-2-yl) cyclopropane carbohydrazides (5a-t). These compounds were screened for their anticancer activity against a panel of four cancer cell lines and four compounds showed promising activity at micromolar concentration against all the tested cell lines with IC50 values ranging between 1.9-8.45 μM. These compounds were further validated with in silico methods at the anticancer target, colchicine binding site. [Figure not available: see fulltext.]
Swamy, Ponnapalli Veerabhadra,Kambhampati, Pullaiah China,Chandrasekhar, Kothapalli Bonnoth,Thirupathi, Gugulothu,Sujitha, Pombala,Kumar, Chityal Ganesh,Kumar, Veeramachaneni Ganesh
p. 929 - 939
(2016/07/06)

Synthesis method of furapromide drug intermediate 2-furfuracrylic acid
The invention relates to a synthesis method of a furapromide drug intermediate 2-furfuracrylic acid, which comprises the following steps: adding 3.1mol of 2-furylchloromethanol solution (2), 3.6-3.9mol of malonic acid solution (3) and 300ml of nitroethane into a reaction vessel which is provided with a stirrer and a reflux condenser, controlling the stirring rate at 130-170 rpm, heating the solution to 70-75 DEG C, refluxing for 5-8 hours, lowering the temperature of the solution to 8-13 DEG C, adding 310ml of sodium bromide solution and 200ml of potassium bisulfite solution, reacting for 90-120 minutes, standing for 3-6 hours, precipitating a solid, filtering, washing with a salt solution, washing with toluene, washing with ethylenediamine, dehydrating with a dehydrating agent, and recrystallizing in propionitrile to obtain the crystal 2-furfuracrylic acid.
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Paragraph 0005; 0006; 0014; 0015

(2016/10/31)

Application of chiral ligands: Carbohydrates, nucleoside-lanthanides and other Lewis acid complexes to control regio- and stereoselectivity of the dipolar cycloaddition reactions of nitrile oxides and esters
Chiral Lewis acid mediated 1,3-dipolar cycloaddition reactions of 4-trifluoromethylbenzonitrile oxide to methyl crotonate as well to β-substituted acrylates and (Z)-pent-2-en-1-yl esters were examined. Excellent enantioselectivities with moderate to good regioselectivities were achieved for crotonates with complexes of BiBr3 with (+)-(4,6-benzylidene)methyl-α-d-glucopyranoside C, with the l-ascorbic acid I-FeCl3 system, and with lipase Candida antarctica. High enantiomeric excess was observed for isopropyl ester and benzyl ester. The outstanding ee values were achieved for acrylates with β-t-butyl, cyclohexyl, and 1,3-benzodioxol-5-yl groups in cycloadditions catalyzed by C-Yb(OTf)3 and the (+)-2-hydroxy-3-pinanone N-TiCl4 system. High enantioselectivities were found in reactions of (Z)-pent-2-en-1-yl esters mediated by complexes N-Mg(OTf)2 and N-TiCl4.
Gucma, Miroslaw,Golbiewski, W. Marek,Krawczyk, Maria
p. 13112 - 13124
(2015/02/19)

Synthesis of piperazine derivatives and biological evaluation of its inhibitory activities on vascular smooth muscle cell proliferation
A series of new N-substituted benzyl piperazine derivatives were synthesized using the appropriate synthetic route. The new compounds were characterized by IR, 1H NMR, MS and elemental analysis. All the compounds were screened for their inhibitory activities on vascular smooth muscle cell proliferation. Some of the compounds demonstrated moderate to good inhibition of vascular smooth muscle cell proliferation. The compounds (2h, 6h) were approximately equivalent in activity to heparin as a potent inhibitor. The possible structure-activity relationship of the inhibitory activity of all compounds was also discussed.
Han, Sheng Hua,Chen, Jian Xin,Liu, Hong Yan,Zhang, Hai Rong,Ma, Peng Fei
p. 1299 - 1303
(2015/02/19)

Cu/Fe-Cocatalyzed Formation of β-Ketophosphonates by a Domino Knoevenagel-Decarboxylation-Oxyphosphorylation Sequence from Aromatic Aldehydes and H-Phosphonates
A domino Knoevenagel-decarboxylation-alkene difunctionalization sequence has been developed for the conversion of benzaldehydes into β-ketophosphonates, catalyzed by a cooperative Cu/Fe system, whereby CP and CO bonds are formed simultaneously in a one-pot reaction. The reaction proceeds in good yields and with a broad substrate scope and environmentally benign conditions.
Zhou, Mingxin,Zhou, Yao,Song, Qiuling
supporting information
p. 10654 - 10658
(2015/07/20)

Synthesis and antibacterial activity of 4'3-O-(trans-β-arylacrylamido)carbamoyl azithromycin analogs
Novel 4'3-O-(trans-β-arylacrylamido)carbamoyl azithromycin analogs were designed, synthesized and evaluated for their antibacterial activity against nine significant pathogens using broth microdilution method. A majority of these derivatives maintained the activity of azithromycin against susceptible Streptococcus pyogenes and all the compounds demonstrated remarkably improved activity compared with the references against all the three phenotypes of resistant Streptococcus pneumoniae. In particular, compound 24 exhibited the most potent activity against susceptible Staphylococcus aureus (MIC = 0.5 μg/mL), S. pneumoniae (MIC = 0.06 μg/mL) and S. pyogenes (MIC = 0.25 μg/mL). The most active compound 7 (MIC = 0.015 μg/mL) against resistant S. pneumoniae expressing the mefA gene, exhibited 512 and 256-fold more potent activity than erythromycin and azithromycin, respectively. Compounds 28 (MIC = 0.5 μg/mL), 29 (MIC = 0.25 μg/mL) and 30 (MIC = 0.5 μg/mL) demonstrated potent activity against resistant S. pneumoniae expressing the ermB gene, which were 256, 512 and 256-fold better than the references, respectively.
Yan, Mi,Ma, Xiaodong,Dong, Ruiqian,Li, Xin,Zhao, Can,Guo, Zhenzhen,Shen, Yan,Liu, Fang,Ma, Ruixin,Ma, Shutao
p. 506 - 515
(2015/10/06)

Copper catalyzed oxygen assisted C(CNOH)-C(alkyl) bond cleavage: A facile conversion of aryl/aralkyl/vinyl ketones to aromatic acids
A novel copper-catalyzed aerobic oxidative C(NOH)-C(alkyl) bond cleavage reaction of aryl/aralkyl/vinyl ketones for the synthesis of aromatic/acrylic acids is described. A series of ketones having aryl/aralkyl/vinyl at the one end and methyl to any higher alkyl at the other end can be selectively cleaved and converted into the corresponding acids via oxime intermediates.
Sathyanarayana, Pochampalli,Ravi, Owk,Muktapuram, Prathap Reddy,Bathula, Surendar Reddy
supporting information
p. 9681 - 9685
(2015/09/28)

Synthesis of l -octaarginine through microencapsulated palladium-catalyzed allyl ester deprotection
Octaarginine has been described as a molecular transporter. We report a useful synthesis of orthogonally protected l-octaarginine by using a method based on a microencapsulated palladium catalyst. Known palladium-based methods for allyl ester deprotection have been modified to facilitate purification of the unprotected intermediates. This improvement in the purification step has also been tested with a variety of allyl α-amino esters and allyl α,β-unsaturated esters.
Pérez-López, Ana M.,González-Calderón, Dávir,Occorso, Antonio,Galindo-ángel, Javier,Domínguez-Seglar, José F.,Tamayo, Juan A.,Díaz-Gavilán, Mónica,Gómez-Vidal, José A.
supporting information
p. 2319 - 2322
(2015/08/06)

Alum-Cs2CO3 as a new recyclable solid base catalyst for the efficient syntheses of arylidenemalononitriles, esters and arylcinnamic acids in water
The condensation between aromatic aldehydes and malononitrile, ethylcyanoacetate and malonic acid for the syntheses of arylidenemalononitriles, arylidenemalonic acid esters and aryl cinnamic acids in water using alum-Cs2CO3 as a solid support catalyst has been described. Alum-Cs2CO3 was found to be a highly active, stable and recyclable catalyst under reaction conditions.
Taduri, Ashok Kumar,Devi, B. Rama
p. 1938 - 1942
(2014/06/09)

1-(2-hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile derivatives as potent and tissue selective androgen receptor modulators
We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.
Chekler, Eugene L. Piatnitski,Unwalla, Rayomond,Khan, Taukeer A.,Tangirala, Raghuram S.,Johnson, Mark,St. Andre, Michael,Anderson, James T.,Kenney, Thomas,Chiparri, Sue,McNally, Chris,Kilbourne, Edward,Thompson, Catherine,Nagpal, Sunil,Weber, Gregory,Schelling, Scott,Owens, Jane,Morris, Carl A.,Powell, Dennis,Verhoest, Patrick R.,Gilbert, Adam M.
supporting information
p. 2462 - 2471
(2014/04/17)

An efficient synthesis of conjugated 5-aryl-1,3,4-oxadiazoles from 3-heteroarylacrylohydrazides and acid chlorides
New derivatives of 5-aryl-2-[2-(2-furyl)ethenyl]-1,3,4-oxadiazoles and 5-aryl-2-[2-(2-thienyl)ethenyl]-1,3,4-oxadiazoles are synthesized in a stepwise procedure through intermediate acyclic N′-arylcarbonyl-N-[2-(2-heteroaryl) acryloyl]hydrazines, starting from 3-(2-heteroaryl)acrylic acid hydrazides and acid chlorides. A facile one-pot methodology leading to the final 1,3,4-oxadiazoles is also described.
Kudelko, Agnieszka,Wróblowska, Monika
supporting information
p. 3252 - 3254
(2014/06/09)

Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents
A series of ninety-seven diarylpentanoid derivatives were synthesized and evaluated for their anti-inflammatory activity through NO suppression assay using interferone gamma (IFN-γ)/lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Twelve compounds (9, 25, 28, 43, 63, 64, 81, 83, 84, 86, 88 and 97) exhibited greater or similar NO inhibitory activity in comparison with curcumin (14.7 ± 0.2 μM), notably compounds 88 and 97, which demonstrated the most significant NO suppression activity with IC50 values of 4.9 ± 0.3 μM and 9.6 ± 0.5 μM, respectively. A structure-activity relationship (SAR) study revealed that the presence of a hydroxyl group in both aromatic rings is critical for bioactivity of these molecules. With the exception of the polyphenolic derivatives, low electron density in ring-A and high electron density in ring-B are important for enhancing NO inhibition. Meanwhile, pharmacophore mapping showed that hydroxyl substituents at both meta- and para-positions of ring-B could be the marker for highly active diarylpentanoid derivatives.
Leong, Sze Wei,Mohd Faudzi, Siti Munirah,Abas, Faridah,Mohd Aluwi, Mohd Fadhlizil Fasihi,Rullah, Kamal,Wai, Lam Kok,Abdul Bahari, Mohd Nazri,Ahmad, Syahida,Tham, Chau Ling,Shaari, Khozirah,Lajis, Nordin H.
p. 16058 - 16081
(2015/01/08)

A practical and convenient protocol for the synthesis of (E)-α,β-unsaturated acids
α,β-Unsaturated acids are very useful and versatile reagents in organic synthesis. A novel, practical, and convenient catalytic protocol comprising FeCl3·6H2O (0.5 mol %) and H 2O (1 equiv) in CH3NO2 is described for the rapid synthesis of α,β-unsaturated acids with high E-stereoselectivity under both microwave and conventional heating conditions with high TON and TOF values. This powerful approach efficiently demonstrated the utility of biomass derived aldehydes to build chemical agents used as fuel additives. The method proved to be scalable to gram scale synthesis.
Mohite, Amar R.,Bhat, Ramakrishna G.
p. 4564 - 4567
(2013/09/24)

Discovery of a series of novel compounds with moderate anti-avian H5N1 influenza virus activity in chick embryo
Enlightened by some flavonoid compounds, which had been found as influenza neuraminidase inhibitors, we designed and synthesized a series of novel compounds containing different amino acid fragments. We also reported a simple synthetic route from oseltamivir to prepare its active form which was used as the positive control. The result of enzyme inhibition assay indicated that all the designed compounds displayed weak inhibitory activity against neuraminidase. However, they showed moderate anti-avian H5N1 influenza virus activity in chick embryo. Besides interfering with the function of neuraminidase, these compounds seemed to inhibit the replication of influenza virus by some other mechanism which deserved deep study.
Xie, Yuanchao,Huang, Bing,Yu, Kexiang,Shi, Fangyuan,Xu, Wenfang
p. 3485 - 3496
(2013/07/19)

NHC-catalysed highly selective aerobic oxidation of nonactivated aldehydes
This publication describes a highly selective oxidation of aldehydes to the corresponding acids or esters. The reaction proceeds under metal-free conditions by using N-heterocyclic carbenes as organocatalysts in combination with environmentally friendly oxygen as the terminal oxidation agent.
Moehlmann, Lennart,Ludwig, Stefan,Blechert, Siegfried
p. 602 - 607
(2013/04/24)

Efficient synthesis of 1,3,4-oxadiazoles conjugated to thiophene or furan rings via an ethenyl linker
A novel and efficient synthesis of 5-substituted 2-[2-(2-furyl)ethenyl]-1, 3,4-oxadiazoles and 2-[2-(2-thienyl)ethenyl]-1,3,4-oxadiazoles by cyclocondensation of the appropriate 3-(2-furyl)- and 3-(2-thienyl) acrylohydrazides with triethyl orthoesters in the presence of glacial acetic acid is reported. The formation of symmetrically substituted 2,5-bis[2-(2-furyl)ethenyl]-1,3,4-oxadiazole and 2,5-bis[2-(2-thienyl)ethenyl]- 1,3,4-oxadiazole from the corresponding N,N′-diacylhydrazines under the influence of phosphorus oxychloride is also described. Georg Thieme Verlag Stuttgart. New York.
Kudelko, Agnieszka,Jasiak, Karolina
p. 1950 - 1954
(2013/07/26)

Design, synthesis and biological evaluation of benzothiazepinones (BTZs) as novel non-ATP competitive inhibitors of glycogen synthase kinase-3β (GSK-3β)
Glycogen synthase kinase-3β (GSK-3β) plays a key role in type II diabetes and Alzheimer's diseases, to which non-ATP competitive inhibitors represent an effectively therapeutical approach due to their good specificity. Herein, a series of small molecules benzothiazepinones (BTZs) as novel non-ATP competitive inhibitors of GSK-3β have been designed and synthesized. The in vitro evaluation performed by luminescent assay showed most BTZ derivatives have inhibitory effects in micromolar scale. Among them compounds 6l, 6t and 6v have the IC50 values of 25.0 μM, 27.8 μM and 23.0 μM, respectively. Moreover 6v is devoid of any inhibitory activity in the assays to other thirteen protein kinases. Besides, SAR is analyzed and a hypothetical enzymatic binding mode is proposed by molecular docking study, which would be useful for new candidates design.
Zhang, Peng,Hu, Hai-Rong,Bian, Shi-Hui,Huang, Zhao-Hui,Chu, Yong,Ye, De-Yong
p. 95 - 103
(2013/04/23)

β-alanine-DBU: A highly efficient catalytic system for knoevenagel-doebner reaction under mild conditions
A mild and efficient Knoevenagel-Doebner reaction from malonic acid and a wide range of aldehydes was catalyzed by a catalytic system consisting of β-alanine and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), affording the corresponding (E)-α,β-unsaturated carboxylic acids in good to excellent yields and with high stereoselectivity. The advantage of the method is that the reaction could proceed smoothly at ambient temperature so that it can tolerate a variety of functional groups and avoid unnecessary side reactions. Copyright
Zhu, Lingjian,Lei, Ning,Miao, Zhenyuan,Sheng, Chunquan,Zhuang, Chunlin,Yao, Jianzhong,Zhang, Wannian
experimental part
p. 139 - 143
(2012/03/09)

Synthesis, characterization, antibacterial and antifungal evaluation of novel monosaccharide esters
A novel series of 3-(2-furyl)acrylate monosaccharide esters Ia-f and menthyloxycarbonyl monosaccharide esters IIa-f were designed and synthesized. The chemical structures of the target compounds were confirmed by IR, 1H- and 13C-NMR and ESI-MS, and the target compounds were investigated for their in vitro antibacterial and antifungal activities. The antibacterial screening results showed that the 3-(2-furyl)acrylate monosaccharide ester derivatives Ia-f were either inactive or only weakly active against the three Gram-positive bacterial strains tested, whereas the menthyloxycarbonyl monosaccharide ester derivatives IIa-f exhibited higher levels of activity, with compound IIe being especially potent. The results of the antifungal screening revealed that compounds Ib, Ie, IIb and IIc displayed potent in vitro activities, whereas If and IIf showed promising activities against all of the microorganisms tested, with If exhibiting levels of activity deserving of further investigation.
Shen, Yi,Sun, Yufeng,Sang, Zhipei,Sun, Chengjun,Dai, Ya,Deng, Yong
experimental part
p. 8661 - 8673
(2012/10/08)