33859-00-6Relevant academic research and scientific papers
Sequential Cu(I)/Pd(0)-catalyzed multicomponent coupling and annulation Protocol for the synthesis of indenoisoquinolines
Jayanth, Thiruvellore Thatai,Zhang, Lei,Johnson, Thomas S.,Malinakova, Helena C.
supporting information; experimental part, p. 815 - 818 (2009/07/18)
Copper-catalyzed coupling of imines, vinylstannanes, or alkynes and o-bromoaroyl chlorides followed by Pd(0)-catalyzed annulations afforded indenoisoquinolines. Protocols requiring minimal purifications were developed, providing new methods for the construction of combinatorial libraries.
Resistance-modifying agents. 11. Pyrimido[5,4-d]pyrimidine modulators of antitumor drug activity. Synthesis and structure-activity relationships for nucleoside transport inhibition and binding to α1-acid glycoprotein
Curtin, Nicola J.,Barlow, Hannah C.,Bowman, Karen J.,Calvert, A. Hilary,Davison, Richard,Golding, Bernard T.,Huang, Bing,Loughlin, Peter J.,Newell, David R.,Smith, Peter G.,Griffin, Roger J.
, p. 4905 - 4922 (2007/10/03)
The cardiovascular and antithrombotic agent dipyridamole (DP) has potential therapeutic utility as a modulator of the activity of antimetabolite antitumor agents by virtue of its inhibition of nucleoside transport. However, the activity of DP can be compromised by binding to the acute phase serum protein, α1-acid glycoprotein (AGP). Analogues of DP were synthesized and evaluated as inhibitors of 3H-thymidine uptake into L1210 leukamia cells in the presence and absence of 5 mg/mL AGP. Compounds with potency similar to that of DP were identified where the piperidino substituents at the 4,8-positions were replaced by 4?-methoxybenzylamino, 3?,4?-dimethoxybenzylamino, or piperonylamino groups. Replacement of the diethanolamino groups at the 2,6-positions of DP by alkylamino or alkoxy substituents was tolerated, although at least one oxygen-bearing function (hydroxyl or alkoxy) was required in the side chain for activity comparable to that of DP. Whereas AGP completely ablated the activity of DP, the majority of the newer compounds synthesized retained significant activity in the presence of excess AGP, although replacement of the piperidino groups at the 4,8-positions by N-methylbenzylamino substituents did, in some cases, restore susceptibility to AGP. Selected compounds have been demonstrated to prevent rescue from antifolate cytotoxicity, mediated by nucleoside salvage.
Simple synthetic equivalents for the β-(N,N-disubstituted)ethylamino acyl cation synthon and their applications
Selvamurugan,Aidhen
, p. 2239 - 2246 (2007/10/03)
Various N,N-disubstituted-β-amino-N-methoxy-N-methylpropanamides 3a-i were prepared which served as an excellent β-aminoacyl cation equivalents. These were used to prepare β-amino ketones 1, pharmacologically active tertiary 1-(3,3-diarylpropyl)amines 7a-c, and the interesting C-glycoside 8.
Resistance-modifying agents. Part 7: 2,6-Disubstituted-4,8-dibenzylaminopyrimido[5,4-d]pyrimidines that inhibit nucleoside transport in the presence of α1-acid glycoprotein (AGP)
Barlow, Hannah C.,Bowman, Karen J.,Curtin, Nicola J.,Calvert, A. Hilary,Golding, Bernard T.,Huang, Bing,Loughlin, Peter J.,Newell, David R.,Smith, Peter G.,Griffin, Roger J.
, p. 585 - 589 (2007/10/03)
The synthesis and biological evaluation of potent 4,8-dibenzylaminopyrimidopyrimidine nucleoside transport inhibitors, with reduced binding to α1-acid glycoprotein, is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.
Synthesis of 7,12-dihydro-12-phenyl-5H-6,12-methanodibenz[cf]azocines via N,N-dibenzylphenacylamines
Coskun, Necdet,Bueyuekuysal, Levent
, p. 53 - 59 (2007/10/03)
N,N-DibenzyIphenacylamines (1) were prepared in high yields by a onepot reaction and cyclized at room temperature to give 7,12-dihydro-12-phenyl-5H-6,12-methanodibenz[cf]azocines in high yields. 95% H2SO4 or 70% HClO4 was used as cyclization catalysts. The double-cyclization proceeds smoothly in the cases where electron-donating groups are present in both benzene ring. N-2,3-dimethoxybenzyl-N-benzylphenacylamine (If) gave the corresponding N-benzyl-1,2-dihydro-4-phenylisoquinoline on treatment with 95% H2SO4 while N-3,4-Dimethoxybenzyl-N-benzylphenacylamine (1a) at the same reaction conditions and reaction time cyclized to the corresponding dibenzazocine. However la gave the corresponding dihydroisoquinoline which disproportionates to give N-benzyl-1,2,3,4-tetrahydro-4-phenylisoquinoline and N-benzyl-4-phenylisoquinolinium when treated with 70% perchloric acid at room temperature.
Mechanistic and synthetic aspects of amine oxidations promoted by 3-methyl-5-ethyllumiflavinium perchlorate
Hoegy, Susan E.,Mariano, Patrick S.
, p. 5027 - 5046 (2007/10/03)
Preparative and kinetic aspects of the chemistry of 3-methyl-5-ethyllumiflavinium perchlorate (1) with primary and secondary amines have been investigated. Reactions of! with primary and secondary amines leads to rapid production of modestly stable C4a-adducts. The rates of these processes, determined by stopped-flow kinetic methods, parallel amine nucleophilicities. The C4a-adducts undergo benzylamine promoted elimination reactions to produce N-benzylaldimine products with rates that parallel reactivity profiles expected for E2-elimination processes. Finally, flavinium salt 1 serves as a catalyst for oxidations of primary and secondary amines under aerobic conditions.
Steric and electronic effects on the regioselective formation of platinum(II) metallacycles: Crystal structure of [PtMe(3-MeC6H3CH=NCH2C6H 5)(PPh3)]
Crespo, Margarita,Solans, Xavier,Font-Bardia, Merce
, p. 29 - 36 (2007/10/03)
The reaction of [Pt2Me4(μSMe2)2] (1) with imines 3,4-(OMe)2C6H3CH=NCH2Ph (2e) and 3-MeC6H4CH=NCH2Ph (2e) yields cyclometallated compou
ORGANIC PHOSPHORUS COMPOUNDS 94 PREPARATION, PHYSICAL AND BIOLOGICAL PROPERTIES OF AMINO-ARYLMETHYLPHOSPHONIC- AND -PHOSPHONOUS ACIDS
Maier, Ludwig,Diel, Peter J.
, p. 57 - 64 (2007/10/02)
The preparation, physical and spectroscopic properties of amino-arylmethylphosphonic- and -phosphonous acids, the phosphorus analogues of phenylglycine, are described.It is shown that several of the compounds prepared exhibit antifungal activity at 200 ppm.Thus 1e, 1f, 1g and 1h showed activity against Erysiphe (barley), 2a against Puccinia (wheat) and 6a against Botrytis (apple).Of particular interest is the high gameticidal activity of 3a in the greenhouse.
