- Generation of the furan analogue of ortho-quinodimethane by 1,4-elimination of 3-acetoxymethyl-2-tributylstannylmethylfuran
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2,3-Dimethylene-2,3-dihydrofuran is generated in situ by boron trifluoride induced 1,4-conjugative elimination of tributylstannylmethyl acetate and then trapped with dienophiles to give the corresponding Diels-Alder cycloadducts.
- Liu, Guo-Bin,Mori, Hajime,Katsumura, Shigeo
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- New methodology for 2-alkylation of 3-furoic acids: Application to the synthesis of tethered UC-781/d4T bifunctional HIV reverse-transcriptase inhibitors
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New methodology for 2-alkylation of 3-furoic acids is presented involving Wittig reactions of the 3-methoxycarbonyl-2-furanylmethylphosphonium salt. The methodology has been used to prepare a tethered 2-alkylated-UC-781/d4T conjugate as a potentially new type of HIV reverse-transcriptase inhibitor.
- Arnott, Gareth,Hunter, Roger,Mbeki, Linda,Mohamed, Ebrahim
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p. 4023 - 4026
(2007/10/03)
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- On the bromination of methyl 2-methyl-3-furoate
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Methyl 2-methyl-3-furoate was subjected to bromination with N-bromosuccinimide (NBS), a milder brominating reagent, under different reaction conditions to obtain a variety of selective brominated products.
- Khatuya, Haripada
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p. 2643 - 2644
(2007/10/03)
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- Anionic [4+2] cycloaddition strategy to linear furocoumarins: Synthesis of 8 methoxypsoralen and its isoster
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The surfoxide esters 14 and 20d are successfully annulated with bicyclic enone 8 in the presence of (t)BuOLi to provide the pentacyclic ketones 9a and 21a respectively in good yields (≤70%). Flash vacuum pyrolysis of O-methyl derivatives 9b and 21b at - 5000 C/. 1 mm provide furoindacenones 16b and 22b respectively, which in turn are convertible to furocoumarins 1 and 3.
- Mal, Dipakranjan,Bandhyopadhyay, Mousumi,Datta,Murty, Kadiyala V. S. N.
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p. 7525 - 7538
(2007/10/03)
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- N-3-Substituted Pyrimidones as Potent, Orally Active, AT1 Selective Angiotensin II Receptor Antagonists
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A novel series of nonpeptide angiotensin II (A II) antagonists containing a pyrimidinone ring which carries a C-linked biphenyltetrazole moiety and a carboxyheteroaryl group on the 3-position have been prepared.Their affinity for the AT1 receptor was determined in a binding assay on rat adrenal cortical membranes.The in vivo antihypertensive properties were tested by evaluating the inhibition of the pressor response to A II followed by iv and id administration.Extensive molecular modeling studies, including comparison of molecular electrostatic potential distributions, conformational analysis, and overlays on a computational pharmacophore model of A II, were used to evaluate structural parameters of the new compounds, in comparison to other known A II antagonists (e.g., DUP-753 and SKandF 108566).According to the modeling studies, the introduction of a (carboxyheteroaryl)methyl moiety at the 3-position of the pyrimidinone ring led to derivatives with increased potency.Methyl 2-methyl>-1-(6H)-pyrimidinyl>methyl>-3-thiophenecarboxylate (3k, LR-B/081), one of the most potent compounds in the series (Ki = 1.4 nM), exhibited a marked antihypertensive activity on oral administration to conscious renal hypertensive rats, with long duration of action.It was selected for clinical evaluation in the treatment of hypertension in man.
- Salimbeni, Aldo,Canevotti, Renato,Paleari, Fabio,Poma, Davide,Caliari, Saturnino,et al.
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p. 4806 - 4820
(2007/10/03)
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