- Novel chemoselective reduction of aryldiazonium fluoroborates with Zn- NiCl2·6H2O-THF
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Substituted aryldiazonium fluoroborates are selectively reduced to the corresponding phenylhydrazines by using Zn-NiCl2·6H2O in THF as a reducing agent.
- Bandgar,Uppalla
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- Tuned structure and DNA binding properties of metal complexes based on a new 4-acylpyrazolone derivative
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It is common knowledge that the spatial structure of substrates is the major influencing factor in DNA binding. To tune the binding affinity of DNA, a new 4-acylpyrazolone derivative ligand, (2-hydroxy-N′-((5-hydroxy-3-methyl-1-(4-nitrophenyl)-4,5-dihydro-1H-pyrazol-4-yl)(phenyl)methylene)benzohydrazide) (H2L) and its three complexes have been prepared and well characterized. Reaction of H2L with CuCl2 resulted in a mononuclear compound with tetra-coordinated quadrilateral plane, [Cu(HL)Cl] (1). When H2L was coordinated to Cu(OAc)2, a dinuclear Cu(ii) compound with chemical formula of [Cu2L2(CH3OH)2]·CH3OH (2) was obtained, and the coordination geometry of Cu(ii) is a square pyramid. Upon assembly of H2L with Mn(OAc)2, a quite different dinuclear compound with chemical composition of [Mn2L2(O CH3)2(H2O)2]·CH3OH (3) was afforded, where Mn(iii) displayed distorted octahedral configurations. DNA binding studies were performed on H2L and its three complexes by means of electron absorption titration and EB-DNA competition experiments, and the results indicate they all bind DNA in an intercalation mode, and their binding affinity follows the order of 1 > 2 > 3 > H2L. In addition, time-dependent density functional theory (TD-DFT) calculations were performed for H2L and its three complexes to better clarify the electronic transitions in the UV-vis spectra.
- Xi, Wei,Song, Fu-Qiang,Xia, Xue-Li,Song, Xue-Qin
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- Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine
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In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.
- Hosseini-Sarvari, Mona,Koohgard, Mehdi
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supporting information
p. 5905 - 5911
(2021/07/12)
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- Amination of Aromatic Halides and Exploration of the Reactivity Sequence of Aromatic Halides
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A base-promoted amination of aromatic halides has been developed using a limited amount of dimethylformamide (DMF) or amine as an amino source. Various aryl halides, including F, Cl, Br, and I, have been successfully aminated in good to excellent yields. Although the amination of aromatic halides with amines or DMF is usually considered as an aromatic nucleophilic substitution (SNAr) process, and the reactivity of an aromatic halide is F > Cl > Br > I, the reactivity of aromatic halides in this system was found to be I > Br a‰ F > Cl. This protocol also showed a good regioselectivity for multihalogenated aromatics. This protocol is valuable for industrial application due to the simplicity of operation, the unrestricted availability of amino sources and aromatic halides, transition metal-free conditions, no requirement for solvent, and scalability.
- Yang, Chu,Zhang, Feng,Deng, Guo-Jun,Gong, Hang
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p. 181 - 190
(2019/01/10)
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- SUBSTITUTED SULFONYL HYDRAZIDES AS INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY
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The present invention relates to substituted sulfonyl hydrazides that have the ability to inhibit lysine biosynthesis via the diaminopimelate pathway in certain organisms. As a result of this activity these compounds can be used in applications where inhibition of lysine biosynthesis is useful applications of this type include the use of the compound as herbicides and/or anti- bacterial agents.
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Paragraph 0202; 0211
(2020/01/24)
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- Oxazolidinones compound and application thereof
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The invention provides an oxazolidinones compound shown as the formula VI, or salt, an aquo-complex, or a crystal form of the oxazolidinones compound, which are pharmaceutically acceptable. The invention also provides a preparation method of the compound. In the current field of a chemical drug, activity of most compounds with changed structures becomes better, while toxicity is obviously enhanced, so that the compounds cannot be used as drugs. Compared with a compound in the prior art, the oxazolidinones compound provided in the invention has excellent anti-drug-resistance and antimicrobial activity. What is unexpected is that the oxazolidinones compound has better safety and benefits safe drug use and therapy of a patient.
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Paragraph 0087;0091-0092
(2016/10/10)
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- Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones
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Opportunistic fungal infections caused by the Candida spp. are the most common human fungal infections, often resulting in severe systemic infections - a significant cause of morbidity and mortality in at-risk populations. Azole antifungals remain the mainstay of antifungal treatment for candidiasis, however development of clinical resistance to azoles by Candida spp. limits the drugs' efficacy and highlights the need for discovery of novel therapeutics. Recently, it has been reported that simple hydrazone derivatives have the capability to potentiate antifungal activities in vitro. Similarly, pyrimidinetrione analogs have long been explored by medicinal chemists as potential therapeutics, with more recent focus being on the potential for pyrimidinetrione antimicrobial activity. In this work, we present the synthesis of a class of novel hydrazone-pyrimidinetrione analogs using novel synthetic procedures. In addition, structure-activity relationship studies focusing on fungal growth inhibition were also performed against two clinically significant fungal pathogens. A number of derivatives, including phenylhydrazones of 5-acylpyrimidinetrione exhibited potent growth inhibition at or below 10 μM with minimal mammalian cell toxicity. In addition, in vitro studies aimed at defining the mechanism of action of the most active analogs provide preliminary evidence that these compound decrease energy production and fungal cell respiration, making this class of analogs promising novel therapies, as they target pathways not targeted by currently available antifungals.
- Neumann, Donna M.,Cammarata, Amy,Backes, Gregory,Palmer, Glen E.,Jursic, Branko S.
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p. 813 - 826
(2014/01/23)
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- Efficient synthesis of aryl hydrazines using copper-catalyzed cross-coupling of aryl halides with hydrazine in PEG-400
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An efficient and convenient method for the synthesis of aryl hydrazines is described via copper-catalyzed cross-coupling of aryl halides with aqueous hydrazine in PEG-400. This protocol is applicable to both electron-deficient and electron-rich aryl iodides and bromides, and even to sterically hindered substrates, giving aryl hydrazines in good to excellent yields.
- Chen, Junmin,Zhang, Yimin,Hao, Wenyan,Zhang, Rongli,Yi, Fei
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p. 613 - 617
(2013/07/25)
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- One-pot synthesis of pyrrolo[3,2-f]-and pyrrolo[2,3-h]quinoline derivatives: Observation of an unexpected mechanistic pathway
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One-pot synthesis of pyrrolo[3,2-f]- and pyrrolo[2,3-h]quinolines were obtained starting from substituted 5-aminoindoles, benzaldehydes, and phenylacetylenes in the presence of La(OTf)3 as a catalyst in good yields. The indole moiety in 5-aminoindole is believed to be mainly responsible for the observation of unexpected mechanistic pathway to the formation of pyrrolo[2,3-h]quinoline. Georg Thieme Verlag Stuttgart · New York.
- Ramesh, Subburethinam,Nagarajan, Rajagopal
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supporting information; scheme or table
p. 717 - 722
(2012/07/03)
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- Synthesis and biological activity of pyrazolidine-3,5-dione substituted benzimidazole derivatives
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Condensation of o-phenylene diamine with chloro acetic acid gave 2-chloromethyl benzimdazole, which undergoes halide replacement with phenylhydrazines to give the corresponding N,N'-disubstituted hydrazines. Later these compounds were treated with diethyl malonate in presence of acetic acid to get the pyrazolidine-3,5-dione substituted benzimidazole derivatives. The synthesized compounds were subjected to microbiological screening and in vitro antiinflammatory activity.
- Tiwari, Abhishek,Tiwari, Varsha,Venkataramana,Madhavan
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experimental part
p. 1179 - 1182
(2012/01/05)
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- Synthesis and biological evaluation of some new aryl pyrazol-3-one derivatives as potential hypoglycemic agents
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Several new aryl substituted pyrazol-3-one 3 derivatives were prepared by the reaction of substituted phenyl hydrazine 1 with diethylethoxymethylene malonate (DEEM) 2. The compounds were synthesized by Michael addition reaction, which is a nucleophilic addition of enolate anions to the carbon-carbon double bond of α,β-unsaturated carboxylic acid derivatives. All the compounds were characterized by UV, IR and NMR spectroscopy and tested for hypoglycemic activity on alloxan induced diabetic rats. Among the tested compounds ethyl-2-para nitrophenyl-2,3-dihydro-1H-pyrazol-3-one-4-carboxylate 3c and ethyl-2-meta nitrophenyl-2,3-dihydro-1H-pyrazol-3-one-4-carboxylate 3d are identified as potent hypoglycemic agents and their activities are comparable with the standard drug metformin.
- Das, Nirupam,Verma, Abhilasha,Shrivastava, Prabhat K.,Shrivastava, Sushant K.
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experimental part
p. 1555 - 1558
(2009/04/07)
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- Selective reduction of aryl diazonium fluoroborates
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Substituted aryl diazonium fluoroborates have been selectively reduced to the corresponding phenylhydrazines by using borohydride exchange resin (BER).
- Bandgar,Thite
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p. 635 - 639
(2007/10/03)
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- Synthesis and adenosine receptor affinity of a series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine
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Pyrazolo[3,4-d]pyrimidines are pyrazolo analogues of purines. They have been shown to be a general class of compounds which exhibit A1 adenosine receptor affinity. Two series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine have been synthesized. The first involved substitution of the N1-position while the second involved substitution of the N5-position. Both alkyl and aryl substituents were examined. All compounds were tested for A1 adenosine receptor affinity by using a (R)-[3H]-N6-(phenylisopropyl)adenosine binding assay. The 3-chlorophenyl group showed the greatest activity in the N1-position and the butyl group produced the greatest activity in the N5-position. Combination of the best substituent in each of these positions enhanced the overall activity. The most potent compound was 4-amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one with an IC50 of 6.4 X 10-6 M. Selectivity at the receptor subclasses was examined by performing an A2 adenosine receptor affinity assay with [3H]CGS 21680. This series of compounds were slightly less potent at A2 receptors. 4-Amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one was the most potent compound with an IC50 of 19.2 X 10-6 M.
- Harden,Quinn,Scammells
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p. 2892 - 2898
(2007/10/02)
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- AN EFFICIENT METHOD FOR THE CONVERSION OF ARYLHYDRAZINES INTO 2-ARYL-4,4-DIALKYLSEMICARBAZIDES
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Arylhydrazines are converted into 2-aryl-4,4-dialkylsemicarbazides by subsequent reaction with chloroformate, phosgene, dialkylamine, and alkaline hydrolysis.
- Pilgram, K. H.
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p. 697 - 706
(2007/10/02)
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- THIOSULFONIC ACIDS. XXXI. ARYLAZOARENETHIOSULFONATES
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Arylazoarenethiosulfonates were obtained, and their structures and chemical characteristics were studied.It was shown that arylazoarenethiosulfonates have a nonionic structure, and this explains their high stability.It was established that they enter with difficulty into reactions with the release of nitrogen, but they enter readily into azo-coupling and reduction reactions.
- Boldyrev, B. G.,Grivnak, L. M.
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p. 324 - 330
(2007/10/02)
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- Antiimplantation Agents: Part I - 1-Arylthiosemicarbazides
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Several 1-arylthiosemicarbazides, 2-arylhydrazinothiazolines and 2-arylhydrazinodihydrothiazines have been examined for their antiimplantation activity in rats.Among the active compounds, 4-methyl-1-(3,5-bistrifluoromethylphenyl)thiosemicarbazide (3, C 2696-Go) and the corresponding 4,4-dimethyl (47), ethyl (4), n-butyl (5) and allyl (6) derivatives completely inhibit implantation at doses 10, 3, 20, 20 and 30 mg/kg respectively.The 3,4-dichlorophenyl analogue (32) is effective at a dose of 30 mg/kg. 2-(3,5-Bistrifluoromethylphenyl)hydrazinothiazoline (51) and the corresponding dihydrothiazine (63) show a weaker activity.The biological profile of C 2696-Go has been investigated in detail.It appears to prevent implantation by its antiuterotropic activity and ability to inhibit desiduoma formation.
- Nagarajan, K.,Talwalker, P.K.,Kulkarni, C.L.,Venkateswarlu, A.,Prabhu, S.S.,Nayak, G.V.
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p. 1243 - 1257
(2007/10/02)
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- Phenyl-1,2,3,4-tetrahydrocarbazoles and use thereof
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This application relates to phenyl-substituted 1,2,3,4-tetrahydrocarbazoles and to their use as anti-depressant agents useful in the treatment of mental depression of either endogenous or reactive nature.
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