- Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids
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We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.
- Begam, Hasina Mamataj,Jana, Ranjan,Manna, Kartic,Samanta, Krishanu
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supporting information
p. 7443 - 7449
(2020/10/09)
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- RE[N(SiMe3)2]3-Catalyzed Guanylation/Cyclization of Amino Acid Esters and Carbodiimides
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The example of rare-earth metal-catalyzed guanylation/cyclization of amino acid esters and carbodiimides is well-established, forming 4(3H)-2-alkylaminoquinazolinones in 65-96% yields. The rare-earth metal amides RE[N(TMS)2]3 (RE = Y, Yb, Nd, Sm, La; TMS = SiMe3) showed high activities, and La[N(TMS)2]3 performed best for a wide scope of the substrates.
- Lu, Chengrong,Gong, Chao,Zhao, Bei,Hu, Lijuan,Yao, Yingming
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p. 1154 - 1159
(2018/02/10)
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- Design, synthesis and biological characterization of a new class of osteogenic (1H)-quinolone derivatives
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Smoothened (Smo) is the signal transducer of the Hedgehog (Hh) pathway and its stimulation is considered a potential powerful tool in regenerative medicine to treat severe tissue injuries. Starting from GSA-10, a recently reported Hh activator acting on Smo, we have designed and synthesized a new class of quinolone-based compounds. Modification and decoration of three different portions of the original scaffold led to compounds able to induce differentiation of multipotent mesenchymal cells into osteoblasts. The submicromolar activity of several of these new quinolones (0.4–0.9?μM) is comparable to or better than that of SAG and purmorphamine, two reference Smo agonists. Structure-activity relationships allow identification of several molecular determinants important for the activity of these compounds.
- Manetti, Fabrizio,Petricci, Elena,Gabrielli, Annalisa,Mann, Andrè,Faure, Hélène,Gorojankina, Tatiana,Brasseur, Laurent,Hoch, Lucile,Ruat, Martial,Taddei, Maurizio
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supporting information
p. 747 - 757
(2016/07/21)
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- Synthesis and evaluation of quinazolines as inhibitors of the bacterial cell division protein FtsZ
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The bacterial cell division protein FtsZ is one of many potential targets for the development of novel antibiotics. Recently, zantrin Z3 was shown to be a cross-species inhibitor of FtsZ; however, its specific interactions with the protein are still unknown. Herein we report the synthesis of analogues that contain a more tractable core structure and an analogue with single-digit micromolar inhibition of FtsZs GTPase activity, which represents the most potent inhibitor of Escherichia coli FtsZ reported to date. In addition, the zantrin Z3 core has been converted to two potential photo-cross-linking reagents for proteomic studies that could shed light on the molecular interactions between FtsZ and molecules related to zantrin Z3.
- Nepomuceno, Gabriella M.,Chan, Katie M.,Huynh, Valerie,Martin, Kevin S.,Moore, Jared T.,Obrien, Terrence E.,Pollo, Luiz A. E.,Sarabia, Francisco J.,Tadeus, Clarissa,Yao, Zi,Anderson, David E.,Ames, James B.,Shaw, Jared T.
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supporting information
p. 308 - 312
(2015/03/30)
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- Synthesis of symmetric diester-functionalised Troeger's base analogues
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The yields of ester-functionalised Troeger's base analogues are dramatically improved by incorporating an electron-donating group on the aromatic ring and/or enhancing solubil- ity of the aniline unit. In addition to 2,8-diester compounds, 1,7-, 3,9- and 4,10-diester-functionalised Troeger's base analogues have been prepared for the first time.
- Bhuiyan, M. Delower H.,Zhu, Kai-Xian,Jensen, Paul,Try, Andrew C.
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supporting information; experimental part
p. 4662 - 4670
(2010/10/19)
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- AZABIPHENYLAMINOBENZOIC ACID DERIVATIVES AS DHODH INHIBITORS
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New azabiphenylaminobenzoic acid derivatives having the chemcial structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of the dehydroorotate dihydrogenase (DHODH)
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Page/Page column 66
(2009/04/25)
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- Substituted imidazo [1,5-a] pyrimido [5,4-d] [1] benzazepine derivatives
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The present invention is a compound of formula wherein R1 is halogen or lower alkyl; R2 is hydrogen, lower alkyl, cycloalkyl, —(CH2)m-phenyl, wherein the phenyl ring may be substituted by lower alkoxy, or is —(CH2)m-indolyl; R3 is —C(O)O-lower alkyl, —C(O)OH, or a five membered heteroaromatic group, which rings may be substituted by lower alkyl or cycloalkyl; n is 0, 1 or 2; m is 0, 1 or 2; or a pharmaceutically acceptable acid addition salt thereof. Compound I shows high affinity and selectivity for GALA A α5 receptor binding sites.
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- Investigation into a By-product from the Reaction of 2-Amino-5-methylbenzoic Acid with Ammonium Thiocyanate
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One of the by-products from the reaction of 2-amino-5-methylbenzoic acid with ammonium thiocyanate is shown to be 2,3-dihydro-5-methyl-2-thioxo-3-p-tolylquinazolin-4(1H)-one (6).This reacts with hydrazine to give three products (21)-(23), which have been converted into tetrazolo- (27) and 1,2,4-triazolo-quinazolino-derivatives (20) and (30).The products from the reaction of o-aminoacetophenone with an aryl isothiocyanate are converted into a reactive 1-azabuta-1,3-diene intermediate (34), which undergoes a ? cycloaddition reaction with dimethyl acetylenedicarboxylate, followed by a retro-Diels-Alder reaction, to give dimethyl 4-methylquinoline-2,3-dicarboxylate.
- Kennewell, Peter D.,Scrowston, Richard M.,Shenouda, Ibrahim G.,Tully, W. Roger,Westwood, Robert
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p. 2001 - 2025
(2007/10/02)
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