2013 Volume 24 Issue 5

Recent advances in biocompatible supramolecular assemblies for biomolecular detection and delivery
Lei Wang , Li-Li Li , Horse L. Ma , Hao Wang
2013, 24(05): 351-358
[Abstract](276) [FullText HTML] [PDF 4901KB](0)
Inspired by sophisticated biological structures and their physiological processes, supramolecular chemistry has been developed for understanding and mimicking the behaviors of natural species. Through spontaneous self-assembly of functional building blocks, we are able to control the structures and regulate the functions of resulting supramolecular assemblies. Up to now, numerous functional supramolecular assemblies have been constructed and successfully employed as molecular devices, machines and biological diagnostic platforms. This review will focus on molecular structures of functional molecular building blocks and their assembled superstructures for biological detection and delivery.
A 4-aminonaphthalimide based environmentally sensitive fluorescence probe
Zhi-Yong Wu , Jing-Nan Cui , Xu-Hong Qian , Tian-Yu Liu
2013, 24(05): 359-361
[Abstract](277) [FullText HTML] [PDF 563KB](0)
A simply synthesized 4-aminonaphthalimide derivative 1 expresses both polarity and viscosity sensitive fluorescence spectra, indicating its potential usage as an environmentally sensitive fluorescence probe. By comparing the fluorescence behavior of 1 with that of a known 4-aminonaphthalimide derivative 2, it was found that the substitution of the 4-amino group has profound influence on the environmentally sensitive fluorescence properties of 4-aminonaphthalimide.
Complexation of sym-bis(benzimidazole)-2, 2’-ethylene salts with cucurbit[6]uril derivatives:A potential axle molecule for pseudorotaxanes
Jun-Ming Yi , Xin-Long Ni , Xin Xiao , Li-Bing Lu , Sai-Feng Xue , Qian-Jiang Zhu , Zhu Tao
2013, 24(05): 362-366
[Abstract](337) [FullText HTML] [PDF 2598KB](0)
Sym-bis(benzimidazole)-2,2'-ethylene cations act as a new axle template for threading cucurbit[6]uril derivatives on, forming [2]pseudorotaxane and [3]pseudorotaxane. These new complexes have been studied using 1H NMR, UV-vis absorption spectroscopy and X-ray analysis. Changes in the 1H NMR spectra indicate that the two types of pseudorotaxane can be formed by varying the host concentration. UV-vis absorption titration experiments at different pH values demonstrate that interesting pKa shifts of the bis-benzimidazole derivatives can be induced by the host-guest complexation. The associated constants were calculated to be 2.81×104 L/mol and 9.06×106 L/mol for the [2]pseudorotaxanes and [3]pseudorotaxanes, respectively. Furthermore, X-ray diffraction studies of the solid state structures provide unequivocal proof of the host concentration dependent pseudorotaxane, which is strongly in line with the evidences in solution.
Efficient synthesis of water-soluble calix[4]arenes via thiol-ene “click” chemistry
Hong Chen , Zhi-Long Zou , Shi-Liang Tan , Jia-Hai Bi , De-Mei Tian , Hai-Bing Li
2013, 24(05): 367-369
[Abstract](284) [FullText HTML] [PDF 340KB](0)
Several water-soluble calix[4]arenes were synthesized via radical addition reaction between thiols and alkenes under UV lamp irradiation (λ= 365 nm) in good yields. The structures of these compounds synthesized herein were fully confirmed by 1H NMR, ESI-MS and elemental analysis.
Nano-Fe3O4 encapsulated-silica particles bearing sulfonic acid groups as a magnetically separable catalyst for green and efficient synthesis of functionalized pyrimido[4, 5-b]quinolines and indeno fused pyrido[2, 3-d]pyrimidines in water
Firouzeh Nemati , Raheleh Saeedirad
2013, 24(05): 370-372
[Abstract](282) [FullText HTML] [PDF 377KB](0)
The magnetic nanoparticles supported silica sulfuric acid was used as an efficient catalyst for the synthesis of pyrimido[4,5-b]quinolines and indeno fused pyrido[2,3-d]pyrimidines in water. The desired products were obtained in excellent yields. Fe3O4@SiO2-SO3H was readily recovered using an external magnet and could be reused several times without significant loss of reactivity.
Efficient photocatalytic properties of a dinuclear iron complex with bis[2-hydroxybenzaldehyde]hydrazonate ligand
Jing-Wen Ran , Shao-Wen Liu , Peng Wua , Jun Pei
2013, 24(05): 373-375
[Abstract](266) [FullText HTML] [PDF 1721KB](0)
A novel photooxidative system for degrading toxic organic pollutants is reported. A new complex of Fe2L3(L = bis[2-hydroxybenzaldehyde]hydrazone) synthesized can efficiently activate hydrogen peroxide (H2O2) to oxidize and mineralize the target complexes rhodamine B (RhB) and methyl orange (MO) in aqueous media under ambient temperature and normal pressure and with visible light irradiation.
Multicomponent reactions for the synthesis of functionalized 1, 4-oxathiane-3-thiones under microwave irradiation in water
Zinatossadat Hossaini , Faramarz Rostami-Charati , Samereh Seyfi , Mehdi Ghambarian
2013, 24(05): 376-378
[Abstract](294) [FullText HTML] [PDF 551KB](0)
A series of substituted 1,4-oxathiane-3-thione derivatives were synthesized via one-pot multicomponent reactions of nitromethane, carbon disulfide and oxiranes in the presence of Et3N in water as the solvent under microwave irradiation. Particularly valuable features of this method include high yields of products, broad substrate scope, short reaction time and straightforward procedure.
A total synthesis of mycalisine A
Yan-Hui Dou , Hai-Xin Ding , Ru-Chun Yang , Wei Li , Qiang Xiao
2013, 24(05): 379-382
[Abstract](331) [FullText HTML] [PDF 379KB](0)
In this paper, we report a total synthesis of a naturally occurring pyrrolo[2,3-d]pyrimidine nucleoside, mycalisine A. Our synthetic strategy uses D-xylose as the startingmaterial and Vorbrüggen glycosylation as the key step. Mycalisine A was synthesized in 11 steps with a 15% overall yield.
Preparation of new spongy adsorbent for removal of EDTA-Cu(Ⅱ) and EDTA-Ni(Ⅱ) from water
Xin Yang , Jin-Nan Wang , Cheng Cheng
2013, 24(05): 383-385
[Abstract](270) [FullText HTML] [PDF 608KB](0)
A new spongy adsorbent (PU-DTC) was prepared with a polyurethane (PU) adsorbent for removal of EDTA-Cu(Ⅱ) and EDTA-Ni(Ⅱ) from water. This new spongy adsorbent was characterized by using SEM and 13C NMR and FT-IR spectroscopy. Adsorption kinetic curve indicated that this new spongy adsorbent could quickly remove EDTA-Cu(Ⅱ) and EDTA-Ni(Ⅱ) from water, and adsorption isotherm also indicated that PU-DTC had high equilibrium adsorption capacity for EDTA-Cu(Ⅱ) and EDTA-Ni(Ⅱ).
Synthesis and in vitro antitumor activity of novel diaryl urea derivatives
Yan-Fang Zhao , Zi-Jian Liu , Xin Zhai , Dan-Dan Ge , Qiang Huang , Ping Gong
2013, 24(05): 386-388
[Abstract](262) [FullText HTML] [PDF 352KB](0)
A series of novel diaryl ureas containing 4-[(2-amino-6-trifluromethyl)pyrimidine-4-yl]piperazine-1-yl group were synthesized and evaluated for their cytotoxic activities in a panel of human cancer cell lines. Compared with the reference drug Sorafenib, some compounds showed more potent and a broader spectrum of anti-cancer activities. Among them, compound 2p demonstrated significant inhibitory activities against MDA-MB-231, HT-29 and MCF-7 cell lines with IC50 values of 0.016, 0.63, 0.001 mmol/L, respectively.
One-pot synthesis of 1, 3-thiazolidin-4-one using Bi(SCH2COOH)3 as catalyst
Naser Foroughifar , Sattar Ebrahimi
2013, 24(05): 389-391
[Abstract](289) [FullText HTML] [PDF 382KB](0)
A catalytic multi-component reaction involving aromatic amine, aromatic aldehydes, mercapto acid as substrates and Bi(SCH2COOH)3 as catalyst under solvent free conditions, afforded thiazolidin-4-one in good yields. The efficiency of the catalyst was proved with a variety of substrates, ranging from electrondeficient to electron-rich aldehydes.
Synthesis of novel copolymer:Poly(p-dioxanone-co-L-phenylalanine)
Bing Wang , Chi Ma , Zuo-Chun Xiong , Cheng-Dong Xiong , Quan-Hua Zhou , Dong-Liang Chen
2013, 24(05): 392-396
[Abstract](274) [FullText HTML] [PDF 686KB](0)
In order to expand the application of poly(p-dioxanone) or PPDO in biomedical area, a series of novel copolymers were synthesized successfully by one-step, melted copolymerization of p-dioxanone (PDO) and L-phenylalanine N-carboxyanhydride (L-Phe-NCA) monomers. With the in-feedmolar ratio of L-Phe-NCA/PDO equal to 1/20, the conversions of the two kinds of monomers were calculated from 1H NMR. The average molecular weight and polydispersity of the copolymer increase with the increasing reaction time and catalyst concentration. However, the conversions of the two kinds of monomers did not change with the reaction conditions. A three-step mechanism is presented and proved by high resolution 1H NMR and IR spectrums.
Effects of molecular configuration of a chiral trimeric phenylene vinylene on its liquid crystalline properties
Ping Yu , Zhen-Lin Zhang , Lei Wang , Chun-Luan Liu , Shi-Min Liu , Hai-Quan Zhang
2013, 24(05): 397-400
[Abstract](296) [FullText HTML] [PDF 1230KB](0)
Based on an analysis of the 1H NMR, FT-IR, UV-vis spectra, a chiral trimeric phenylene vinylene derivative (ChTPV) synthesized by a Wittig reaction was determined to have a trans-cis configuration, and it could be isomerized to the trans-trans isomer when treated with iodine. The melting point of ChTPV with a trans-trans configuration increased by 162.1℃ compared to the trans-cis isomer, and the ChTPV with trans-trans configuration exhibited the typical liquid-crystalline texture of the smectic A in the heating process. The results indicated that the molecular configuration can influence the formation of the liquid crystalline phase of ChTPV.
The SBA-15/SO3H nanoreactor as a highly efficient and reusable catalyst for diketene-based, four-component synthesis of polyhydroquinolines and dihydropyridines under neat conditions
Sadegh Rostamnia , Fatemeh Pourhassan
2013, 24(05): 401-403
[Abstract](328) [FullText HTML] [PDF 1019KB](0)
An efficient diketene ring-opening synthesis of polyhydroquinoline derivatives using SBA-15 sulfonic acid modified mesoporous substrates a green and reusable catalyst in a single-pot four-component coupling reaction of diketene, alcohol, enamine, and aldehydes is reported. Dihydropyridine derivatives based on neat adduct of diketene, alcohols and aldehydes using SBA-15/SO3H nanoreactor as catalyst via a four-component reactions are also synthesized. The advantages of the present method include the use of a small amount catalyst, simple procedure with an easy filterable work-up, waste-free, green and direct synthetic method with an excellent yield of products with efficient use of catalyst and a short reaction time.
Silicon-mediated highly efficient synthesis of 1, 8-dioxo-octahydroxanthenes and their transformation to novel functionalized pyrano-tetrazolo [1, 5-a] azepine derivatives
Hanan A. Soliman , Tarek A. Salama
2013, 24(05): 404-406
[Abstract](297) [FullText HTML] [PDF 393KB](0)
A facile and highly efficient protocol for the synthesis of 1,8-dioxo-octahydroxanthene derivatives was achieved through cascade Knoevenagel-Michael condensations and cyclo-dehydration reaction utilizing tetrachlorosilane (TCS) as catalyst under mild conditions. Reaction of the titled compounds with TCS-NaN3 to give novel functionalized pyrano[3,2-c]tetrazolo[1,5-a]azepine derivatives is also described.
Synthesis of symmetrical 1, 3-diynes via tandem reaction of (Z)-arylvinyl bromides in the presence of DBU and CuI
Wen-Sheng Zhang , Wen-Jing Xu , Fei Zhang , Gui-Rong Qu
2013, 24(05): 407-410
[Abstract](452) [FullText HTML] [PDF 722KB](0)
Microwave-assisted tandem reaction of (Z)-arylvinyl bromides involving an elimination and homocoupling in the presence of DBU and CuI in DMF affords a variety of symmetrical 1,3-diynes in good to excellent yields. This tandem process, eliminating the need of volatile and savory terminal alkynes, provides an alternative to the conventional homocoupling methods for the synthesis of symmetrical 1,3-diynes.
Entirely green protocol for the synthesis of β-aminoketones using saccharose as a homogenous catalyst
Mir Rasul Mousavi , Nourallah Hazeri , Malek Taher Maghsoodlou , Sajjad Salahi , Sayyed Mostafa Habibi-Khorassani
2013, 24(05): 411-414
[Abstract](274) [FullText HTML] [PDF 354KB](0)
Saccharose was applied as an efficient and homogenous catalyst for a one-pot, three-component Mannich reaction for the formation of β-aminoketones from aromatic aldehydes, anilines, and acetophenone at ambient temperature in excellent yields. This protocol has the following advantages: mild conditions, high yields, clean reaction profiles, operational simplicity, and environmentally benign and simple work-up procedures.
Synthesis and in vitro biological evaluation of nitric oxide-releasing derivatives of hydroxylcinnamic acids as anti-tumor agents
Ming-Dong Lu , Xiao Zhou , Yao-Jun Yu , Pi-Hong Li , Wei-Jian Sun , Cheng-Guang Zhao , Zhi-Qiang Zheng , Tao You , Fei-Hai Wang
2013, 24(05): 415-418
[Abstract](303) [FullText HTML] [PDF 535KB](0)
Novel furoxan-based nitric oxide-releasing derivatives 6a-p of hydroxylcinnamic acids were synthesized by coupling the carboxyl group of hydroxylcinnamic acids with furoxan through various alkylol amines. Compounds 6a, e-i and m-p displayed more potent anti-tumor activities superior to control 5-fluorouracil (5-FU) in most cancer cells tested. Furthermore, 6f could selectively inhibit tumor cells, but not non-tumor cell proliferation. This inhibition was attributed to high levels of NO released in cancer cells and potentially synergistic effect of NO donor moieties and the bioactivity of hydroxylcinnamic acids.
Resolution enhancement in hydrophobic interaction chromatography via electrostatic interactions
Dong Gao , Fu-Chun Tan , Wen-Peng Wang , Li-Li Wang
2013, 24(05): 419-421
[Abstract](280) [FullText HTML] [PDF 872KB](0)
In this work, a new type of hydrophobic stationary phase that provide electrostatic interactions with analytes was developed by bonding β-phenylethylamine as a functional ligand to silica. This stationary phase can separate proteins with similar hydrophobicity that traditional hydrophobic resins cannot. Hen egg white was separated to examine the selectivity. The results show that the introduced electrostatic interactions are an important factor for the resolution enhancement and the new resin could have important applications in separation and purification of biological macromolecules.
A convenient one-pot three component synthesis of 3-aminoalkylated indoles catalyzed by 3-chlorophenylboronic acid
Santosh V. Goswami , Prashant. B. Thorat , Vijay N. Kadam , Sachin A. Khiste , Sudhakar R. Bhusare
2013, 24(05): 422-424
[Abstract](276) [FullText HTML] [PDF 369KB](0)
An efficient protocol was developed for the synthesis of 3-aminoalkylated indoles using 3-chlorophenylboronic acid as a catalyst under ambient temperature conditions. The three-component reaction of indoles, aromatic aldehydes and N-methyl aniline offered corresponding 3-aminoalkylated indoles in excellent yields. This protocol presents some remarkable features such as mild reaction conditions, simple workup procedure and excellent yields.
Novel azo dyes derived from 8-methyl-4-hydroxyl-2-quinolone:Synthesis, UV-vis studies and biological activity
E.O. Moradi Rufchahi , H. Pouramir , M.R. Yazdanbakhsh , H. Yousefi , M. Bagheri , M. Rassa
2013, 24(05): 425-428
[Abstract](300) [FullText HTML] [PDF 476KB](0)
In this study, N,N'-di-(2-methylphenyl)malonamide was synthesized and reacted with polyphosphoric acid to afford 8-methyl-4-hydroxyl-2-quinolone. Eight novel azo disperse dyes were then synthesized by linking diazotized p-substituted aniline derivatives with 8-methyl-4-hydroxyl-2-quinolone. The solvatochromism of these azo dyes in various solvents was evaluated. All the compounds were then evaluated for their antibacterial activity against four bacteria, namely, Bacillus subtilis, Micrococcus luteus, Salmonella enterica, and Pseudomonas aeruginosa. The results showed that some of these compounds have high levels of antibacterial activity.
Design, synthesis and biological activity of cyclohexane-bearing C-glucoside derivatives as SGLT2 inhibitors
Shuo Zhang , Yu-Li Wang , Qun-Chao Wei , Wei-Ren Xu , Li-Da Tang , Gui-Long Zhao , Jian-Wu Wang
2013, 24(05): 429-432
[Abstract](346) [FullText HTML] [PDF 545KB](0)
Seven cyclohexane-bearing C-glucoside derivatives (7, 9, 12, 13 and 17-19) were designed and synthesized as SGLT2 inhibitors starting from a potent SGLT2 inhibitor we discovered in earlier work, (1S)-1-deoxy-1-[4-methoxy-3-(trans-n-propylcyclohexyl)methylphenyl]-D-glucose (1). The in vitro and in vivo biological activities were evaluated by hSGLT2/hSGLT1 inhibition and urinary glucose excretion (UGE), respectively. Among the synthesized compounds 12, the 6-deoxy derivative of 1 was the most active and selective SGLT2 inhibitor (IC50 = 1.4 nmol/L against hSGLT2; selectivity = 1576). Compound 12 was a potent SGLT2 inhibitor, which could induce more urinary glucose than 1 and dapagliflozin in UGE.
Efficient imidazolium salts for palladium-catalyzed Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions
Mojtaba Amini , Mojtaba Bagherzadeh , Sadegh Rostamnia
2013, 24(05): 433-436
[Abstract](281) [FullText HTML] [PDF 360KB](0)
The system, Pd(OAc)2/imidazolium salts (L2), was found as an efficient catalyst in the Heck coupling reaction of olefins with aryl halides and Suzuki reactions of various aryl halides with aryl boronic acids under aerobic condition. This catalytic system demonstrates great tolerance to a wide range of groups on all substrates of aryl halides, alkenes and aryl boronic acids.
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