- Preparation of amidines from amidoximes via transfer hydrogenation
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Amidoximes are reduced into amidine using triethyl silane and PdCl 2 in acetic acid. Copyright
- Mahajan, Umesh S.,Godinde, Rupesh R.,Mandhare
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- Silver-catalyzed [3+2+1] annulation of aryl amidines with benzyl isocyanide
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A silver-catalyzed [3+2+1] annulation of amidines with benzyl isocyanide toward 2,4-diaryl-1,3,5-triazines was developed. A variety of symmetrical and unsymmetrical products were obtained in moderate to good yields. This work also features an oxidant-free approach to 2,4-disubstituted triazines.
- Lu, Xiaodong,Xin, Xiaoyi,Wan, Boshun
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supporting information
p. 361 - 364
(2018/01/08)
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- Investigation of new 2-aryl substituted Benzothiopyrano[4,3-d[pyrimidines as kinase inhibitors targeting vascular endothelial growth factor receptor 2
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Vascular Endothelial Growth Factor (VEGF) pathway has emerged as one of the most important positive modulators of Angiogenesis, a central process implicated in tumour growth and metastatic dissemination. This led to the design and development of anti-VEGF monoclonal antibodies and small-molecule ATP-competitive VEGFR-inhibitors. In this study, we describe the synthesis and the biological evaluation of novel 2-aryl substituted benzothiopyrano-fused pyrimidines 1a-i, 2a-i and 3a-i. The ability of the compounds to target the VEGF pathway was determined in vitro exploiting the compounds' antiproliferative efficacy against HUVEC cells. The VEGFR-2 inhibition was confirmed by enzymatic assays on recombinant human kinase insert domain receptor (KDR), by cell-based phospho-VEGFR-2 inhibition assays, and by ex vivo rat aortic ring tests. The selectivity profile of the best performing derivatives belonging to series 2 was further explored combining modeling studies and additional assays in a panel of human cell lines and other kinases.
- Salerno, Silvia,Marini, Anna Maria,Fornaciari, Giacomo,Simorini, Francesca,La Motta, Concettina,Taliani, Sabrina,Sartini, Stefania,Da Settimo, Federico,Garciá-Argaéz, Aída Nelly,Gia, Ornella,Cosconati, Sandro,Novellino, Ettore,D'Ocon, Pilar,Fioravanti, Anna,Orlandi, Paola,Bocci, Guido,Dalla Via, Lisa
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- Transition-metal-free approach to 4-ethynylpyrimidines via alkenynones
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A practical approach to the synthesis of 4-ethynylpyrimidines by the condensation of arylamidines with 2-aryl-1-ethoxy-5-(trimethylsilyl)pent-1-en-4- yn-3-ones has been developed. As these latter ketones are easily accessible from bis(trimethylsilyl)acetylene and arylacetyl chlorides, the regioselective condensation reported herein provides a facile access to both TMS-protected and unprotected 4-ethynylpyrimidines in yields of up to 85%. Copyright
- Golubev, Pavel R.,Pankova, Alena S.,Kuznetsov, Mikhail A.
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p. 3614 - 3621
(2014/06/23)
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- Discovery and biological evaluation of novel 4-amino-2-phenylpyrimidine derivatives as potent and orally active GPR119 agonists
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Novel 4-amino-2-phenylpyrimidine derivatives were synthesized and evaluated as GPR119 agonists. Optimization of the substituents on the phenyl ring at the 2-position and the amino group at the 4-position led to the identification of 3,4-dihalogenated and
- Negoro, Kenji,Yonetoku, Yasuhiro,Misawa-Mukai, Hana,Hamaguchi, Wataru,Maruyama, Tatsuya,Yoshida, Shigeru,Takeuchi, Makoto,Ohta, Mitsuaki
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p. 5235 - 5246
(2012/11/07)
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- Synthesis and structure of aroylamidines and N-arylbenzamidines hydrochlorides
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Aroylamidines can be obtained as salts in a reaction of the corresponding arylcarbonitriles with anhydrous ethanol in the presence of dry HCl followed by treating intermediate imidoesters with alcoholic solution of ammonia. N-Arylbenzamidines are obtained by reacting benzonitrile with arylamines in the presence of AlCl3. The structure of arylamines and the reaction conditions signifi cantly affect the yield of the target product, and sometimes the very possibility of its preparation. Pleiades Publishing, Ltd., 2012.
- Kuvaeva,Fedorova,Zaitsev,Yakovlev,Zakharov,Semakova
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experimental part
p. 209 - 213
(2012/06/01)
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- Access to variously substituted 5,6,7,8-tetrahydro-3H-quinazolin-4-ones via Diels-Alder adducts of phenyl vinyl sulfone to cyclobutene-annelated pyrimidinones
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Under basic conditions (Et3N, dioxane), the aromatic amidines 4 and also S-methylisothiourea 4g cleanly undergo Michael addition to methyl 2-chloro-2-cyclopropylideneacetate (5), followed by intramolecular nucleophilic substitution, cyclopropyl
- Dalai, Suryakanta,Belov, Vladimir N.,Nizamov, Shamil,Rauch, Karsten,Finsinger, Dirk,De Meijere, Armin
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p. 2753 - 2765
(2007/10/03)
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- TETRAHYDRO- AND DIHYDROQUINAZOLINONES
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The present invention relates to the use of tetrahydro- and dihydroquinazolinones of formula (I) as protein kinase activators or inhibitors, a method for their manufacture, their use for the preparation of a medicament for the treatment of diseases, their
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Page/Page column 62; 63; 72; 73
(2010/11/23)
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- 2-aryl dihydropyrimidine compounds
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There are provided novel compounds of formula (I) including their 3,4-dihydropyrimidine tautomer form, wherein R1, R2, R3, R4, R5, X and n are as defined in the specification, and optical isomers and
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- Preparation of N,N,N'-tris(trimethylsilyl)amidines; a convenient route to unsubstituted amidines
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The tris(trimethylsilyl)amidines RC(NSiMe3)N(SiMe3)2 (R = C6H5, p-CH3C6H4, p-ClC6H4, p-MeOC6H4, p-Me2NC6H4, p-CF3C6H4, p-C6H5C6H4 and CF3) are prepared by the reaction of the respective nitriles with (Me3Si)2NLI.OEt2 in ether to give intermediates RC(NLi)N(SiMe3)2.Heating these intermediates with ClSiMe3 in toluene affords the products, which are isolated by vacuum distillation, in high yield.With 1,4-dicyanobenzene, two equivalents of reagents affords the per(trimethylsilyl)-1,4-diamidine.Hydrolysis of the intermediates with 6N ethanolic HCl affords the unsubstituted amidine hydrochlorides RC(NH)NH2.HCl (R = C6H5, p-MeOC6H4, p-ClC65H4, p-O2NC6H4) in high yield.
- Boere, Rene T.,Onkley, Richard T.,Reed, Robert W.
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p. 161 - 168
(2007/10/02)
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- AZIDE AND FLUORIDE EXCHANGE REACTIONS OF HALODIAZIRINES
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Reactions of 3-aryl-3-bromodiazirines (11) with molten tetrabutylammonium fluoride at 25degC provide 65-74percent isolated vields of the novel corresponding 3-aryl-3-fluorodiazirines (12) Related reactions of 11 with tetrabutylammonium azide afford high yields of aryl nitriles.The latter reactions are believed to proceed through unstable intermediate 3-aryl-3-azidodiazirines (7).These reactions involve rate-determining formation of 7 and display kinetics which are first order in azide ion and bromodiazirine.The likely intermediacy of aryldiazirinium bromide ion pair between 11 and 7 is supported by a combination of salt effect, leaving group effect and Hammett studies.Molecular orbital calculations are employed to characterize azidodiazirines as well as the mode of their decomposition to nitriles.In particular, we consider the possible itermediacy of a 3-nitrenodiazirine or an azidocarbene.
- Moss, Robert A.,Terpinski, Jacek,Cox, D. Phillip,Denneey, Dorothy Z.,Krogh-Jespersen, Karsten
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p. 2743 - 2748
(2007/10/02)
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- 2,4,5-Triaryl pyrimidines and a method of treating pain, fever, thrombosis, inflammation and arthritis
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This invention provides for certain novel 2,4,5-triaryl pyrimidine derivatives, their pharmaceutical formulations, and a method of treating pain, fever, thrombosis, inflammation, and arthritis.
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