- Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones
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Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.
- Daniliuc, Constantin,Glorius, Frank,Hu, Tianjiao,Lückemeier, Lukas
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supporting information
p. 23193 - 23196
(2021/09/25)
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- Discovery and Optimization of Novel, Selective Histone Methyltransferase SET7 Inhibitors by Pharmacophore- and Docking-Based Virtual Screening
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Histone methyltransferases are involved in various biological functions, and these methylation regulating enzymes' abnormal expression or activity has been noted in several human cancers. Within this context, SET domain-containing (lysine methyltransferase) 7 (SET7, also called KMT7, SETD7, SET9) is of increasing significance due to its diverse roles in biological functions and diseases, such as diabetes, cancers, alopecia areata, atherosclerotic vascular disease, HIV, and HCV. In this study, DC-S100, which was discovered by pharmacophore- and docking-based virtual screening, was identified as the hit compound of SET7 inhibitor. Structure-activity relationship (SAR) analysis was performed on analogs of DC-S100 and according to the putative binding mode of DC-S100, structure modifications were made to improve its activity. Of note, compounds DC-S238 and DC-S239, with IC50 values of 4.88 and 4.59 μM, respectively, displayed selectivity for DNMT1, DOT1L, EZH2, NSD1, SETD8, and G9a. Taken together, DC-S238 and DC-S239 can serve as leads for further investigation as SET7 inhibitors and the chemical toolkits for functional biology studies of SET7.
- Meng, Fanwang,Cheng, Sufang,Ding, Hong,Liu, Shien,Liu, Yan,Zhu, Kongkai,Chen, Shijie,Lu, Junyan,Xie, Yiqian,Li, Linjuan,Liu, Rongfeng,Shi, Zhe,Zhou, Yu,Liu, Yu-Chih,Zheng, Mingyue,Jiang, Hualiang,Lu, Wencong,Liu, Hong,Luo, Cheng
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p. 8166 - 8181
(2015/11/09)
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- Nucleic acid binding dyes and uses therefor
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The invention provides novel compounds and compositions of Formulas I and II, as well as methods of using them. The compounds can be used, for example, to quantify an amount of double stranded DNA in a sample subjected to nucleic acid amplification, or fo
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Page/Page column 38
(2015/12/25)
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- An efficient green protocol for the preparation of acetoacetamides and application of the methodology to a one-pot synthesis of Biginelli dihydropyrimidines. Expansion of dihydropyrimidine topological chemical space
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The present study describes the preparation of N-aryl-(15) and N-alkyl-(17) acetoacetamides, in good to excellent yields, using both conventional and microwave heating, by reaction of amine derivatives (14 and 16) with 2,2,6-trimethyl-4H-1,3-dioxin-4-one (TMD, 12) in aqueous medium. The acetoacetamides were used to prepare novel Biginelli dihydropyrimidine derivatives. The introduction of the amino acid derivatives potentially allows for the exploration of new structural complexity and topologically diversifies the chemical space occupied by this versatile chemical scaffold.
- Gama, Fernando H. S.,De Souza, Rodrigo O. M. A.,Garden, Simon J.
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p. 70915 - 70928
(2015/09/08)
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- Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties
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Rapid and facileaccess to novel chromeno[4,3-b]pyridine-2,5-dione derivatives was achieved by a mild base catalysed reaction of 4-chloro-3-formylcoumarin and acetoacetamides in PEG-300 as recyclable solvent. The compounds were evaluated for their antimicrobial activities against 3 Gram-positive and 3 Gram-negative bacteria (Staphylococcus epidermis, Vibrio parahaemolyticus, Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Klebsiella pneumonia) with Cefotaxime control. They were further subjected to antioxidant studies using DPPH test with ascorbic acid control. While compounds 5d and 5k showed promising broad spectrum antibacterial properties against all the evaluated bacteria, compound 5g exhibited good antioxidant properties. Indian Academy of Sciences.
- Jaggavarapu, Satyanarayana Reddy,Kamalakaran, Anand Solomon,Jalli, Ventkata Prasad,Gangisetty, Sravan Kumar,Ganesh, Munusswamy Ramanujam,Gaddamanugu, Gopikrishna
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p. 187 - 195
(2014/04/03)
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- Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties
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Rapid and facile access to novel chromeno[4,3-b]pyridine-2,5-dione derivatives was achieved by a mild base catalysed reaction of 4-chloro-3-formylcoumarin and acetoacetamides in PEG-300 as recyclable solvent. The compounds were evaluated for their antimicrobial activities against 3 Gram-positive and 3 Gram-negative bacteria (Staphylococcus epidermis, Vibrio parahaemolyticus, Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Klebsiella pneumonia) with Cefotaxime control. They were further subjected to antioxidant studies using DPPH test with ascorbic acid control. While compounds 5d and 5k showed promising broad spectrum antibacterial properties against all the evaluated bacteria, compound 5g exhibited good antioxidant properties. [Figure not available: see fulltext.]
- Jaggavarapu, Satyanarayana Reddy,Kamalakaran, Anand Solomon,Jalli, Ventkata Prasad,Gangisetty, Sravan Kumar,Ganesh, Munusswamy Ramanujam,Gaddamanugu, Gopikrishna
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p. 187 - 195
(2016/02/26)
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- Ligand-enabled γ-C-H olefination and carbonylation: Construction of β-quaternary carbon centers
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Monoselective γ-C-H olefination and carbonylation of aliphatic acids has been accomplished by using a combination of a quinoline-based ligand and a weakly coordinating amide directing group. The reaction provides a new route for constructing richly functionalized all-carbon quaternary carbon centers at the β-position of aliphatic acids.
- Li, Suhua,Chen, Gang,Feng, Chen-Guo,Gong, Wei,Yu, Jin-Quan
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supporting information
p. 5267 - 5270
(2014/05/06)
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- One-pot synthesis of 3-hydroxyquinolin-2(1 H)-ones from N-phenylacetoacetamide via PhI(OCOCF3)2-mediated α-hydroxylation and H2SO4-promoted intramolecular cyclization
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A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF 3)2-mediated α-hydroxylation and a H 2SO4-promoted intramolecular condensation. The hydroxyl group in the generated α-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.
- Yuan, Yucheng,Yang, Rui,Zhang-Negrerie, Daisy,Wang, Junwei,Du, Yunfei,Zhao, Kang
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p. 5385 - 5392
(2013/07/26)
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- Facile synthesis of furoquinoline and effects on radical-induced oxidation of DNA
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The aim of this work was to clarify the influences of the position of hydroxyl group and furo[2,3-b] moiety on the antioxidant effectiveness of quinoline. Thus, 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-6-ol (PFQ), 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-8-ol (OFQ), and 4-methyl-2,3- dihydrofuro[2,3-b]quinolin-7-ol (MFQ) were synthesized by a recyclization reaction of 1-acetyl-N-phenylcyclopropanecarboxamide in the presence of SnCl4 as the catalyst. The antioxidant capacities of PFQ, OFQ, and MFQ were evaluated in the experimental system of the oxidation of DNA caused by Cu2+/glutathione (GSH), ?OH, and 2,2′-azobis(2- amidinopropane hydrochloride) (AAPH). OFQ and PFQ were able to protect DNA against Cu2+/GSH- and ?OH-induced oxidation because the furo[2,3-b] moiety was beneficial for stabilizing the produced furoquinoline radical. Moreover, MFQ can decrease the oxidation rate of AAPH-induced oxidation of DNA, while PFQ and OFQ can inhibit AAPH-induced oxidation of DNA for a period. The data obtained from AAPH-induced oxidation of DNA were treated by chemical kinetic method; it was found that PFQ and OFQ can trap 1.3 and 1.5 radicals, respectively. Therefore, the hydroxyl group at different positions changed the mechanism of furoquinoline in protecting DNA against radical-induced oxidation. Graphical Abstract: Effects on Cu2+/glutathione-, ?OH-, and peroxyl radical-induced oxidation of DNA.[Figure not available: see fulltext.]
- Wang, Rui,Liu, Zai-Qun
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p. 1563 - 1569
(2013/07/26)
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- Characterization of 4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate as an effective antiplatelet agent
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We have studied earlier a membrane bound novel enzyme Acetoxy Drug: protein transacetylase identified as Calreticulin Transacetylase (CRTAase) that catalyzes the transfer of acetyl groups from polyphenolic acetates (PAs) to the receptor proteins and thus modulating their biological activities. In this communication, we have reported for the first time that acetoxy quinolones are endowed with antiplatelet action by virtue of causing CRTAase catalyzed activation of platelet Nitric Oxide Synthase (NOS) by way of acetylation leading to the inhibition of ADP/Arachidonic acid (AA)-dependent platelet aggregation. The correlation of specificity of platelet CRTAase to various analogues of acetoxy quinolones with intracellular NO and consequent effect on inhibition of platelet aggregation was considered crucial. Among acetoxy quinolones screened, 6-AQ (4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate/6-acetoxyquinolin-2-one, 22) was found to be the superior substrate to platelet CRTAase and emerged as the most active entity to produce antiplatelet action both in vitro and in vivo. 6-AQ caused the inhibition of cyclooxygenase-1 (Cox-1) resulting in the down regulation of thromboxane A2 (TxA2) and the inhibition of platelet aggregation. Structural modification of acetoxy quinolones positively correlated with enhancement of intracellular NO and antiplatelet action.
- Priya, Nivedita,Gupta, Anjali,Chand, Karam,Singh, Prabhjot,Kathuria, Abha,Raj, Hanumantharao G.,Parmar, Virinder S.,Sharma, Sunil K.
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experimental part
p. 4085 - 4094
(2010/08/06)
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- NUCLEIC ACID BINDING DYES AND USES THEREFOR
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The invention provides novel compounds and compositions of Formulas I and II, as well as methods of using them. The compounds can be used, for example, to quantify an amount of double stranded DNA in a sample subjected to nucleic acid amplification, or fo
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- Short, efficient syntheses of pyrrole α-amides
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We report an inexpensive method for producing a diverse array of pyrrole amides on a large scale and in good yield. The synthetic sequence allows for the preparation of a number of pyrrole amide derivatives in excellent to moderate yields from commercially available compounds. The diketene adduct, in the presence of an amine nucleophile, provides an excellent method for acetoacetylation. For diversity and versatility, a second method utilizing Meldrum's acid was successfully employed for the preparation of additional acetoacetamide derivatives. Using the Knorr pyrrole synthesis, pyrrole amides were readily prepared from the oxime of the acetoacetamides. Copyright Taylor & Francis Group, LLC.
- Huggins, Michael T.,Barber, Patrick S.,Florian, David,Howton, William
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experimental part
p. 4226 - 4239
(2009/04/11)
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- THERAPEUTIC AGENTS I
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Compounds of formula(I), processes for preparing such compounds, their use in the treatment of obesity, psychiatric disorders, cognitive disorders, memory disorders, schizophrenia, epilepsy, and related conditions, and neurological disorders such as dementia, multiple sclerosis, Parkinson's disease, Huntington's chorea and Alzheimer's disease and pain related disorders, and pharmaceutical compositions containing them.
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Page/Page column 40
(2010/02/12)
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- Synthesis, X-ray diffraction study and biological activity of 7-hydroxy-4-methylquinolin-2(1H)-one
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The compound 7-hydroxy-4-methylquinolin-2(1H)-one (HMQ) has been synthesized by an easy and efficient microwave-assisted method. The structure of the compound has been confirmed on the basis of its IR, 1H NMR spectral data and elemental analyses. The sample has been subjected to X-ray diffractometry to elucidate structural information. The structure of the compound has been found to be orthorhombic belonging to base centered system. The accountability of strain broadening effects with respect to natural particle size is also examined and discussed. The compound has been screened for the antibacterial and antifungal activities.
- Deshmukh,Dhongade-Desai, Savita,Chavan
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p. 1659 - 1662
(2007/10/03)
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- Substituent effects on absorption and fluorescence spectra of carbostyrils
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Absorption and fluorescence spectra as well as quantum yields of a series of differently substituted carbostyrils (quinolin-2(1H)-ones) are reported. Especially for compounds containing donor substituents in position 6, substantial bathochromic shifts (comparable to analogous coumarins) of both absorption as well as fluorescence transitions are obtained. High absorption intensities and quantum yields are found for 7-donor substituted isomers. Semiempirical molecular orbital calculations (AMI for structures, ZINDO for electronic transition energies) prove to be a suitable tool for the prediction of absorption and fluorescence properties of these compounds. Ab initio and density functional calculations establish the lactam form as the dominant tautomer of the parent quinolin-2(1H)-one.
- Fabian, Walter M.F.,Niederreiter, Karlheinz S.,Uray, Georg,Stadlbauer, Wolfgang
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p. 209 - 220
(2007/10/03)
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- Synthesis and immunosuppressant activity of pyrazole carboxamides
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A series of novel pyrazole carboxamides sis disclosed that demonstrate strong immunosuppressant activity in rodent and human mixed leukocyte response (MLR) assays (IC50 1 μM). The synthesis, biological activity, mode of action, and pharmacokinetic properties of this new lead series are discussed.
- Wang, Alan X.,Xie, Qinghua,Lane, Ben,Mollison, Karl W.,Hsieh, Gin C.,Marsh, Kennan,Sheets, Michael P.,Luly, Jay R.,Coghlan, Michael J.
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p. 2787 - 2792
(2007/10/03)
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- New synthetic applications of aryllead triacetates. N-arylation of amides
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p-Tolyllead triacetate efficiently arylates the nitrogen atom of carboxamide, sulfonamide, imide, and hydantoin anions under mild conditions. This reaction did not interfere with the arylation of amino and β-dicarbonyl groups.
- López-Alvarado, Pilar,Avenda?o, Carmen,Menéndez, J. Carlos
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p. 5865 - 5870
(2007/10/03)
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- MECHANISM OF ACETOACETYLATION OF SUBSTITUED ANILINES
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Kinetics have been studied of the reaction of diketene with substituted anilines, and the reaction rate has been found to depend on relative permitivity of the system.The rate and equilibrium constants have been calculated by combination of rate and equilibrium relations with the relation by Amis; the constants correlate with the Hammett substituent constants.The reaction does not proceed as a simple bimolecular process.A reaction mechanism has been suggested.
- Knizek, Jiri,Lejdar, Erhard,Vetesnik, Pavel
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p. 365 - 374
(2007/10/02)
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