Archives of Journal Articles

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A Stereoselective Synthesis of dl-threo-Methylphenidate: Preparation and Biological Evaluation of Novel Analogues

Axten, J. M.; Krim, L.; Kung, H. F.; Winkler, J. D.;
J. Org. Chem.; (Communication); 1998; 63(26); 9628-9629.
DOI: 10.1021/jo982214t
http://rapidshare.de/files/3012877/axten.djvu.html

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The First Enantioselective Synthesis of (2R,2'R)-threo-(+)-Methylphenidate Hydrochloride

Prashad, M.; Kim, H.-Y.; Lu, Y.; Liu, Y.; Har, D.; Repic, O.; Blacklock, T. J.; Giannousis, P.;
J. Org. Chem.; (Technical Note); 1999; 64(5); 1750-1753.
DOI: 10.1021/jo9821473

http://rapidshare.de/files/3012894/prashad.djvu.html

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Neoclerodane Diterpenes as a Novel Scaffold for Opioid Receptor Ligands

Wayne W. Harding, Kevin Tidgewell, Nathan Byrd, Howard Cobb, Christina M. Dersch, Eduardo R. Butelman, Richard B. Rothman, and Thomas E. Prisinzano*
J Med. Chem., 48 (15), 4765
http://rapidshare.de/files/4142862/jm048963m.pdf.html

Abstract:

Structural modification of salvinorin A, the active component of Salvia divinorum, has resulted in the synthesis of novel neoclerodane diterpenes with opioid receptor affinity and activity. We report in this study a nonnitrogenous neoclerodane diterpene with opioid receptor affinity (13) that is an agonist at opioid receptors. This represents the identification of a novel structural class of opioid receptor agonists.

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Degradation of a-Methyl-3,P-dihydroxyphenylalanine (a-MethylDOPA)
H. L. SLATESD, . TAUBC, . H. Kuo, AND N. L. WENDLER
Journal of Organic Chemistry Table of Contents Vol. 29,pg.1424-1429, No. 6: June 1964
http://rapidshare.de/files/4395881/jo01029a039.pdf.html

Abstract

a-MethylDOPA has been degraded in high yield by several pathways to derivatives of 3,4dihydroxyphenyl-
acetone. These degradations comprise recycle routes for the utilization of D-( +)-a-methylDOPA in the synthesis
of L-( - )-a-methylDOPA.

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Studies on Amino Alcohols. I. The Preparation and Dehydration of Certain Aliphatic Tertiary Amino Alcohols
Barbara Knapp Campbell and Kenneth N. Campbell
Journal of the American Chemical Society Table of Contents(1938) Vol. 60, No. 6: , pp 1372 - 1376;

DOI: 10.1021/ja01273a028

http://rapidshare.de/files/4435033/Studies_on_Amino_Alcohols._I.pdf.html
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The Condensation of Aliphatic Alcohols with Aromatic Hydrocarbons. I. The Preparation of Mesitylene and sym-Triethylbenzene
James F. Norris and John N. Ingraham
journal of the American Chemical Society (1938),Vol. 60, No. 6:,pp 1421 - 1423;

DOI: 10.1021/ja01273a04

http://rapidshare.de/files/4435062/The_Condensation.pdf.html

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Stereoisomers of N-[1-(2-hydroxy-2-phenylethyl)-3-methyl-4-peperidyl]-N-phenyloropanamide: synthesis, stereochemistry, analgesic activity, and opioid receptor binding characteristics.
Wang ZX, Zhu YC, Jin WQ, et al.
[red]J Med Chem 1995; 38:3652-9[/red]

http://rapidshare.de/files/4887190/jm00018a026.pdf.html

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Isolation and structure of a brain constituent that binds to the cannabinoid receptor.
Devane WA, Hanus L, Breuer A, Pertwee RG, Stevenson LA, Griffin G, Gibson D, Mandelbaum A, Etinger A, Mechoulam R.
Science, 1992, 258(5090), 1946-1949
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=1470919

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Production of a new lysergic acid derivative in submerged culture by a strain of Claviceps Paspali Stevens and Hall
Arcamone, F.; Chain, E. B.; Ferretti, A.; Minghetti, A.; Pennella, P.; Tonolo, A.; Vero, Lidia
Proceedings of the Royal Society 155B: 26-54, 1961
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Abstract
1. The production of a new lysergic acid derivative, identified as D-lysergic acid ? -hydroxyethylamide, in submerged culture and in yields up to 1 mg/ml. and above, by a strain of Claviceps paspali Stevens & Hall is reported; this substance can be converted in high yields into D-lysergic acid amide. 2. The morphological properties of this strain under different culture conditions are examined and it is shown that it grows in a form resembling natural sclerotia. 3. The biochemical culture conditions for the production of the new lysergic acid derivative in shake flasks and in stirred fermenters, the course of the fermentation, the methods for the isolation and purification of the substance and its transformation products and some of its chemical and physical properties are described.

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Synthesis, in Vitro Characterization, and Radiolabeling of N,N-Dimethyl-2-(2'-amino-4'-substituted-phenylthio)benzylamines: Potential Candidates as Selective Serotonin Transporter Radioligands
Nachwa Jarkas, Jonathan McConathy, Ronald J. Voll, and Mark M. Goodman*
J. Med. Chem., 48 (13), 4254 -4265, 2005

http://ripway.com/members/getfile.asp?file=\2005-6\328117\JMEDCHEM2005%2E48%2E4256%2D4265%2Epdf

Abstract:
A series of N,N-dimethylated and N-monomethylated analogues of N,N-dimethyl-2-(2'-amino-4'-iodophenylthio)benzylamine substituted at the 4'-phenyl position have been prepared and evaluated in vitro for serotonin transporter (SERT) selectivity. Several derivatives were prepared where the 4'-position was either unsubstituted 13 and 33a or substituted with methyl 14a and 33b, ethenyl 14b and 34, ethyl 16 and 35, hydroxymethyl 20 and 41, hydroxyethyl 22, fluoroethyl 23, hydroxypropyl 27, and fluoropropyl 28. Competition binding in cells stably expressing the transfected human SERT, dopamine transporter (DAT), and norepinephrine transporter (NET) using [3H]citalopram, [3H]WIN 35,428 or [125I]RTI-55, and [3H]nisoxetine, respectively, demonstrated the following order of SERT affinity (Ki (nM)): 14a (0.25) > 16 (0.49) > 20 (0.57) > 14b (1.12) > 13 (1.59) > 33b (1.94) = 35 (2.04) 23 (8.50) = 28 (8.55) > 41 (15.11) 22 (51) > 33a (83.43) > 27 (92). The Ki values revealed that most of these derivatives displayed a high affinity for the SERT and a high selectivity over the DAT and NET. Moreover, substitution at the 4'-position of the dimethylated and monomethylated benzylamines differently influenced SERT binding: (i) the dimethylated benzylamines exhibited higher SERT affinity than the monomethylated ones, (ii) alkyl, alkenyl, or hydroxymethyl functions at the 4'-position afford compounds with high SERT affinity, and (iii) -hydroxy and fluoro-substituted ethyl and propyl groups at the 4'-position decrease the SERT affinity. From this series, the dimethylated derivatives 13, 14a, 14b, 16, and 20 were radiolabeled with carbon-11 and their log P7.4 was calculated as a measure of their potential brain penetrance as positron emission tomography SERT imaging agents.

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Quinazolines and 1,4-benzodiazepines. 5-Pyrimidyl-and 5-pyrazinylbenzodiazepines.
J.Med.Chem. 1977 Oct;20(10):1312-7.

http://rapidshare.de/files/3568361/jm00220a017.pdf.html

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A Convenient Method for Synthesis of Enantiomerically Enriched Methylphenidate from N-Methoxycarbonylpiperidine

Matsumura, Y.; Kanda, Y.; Shirai, K.; Onomura, O.; Maki, T.;
Org. Lett.; (Communication); 1999; 1(2); 175-178. DOI: 10.1021/ol9905046

Synthesis and Pharmacology of Ethylphenidate Enantiomers: The Human Transesterification Metabolite of Methylphenidate and Ethanol

Patrick, K. S.; Williard, R. L.; VanWert, A. L.; Dowd, J. J.; Oatis, J. E., Jr.; Middaugh, L. D.;
J. Med. Chem.; (Article); 2005; 48( 8 ); 2876-2881. DOI: 10.1021/jm0490989

Synthesis and Evaluation of Dopamine and Serotonin Transporter Inhibition by Oxacyclic and Carbacyclic Analogues of Methylphenidate

Meltzer, P. C.; Wang, P.; Blundell, P.; Madras, B. K.;
J. Med. Chem.; (Article); 2003; 46( 8 ); 1538-1545. DOI: 10.1021/jm0205292

Investigations in Heterocycles. XV. Methylphenidate: A Versatile Intermediate in the Synthesis of Bicyclic Heterocycles with a Bridgehead Nitrogen Atom

George DeStevens, Marcel Bernier;
J. Med. Chem.; 1964; 7(2); 146-149.

Synthesis and Pharmacology of Potential Cocaine Antagonists. 2. Structure-Activity Relationship Studies of Aromatic Ring-Substituted Methylphenidate Analogs

Deutsch, H. M.; Shi, Q.; Gruszecka-Kowalik, E.; Schweri, M. M.;
J. Med. Chem.; (Article); 1996; 39(6); 1201-1209. DOI: 10.1021/jm950697c

Asymmetric Synthesis and Pharmacology of Methylphenidate and Its Para-Substituted Derivatives

Thai, D. L.; Sapko, M. T.; Reiter, C. T.; Bierer, D. E.; Perel, J. M.;
J. Med. Chem.; (Article); 1998; 41(4); 591-601. DOI: 10.1021/jm970620

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An Efficient Fischer Indole Synthesis of Avitriptan, a Potent 5-HT1D Receptor Agonist
Paul R. Brodfuehrer, Bang-Chi Chen, Thomas R. Sattelberg, Sr., Patrick R. Smith, Jayachandra P. Reddy, Derron R. Stark, Sandra L. Quinlan, J. Gregory Reid, John K. Thottathil, and Shaopeng Wang
J. Org. Chem., 62 (26), 9192 -9202, 1997

Direct Link URL: http://home.ripway.com/2005-1/247174/AnEfficientFischerIndoleSynthesisofAvitriptanaPotent5-HT1DReceptorAgonist.pdf
Alternate URL: http://host.picturewizard.com/2005-1/247174/AnEfficientFischerIndoleSynthesisofAvitriptanaPotent5-HT1DReceptorAgonist.pdf

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Synthesis and Biological Activity of 3-[2-(Dimethylamino)ethyl]-5-[(1,1-dioxo-5-methyl-1,2,5-thiadiazolidin-2-yl)methyl]-1H-indole and Analogs: Agonists for the 5-HT1D Receptor
Jose L. Castro, Raymond Baker, Alexander R. Guiblin, Sarah C. Hobbs, Matthew R. Jenkins, Michael G. N. Russell, Margaret S. Beer, Josephine A. Stanton, Kate Scholey, and et al.
Journal of Medicinal Chemistry Vol. 37, No. 19: 1994,3023 - 3032

Direct Link URL: http://home.ripway.com/2005-1/247174/SynthesisandBiologicalActivityof3-[2-(Dimethylamino)ethyl]-5(-l[l-dioxo-5-methy1l-25-thiadiazolidin-2-y1)-methyl]-lH-indoleandAnalogues-Agonistsforthe5-HTIDReceptor.pdf
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Direct Halogenation of Alcohols and Their Derivatives with tert-Butyl Halides in the Ionic Liquid [pmIm]Br under Sonication Conditions - A Novel, Efficient and Green Methodology
Brindaban C. Ranu *, Ranjan Jana
European Journal of Organic Chemistry Volume 2005, Issue 4 , Pages 755 - 758

Direct Link URL: http://home.ripway.com/2005-1/247174/DirectHalogenationofAlcoholsandTheirDerivativeswithtert-ButylHalidesintheIonicLiquid[pmIm]BrunderSonicationConditions–ANovelEfficientandGreenMethodology.pdf
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Abstract
A novel halogenating reagent system for direct halogenation of alcohols has been developed. tert-Butyl bromide, chloride and iodide in combination with the ionic liquid [pmIm]Br have been found to convert alcohols into the corresponding bromides, chlorides and iodides under sonication conditions (or heating) in good yields. Although a variety of primary and secondary alcohols participated in this reaction without any difficulty, tertiary alcohols remained inert. Several alcohol derivatives such as OTMS, OTBDMS, OAc, OTS and OTHP are also transformed into the corresponding halides in one-pot fashion by this procedure. A plausible rationale for this transformation is also presented. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Proton NMR configurational correlation for retro-inverso dipeptides: application to the determination of the absolute configuration of "enkephalinase" inhibitors. Relationships between stereochemistry and enzyme recognition
M. C. Fournie-Zaluski, E. Lucas-Soroca, J. Devin, B. P. Roques
J. Med. Chem., 1986, 29(5), 751-757
http://rapidshare.de/files/5143598/J._Med._Chem.__1986__29_5___751-757.pdf.html

New bidentates as full inhibitors of enkephalin-degrading enzymes: synthesis and analgesic properties
Marie Claude Fournie-Zaluski, Annie Coulaud, Romaine Bouboutou, Pierre Chaillet, Jocelyne Devin, Gilles Waksman, Jean Costentin, Bernard P. Roques
J. Med. Chem., 1985, 28(9), 1158-1169
http://rapidshare.de/files/5143707/J._Med._Chem.__1985__28_9___1158-1169.pdf.html

New carboxyalkyl inhibitors of brain enkephalinase: synthesis, biological activity and analgesic properties
Marie Claude Fournie-Zaluski, Pierre Chaillet, Evelyne Soroca-Lucas, Helene Marcais-Collado, Jean Costentin, Bernard P. Roques
J. Med. Chem., 1983, 26(1), 60-65
http://rapidshare.de/files/5143763/J._Med._Chem.__1983__26_1___60-65.pdf.html

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