112656-95-8Relevant academic research and scientific papers
Structural studies with antimicrobial and antifertility activity of a monofunctional bidentate ligand with its boron(III), palladium(II), and platinum(II) complexes
Singh,Biyala
, p. 1477 - 1491 (2006)
The reaction of the sulfur donor Schiff base ligand, 7-nitro-3-(indolin-2- one) hydrazinecarbo-thioamide, with phenyldihydroxyboron in benzene, palladium(II)chloride, and platinum(II) chloride, in ethanol, gave the mononuclear tetracoordinated and hexacoordinated complexes. The Schiff base ligand coordinated to the boron atom in 1:1 and 1:2 molar ratios and to the palladium and platinum metals in only 1:2 molar ratios in the presence of an acidic and basic medium. Tentative structural conclusions are drawn for reaction products based upon elemental analysis, electrical conductance, and spectral (electronic, infrared, 1H NMR, 13C NMR, and 11B NMR) data. The antifertility activity of the ligand and its nonmetal/metal complexes is discussed with a comparative study in an effective manner. Copyright Taylor & Francis Group, LLC.
Effect of the piperazine unit and metal-binding site position on the solubility and anti-proliferative activity of ruthenium(II)- and osmium(II)-arene complexes of isomeric indolo[3,2-c ]quinoline - Piperazine hybrids
Filak, Lukas K.,Kalinowski, Danuta S.,Bauer, Theresa J.,Richardson, Des R.,Arion, Vladimir B.
, p. 6934 - 6943 (2014)
In this study, the indoloquinoline backbone and piperazine were combined to prepare indoloquinoline-piperazine hybrids and their ruthenium- and osmium-arene complexes in an effort to generate novel antitumor agents with improved aqueous solubility. In addition, the position of the metal-binding unit was varied, and the effect of these structural alterations on the aqueous solubility and antiproliferative activity of their ruthenium- and osmium-arene complexes was studied. The indoloquinoline-piperazine hybrids L1-3 were prepared in situ and isolated as six ruthenium and osmium complexes [(η6-p-cymene)M(L1-3)Cl]Cl, where L1 = 6-(4-methylpiperazin-1-yl)-N-(pyridin-2-yl-methylene)-11H-indolo[3,2-c] quinolin-2-N-amine, M = Ru ([1a]Cl), Os ([1b]Cl), L2 = 6-(4-methylpiperazin-1-yl)-N-(pyridin-2-yl-methylene)-11H-indolo[3,2-c] quinolin-4-N-amine, M = Ru ([2a]Cl), Os ([2b]Cl), L3 = 6-(4-methylpiperazin-1-yl)-N-(pyridin-2-yl-methylene)-11H-indolo[3,2-c] quinolin-8-N-amine, M = Ru ([3a]Cl), Os ([3b]Cl). The compounds were characterized by elemental analysis, one- and two-dimensional NMR spectroscopy, ESI mass spectrometry, IR and UV-vis spectroscopy, and single-crystal X-ray diffraction. The antiproliferative activity of the isomeric ruthenium and osmium complexes [1a,b]Cl-[3a,b]Cl was examined in vitro and showed the importance of the position of the metal-binding site for their cytotoxicity. Those complexes containing the metal-binding site located at the position 4 of the indoloquinoline scaffold ([2a]Cl and [2b]Cl) demonstrated the most potent antiproliferative activity. The results provide important insight into the structure-activity relationships of ruthenium- and osmium-arene complexes with indoloquinoline-piperazine hybrid ligands. These studies can be further utilized for the design and development of more potent chemotherapeutic agents.
Method for synthesizing 7-nitroindole
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, (2020/03/09)
The invention relates to a method for synthesizing 7-nitroindole. The method comprises the following steps: subjecting oxime generated by condensation of o-nitroaniline, hydroxylamine and chloral to anucleophilic substitution reaction in a solvent under the action of an acidic substance and a drying agent, and performing hydrolyzing under alkaline conditions to generate an oximido intermediate; preparing 7-nitroisatin from the oximido intermediate in the presence of an acidic substance; and subjecting the 7-nitroisatin to reduction in a solvent by a system consisting of sodium borohydride andzirconium chloride so as to obtain the product 7-nitroindole. According to the method for synthesizing the 7-nitroindole, the product is obtained through three steps, so a production cycle is remarkably shortened and productivity is improved; used materials are simple and easily-available, so cost is low; reaction conditions are mild; the method is suitable for industrial mass production; meanwhile, the system of sodium borohydride and zirconium tetrachloride is used for replacing borane in the reduction step, so virulent, flammable and combustible raw materials are avoided, and the method issafer and environmentally friendlier.
Oxindole-based intraocular pressure reducing agents
Zaryanova, Ekaterina V.,Lozinskaya, Nataly A.,Beznos, Olga V.,Volkova, Maria S.,Chesnokova, Nataly B.,Zefirov, Nikolay S.
, p. 3787 - 3793 (2017/07/27)
The study represents the new findings at the crossroads of chemistry and medicine, particularly between medicinal and organic chemistry and ophthalmology. In this work we describe how the chemical reactivity of indolinone scaffold may be used to create small molecule ligands with strong biological response comparable with and larger than that of endogenous hormone. The synthesis of oxindole-based melatonin and 5-methoxycarbonylamino-N-acetyltryptamine (5-MCA-NAT) analogues was proposed and their ability to influence intraocular pressure (IOP) was studied in vivo. Time-dependent study revealed the prolonged effect (more than 6?h) of the lead-compound. This effect in combination with high IOP reducing effect (41?±?6%) in low concentrations of the active compound (0.1?wt%) and with high water solubility represents a great potential of low-cost oxindole derivatives as potent antiglaucoma agents.
Catalytic formation of ketones from unactivated esters through rhodium chelation-assisted C-O bond activation
Wang, Jingjing,Zuo, Sujing,Chen, Weiqiang,Zhang, Xinrui,Tan, Kaixin,Tian, Yun,Wang, Jianhui
, p. 8217 - 8231 (2013/09/24)
A new method for building aryl aryl ketones containing heterocyclic rings through chelation-assisted C-O bond activation catalyzed by a rhodium complex has been developed. In this reaction, methyl quinoline-8-carboxylate, methyl quinoxaline-5-carboxylate, and their derivatives were reacted with an excess amount of a substituted phenyl boronic acid in the presence of a rhodium(I) complex to give substituted phenyl(quinolin-8-yl)methanone, phenylquinoxalin-5- ylmethanone, and their derivatives in medium to high yields. The current method offers a highly favorable synthetic pathway to efficiently build related drugs with an 8-benzoylquinoline core structure. This method may prove especially valuable for medicinal chemists for the late-stage introduction of versatile ketone moieties into complex scaffolds for diversity-oriented synthetic strategies.
DIHYDROOROTATE DEHYDROGENASE INHIBITORS
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Page/Page column 61-62, (2010/11/03)
The invention relates to compounds of formula (I) wherein R1, R2, X1, X2, Y, Ra, Rb, Q have the meanings given in claim 1. The compounds are useful e.g. in the treatment of autoimmune disorders, such as multiple sclerosis and also in the treatment of cancer disorders.
Use of pyridinium chlorochromate and reusable polyaniline salt catalyst combination for the oxidation of indoles
Kumar, Chebolu Naga Sesha Sai Pavan,Devi, Chebrolu Lavanya,Rao, Vaidya Jayathirtha,Palaniappan, Srinivasan
scheme or table, p. 2023 - 2027 (2009/04/07)
A novel method is described herein for the simple, convenient and efficient oxidation of indoles to isatins using pyridinium chlorochromate with the aid of polyaniline salt catalyst at room temperature or at reflux in dichloroethane. Interestingly, oxidation of 3-alkyl indoles by this procedure gave 3-hydroxy 3-alkyl oxindoles. On the other hand, indol-3-alkanols gave mixtures of isatins and 3-formyl indoles. This is the first example of use of polyaniline as a catalyst in oxidation reaction.
