Nucleocyclitols. Coupling of Heterocyclic Bases to Cyclitol Oxiranes

Cadenas, Raúl A.; Grass, Margarita Yaber; Mosettig, Jorge; Gelpi, María E.

doi:10.1080/07328319008045106

Cited by 6 publications

(1 citation statement)

References 22 publications

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“…Their structures are shown in figure 1: No. 1:3'-(6-methylmercaptopurine-9-yl)-3'-deoxyl',5',6'-tri-0-(mcthylsulfonyl)mucoinositol (MPI) [ 10]; [11]; No. 5: l,5-dichloro-6-N-bis(2-chloroethyl)aminol',5',6/-tridcoxy-2,3,4-tri-0-(methylsulfonyl)mucoinositol (DEI) [13]; No.…”

Section: Compoundsmentioning

confidence: 99%

Action of Nitrogenated and Sulfonylated Inositol Derivatives upon the Proliferation in vitro of Normal Mouse Cells and Tumor Mouse Cells

Eiján

Puricelli²,

Joffé³

et al. 1994

Tumor Biol

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Despite the major advances of cancer chemotherapy during the past 40 years, host toxicities and drug resistance justify the need to continue the search for new antineoplastic agents. In the present work, we have studied the effect of six synthetic drugs on the in vitro growth of two murine mammary adenocarcinomas (M3 and MM3), as well as on normal embryonic cells. AI, MIC and MPI are purines coupled to a sulfonylated inositol, while DIC and DEI have nitrogen mustard as substituent. Methylsulfonylmucoinositol was the common substituent. Our results indicated that only drugs substituted with nitrogen mustards had an antiproliferative effect. DEI was more effective on tumor cells than on normal cells.

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Section: Compoundsmentioning

confidence: 99%

Action of Nitrogenated and Sulfonylated Inositol Derivatives upon the Proliferation in vitro of Normal Mouse Cells and Tumor Mouse Cells

Eiján

Puricelli²,

Joffé³

et al. 1994

Tumor Biol

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On the Regio‐ and Stereoselective Synthesis of Aminocyclitols from Cyclitol Epoxides: The Effect of Li as a Chelating Agent

Serrano

Llebaría

Vázquez

et al. 2005

Chemistry A European J

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One of the general procedures given in the Experimental Section of this paper contains incorrect information. The correct procedure is given below. The authors apologise for this error. General synthetic methods and compound characterization-Reaction of epoxides with nucleophiles in the presence of LiClO 4 : A solution of the starting epoxides 1 or 2 (0.5 mmol) in CH 3 CN (5 mL) was added dropwise under argon over LiClO 4 (1.28 g, 5 mmol) at RT. A solution of NaN 3 (5 mmol) or the corresponding amine (see Table 1) in CH 3 CN (1 mL) was added next and the reaction mixture was stirred at 80 8C under argon. After 18 h, the reaction mixture was cooled to RT, quenched with H 2 O (10 mL), extracted with CH 2 Cl 2 (3 × 20 mL), and dried over anhydrous Na 2 SO 4. Filtration and evaporation afforded crude aminoalcohols (see Table 1), which were purified as indicated below.

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Nucleocyclitols. Synthesis of substituted purinyl‐muco‐inositol derivatives

Aguilar

Gelpi

Cadenas

1992

Journal of Heterocyclic Chem

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Several carbocyclic nucleoside analogs possessing a 6‐substituted purine linked to a mesylated muco‐inositol were synthesized. The coupling of triethylamine‐activated 6‐chloropurine with 2,3‐anhydro‐l,5,6‐tri‐O‐(methanesulfonyl)‐epi‐inositol gave a 6‐chloro purinyl muco‐inositol amenable to further synthetic transformations in the heterocyclic moiety by substitution of the chlorine atom by nitrogen nucleophiles such as methylamino, diethylamino, benzylamino, hydrazino, morpholino, hydroxylamino, piperidino, and glycyl groups.

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Nucleocyclitols. Coupling of Heterocyclic Bases to Cyclitol Oxiranes

Cited by 6 publications

References 22 publications

Action of Nitrogenated and Sulfonylated Inositol Derivatives upon the Proliferation in vitro of Normal Mouse Cells and Tumor Mouse Cells

Action of Nitrogenated and Sulfonylated Inositol Derivatives upon the Proliferation in vitro of Normal Mouse Cells and Tumor Mouse Cells

On the Regio‐ and Stereoselective Synthesis of Aminocyclitols from Cyclitol Epoxides: The Effect of Li as a Chelating Agent

Nucleocyclitols. Synthesis of substituted purinyl‐muco‐inositol derivatives

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