- Imidazolone and imidazolidinone artifacts of a pivotal imidazolthione, zyzzin, from the poecilosclerid sponge Zyzza massalis from the Coral Sea. The first thermochromic systems of marine origin
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Dry acetone extracts of the freeze-dried, deep-red powder of the poecilosclerid sponge Zyzza massalis (Dendy) from the Coral Sea gave the orange alkaloid zyzzin (=4-(1H-indol-3-yl)-1,5-dihydro-5-thioxo-1H-imidazol-2-one; 14), which underwent exchange of the 5-thioxo for the 5-oxo group during aqueous chromatographic workup, giving yellow 13. Both 13 and 14 added hydroxylic solvents at C(4)=N giving colourless, racemic products, 3 and 8, respectively, by incorporation of MeOH and 10 and 11, respectively, by incorporation of H2O. On warming 3 or 10 in DMSO, 13 was recovered, thus furnishing a novel thermochromic system. Optically active (±)-12, which may be viewed to derive from enzymatic reduction of 14 at C(4)=N followed by S→O exchange, was also isolated from this sponge, along with the linear amides 16 and 19. Compound 3 proved to have antibacterial and antifungal activities.
- Mancini,Guella,Debitus,Duhet,Pietra
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- PYRIMIDINE COMPOUND, PREPARATION METHOD THEREOF AND MEDICAL USE THEREOF
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The present invention discloses a pyrimidine compound, a preparation method thereof and a medical use thereof. Specifically, the present invention discloses a pyrimidine compound represented by formula (I), pharmaceutically acceptable salts thereof, a preparation method thereof, and a use thereof as a cyclin-dependent kinase 9 (CDK9) inhibitor, particularly for the treatment of cancer. The definition of each group in formula (I) is the same as that in the specification.
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Paragraph 0359; 0362; 0364
(2021/04/10)
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- Efficient Synthesis and Biological Activity of Novel Indole Derivatives as VEGFR-2 Tyrosine Kinase Inhibitors
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A series of novel indole derivatives were synthesized as potent inhibitors for the vascular endothelial growth factor receptor 2 (VEGFR-2) tyrosine kinase. Among those, compound 10b demonstrated the highest growth inhibition rate of 66.7% against the VEGFR-2 tyrosine kinase at 10 μM which indicates that indole-benzothiazole might be the favorable structure. The binding mode of compound 10b with VEGFR-2 tyrosine kinase was evaluated by molecular docking.
- Zhang,Xu,Wang,Kang
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p. 3006 - 3016
(2018/02/21)
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- Bis(allyl)-ruthenium(IV) complexes with phosphinous acid ligands as catalysts for nitrile hydration reactions
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Several mononuclear ruthenium(iv) complexes with phosphinous acid ligands [RuCl2(η3:η3-C10H16)(PR2OH)] have been synthesized (78-86% yield) by treatment of the dimeric precursor [{RuCl(μ-Cl)(η3:η3-C10H16)}2] (C10H16 = 2,7-dimethylocta-2,6-diene-1,8-diyl) with 2 equivalents of different aromatic, heteroaromatic and aliphatic secondary phosphine oxides R2P(O)H. The compounds [RuCl2(η3:η3-C10H16)(PR2OH)] could also be prepared, in similar yields, by hydrolysis of the P-Cl bond in the corresponding chlorophosphine-Ru(iv) derivatives [RuCl2(η3:η3-C10H16)(PR2Cl)]. In addition to NMR and IR data, the X-ray crystal structures of representative examples are discussed. Moreover, the catalytic behaviour of complexes [RuCl2(η3:η3-C10H16)(PR2OH)] has been investigated for the selective hydration of organonitriles in water. The best results were achieved with the complex [RuCl2(η3:η3-C10H16)(PMe2OH)], which proved to be active under mild conditions (60 °C), with low metal loadings (1 mol%), and showing good functional group tolerance.
- Tomás-Mendivil, Eder,Francos, Javier,González-Fernández, Rebeca,González-Liste, Pedro J.,Borge, Javier,Cadierno, Victorio
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p. 13590 - 13603
(2016/09/04)
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- Synthesis and antitumor activity of new thiazole nortopsentin analogs
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New thiazole nortopsentin analogs in which one of the two indole units was replaced by a naphthyl and/or 7-azaindolyl portion, were conveniently synthesized. Among these, three derivatives showed good antiproliferative activity, in particular against MCF7 cell line, with GI50 values in the micromolar range. Their cytotoxic effect on MCF7 cells was further investigated in order to elucidate their mode of action. Results showed that the three compounds act as pro-apoptotic agents inducing a clear shift of viable cells towards early apoptosis, while not exerting necrotic effects. They also caused cell cycle perturbation with significant decrease in the percentage of cells in the G0/G1 and S phases, accompanied by a concomitant percentage increase of cells in the G2/M phase, and appearance of a subG1-cell population.
- Attanzio, Alessandro,Barraja, Paola,Carbone, Anna,Cascioferro, Stella,Cirrincione, Girolamo,Diana, Patrizia,Montalbano, Alessandra,Parrino, Barbara,Spanò, Virginia,Tesoriere, Luisa
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- Screening of NOS activity and selectivity of newly synthesized acetamidines using RP-HPLC
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Nitric Oxide Synthase (NOS) inhibitors could play a powerful role in inflammatory and neurodegenerative diseases. In this work, novel acetamidine derivatives of NOS were synthesized and the inhibitor activity was evalued. To screen the activity and selectivity, the l-citrulline residue, after the enzymatic NOS assay, was derivatized with o-phthaldialdehyde/N-acetyl cysteine (OPA/NAC) and then evaluated by RP-HPLC method with fluorescence detection.All compounds did not affect the activity of endothelial and neuronal isoforms, while nine of them possessed a percentage of iNOS activity at 10 μM lower than 50%, and were selected for IC50 evaluation. Among them, a compound emerged as a very potent (IC50 of 53 nM) and selective iNOS inhibitor.
- Fantacuzzi, Marialuigia,Maccallini, Cristina,Di Matteo, Mauro,Ammazzalorso, Alessandra,Bruno, Isabella,De Filippis, Barbara,Giampietro, Letizia,Mollica, Adriano,Amoroso, Rosa
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p. 419 - 424
(2016/02/16)
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- Direct oxidative esterification of alcohols and hydration of nitriles catalyzed by a reusable silver nanoparticle grafted onto mesoporous polymelamine formaldehyde (AgNPs@mPMF)
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A nitrogen-rich mesoporous organic polymer was synthesized as a novel support. A silver nanoparticle was synthesized and grafted onto it. The prepared catalyst (AgNPs@mPMF) was characterized by powder X-ray diffraction (XRD), scanning electron microscopy(SEM) and energy dispersive X-ray spectrometry (EDS), thermogravimetric analysis (TGA), high-resolution transmission electron microscopy (HRTEM), UV-vis diffuse reflectance spectroscopy (DRS), N2 adsorption, Raman spectroscopy and EPR study. The catalytic activity was evaluated for the oxidative esterification reaction of alcohols and hydration of nitriles. The oxidative esterification reaction was carried out for various activated alcohols giving excellent yields of the corresponding ester products. The catalyst was also efficient in the hydration of nitriles. Both reactions were optimized by varying the bases, temperatures and solvents. The catalyst can be facilely recovered and reused six times without a significant decrease in its activity and selectivity.
- Ghosh, Kajari,Iqubal, Md. Asif,Molla, Rostam Ali,Mishra, Ashutosh,Kamaluddin,Islam, Sk Manirul
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p. 1606 - 1622
(2015/04/27)
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- Polymer-anchored Ru(II) complex as an efficient catalyst for the synthesis of primary amides from nitriles and of secondary amides from alcohols and amines
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A polymer-anchored ruthenium(II) catalyst was synthesized and characterized. Its catalytic activity was evaluated for the preparation of primary amides from aqueous hydration of nitriles in neutral condition. A range of nitriles were successfully converted to their corresponding amides in good to excellent yields. The catalyst was also effective in the preparation of secondary amides from the coupling of alcohols and amines. The catalyst can be facilely recovered and reused six times without a significant decrease in its activity.
- Islam, Sk Manirul,Ghosh, Kajari,Roy, Anupam Singha,Molla, Rostam Ali
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p. 900 - 907
(2015/02/19)
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- Transition metal-free sodium borohydride promoted controlled hydration of nitriles to amides
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A transition metal-free process, promoted by sodium borohydride, has been developed for convenient and selective hydration of nitriles to corresponding amides. The present process converts the aromatic, aliphatic, and heteroaromatic nitriles with wide functional group tolerance. The regioselective hydration of one nitrile moiety in the presence of an other nitrile group makes high impact in the present protocol.
- Verma, Praveen Kumar,Kumar, Neeraj,Sharma, Upendra,Bala, Manju,Kumar, Vishal,Singh, Bikram
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p. 2867 - 2875
(2013/09/02)
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- Transition metal-free 1,3-dimethylimidazolium hydrogen carbonate catalyzed hydration of organonitriles to amides
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An efficient hydration of organonitriles to the corresponding amides was accomplished using 1,3-dimethylimidazolium hydrogen carbonate as an organocatalyst. The developed catalytic method was also applicable for the synthesis of metal phthalocyanines.
- Verma, Praveen Kumar,Sharma, Upendra,Bala, Manju,Kumar, Neeraj,Singh, Bikram
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p. 895 - 899
(2013/04/23)
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- Au/Ag-cocatalyzed aldoximes to amides rearrangement under solvent- and acid-free conditions
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(Chemical Equation Presented) The gold/silver-cocatalyzed conversion of aldoximes into primary amides is reported. The reaction, which proceeds under neat and acid-free conditions, allows for the conversion of a range of aldoximes, and is a rare example of cooperative catalysis involving well-defined gold species.
- Ramon, Ruben S.,Bosson, Johann,Diez-Gonzalez, Silvia,Marion, Nicolas,Nolan, Steven P.
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experimental part
p. 1197 - 1202
(2010/04/02)
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- Structural modification of diketo acid portion in 1H-benzylindole derivatives HIV-1 integrase inhibitors
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Our previous studies led to discovery of a very potent benzylindoldiketo acid (CHI-1043) acting as HIV-1 integrase strand transfer inhibitor. We herein report the synthesis of new structurally different compounds in which the 1,3-diketo acid moiety has been substituted with other functionalities. The synthesized derivatives were evaluated for their activity on the IN enzyme and in MT-4 cells but only 4-[l-(4-fluorobenzyl)-4-methoxy-1H-indol-3-yl)-3-hydroxyfuran-2(5H)-one (12) was able to strongly inhibit HIV-1 probably by biotransformation into CHI-1043.
- Ferro, Stefania,De Grazia, Sara,De Luca, Laura,Barreca, Maria Letizia,Debyser, Zeger,Chimirri, Alba
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experimental part
p. 947 - 959
(2009/09/30)
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- NITROGENATED HETEROCYCLIC COMPOUND AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
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The present invention relates to novel compounds having a xanthine oxidase inhibitory effect and an uricosuric effect and pharmaceutical compositions comprising the same as an active ingredient. That is, the present invention relates nitrogen-containing heterocyclic compounds represented by the following general formula (I): wherein Y1 represents N or C(R4) ; Y2 represents N or C(R5) ; R4 and R5 independently represent an alkyl group, a hydrogen atom etc. ; one of R1 and R2 represents an optionally substituted aryl group, an alkoxygroup or an optionally substituted heterocyclic group; the other of R1 and R2 represents a haloalkyl group, a cyanogroup, ahalogenatometc.; and R3 represents a 5-tetrazolyl group or a carboxy group, and pharmaceutically acceptable salts thereof, and pharmaceutical compositions comprising the same as an active ingredient.
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Page/Page column 12; 14
(2008/12/06)
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- Low molecular weight indole fragments as IMPDH inhibitors
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The study of non-oxazole containing indole fragments as inhibitors of inosine monophosphate dehydrogenase (IMPDH) is described. The synthesis and in vitro inhibitory values for IMPDH II are discussed.
- Beevers, Rebekah E.,Buckley, George M.,Davies, Natasha,Fraser, Joanne L.,Galvin, Francis C.,Hannah, Duncan R.,Haughan, Alan F.,Jenkins, Kerry,Mack, Stephen R.,Pitt, William R.,Ratcliffe, Andrew J.,Richard, Marianna D.,Sabin, Verity,Sharpe, Andrew,Williams, Sophie C.
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p. 2535 - 2538
(2007/10/03)
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- Isocyanatophosphoryl Dichloride as Reagent for Introduction of Carbamoyl Group into Molecules of π-Excessive Heterocycles and Enamines
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A study on the stepwise hydrolysis of hetarene- and cycloalkenecarboxamidophosphoryl dichlorides afforded the synthesis of hitherto unknown hetarene- and cycloalkene-carboxamidophosphoric acids as well as allowing the introduction of unsubstituted carbamoyl group in the molecules of pyrroles, indoles, indolizines, and some enamines.
- Smaliy, Radomir V.,Chaikovskaya, Aleksandra A.,Pinchuk, Aleksandr M.,Tolmachev, Andrei A.
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p. 2525 - 2529
(2007/10/03)
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- Reactions of Vilsmeier Haack reagent with aromatic and heterocyclic aldoximes
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Reactions of Vilsmeier Haack reagent with various aromatic and heterocyclic aldoximes give amides. Nitriles are shown to be the intermediates in this reaction. Vilsmeier Haack reaction with amides in turn furnishes nitriles.
- Kusurkar, Radhika,Goswami, Shailesh,Vyas, Sandhya
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p. 3148 - 3151
(2007/10/03)
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- Biotransformation of the phytoalexin camalexin by the phytopathogen Rhizoctonia solani
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The unusual metabolism of the cruciferous phytoalexin camalexin by virulent and weakly virulent isolates of the root rot fungus Rhizoctonia solani Kuhn is reported. This biotransformation proceeded via 5- hydroxycamalexin, which was further biotransformed into more polar metabolites. Importantly, the metabolites resulting from transformation of camalexin were significantly less toxic to the pathogen than camalexin. Thus, it was concluded that R. solani can detoxify camalexin through oxidation of the indole ring. The chemistry involved in the structure determination of the intermediates of this pathway, their synthesis as well as antifungal activity is described.
- Pedras, M. Soledade C.,Khan, Abdul Q.
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- SYNTHESIS AND PROPERTIES OF AZOLES AND THEIR DERIVATIVES. 32. SYNTHESIS AND SOME TRANSFORMATIONS OF HYDROCHLORIDES OF IMIDO ESTERS OF INDOLECARBOXYLIC ACIDS
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The Pinner reaction with the nitriles of indole-3-carboxylic and 3-indolylacetic acids was studied.The hydrochlorides of the imide esters of these acids, which were converted to the free bases, amides, and esters, were synthesized.Imidazolines, benzimidazoles, and benzoxazoles that contain indole substituents were obtained by condensation of the hydrochlorides of the imido esters of the indolecarboxylic acids with ethylenediamine, o-phenylenediamine, and o-aminophenol.
- Kelarev, V. I.,Shvekhgeimer, G. A.
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p. 501 - 506
(2007/10/02)
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