Organic disulfide and related substances. XXII. Substituted benzyl 2-(n-decylamino)ethyl disulfide hydrochlorides. A possible neighboring-group effect involving sulfur

Bellas, M.; Tuleen, David L.; Field, Lamar

doi:10.1021/jo01283a051

Cited by 14 publications

(9 citation statements)

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“…Subsequent treatment with methanolic ammonia gave 6-chloro-9-β- d -ribofuranosyl-9 H -purine ( 3 ), which on coupling with trityl chloride resin gave the key intermediate 4 . Nucleophilic displacement with the appropriate thiols led the resin-linked 6-(substituted benzylthio)purine 5 . Cleavage from the resin with 2% trifluoroacetic acid and 5% triisopropylsilane afforded the nearly pure 6-(substituted benzylthio)purines 6 in excellent overall yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Activity and Molecular Modeling of 6-Benzylthioinosine Analogues as Subversive Substrates ofToxoplasmagondiiAdenosine Kinase

et al. 2004

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Toxoplasma gondii is the most common cause of secondary CNS infections in immunocompromised persons such as AIDS patients. The major route of adenosine metabolism in T. gondii is direct phosphorylation to adenosine 5'-monophosphate (AMP) catalyzed by the enzyme adenosine kinase (EC 2.7.1.20). Adenosine kinase in T. gondii is significantly more active than any other purine salvage enzyme in this parasite and has been established as a potential chemotherapeutic target for the treatment of toxoplasmosis. Subversive substrates of T. gondii,but not the human, adenosine kinase are preferentially metabolized to their monophosphorylated forms and become selectively toxic to the parasites but not their host. 6-Benzylthioinosine (BTI) was identified as an excellent subversive substrate of T. gondii adenosine kinase. Herein, we report the synthesis of new analogues of BTI as subversive substrates for T. gondii adenosine kinase. These new subversive substrates were synthesized starting from tribenzoyl protected d-ribose. To accomplish the lead optimization process, a divergent and focused combinatorial library was synthesized using a polymer-supported trityl group at the 5'-position. The combinatorial library of 20 compounds gave several compounds more active than BTI. Structure-activity relationship studies showed that substitution at the para position plays a crucial role. To investigate the reasons for this discrimination, substrates with different substituents at the para position were studied by molecular modeling using Monte Carlo Conformational Search followed by energy minimization of the enzyme-ligand complex.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Activity and Molecular Modeling of 6-Benzylthioinosine Analogues as Subversive Substrates ofToxoplasmagondiiAdenosine Kinase

et al. 2004

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“…para-Cyanobenzylmercaptan (pCBM) was synthesized using a procedure as described in ref. 23. Ethanol (Roth; analytical grade, 99.8%) was used as received.…”

Section: Experimental Chemicalsmentioning

confidence: 99%

“…Synthesis of para-cyanobenzylmercaptan (pCBM) pCBM was prepared using para-cyanobenzylbromide and thiourea. 23 para-Cyanobenzylbromide (9.8 g, 0.05 mole) and thiourea (3.8 g, 0.05 mole) were dissolved in 40 ml of ethanol and the solution was heated to about 100 1C under reflux for 1 h. The excess of solvent was removed by pumping and the residual creamy white thiuronium salt was washed with ethyl acetate. The dried solid substance was dissolved in distilled water.…”

Section: Experimental Chemicalsmentioning

confidence: 99%

Self-assembled monolayers of benzylmercaptan and para-cyanobenzylmercaptan on gold: surface infrared spectroscopic characterization

Rajalingam

Hallmann

Strunskus

et al. 2010

Phys. Chem. Chem. Phys.

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Self-assembled monolayers (SAMs) on gold substrates were prepared from benzylmercaptan (BM) and para-cyanobenzylmercaptan (pCBM), and the resulting surfaces were investigated using conventional infrared reflection-absorption spectroscopy (IRRAS) as well as polarization modulation infrared reflection-absorption spectroscopy (PM-IRRAS). IRRAS data are analyzed by comparison with transmission IR spectra and theoretical (DFT) simulations. The spectroscopic results indicate the presence of well-ordered monolayers of BM and pCBM with an orientation perpendicular to the surface. IRRAS and PM-IRRAS data are compared to each other and the respective merits of both methods are discussed.

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“…The relative stabilities of some disulfides towards disproportionation have been studied in detail [2][3][4]. The treatment of two mercaptans with bromine has been reported to give a mixture of three disulfides, one of which is unsymmetrical (Scheme 2) [5].…”

Section: Introductionmentioning

confidence: 99%

<b>Synthesis and fungicidal activity of acetyl substituted benzyl disulfides</b>

Ayodele

Olajire

Amuda

et al. 2003

Bull. Chem. Soc. Eth.

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Organic disulfide and related substances. XXII. Substituted benzyl 2-(n-decylamino)ethyl disulfide hydrochlorides. A possible neighboring-group effect involving sulfur

Cited by 14 publications

References 0 publications

Synthesis, Biological Activity and Molecular Modeling of 6-Benzylthioinosine Analogues as Subversive Substrates ofToxoplasmagondiiAdenosine Kinase

Synthesis, Biological Activity and Molecular Modeling of 6-Benzylthioinosine Analogues as Subversive Substrates ofToxoplasmagondiiAdenosine Kinase

Self-assembled monolayers of benzylmercaptan and para-cyanobenzylmercaptan on gold: surface infrared spectroscopic characterization

<b>Synthesis and fungicidal activity of acetyl substituted benzyl disulfides</b>

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