Shouxin Liu

Hebei University of Science and Technology

Visible light-promoted C(sp ³ )–H bond chlorination with MgCl 2 as a chlorine source in AcOH/CH 3 CN in the presence of FeCl 3 is reported.

A novel [c2] daisy chain was successfully constructed by the hermaphroditic monomer of dibenzo[24]-crown-8 (DB24C8) derivative bearing secondary ammonium salt (1) from the analysis of the solution-phase behavior of parent monomers and single-crystal X-ray analysis. ¹H NMR spectroscopy was employed to show that the crown ether moiety and the seconda...

A convenient and efficient trans-stereoselective and β-regioselective hydroboration of propargyl alcohols was achieved simply with LiOtBu as the base and (Bpin)2 as the boron reagent in dimethyl sulfoxide at room temperature. Both terminal and internal propargyl alcohols with diverse structures and functional groups underwent the transformation smo...

A novel [c2] daisy chain was successfully constructed by the hermaphroditic monomer of dibenzo[24]-crown-8 (DB24C8) derivative bearing secondary ammonium salt (1) from the analysis of the solution-phase behavior of parent monomers and single-crystal X-ray analysis. ¹ H NMR spectroscopy was employed to show that the crown ether moiety and the second...

Tumescenamide A (1), isolated from Streptomyces tumescens YM23-20, consists of a cyclic depsipeptide and a side-chain 2,4-dimethylheptanoate (Dmh).

Cyclization–aromatization of enamines is a powerful method for the establishment of aza-aromatic cycles. We report herein the development of a simple and practical [3+3] aldol cyclization–aromatization of ,γ-dioxobutanoate with amines...

Background The Paracoccus sp. strain isolated from sludge was identified and evaluated for catalytic activity in the degradation of penicillin G. Results High degradation efficiency and synergistic catalytic effects of the whole cell and visible light without additional catalysts were observed. The key factors influencing the degradation and kinet...

A highly selective, green and sustainable chlorination of aliphatic C-H bonds is reported using MCln under the co-catalysis of visible light and nano-Cu@CuCl, which was synthesised via a one-step, hydrothermal...

The control of regioselectivities has been recognized as the elementary issue for alkene hydroboration. Despite considerable progress, the specificity of alkene substrates or the adjustment of ligands was necessary for specific regioselectivities, which restrict the universality and practicability. Herein, we report a ligand-free iron-catalyzed reg...

Substantial concentrations of penicillin V potassium (PVK) have been found in the environment, which may pose potential threats to human health and contribute to the emergence of penicillin-resistant bacterial strains. In this study, antibiotic-degrading bacterial strains for PVK were isolated from sludge and characterized. Ochrobactrum tritici was...

Background: An efficient biodegradation-strengthening approach was developed to improve penicillin G degradation from industrial bacterial residue in an expanded bed adsorption bioreactor (EBAB) is reported in this paper. Results: Paracoccus sp. strain KDSPL-02 was isolated based on its ability to use penicillin G as the sole carbon and nitrogen...

The control of regioselectivities has been recognized as the elementary issue for alkene hydroboration. Despite considerable progress, the specificity of alkene substrates or the adjustment of ligands were necessary for specific regioselectivities, which restrict the universality and practicability. Herein, we report a ligand-free iron-catalyzed re...

Direct conversion of the readily available alkyl bromides and alcohols to value-added epoxides using DMSO under mild reaction conditions has been developed. Benzyl and allyl bromides, activated and unactivated alcohols all proceeded smoothly to give epoxides in high to excellent yield. Dimethyl sulfide, generated by DMSO oxidations, was in situ ela...

The direct selective halogenation of unactivated C(sp3)–H bonds into C-halogen bonds was achieved using a nano Ag/AgCl catalysis at RT under visible light or LED irradiation in the presence of an aqueous solution of NaX/HX as halide source, in air. The halogenation of hydrocarbons provided mono-halide substituted products with 95% selectivity and y...

Melanoma is highly resistant to most traditional treatments; therefore, its incidence and mortality rates are rapidly increasing. The effect of a novel sansalvamide A analogue named LY-15 on the growth and induction of apoptosis in B16 cancer cells was investigated in vitro. The inhibitory effects of LY-15 on B16 cells occurred in a concentration-...

Palladium-catalyzed asymmetric allylic alkylation of acyclic ketones represents a significant challenge in organic synthesis. We report herein that the synthesis of chiral 2,2-disubsituted pyrrolidines from acyclic ketones has been accomplished by using catalytic asymmetric method in the presence of Pd(dba)2 and (R)-binap ligand. Theses reactions o...

Most of polypeptides containing α,β-dehydroamino acids have important biological activity, so exploration of synthetic method has practical significance. In this paper, dipeptides were prepared from l-threonine by protecting of c-terminal allyl acetate, and condensing reaction with a series of N-Boc amino acid. Then, treatment of dipeptides obtaine...

A series of arylidene N-alkoxydiketopiperazines was designed and stereoselectively synthesized via oxime-ether formation and intramolecular acylation. Possible cyclization and acid-catalyzed rearrangement-fragmentation mechanisms were discussed. The crystal structure of the novel diketopiperazine further confirmed the rearrangement mechanism. Most...

A general and direct C3 functionalization of free (N-H) indoles with readily available electrophiles such as acid chlorides, chloroformates, thionyl chloride, and methylsulfonyl chloride via a common N-indolyl triethylborate intermediate is reported. The reaction proceeds smoothly under mild conditions in up to 93% yield. Indoles with substituents...

A convenient method of synthesizing a tripeptide-containing N-methyl group amino acid was developed using O-benzotriazole-N,N,N′,N′-tetramethyluronium-hexafluorophosphate as the condensing agent. The crystals of tripeptide had white needles belonging to the orthorhombic space group P212121. The conformational preference for homochiral tripeptides w...

(E)-Ethyl 2-(hydroxyimino)-3-(4-methoxyphenyl)-3-oxopropanoate has been synthesized by the oximation of ethyl 3-(4-methoxyphenyl)- 3-oxopropanoate with ethyl nitrite in the presence of multi-pore activated-K2CO3. A one-pot procedure has also been developed for the conversion of this oxime to the corresponding erythro-2-acetamido-3-hydroxy-3-(4-meth...

A novel base, nano-K2CO3, was easily prepared by ultrafine wet milling. The surface properties and the reactive activities of nano-K2CO3 were characterized. It was found that such a base showed higher basicity than normal K2CO3 and could replace sodium (or potassium) alkoxide to carry out monoalkylation and oximation of active methylene compounds....

Sansalvamide A is a cyclic depsipeptide that is isolated from a marine fungus of the Fusarium genus. Sansalvamide A exhibits significant antitumor ability. The molecular formula and molecular weight of the novel sansalvamide A derivative H-15 are C29H44BrN5O6 and 637.2475, respectively. In the present study, H-15 was found to inhibit the proliferat...

Enantiopure (2R,3R)-β-methoxytyrosine was stereoselectively synthesized from ethyl 3-(4-hydroxyphenyl)-3-oxopropanoate protected by 2-methoxyethoxymethyl (MEM) (ee >98%). l-Aminoacylase-catalyzed resolution of the corresponding erythro-N-acetyl derivatives afforded (2S,3S)-(4-MEM)-β-methoxytyrosine (ee >99%). The conversion increased to 98% by opti...

An efficient, photocatalytic chlorination of alkylarene α-H groups using NaCl/HCl as a chlorine source has been developed, which involves a radical mechanism under visible-light (including sunlight) conditions. A chlorine radical is proposed to be formed by an electron transfer from chloride ion to O2 in air through the bandgap hole of the semicond...

A series of open-chain analogs of cyclic peptides was designed and synthesized using sansalvamide A as a model compound. All compounds exhibited low antitumor activity. Furthermore, the evaluation of their inhibitory potency toward IMPDH, SHP2, ACHE, proteasome, MAGL, and cathepsin B showed that all of the compounds were potent against protein tyro...

An efficient fermentation-strengthening approach was developed to improve the anaerobic production of vitamin B12 by cultivation process optimization with Propionibacterium freudenreichii. The effects of the byproduct propionic acid and the precursor 5,6-dimethylbenzimidazole (DMB) on vitamin B12 biosynthesis were investigated. Byproduct inhibition...

This paper describes an efficient procedure for the synthesis of micromide, a natural product that shows anti-solid-tumor activity. Our strategy involved the synthesis of N-nosyl-protected amino acids and their N-methylation with iodomethane. The hindered oligopeptides containing N-methyl amino acids were synthesized in excellent yields and high pu...

An efficient fermentation-strengthening approach was developed to improve the anaerobic production of propionic acid and vitamin B12 by co-fermentation with Propionibacterium freudenreichii. Vitamin B12 production from glucose resulted in relatively high productivity (0.35 mg/L h) but a low propionic acid yield (0.55 g/g). By contrast, glycerol gav...

Chiral β-hydroxy-β-arylalanine and β-methoxy-β-arylalanine derivatives, which occur widely in marine nature products, were stereoselectively synthesized with 99 % ee values. The two erythro isomers were prepared by L- or D-aminoacylase-catalyzed resolution of the corresponding N-acetyl derivatives, whereas the two threo isomers were obtained only b...

N-(α-Alkyloxime-3-phenylpropionyl) proline was designed and synthesized as an acylating agent to modify the 6-OH of 1-O-acetylbritannilactone. Eight intermediates and eight target compounds were obtained. The structures of sixteen novel compounds were characterized by 1HNMR, IR and HRMS. The activities against HL-60 and Bel-7402 cell lines were tes...

Sansalvamide A, a cyclic depsipeptide isolated from a marine fungus of the Fusarium genus, exhibits significant antitumor activity. In the present study, H-10 (molecular formula, C38H55N5O6; molecular weight, 677.8732), a novel sansalvamide A derivative, demonstrated an inhibitory effect on the proliferation of murine melanoma B16 cells. It was con...

Eight sansalvamide A peptide analogues with 4′-fluoride, 4′-chloride, 4′-bromide, 4′-iodide, and 4′-methoxyphenylalanine moieties were synthesized. The effect of these para-substitutions of sansalvamide A peptide on their cytotoxicity was evaluated using HCT-116, MDA-MB-231, HT-29, HCT-15, K562, HeLa, and A549 cell lines. The 4′-methoxyphenylalanin...

Two novel alkali cation sandwich complexes have been constructed by reaction of potassium and cesium picrate with double-armed benzo-15-crown-5 ether 1. Crystals of the K+Pic−2(B15C5) and Cs+Pic−2(B15C5) complexes (Mr = 1339.81, 2865.23) are all yellow prisms which belong to the orthorhombic space group Pna2(1) with a = 25.757(5), b = 12.927(3), c...

The direct amidation of amino acid derivatives catalyzed by arylboronic acids has been examined. The reaction was generally slow relative to simple amine-carboxylic acid combinations though proceeded at 65–68 °C generally avoiding racemization. 3,4,5-Trifluorophenylboronic and o-nitrophenylboronic acids were found to be the best catalysts, though f...

A formal synthesis of cephalotaxine, the parent member of the Cephalotaxus alkaloids, was achieved. It features a practical four-step assembly of the benzazepine-bearing pentacyclic ring system through two alkylation reactions, acidic hydrolysis and aldolization.

A practical method has been developed for reduction of C-N double bond in oximes, imines and hydrazones with sodium borohydride catalyzed by Raney Ni. The reactions were carried out in basic aqueous solution and the desired products were obtained in moderate yields after a simple procedure. This method can be applied to synthesize simpler aliphatic...

An efficient, convenient synthesis method has been introduced for the preparation of phenylalanine containing crown ether ring by nucleophilic substitution, nitrosation and reduction reaction using benzo-crown ether and dimethyl malonate as material. The structures of the product are characterized by 1HNMR, MS and element analysis.

Dodecyl benzenesulfonic acid functionalized silica-coated magnetic nanoparticles (γ-Fe(2)O(3)@SiO(2)-DDBSA) were readily prepared and identified as an efficient catalyst for the synthesis of a library of spirooxindole-pyrimidine derivatives by three-component condensation reaction of barbituric acids, isatins and cyclohexane-1,3-diones. The aqueous...

Double-armed crown ether 15,16-bis((4-nitrophenoxy)methyl)-2,3,5,6,8,9,11, 12- octahydrobenzo[b][1,4,7,10,13] pentaoxacyclopentadecine F.W. 570.54 was synthesized by dibromomethyl benzo-15-crown-5 with 4-nitrophenol in the presence of anhydrous K 2CO 3, characterized by spectroscopic techniques and confirmed by X-ray crystal structure analysis. The...

Amorphous nickel powder (Ni(0)) was utilised as a catalyst under mild, aqueous, basic conditions for enhancing the sodium borohydride-mediated reduction of C-N multiple bonds such as oximes, imines, hydrazones and nitriles to produce the corresponding amines in good to excellent yields.

A series of novel N-(pyrimidin-4-yl)thiazol-2-amine derivatives have been synthesized and evaluated as glucokinase (GK) activators. Ethyl 2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl-amino)thiazole-5-carboxylate was found to be a potent dual-acting hypoglycemic agent activating both GK and PPARγ. When given orally to normal mice,...

A stereoselective synthesis of arylidene N-alkoxydiketopiperazines via oxime-ether formation and intramolecular acylation is described, followed by an acid-catalysed rearrangement-fragmentation to give novel diketopiperazine hemiaminal derivatives with useful bioactivity against certain tumour cell lines.

In the title compound, C(22)H(20)N(+)·Cl(-), the anthracene system makes a dihedral angle of 72.65 (4)° with the benzene ring. The C-N-C-C torsion angles in the chain connecting the benzene ring and anthracene system are 52.24 (15) and -170.73 (11)°. The crystal structure is stabilized by inter-molecular N-H⋯Cl and C-H⋯Cl hydrogen bonds, which link...

dl-Gylcerol monoester of pivalic acid was synthesized by alcoholysis reaction of pivalyl chloride with acetone ketal of glycerine. The effect of molar ratio, reaction time, reaction temperature and catalyst dosage on the yield was investigated. The product structure was characterized by IR and 1HNMR. Results indicated that yield of dl-gylcerol mono...

As intermediates of light stabilizer malonate, diethyl 3,5-di-t-butyl-4-hydroxybenzyl phenyl malonates (F.W. 454.58) was synthesized, characterized by 1H NMR, element analysis and confirmed by X-ray crystal structure analysis. This compound crystallizes in monoclinic class under the space group P21/c with cell parameters, a = 9.8218(4) Å, b = 13.55...

In the title compound, C(15)H(15)NO(4), the quinoline ring system and one of the malonate side chains are essentially coplanar (r.m.s. deviation = 0.0297 Å). The two malonate C-C(=O)-O-CH(3) side chains are oriented at right angles [89.68 (8)°] with respect to each other. The crystal packing is stabilized by weak non-classical inter-molecular C-H⋯O...

In the title compound, C(15)H(20)O(7), the benzene ring makes dihedral angles of 69.17 (5) and 80.81 (4)° with the two side chains of malonate. The two malonate side chains comprising C/C/O/C atoms are oriented at right angles [86.26 (6)°] with respect to each other. In the crystal structure, the crystal packing is stabilized by weak non-classical...

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and...

Abstract As precursors of α-amino acids, methyl 2-hydroxyimino-3-phenyl-propionate (F.W. 193.20) was synthesized, characterized by 1H NMR, IR, element analysis and confirmed by X-ray crystal structure analysis. This compound crystallizes in monoclinic class under the space group P21/c with cell parameters, a = 8.6435(17) Å, b = 5.4957(11) Å, c = 21...

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In the title compound, C(25)H(23)N(3)O(5)S, the central 1,3,4-oxadiazole ring makes dihedral angles of 35.05 (7), 23.68 (7) and 82.55 (8)°, with the three benzene rings. In the crystal structure, the packing is stabilized by weak non-classical inter-molecular C-H⋯O hydrogen bonds, which link the mol-ecules into an infinite network.

In the title compound, C(20)H(22)N(2)O(5), the central 1,3,4-oxadiazole ring is essentially planar [r.m.s. deviation from the best plane of 0.0011 Å] and makes dihedral angles of 4.10 (3) and 13.32 (4)° with the two benzene rings. In the crystal structure, the packing is stabilized by weak non-classical inter-molecular C-H⋯N hydrogen bonds, which l...

An effective method to prepare racemic alpha-amino acids was developed. The key reactions involve nitrosation of malonate under basic conditions and reduction of alpha-hydroxyimino ester derivatives with zinc powder in the presence of acetic anhydride.

In the title compound, C(24)H(20)BrN(3)O(4)S, the central benzene ring makes dihedral angles of 17.13 (13), 39.83 (13) and 58.37 (13)°, respectively, with the pyrazolone ring, the bromo-benzene ring and the terminal phenyl ring. In the crystal structure, the packing is stabilized by a weak non-classical inter-molecular C-H⋯O hydrogen bond which lin...

In the title compound, C(25)H(22)N(4)O(4), the central benzene ring, makes dihedral angles of 74.35 (6), 17.01 (8) and 62.19 (7)°, respectively, with the nitro-benzyl ring, the pyrazolone ring and the terminal phenyl ring. Inter-molecular C-H⋯O hydrogen bonds help to consolidate the crystal packing.

In the title compound, C15H13ClO3, the vanillin group makes a dihedral angle of 72.79 (9)° with the chlorobenzene ring. The crystal structure is stabilized by weak non-classical intermolecular C—H...O hydrogen bonds that form centrosymmetric dimers.

In the title compound, C26H24ClN3O5S·C2H3N, the o-vanillin group makes dihedral angles of 25.87 (4), 11.93 (3) and 72.05 (7)° with the pyrazolone, benzene and phenyl rings, respectively. The crystal structure is stabilized by weak intermolecular C—H...O interactions that link molecules into centrosymmetric dimers.

In the title compound, C23H20Cl2N2O4 center dot 1.5H(2)O, the vanillin group makes dihedral angles of 0.52 ( 14) and 81.22 ( 7)degrees with the benzohydrazide residue and the dichlorobenzene ring, respectively. An intramolecular N-H center dot center dot center dot O hydrogen bond helps to stabilize the molecular conformation, while intermolecular...

In the title compound, C25H20ClN3O3, the central benzene ring makes dihedral angles of 7.56 (10), 39.46 (7) and 63.03 (7)° with the pyrazolone ring, the chlorobenzene ring and the terminal phenyl ring, respectively. The packing is stabilized by weak C—H...O intermolecular hydrogen bonds that link molecules into chains running along the b axis.

In the title compound, C25H20ClN3O3, the central benzene ring makes dihedral angles of 7.56 (10), 39.46 (7) and 63.03 (7)

In the title compound, C15H12Cl2O3, the isovanillin group makes a dihedral angle of 3.12 (12)degrees with the dichlorobenzene ring. Intermolecular C-H center dot center dot center dot O hydrogen bonds help to consolidate the crystal packing.

In the title compound, C16H14Cl2O3, the ethylvanillin group makes a dihedral angle of 6.15 (3)degrees with the dichlorobenzene ring. Intermolecular C-H center dot center dot center dot O interactions lead to trimeric associations of molecules.

The title compound, C21H18N4O5, crystallizes with two mol­ecules in the asymmetric unit. The conformations of these non-planar mol­ecules are simlilar. Intra- and inter­molecular N—H⋯(O,N) hydrogen-bond systems and inter­molecular C—H⋯O and C—H⋯N hydrogen bonds help to consolidate the crystal packing.

In the title compound, C15H12Cl2O3, the vanillin group makes a dihedral angle of 4.47 (8)° with the dichloro­benzene ring. Inter­molecular C—H⋯O hydrogen bonds help to consolidate the crystal structure.

In the title compound, C26H23Cl2N3O3, the central vanillin group makes dihedral angles of 51.19 (8), 7.51 (11) and 45.65 (11)° with the dichloro­benzene ring, the pyrazolone ring and the terminal phenyl ring, respectively. Inter­molecular C—H⋯O inter­actions help to consolidate the crystal packing.

In the title compound, C23H22N2O6, the vanillin group makes dihedral angles of 81.15 (6) and 23.52 (7)°, respectively, with the phenyl ring and the benzohydrazide mean plane. An intra­molecular N—H⋯O hydrogen bond helps to stabilize the mol­ecular conformation, while the water mol­ecule inter­acts with the organic mol­ecule by way of a bifurcated O...

The title compound, C10H9NO3, crystallizes with two mol­ecules in the asymmetric unit. Inter­molecular C—H⋯O and C—H⋯(O,O) inter­actions help to consolidate the crystal packing.

In the title compound, C25H21Cl2N3O2, the central benzene ring makes dihedral angles of 65.61 (10), 12.95 (15) and 39.49 (14)degrees, respectively, with the dichlorobenzene ring, the pyrazolone ring and the terminal phenyl ring. Intermolecular C-H center dot center dot center dot O interactions help to consolidate the crystal packing.

In the title compound, C23H22N2O6, the vanillin group makes dihedral angles of 81.15 (6) and 23.52 (7)degrees, respectively, with the phenyl ring and the benzohydrazide mean plane. An intramolecular N-(HO)-O-... hydrogen bond helps to stabilize the molecular conformation, while the water molecule interacts with the organic molecule by way of a bifu...

Total synthesis of N-methylsansalvamide A was accomplished in solution phase by a convergent approach. An N-Boc-tri-depsipepide 6 and a dipeptide ester 10 were prepared in the yield of 89% and 91%, respectively. Cyclization of the linear penta-depsipetide was achieved with PyBOP and DIPEA in DMF-CH 2Cl2.