- New metal complex systems as electrode active components of ion selective electrode membranes
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New donor-acceptor 3d-transition metal complexes were synthesized and the cobalt and nickel complexes were studied by X-ray diffraction; CIF files CCDC no. 1516693 (III(Ni)) and 1516694 (III(Co)). The crystal structure details of the reactants were discussed. The proposed compounds were tested as the active components of ion selective electrode membranes for determination of thiocyanate ions. The selectivity of the SCN-SE with metal complex-based membranes depends on the ligand structure and the central metal ion type. The proposed electrode is suitable for determination of thiocyanate ions in the presence of sulfate, chloride, nitrate, nitrite, bromide, and iodide ions.
- Nemilova, M. Yu.,Shvedene,Mikhalev,Fedyanin,Shpakovsky
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Read Online
- Synthesis and properties of low-surface-energy polyimides
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An aromatic diamine monomer, 1H,1H-perfluorooctyl 3,5-diaminobenzoate (PFD), was synthesized in three steps, which was used to prepare the polyimides containing pendant perfluoroalkyl chains via the polymerization of PFD with commercial 4,4′-(hexafluoroisopropylidene)diphthalic anhydride. Various characterization techniques including thermogravimetric analysis, infrared spectroscopy, and X-ray photoelectron spectroscopy were used to characterize the new polyimides with perfluoroalkyl chains. The resulting polyimide film exhibits hydrophobicity with a contact angle of 95° for water, and the calculated surface free energy is 37.4mNm-1. Superhydrophobic surfaces were also demonstrated by coating the polyimide containing pendant perfluorooctyl chains on rough alumina substrate.
- Wang, Hai-Zhong,Ye, Qian,Wang, Xiao-Long
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Read Online
- Lead derivatization of ethyl 6-bromo-2-((dimethylamino)methyl)-5-hydroxy-1-phenyl-1H-indole-3-carboxylate and 5-bromo-2-(thiophene-2-carboxamido) benzoic acid as FabG inhibitors targeting ESKAPE pathogens
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Our previous studies on FabG have identified two compounds 5-bromo-2-(thiophene-2-carboxamido) benzoic acid (A) and ethyl 6-bromo-2-((dimethylamino)methyl)-5-hydroxy-1-phenyl-1H-indole-3-carboxylate(B) as best hits with allosteric mode of inhibition. FabG is an integral part of bacterial fatty acid biosynthetic system FAS II shown to be an essential gene in most ESKAPE Pathogens. The current work is focussed on lead expansion of these two hit molecules which ended up with forty-three analogues (twenty-nine analogues from lead compound A and fourteen compounds from lead compound B). The enzyme inhibition studies revealed that compound 15 (effective against EcFabG, AbFabG, StFabG, MtFabG1) and 19 (inhibiting EcFabG and StFabG) had potency of broad-spectrum inhibition on FabG panel.
- Varakala, Saiprasad Dasugari,Reshma, Rudraraju Srilakshmi,Schnell, Robert,Dharmarajan, Sriram
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- Synthesis, computational studies and enzyme inhibitory kinetics of benzothiazole-linked thioureas as mushroom tyrosinase inhibitors
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Herein, we report synthesis of a set of benzothiazole-thiourea hybrids with aromatic and aliphatic side chains (BT1 to BT9) using an elegant synthetic strategy. The newly synthesized benzothiazole-thiourea conjugates were subjected to In-vitro tyrosinase inhibition and free radical scavenging activity. Majority of the compounds indicated inhibition considerably improved than the standard; compound (Kojic acid with IC50 = 16.8320 ± 1.1600 μM) BT2 with IC50 = 1.3431 ± 0.0254 μM was found to be the best inhibitor. A non-competitive mode of inhibition of BT2 was disclosed with Ki value of 2.8 μM. In order to study enzyme-inhibitor interactions SAR analysis molecular docking was carried out. The amino groups of thiourea were involved in hydrogen bonding with Glu322 showing the bond length of 1.74 and 2.70 ?, respectively. Moreover, the coupling of π-π was displayed between benzothiazole and benzene rings of His244 and His263, respectively. The outcome of this study might help to develop new inhibitors of melanogenesis, important for cosmetic and food products. Communicated by Ramaswamy H. Sarma.
- Ujan, Rabail,Saeed, Aamer,Ashraf, Saba,Channar, Pervaiz Ali,Abbas, Qamar,Rind, Mahboob Ali,Hassan, Mubashir,Raza, Hussain,Seo, Sung-Yum,El-Seedi, Hesham R.
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p. 7035 - 7043
(2020/08/12)
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- Benzimidazole tethered thioureas as a new entry to elastase inhibition and free radical scavenging: Synthesis, molecular docking, and enzyme inhibitory kinetics
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The porcine pancreatic elastase inhibition and free-radical scavenging play a crucial role in age progression. All the series of 10 newly synthesized benzimidazole thioureas (4a-j) were assessed for elastase inhibition and radical scavenging activity to identify the suitable anti-aging ingredient for cosmetics products. The compounds 4e, 4f, 4g, and 4h showed inhibition better than the standard, while compound 4f showed the most significant elastase inhibition with the IC50 value of 1.318 ± 0.025 μM compared with oleanic acid IC50 13.451 ± 0.014 used ±1.989 and 41.563 ± 0.824, respectively, as standard. Molecular docking studies were performed and the compound 4f showed binding energy of 7.2 kcal/mol. Kinetics studies revealed inhibition of the pancreatic elastase in a competitive manner. The relative binding energy and structure activity relationship (SAR) identified compound 4f as an effective inhibitor of porcine pancreatic elastase. Compounds 4e and 4i showed remarkable free-radical scavenging activity with SC50 values of 26.421.
- Abbas, Qamar,Ashraf, Saba,Channar, Pervaiz Ali,Hassan, Abbas,Hassan, Mubashar,Rafique, Hummera,Raza, Hussain,Rind, Mahboob Ali,Saeed, Aamer,Seo, Sung-Yum,Ujan, Rabail,Ul-Hamid, Anwar
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- Br?nsted acid-catalyzed chlorination of aromatic carboxylic acids
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The chlorination of aromatic carboxylic acids with SOCl2 has been effectively performed by reacting with a Br?nsted acid as the catalyst. Based on this discovery, an efficient catalytic method that is cheaper than traditional catalytic methods was developed. 20 substrates were chlorinated offering excellent yields in a short reaction time. And the SOCl2/Br?nsted acid system has been used in a larger scale preparative reaction. A dual activation mechanism was proposed to prove the irreplaceable system of SOCl2/Br?nsted acid.
- Yu, Zhiqun,Yao, Hongmiao,Xu, Qilin,Liu, Jiming,Le, Xingmao,Ren, Minna
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supporting information
p. 685 - 689
(2021/04/09)
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- Preparation method and application of tetrahydrobenzothiophene compound and pharmaceutical composition
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The invention belongs to the field of medicines, and particularly relates to a tetrahydrobenzothiophene compound as well as a pharmaceutical composition and a preparation method and application thereof. The tetrahydrobenzothiophene compound is a compound I as shown I. In-flight R1 And R2 The C1 -4 is a saturated/unsaturated hydrocarbon group. - OCH3 , OCH2 CH3 Phenyl, substituted phenyl, NO2 One - COR of - OH - F, Cl - Br. I - H R1 AND R2 Or different. R3 It is-F. - Cl, Br, I, OH, Amino, C1 -4 saturated/unsaturated hydrocarbon group, OCH3 , OCH2 CH3 , H, Wherein one of them is, n ≥ 5, n Being an integer. The compound effectively inhibits salmonella by inhibiting the synthesis of ATP-dependent transporter in the lipopolysaccharide synthesis pathway. Aeruginosa, escherichia coli and staphylococcus aureus.
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Paragraph 0178; 0181-0182
(2021/10/16)
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- Synthesis, in silico study and antimicrobial activity of new piperine derivatives containing substituted δ-esters
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A series of fifteen new piperine-derived diesters was synthesized through the substitution reaction between the salt of piperic acid, obtained through piperine basic hydrolysis, with the δ-chloro-esters, obtained through the cleavage of tetrahydrofuran (THF) with acyl chlorides in the presence of ZnCl2. The final compounds were obtained with yields ranging from 50 to 84% and were characterized by infrared (IR) and 1H and 13C nuclear magnetic resonance spectroscopy (NMR). The new compounds were evaluated in silico in regard to their ADME (absorption, distribution, metabolism, and excretion) properties, and in vitro for their antimicrobial activity against bacteria strains (Staphylococcus aureus and Pseudomonas aeruginosas), yeast fungi (Candida albicans and C. tropicalis) and filamentous fungi (Aspergillus fumigatus, A. flavus and A. niger). The results from the in silico studies of Lipinski's rule of five showed that most compounds present good pharmacological possibilities, and the results from in vitro antimicrobial activity showed that 8 of the 15 synthesized compounds displayed antimicrobial activity, inhibiting the growth of 40-80% of tested strains, with a minimum inhibitory concentration (MIC) interval ranging from 1024 to 256 μg mL-1
- Barbosa-Filho, José M.,Brandao, Maria C. R.,De Athayde-Filho, Petr?nio F.,Dutra, Thalisson F.,Lima, Edeltrudes O.,Lira, Bruno F.,Neto, Hermes Diniz,Trindade, Emmely O.
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p. 2590 - 2602
(2020/11/18)
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- Novel method for synthesizing 3, 5-dinitrobenzyl chloride
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The invention provides a novel method for synthesizing 3, 5-dinitrobenzyl chloride. The novel method comprises the following steps: a, carrying out reduction reaction on 3, 5-dinitrobenzoyl chloride and a reducing agent in a first solvent to obtain 3, 5-dinitrobenzene methanol; and b, carrying out chlorination reaction on the 3, 5-dinitrobenzene methanol, a chlorination reagent and a catalyst in asecond solvent to obtain the 3, 5-dinitrobenzyl chloride. According to the method, the reduction process of the 3, 5-dinitrobenzoyl chloride is remarkably improved, a simple reducing agent is used, nitro reduction is avoided under the assistance of Lewis acid and Lewis alkali, and the reaction selectivity and the product yield are improved.
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Paragraph 0026-0033
(2020/07/21)
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- Aroylthiourea derivatives of ciprofloxacin drug as DNA binder: Theoretical, spectroscopic and electrochemical studies along with cytotoxicity assessment
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Aroylthiourea derivatives of ciprofloxacin drug — [1-cyclopropyl-6-fluoro-7-(4-((4-methoxybenzoyl)carbamothioyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid] ATU-1, [1-cyclopropyl-7-(4-((2,4-dibromobenzoyl)carbamothioyl)piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid] ATU-2, and [1-cyclopropyl-7-(4-((3,5-dinitrobenzoyl)carbamothioyl)piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid] ATU-3 were synthesized, characterized and investigated for DNA binding at stomach pH (4.7) and at 37 °C. All findings by using DFT, molecular docking, spectroscopic (UV-, fluorescence; FL-), cyclic voltammetric (CV) and viscometric techniques revealed that these compounds have the potency to bind with DNA via a mixed mode of interaction. The binding affinity of ATU-1 was evaluated comparatively greater with Kb × 104/M?1 (docking; 5.55, UV-; 7.93, FL-; 5.62, CV; 6.06), ΔG/kJmol?1(docking; ?27.07, UV-; ?29.07, FL-; ?28.18, CV; ?28.38) and n (FL-; 1.20, CV; 2.72). Stern-Volmer quenching constant (Ksv) further pointed towards comparatively greater binding affinity of ATU-1 for DNA, while bimolecular quenching constant (Kq) values showed the involvement of static quenching mechanism in the compound — DNA interaction. Comparatively lesser IC50 (7.1 μM) value obtained from biological work on Huh-7 cancer cell line further confirmed the greater anticancer potential of ATU-1 than that of ATU-2&3.
- Farooqi, Shahid Iqbal,Arshad, Nasima,Perveen, Fouzia,Channar, Pervaiz Ali,Saeed, Aamer,Javeed, Aneela
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- A halogen-bonding foldamer molecular film for selective reagentless anion sensing in water
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We describe self-assembled monolayers of novel halogen-bonding and hydrogen-bonding foldamer receptors capable of selectively recruiting perrhenate, iodide and thiocyanate in water. Unprecedented anion sensing via impedance-derived capacitance spectroscopy enables subsequent sensitive and selective anion detection without the need for a redox probe. Importantly, the sensing of any anion should be possible using this novel electrochemical approach.
- Hein, Robert,Borissov, Arseni,Smith, Martin D.,Beer, Paul D.,Davis, Jason J.
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supporting information
p. 4849 - 4852
(2019/05/02)
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- Design, Synthesis and in Vitro Tumor Cytotoxicity Evaluation of 3,5-Diamino-N-substituted Benzamide Derivatives as Novel GSK-3β Small Molecule Inhibitors
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Glycogen synthase kinase-3 (GSK-3) plays an important regulatory role in various signaling pathways; such as PI3 K/AKT, which is closely related to the occurrence and development of tumors. At present, the most reported active GSK-3 inhibitors have the same structure: lactam ring or amide structure. To find out the GSK-3β small molecule inhibitor with novel, safe, efficient and more uncomplicated synthesis method, we analyzed in-depth reported crystal-binding patterns of GSK-3β small molecule inhibitor with GSK-3β protein, and designed and synthesized 17 non-reported 3,5-diamino-N-substituted benzamide compounds. Their structures were confirmed by 1H-NMR, 13C-NMR, and HR-MS. The preliminary screening of tumor cytotoxicity of compounds in vitro was detected by MTT, and their structure–activity relationships were illustrated. The results have shown that 3,5-diamino-N-[3-(trifluoromethyl)phenyl]benzamide (4d) exhibited significant tumor cytotoxicity against human colon cancer cells (HCT-116) with IC50 of 8.3 μm and showed commendable selectivity to GSK-3β. In addition, Compound 4d induced apoptosis to some extent and possessed modest PK properties.
- Zhou, Yanping,Zhang, Lijuan,Fu, Xiujuan,Jiang, Zhongliang,Tong, Rongsheng,Shi, Jianyou,Li, Jian,Zhong, Lei
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- Synthesis and enzyme inhibitory kinetics of some novel 3-(substituted benzoyl)-2-thioxoimidazolidin-4-one derivatives as α-glucosidase/α-amylase inhibitors
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The present work describes an efficient and convenient synthesis of a library of novel 3-(substituted benzoyl)-2-thioxoimidazolidin-4-ones (3a–j). The benzoyl isothiocyanates were treated with glycine in the presence of pyridine, the reactants got consumed giving a variety of thioxoimidazolidin-4-ones derivatives under mild reaction conditions. The structures of the compounds were determined by elemental analysis, FTIR, 1H, 13C NMR and mass spectral data. The title compounds were tested for their potential to inhibit the activity of enzymes α-glucosidase and α-amylase. It was found that most of the derivatives showed good enzyme inhibitory activity while compound 3j exhibited excellent activity with IC50 values 0.051 and 0.0082 mM for α-glucosidase and α-amylase, respectively. The presence of 3,5-di-NO2 functional groups at aromatic ring in compound 3j play important role in enzyme inhibitory activity. The enzyme inhibitory kinetic analysis of the most potent derivative 3j revealed that it is a mixed type inhibitor of α-glucosidase with Ki and Ki? values 0.0339 and 0.1562 mM, respectively. It was further investigated that compound 3j formed reversible enzyme inhibitor complex with α-glucosidase. The cytotoxicity of all the synthesized compounds was also evaluated and results showed that none of these compounds displayed toxicity against brine shrimps. Based upon results, it is suggested that compound 3j may act as a lead structure for the development of most potent α-glucosidase inhibitors.
- Qamar, Rabia,Saeed, Aamer,Saeed, Maria,Shah, Babar Hussain,Ashraf, Zaman,Abbas, Qamar,Seo, Sung Yum
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p. 1528 - 1537
(2018/04/02)
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- Hemozoin inhibiting 2-phenylbenzimidazoles active against malaria parasites
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The 2-phenylbenzimidazole scaffold has recently been discovered to inhibit β-hematin (synthetic hemozoin) formation by high throughput screening. Here, a library of 325,728 N-4-(1H-benzo[d]imidazol-2-yl)aryl)benzamides was enumerated, and Bayesian statistics used to predict β-hematin and Plasmodium falciparum growth inhibition. Filtering predicted inactives and compounds with negligible aqueous solubility reduced the library to 35,124. Further narrowing to compounds with terminal aryl ring substituents only, reduced the library to 18, 83% of which were found to inhibit β-hematin formation 100 μM and 50% parasite growth 2 μM. Four compounds showed nanomolar parasite growth inhibition activities, no cross-resistance in a chloroquine resistant strain and low cytotoxicity. QSAR analysis showed a strong association of parasite growth inhibition with inhibition of β-hematin formation and the most active compound inhibited hemozoin formation in P. falciparum, with consequent increasing exchangeable heme. Pioneering use of molecular docking for this system demonstrated predictive ability and could rationalize observed structure activity trends.
- L'abbate, Fabrizio P.,Müller, Ronel,Openshaw, Roxanne,Combrinck, Jill M.,de Villiers, Katherine A.,Hunter, Roger,Egan, Timothy J.
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p. 243 - 254
(2018/10/15)
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- Synthesis and antibacterial evaluation of 3,5-Diaryl-1,2,4-oxadiazole derivatives
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This manuscript reports the synthesis of twenty 3,5-diaryl-1,2,4-oxadiazole derivatives, nine of which are novel compounds. The amidoxime reaction with acyl chlorides obtained from substituted benzoic acids was used. All compounds were tested against five standard (American Type Culture Collection (ATCC)) bacteria: Escherichia coli, Pseudomonas aeruginosa, Enterococcus faecalis, Proteus mirabilis and Staphylococcus aureus. Screening assays were carried out using agar-diffusion technique, in which 100 μM heterocyclic compounds solutions (20percent dimethylsulfoxide/water) were employed. The minimum inhibitory concentrations (MIC) of the active compounds were determined by serial dilutions at decreasing concentrations in microtiter plates. The nitrated derivatives gave the best test results, where MIC = 60 μM (E. coli) was the lowest value found for an ortho-nitrated derivative. The activity of these compounds possibly involves a mechanism via free radicals. S. aureus and P. aeruginosa were resistant to all compounds.
- Cunha, Felipe S.,Nogueira, Joseli M. R.,De Aguiar, Alcino P.
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p. 2405 - 2416
(2018/10/20)
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- Synthesis, carbonic anhydrase inhibitory activity and antioxidant activity of some 1,3-oxazine derivatives
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(Table presented.). A series of 1-(6-methyl-2-substituted phenyl-4-thioxo-4H-1,3-oxazin-5-yl)ethanones (3a-n) were synthesized by the reaction of benzoyl isothiocyanates with active methylene compound acetylacetone in the presence of triethyl amine in a one-pot process. The structures of the products were elucidated by elemental analyses, FT-IR, 1H NMR, 13C NMR, and mass spectroscopy. These new 1,3-oxazine derivatives were evaluated for their inhibitory activity against carbonic anhydrase II. Results for in vitro assay revealed that compound 3b having 4-methoxy phenyl moiety was the most potent inhibitor with IC50 value of 0.144 ± 0.008 μM. It exhibited higher enzyme inhibitory activity as compared to the standard acetazolamide (IC50 = 0.997 ± 0.061 μM). The compounds 3c, 3h, and 3n also displayed superior inhibitory activities compared to the rest of the synthesized oxazine derivatives. The radical scavenging activity of oxazine derivatives was also performed and it was found that compounds showed moderate antioxidant activity. Lipinski rule confirmed the therapeutic potential of the synthesized compounds. Molecular docking studies were also performed to further understand the binding affinity of these compounds with PDBID 1V9E which confirmed that the synthesized derivatives bind in the active binding site of the target protein. Based upon our results, it is proposed that compound 3b may serve as a lead structure to design more potent carbonic anhydrase inhibitors.
- Qamar, Rabia,Saeed, Aamer,Saeed, Maria,Ashraf, Zaman,Abbas, Qamar,Hassan, Mubashir,Albericio, Fernando
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p. 352 - 361
(2018/10/20)
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- MONOMER, POLYMER, COMPENSATION FILM, OPTICAL FILM, AND DISPLAY DEVICE
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A monomer represented by Chemical Formula 1-1 wherein in Chemical Formula 1-1, Z, L1, L2, R1 to R6, n, m, p, and a to f are the same as defined in the detailed description.
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Paragraph 0257; 0258
(2017/03/21)
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- Design and synthesis of antimicrobial active new molecular entities of N-substituted pipradol derivatives
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Synthesis of antimicrobial 4-(hydroxyldiphenyl methyl)piperidin-1-yl)(substituted phenyl)methanone derivatives by using conventional chemical reactions to produces feasible and entirely new chemical entities (NCE’S) which were having a great potential microbial activities equivalent to fexofenidine used as a biological standard. This invention may help full for derive more potential pipradol molecules with peptide bond linkage.
- Sri Ramudu,Ramachandran,Venkat Rao,Murali Krishna,Satya Narayana,Reddy, Kallam Naveen
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p. 2113 - 2115
(2017/10/06)
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- Synthesis, characterization, and anti-inflammatory activities of methyl salicylate derivatives bearing piperazine moiety
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In this study, a new series of 16 methyl salicylate derivatives bearing a piperazine moiety were synthesized and characterized. The in vivo anti-inflammatory activities of target compounds were investigated against xylol-induced ear edema and carrageenan-induced paw edema in mice. The results showed that all synthesized compounds exhibited potent anti-inflammatory activities. Especially, the anti-inflammatory activities of compounds M15 and M16 were higher than that of aspirin and even equal to that of indomethacin at the same dose. In addition, the in vitro cytotoxicity activities and anti-inflammatory activities of four target compounds were performed in RAW264.7 macrophages, and compound M16 was found to significantly inhibit the release of lipopolysaccharide (LPS)-induced interleukin (IL)-6 and tumor necrosis factor (TNF)-α in a dose-dependent manner. In addition, compound M16 was found to attenuate LPS induced cyclooxygenase (COX)-2 up-regulation. The current preliminary study may provide information for the development of new and safe anti-inflammatory agents.
- Li, Jingfen,Yin, Yong,Wang, Lisheng,Liang, Pengyun,Li, Menghua,Liu, Xu,Wu, Lichuan,Yang, Hua
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- Design, synthesis and evaluation of rhodanine derivatives as aldose reductase inhibitors
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Aldose reductase (ALR) enzyme plays a significant role in conversion of excess amount of glucose into sorbitol in diabetic condition, inhibitors of which decrease the secondary complication of diabetes mellitus. To understand the structural interaction of inhibitors with ALR enzyme and develop more effective ALR inhibitors, a series of substituted 5-phenylbenzoate containing N-substituted rhodanine derivatives were synthesized and evaluated for their in vitro ALR inhibitory activity. Docking studies of these compounds were carried out, which revealed that the 5-phenylbenzoate moiety deeply influenced the key π-π stacking while 4-oxo-2-thioxothiazolidines contributed in hydrogen bond interactions. The phenyl ring of benzylidene system occupied in specific pocket constituted from Phe115, Phe122, Leu300 and Cys303 while the rhodanine ring forms a tight net of hydrogen bond with Val47 at anionic binding site of the enzyme. The structural insights obtained from the docking study gave better understanding of rhodanine and macromolecular interaction and will help us in further designing and improving of ALR inhibitory activity of rhodanine analogs. Series of substituted 5-phenylbenzoate rhodanine analogs were synthesized and evaluated for their ALR inhibitory activity. The docking study of synthesized compounds was carried out, which revealed that the 5-phenylbenzoate moiety deeply influenced the key π-π stacking while 4-oxo-2-thioxothiazolidines contributed in hydrogen bond interactions.
- Agrawal, Yogesh P.,Agrawal, Mona Y.,Gupta, Arun K.
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p. 172 - 180
(2015/01/30)
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- An efficient synthesis of conjugated 5-aryl-1,3,4-oxadiazoles from 3-heteroarylacrylohydrazides and acid chlorides
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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
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supporting information
p. 3252 - 3254
(2014/06/09)
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- Synthesis and biological evaluation of substituted N-alkylphenyl-3,5- dinitrobenzamide analogs as anti-TB agents
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Here, a medicinal chemistry study of an N-alkylphenyl-3,5-dinitrobenzamide (DNB) scaffold as a potent anti-TB agent is presented. A series of chemical modifications were performed and forty-three new molecules were synthesized to study the structure-activity relationship (SAR) by evaluating against a sensitive strain (H37Rv) of Mycobacterium tuberculosis (MTB). Potent DNB analogs 4b, 7a, 7c, 7d, 7j, 7r and 9a were further tested against resistant strains of MTB. Their intracellular as well as bactericidal potential was also evaluated. Cytotoxicity and in vivo pharmacokinetic studies suggested that DNB analogs have an acceptable safety index, in vivo stability and bio-availability. From the present work, two compounds 7a and 7d have shown nanomolar to sub micro-molar MIC in extracellular and intracellular assays.
- Munagala, Gurunadham,Yempalla, Kushalava Reddy,Aithagani, Sravan Kumar,Kalia, Nitin Pal,Ali, Furqan,Ali, Intzar,Rajput, Vikrant Singh,Rani, Chitra,Chib, Reena,Mehra, Rukmankesh,Nargotra, Ami,Khan, Inshad Ali,Vishwakarma, Ram A.,Singh, Parvinder Pal
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p. 521 - 527
(2014/04/17)
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- Development of 3,5-dinitrobenzoate-based 5-lipoxygenase inhibitors
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Human 5-lipoxygenase (5-LOX) is a well-validated target for anti-inflammatory therapy. Development of novel 5-LOX inhibitors with higher activities is highly demanded. In previous study, we have built a model for the active conformation of human 5-LOX, and identified naphthalen-1-yl 3,5-dinitrobenzoate (JMC-4) as a 5-LOX inhibitor by virtual screening. In the present work, 3,5-dinitrobenzoate-based 5-lipoxygenase inhibitors were developed. Twenty aryl 3,5-dinitrobenzoates, N-aryl 3,5-dinitrobenzamides and analogues were designed and synthesized. Several of them were found with significantly increased activities according to cell-free assay and human whole blood assay. The structure-activity relationship study may provide useful insights for designing effective 5-LOX inhibitors.
- Shang, Erchang,Liu, Ying,Wu, Yiran,Zhu, Wei,He, Chong,Lai, Luhua
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p. 2396 - 2402
(2014/05/06)
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- Design and syntheses of anti-tuberculosis agents inspired by BTZ043 using a scaffold simplification strategy
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Tuberculosis (TB), a disease caused by Mycobacterium tuberculosis (Mtb), is a global public health concern because of the emergence of various resistant strains. Benzothiazin-4-ones (BTZs), represented by BTZ043, are a promising new class of agents for the treatment of tuberculosis and have been shown to kill Mtb in vitro, ex vivo, and in mouse models of TB. Herein we report the design and syntheses of nitroaromatic sulfonamide, reverse-amide, and ester classes of anti-TB agents using a scaffold simplification strategy based on BTZ043. The presented work explores the effect of functional groups such as sulfonamides, reverse-amides, and esters that are attached to the nitroaromatic rings on their anti-TB activity. The in vitro activity of the compounds evaluated against the H37Rv strain of Mtb show that nitroaromatic sulfonamides and nitrobenzoic acid esters with two nitro substituents were most active and highlights the importance of the electronic character (electron deficient aromatic ring) of the nitroaromatic ring as a central theme in these types of nitroaromatic anti-TB agents.
- Tiwari, Rohit,M?llmann, Ute,Cho, Sanghyun,Franzblau, Scott G.,Miller, Patricia A.,Miller, Marvin J.
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supporting information
p. 587 - 591
(2014/06/09)
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- Synthesis and evaluation of some substituted heterocyclic fluconazole analogues as antifungal agents
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A new series of fluconazole analogues of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4- difluoro-phenyl)-3-4-(substituted-heterocyclic ring-1H-1,2,3- triazol-1-yl)-2-propanols (1-10) were designed, synthesized and evaluated as antifungal agents. Preliminary antifungal tests showed that most of the title compounds exhibited moderate activity with broad spectrum against eight human pathogenic fungi in vitro, compounds 1 and 6 had the best antifungal activity against Candida albicans with the value of MIC80 = 0.5 μg/mL respectively.
- Wang, Shudong,Zhang, Lei,Jin, Yongsheng,Tang, Jin Hao,Su, Hua,Yu, Shichong,Ren, Haixiang
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p. 2362 - 2364
(2014/06/09)
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- Synthesis, antimycobacterial, antiviral, antimicrobial activity and QSAR studies of N2-acyl isonicotinic acid hydrazide derivatives
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A series of N2-acyl isonicotinic acid hydrazides (1-17) was synthesized and tested for its in vitro antimycobacterial activity against Mycobacterium tuberculosis and the results indicated that the compound, isonicotinic acid N′- tetradecanoyl-hydrazide (12) was more active than the reference compound isoniazid. The results of antimicrobial activity of the synthesized compounds against S. aureus, B. subtilis, E. coli, C. albicans and A. niger indicated that compounds with dichloro, hydroxyl, tri-iodo and N 2 -tetradecanoyl substituent were the most active ones. The antiviral activity studies depicted that none of the tested compounds were active against DNA or RNA viruses. The multi-target QSAR model was found to be effective in describing the antimicrobial activity of N2-acyl isonicotinic acid hydrazides.
- Judge, Vikramjeet,Narasimhan, Balasubramanian,Ahuja, Munish,Sriram, Dharmarajan,Yogeeswari, Perumal,De Clercq, Erik,Pannecouque, Christophe,Balzarini, Jan
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- Aromatic oligoamide macrocycles with a backbone of reduced constraint
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Oligoamide macrocycles with a backbone partially constrained by hydrogen bonds have been prepared. These macrocycles, carrying multiple H-bonding side chains, underwent strong aggregation in solution and form long fibers in the solid state. In contrast to the strong and specific complexation of the guanidinium ion by analogous macrocycles with fully H-bond-constrained backbones, these macrocycles failed to recognize the same cation, indicating that reducing backbone constraint has led to a drastic change in their cavity.
- Kline, Mark,Wei, Xiaoxi,Gong, Bing
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supporting information
p. 4762 - 4765
(2013/10/08)
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- Synthesis of highly substituted symmetrical 1,3-dienes via organocuprate oxidation
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Oxidation of alkenyl organocuprates formed from alkenyl halides allows the formation of highly substituted symmetrical 1,3-dienes. Cuprates formed from organolithiums and Grignard reagents can be tolerated and the reaction proceeds with retention of alkenyl geometry. Georg Thieme Verlag Stuttgart New York.
- Aves, Sarah. J.,O'Connell, Kieron M. G.,Pike, Kurt G.,Spring, David R.
-
supporting information; experimental part
p. 298 - 300
(2012/03/10)
-
- One-pot formation of aromatic tetraurea macrocycles
-
Treating derivatives of m-phenylenediamine having different electron-richness and reactivities with triphosgene in the presence of triethylamine led to aromatic tetraurea macrocycles in high yields. Factors important for efficiently forming these macrocycles include the molar ratio (2:1) between the diamine and triphosgene, reaction temperature (-75 °C), and solvent (CH2Cl2). By controlling the order and rate for adding diamines, tetraurea macrocycles consisting of two different types of monomeric residues have also been obtained in high yields.
- Wu, Zehui,Hu, Ting,He, Lan,Gong, Bing
-
supporting information; experimental part
p. 2504 - 2507
(2012/07/13)
-
- Supramolecular graft copolymers in moderately polar media based on hydrogen-bonded aromatic oligoamide units
-
By exploiting hetero-complementary aromatic oligoamide units containing hextuple hydrogen bonds, supramolecular graft copolymers were successfully constructed in moderately polar media.
- Pan, Xusong,Chen, Chao,Peng, Jiang,Yang, Yongan,Wang, Yinghan,Feng, Wen,Deng, Pengchi,Yuan, Lihua
-
supporting information
p. 9510 - 9512
(2012/11/06)
-
- Synthesis and bioactivity of N-tert-butyl-N′-acyl-5-methyl-1,2,3- thiadiazole-4-carbohydrazides
-
A series of novel N-tert-butyl-N′-acyl-5-methyl-1,2,3-thiadiazole-4- carbohydrazides were designed and synthesized. Their structures were characterized by melting points, 1H NMR, IR, ESI-MS, and elemental analysis. The bioassay tests indicated that compound 7o exhibited excellent direct anti-TMV activity and induction activity in vivo at 50 μg/mL, which was better than that of Ninamycin and tiadinial. Our studies indicated that 1,2,3-thiadiazole was an active substructure for novel pesticide development.
- Mao, Wu Tao,Zhao, Hui,Fan, Zhi Jin,Ji, Xiao Tian,Hua, Xue Wen,Kalinina, Tatiana,Yury, Yu. Morzherin,Vasiliy, A. Bakulev
-
p. 1233 - 1236,4
(2020/10/15)
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- Alternative strategy for adjusting the association specificity of hydrogen-bonded duplexes
-
A strategy for creating new association specificity of hydrogen-bonded duplexes by varying the spacings between neighboring hydrogen bonds is described. Incorporation of naphthalene-based residues has provided oligoamide strands that pair into duplexes sharing the same H-bonding sequences (e.g., DDAA) but differing in the spacings between their intermolecular hydrogen bonds, leading to homo- or heteroduplexes. The ability to manipulate association-specificity as demonstrated by this work may be extended to other multiple hydrogen bonded systems, thereby further enhancing the diversity of multiple hydrogen-bonded association units for constructing supramolecular structures.
- Zhang, Penghui,Chu, Hongzhu,Li, Xianghui,Feng, Wen,Deng, Pengchi,Yuan, Lihua,Gong, Bing
-
supporting information; experimental part
p. 54 - 57
(2011/03/19)
-
- X-ray, DFT, FTIR and NMR structural study of 2,3-dihydro-2-(R- phenylacylidene)-1,3,3-trimethyl-1H-indole
-
Fischer base derivatives are widely used as precursor in the formation of different chemical switches. Besides, in the presence of acyl chlorides, indole enaminoketone derivatives can be prepared. 2,3-Dihydro-2-(R-phenylacylidene)-1, 3,3-trimethyl-1H-indole, R = 4-NO2, 3,5-(NO2)2 and 4-OCH3, have been characterized previously but only by 1H NMR, thus further characterization was performed by FTIR, 13C NMR and when suitable crystals were obtained by single crystal X-ray diffraction analyses. The structures of the three molecules were additionally analyzed by DFT methods, B3LYP and PW91 functionals, using 6-311G(d,p) basis set. The optimized structures obtained were compared with those determined by crystallographic data. The probable assignments of the anharmonic experimental solid state vibrational frequencies for these molecules have been also made based on the calculated harmonic frequencies in vacuum at the same level of theory for the optimized structures. Correlations between experimental chemical shifts and GIAO calculated magnetic isotropic shielding constants with B3LYP and PW91 functionals using the 6-311++G(3df,3pd) basis set are also reported.
- Vázquez-Vuelvas, Oscar F.,Hernández-Madrigal, Julia V.,Gavi?o, Rubén,Tlenkopatchev, Mikhail A.,Morales-Morales, David,Germán-Acacio, Juan M.,Gomez-Sandoval, Zeferino,Garcias-Morales, Cesar,Ariza-Castolo, Armando,Pineda-Contreras, Armando
-
experimental part
p. 106 - 118
(2011/04/15)
-
- Novel water-soluble red-emitting poly(p -phenylenevinylene) derivative: Synthesis, characterization, and fluorescent acetylcholinesterase assays
-
A new cyano-substituted poly(p-phenylenevinylene) (PPV) derivative, MEOPS-CNPPV, is synthesized through Knoevenagel condensation of anionic diacetonitrile and neutral dialdehyde and characterized by 1H NMR, IR, elemental analysis, and gel-permeation chromatography (GPC). To our knowledge, the polymer is the first water-soluble red-emitting PPV derivative. The absorption and emission wavelength of this water-soluble conjugated polymer (CP) depend on the solvent. In buffer solution, the fluorescence of MEOPS-CNPPV is quenched by cationic dinitrobenzene derivatives. Further research indicates that dinitrobenzene derivative with a more flexible structure exhibits a larger Ksv. Making use of the charge reversal of dinitrobenzene-modified substrate, a "turn-on" method is developed for AChE activity assay with the new polymer as a fluorophore. This convenient and direct fluorometric assay thus provides a platform for novel red-emitting sensory systems.
- Zhang, Wenjun,Zhu, Linna,Qin, Jingui,Yang, Chuluo
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experimental part
p. 12059 - 12064
(2011/12/05)
-
- Design, synthesis, and spectral parameters of transition metal coordination compounds based on organic autocomplexes
-
Organic autocomplexes prepared from 3,5-dinitrobenzoyl chloride and some heterocyclic amines were used to synthesize a series of new coordination compounds with 3d transition metals. The new metal complexes displayed in the electronic absorption spectra charge-transfer bands typical of the initial ligands and an additional long-wave maximum in the region λ 500-625 nm. Pleiades Publishing, Ltd., 2011.
- Il'ina,Mikhalev
-
experimental part
p. 1515 - 1520
(2012/03/11)
-
- Single-pot conversion of an acid to the corresponding 4-chlorobutyl ester
-
A single pot conversion of carboxylic acids into the corresponding 4-chlorobutyl esters has been achieved by a novel procedure. The intermediate acid chlorides are not isolated. The double bond and aromatic methoxy group survive the mild reaction conditions. In almost all the examples studied the products are purified by simple flash chromatography.
- Pal, Sutanuka,Pal, Sudhir Chandra
-
experimental part
p. 596 - 599
(2012/04/18)
-
- Synthesis and thermally stable helix-dimer formation of amidohelicene oligomers
-
Optically active amidohelicene monomer to nonamer were synthesized in high yields by a two-directional method. The CD spectra in chloroform exhibited a large difference between dimer and the higher homologs, and vapor pressure osmometry studies revealed the formation of dimeric aggregates for the latter. It is noted that amidohelicene oligomers possessing two-atom linking groups between helicene and m-phenylene spacer formed helix-dimers in solution as were ethynylhelicene oligomers. The helix-dimer of the amidohelicene octamer in chloroform was very stable, and did not dissociate at 5 × 10-8M on heating to 60 °C. The dissociation of the amidohelicene oligomers to random-coil state took place in hydrogen-bonding breaking solvents, DMSO or THF. The equilibrium between helix-dimer and random-coil changed by varying the ratio in the mixed solvents of chloroform and DMSO. Notably, the equilibriums were not affected by temperature for various mixtures of helix-dimer and random-coil. Thus, the sensitivity toward the environment was quite different between the amido- and ethynylhelicene oligomers.
- Amemiya, Ryo,Ichinose, Wataru,Yamaguchi, Masahiko
-
supporting information; experimental part
p. 809 - 815
(2010/09/06)
-
- Synthesis and biological evaluation of some substituted amino thiazole derivatives
-
Condensation of acetophenone with thiourea in presence of halogen (Iodine) gives 2-amino-4-phenylthiazole (I). 2-Amino-4-phenyl-5-phenylazothizole (II) was prepared by coupling of phenyldiazonium chloride with 2-amino-4-phenylthiazole (I). A series of amide can be synthesized by treatment of appropriate substituted acid chlorides (III) with compound (II) using pyridine as solvent. All the synthesized compounds are characterized by the combination of elemental analysis and standard spectroscopic method. They are screened for anti-bacterial activity against Escherichia coli and Staphylococcus aureus as well as screened for antifungal activity against Aspergillus niger and Apergillus oryzae by cup plate method at 1μg/mL concentration in DMF. All the synthesized compounds showed moderate to good microbial activity.
- Prajapati,Modi, Vishal P.
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experimental part
p. 240 - 243
(2010/11/05)
-
- Synthesis and pharmacological evaluation of novel 1-(2-(benzoyl- substituted-2-phenyl-1h-indol-5-carbony) hydrazinyloxy) vinyl nitrate derivatives as potent non-ulcerogenic, analgesic and anti-inflammatory agents
-
Six derivatives of 1-(2-(benzoyl-(substituted)-2-phenyl-1H-indole-5- carbony) hydrazinyloxy) vinyl nitrate were synthesized and tested in vivo for anti-inflammatory, analgesic, and ulcerogenic properties. Synthesized compounds shown significant anti-inflammatory activity comparable to that of Diclofenac sodium in the carrageenan-induced rat paw edema test and all of the compounds were found to be equipotent to Diclofenac sodium in the acetic acid induced writhing analgesic model. Out of six derivatives two derivatives found to produce no ulceration in stomach specimen of rats; nitric oxide seems to contribute to their excellent safety profile which supports several endogenous GIT defense mechanisms, including increase in mucus, bicarbonate secretions, increase in mucosal blood flow, and inhibition of the activation of pro-inflammatory cells by which NO-Indomethacin protects GI mucosa.
- Mokale, Vinod J.,Raut, Mayuresh K.,Burange, Prashant J.,Dhoot, Navneet S.,Bhandari, Shashikant V.,Bothara, Kailash G.,Naik, Jitendra B.
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experimental part
p. 211 - 218
(2011/09/13)
-
- Novel synthesis and characterization of some new-2-(R) phenyl- 4-(-4-bromo-2-fluoro benzylidene)-oxazol-5-ones
-
In the present study a series of some new 2-(substituted) phenyl- 4-(4-bromo-2-fluoro benz-ylidene)-oxazol-5-ones (2a-2j) were synthesized by the condensation of selected substituted benzoyl glycine (1a-1j) with 4-bromo-2-fluoro benzaldehyde in the presence of fused sodium acetate and acetic anhydride. The constitution of the newly synthesized compounds has been supported by their physical properties, elemental analysis, colour, m.p, IR spectral analysis data.
- Pareek, Alok K.,Joseph,Seth, Daya S.
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experimental part
p. 1533 - 1536
(2011/10/12)
-
- Hansch analysis of substituted benzoic acid benzylidene/furan-2-yl-methylene hydrazides as antimicrobial agents
-
A series of substituted hydrazide derivatives have been synthesized and screened for their in vitro antimicrobial activities against five representative microorganisms. The results of antimicrobial study indicated that the presence of electron withdrawing groups on the benzoic acid moiety improved antimicrobial activity. Further, the presence of heterocyclic ring furan does not improve the antimicrobial activity of substituted hydrazides. To understand the relationship between physicochemical parameters and antimicrobial activity of substituted hydrazide derivatives, QSAR investigation was performed by the development of one-target and multi-target models. The multi-target model was found to be effective in describing the antimicrobial activity of substituted hydrazides in comparison to the one-target models. Further, it indicated the importance of the topological parameter, valence third order molecular connectivity index (3χv) and the electronic parameter, energy of highest occupied molecular orbital (HOMO) in describing the antimicrobial activity of substituted hydrazides.
- Kumar, Pradeep,Narasimhan, Balasubramanian,Sharma, Deepika,Judge, Vikramjeet,Narang, Rakesh
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experimental part
p. 1853 - 1863
(2009/09/30)
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- Novel 3-phenylpropane-1,2-diamine derivates as inhibitors of aminopeptidase N (APN)
-
Aminopeptidase N (APN) is an essential peptidase involved in the process of tumor invasion and metastasis. Here we describe a novel class of inhibitor with 3-phenylpropane-1,2-diamine as scaffold to APN. Preliminary activity evaluation with enzyme inhibition studies showed that compound 12i exhibited potent and selective inhibitory activity towards APN with the IC50 value 15.5 ± 1.2 μM.
- Shang, Luqing,Wang, Qiang,Fang, Hao,Mu, Jiajia,Wang, Xuejian,Yuan, Yumei,Wang, Binghe,Xu, Wenfang
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scheme or table
p. 9984 - 9990
(2009/04/06)
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- 2,6-Dimethyl-4-nitrobenzoic anhydride (DMNBA): An effective coupling reagent for the synthesis of carboxylic esters and lactones
-
Various carboxylic esters are obtained at room temperature in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2,6-dimethyl-4-nitrobenzoic anhydride with triethylamine by the promotion of 4-(dimethylamino)pyridine. The efficiency of the esterification is compared to those of other dehydrations using substituted benzoic anhydrides as coupling reagents. This method was successfully applied to the synthesis of threo-aleuritic acid lactone and the desired 17-membered ring compound was prepared in high yield at room temperature from the corresponding free trihydroxycarboxylic acid using 2,6-dimethyl-4-nitrobenzoic anhydride in the presence of 4-(dimethylamino)pyridine.
- Shiina, Isamu,Miyao, Ryo
-
experimental part
p. 1313 - 1328
(2009/07/05)
-
- Hydrogen-bonded framework structures in 4-[(4-chloro-3-nitrobenzoyl)- hydrazinocarbonyl]pyridinium chloride and N-3,5-dinitrobenzoyl-N′- isonicotinoylhydrazine
-
In 4-[(4-chloro-3-nitrobenzoyl)hydrazinocarbonyl]pyridinium chloride, C13H10ClN4O4 -·Cl-, the component ions are linked into a three-dimensional framework structure by a combination of three N-H...Cl and five C-H...O hydrogen bonds. In N-3,5-dinitrobenzoyl-N′- isonicotinoylhydrazine, C13H9-N5O6, the molecules are linked into a three-dimensional framework structure by one N-H...O and three C-H...O hydrogen bonds, augmented by an aromatic π-π stacking interaction.
- Vasconcelos, Thatyana R. A.,De Souza, Marcus V. N.,Wardell, Solange M. S. V.,Wardell, James L.,Low, John N.,Glidewell, Christopher
-
p. o222-o226
(2007/10/03)
-
- New esters of vanillin and vanillal with some alkane- and arenecarboxylic acids
-
Previously unknown esters were synthesized by the reaction of vanillin and vanillal with carboxylic acid chlorides. Pleiades Publishing, Inc., 2006.
- Dikusar
-
p. 1035 - 1037
(2008/02/05)
-
- Synthesis of esters of D, L-, D(+)-, and L(-)-camphor oximes: Structure-odor correlation
-
Esters of D,L-, D(+)-, and L(-)-camphor oximes were synthesized, and the correlation between their structure and odor was examined.
- Dikusar,Zhukovskaya,Vyglazov
-
p. 1982 - 1985
(2008/02/08)
-
- Synthesis and antibacterial activity of some N-(3-hydroxy-2-pyridyl) benzamides
-
N-(3-Hydroxy-2-pyridyl)benzamides 3(a-J) were synthesized under weak basic solution by reacting of 2-amino-3-pyridinol and an appropriate carboxylic acid chloride, obtained by reaction of carboxylic acids with thionyl chloride. The microbiological activity of these compounds was tested in vitro against Escherichia Coil (PTCC 1338), Pseudomonas aeruginosa (PTCC 1074), Entrococcus faecalis (PTCC 1237) and Staphylococcus aureus (PTCC 1119) bacteria. Compounds 3a, 3e and 3f were the active benzamide derivatives against the Ef and Sa bacteria with a MIC value of 128 μg/ml. Compound 3g was the active entry against Ec and Pa bacteria with a MIC value of 128 μg/.
- Mobinikhaledi,Forughifar,Shariatzadeh,Fallah
-
p. 427 - 430
(2008/02/12)
-
- Synthesis of arylketones using Envirocat EPZG catalyst
-
The Friedel-Crafts acylation reactions of substituted benzene derivatives with substituted acid chlorides proceed smoothly in the presence of a catalytic amount of Envirocat EPZG, a novel supported reagent catalyst, based on montmorillonite K10 clay. This catalyst is eco-friendly, selective and reusable and hence provides a safer and a cost effective approach for large-scale production in industries. The present work involves synthesis of fifteen ketones by using fresh and reused Envirocat EPZG catalyst and a conventional catalyst for Friedel-Crafts reaction, anhyd. AlCl3. The yields of ketones with fresh Envirocat EPZG are always more than that obtained with anhyd. AlCl3. Envirocat EPZG has been reused for the number of reactions in a series, without much loss in its efficiency. Ketones having activating as well as deactivating groups on benzene ring have been synthesized in satisfactory yields.
- Ghatpande, Sonali,Mahajan, Supriya
-
p. 188 - 192
(2007/10/03)
-
- Determining the σ-donor ability of the cyclopropane C-C bond
-
The low temperature crystal structures of ester and ether derivatives of varying electron demand, derived from cyclopropylmethanol 8 and dicyclopropylmethanol 9, have been determined. These structures show a very strong response of the C-OR bond distance to the electron demand of the OR substituent, demonstrating the strong σ-donor ability of the strained C-C bonds in the cyclopropane ring. The Royal Society of Chemistry 2005.
- Fifer, Nathan L.,White, Jonathan M.
-
p. 1776 - 1780
(2007/10/03)
-
- Synthesis of medium-ring and iodinated biaryl compounds by organocuprate oxidation
-
(Chemical Equation Presented) A biaryl banquet! Biphenyls with four ortho substituents, heteroaromatic compounds, iodinated biaryls, and medium rings containing biaryls are all readily synthesized by organocuprate oxidation. The utility of this new methodology is illustrated by the efficient synthesis of the medium-ring core of sanguiin H-5 (see scheme).
- Surry, David S.,Su, Xianbin,Fox, David J.,Franckevicius, Vilius,Macdonald, Simon J. F.,Spring, David R.
-
p. 1870 - 1873
(2007/10/03)
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