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Synlett
Volumn , Issue 13, 2009, Pages 2149-2153
A straightforward route to piloty's acid derivatives: A class of potential nitroxyl-generating prodrugs
Author keywords

HNO; MgO; NO; Piloty's acid; Sulfohydroxamic acids
Indexed keywords

(7,7 DIMETHYL 2 OXOBICYCLO[2.2.1]HEPTAN 1 YL) N HYDROXYMETHANESULFONAMIDE; 4 TERT BUTYL N HYDROXYBENZENESULFONAMIDE; 4 TERT BUTYL N METHOXY N METHYLBENEZENESULFONAMIDE; BENZENESULFONAMIDE DERIVATIVE; N HYDROXY 2 METHYLBENZENESULFONAMIDE; N HYDROXY 2 NITROBENZENESULFONAMIDE; N HYDROXY 2,4,6 TRIISOPROPYLBENZENESULFONAMIDE; N HYDROXY 2,6 DIMETHOXYBENZENESULFONAMIDE; N HYDROXY 4 METHYLBENZENESULFONAMIDE; N HYDROXYTHIOPHENE 2 SULFONAMIDE; UNCLASSIFIED DRUG;
EID: 68949184343     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217565     Document Type: Article
Times cited : (26)
References (64)
  • 4
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    • 2O via a transient hyponitrous acid: (a) Smith, P. A. S.; Hein, G. E. J. Am. Chem. Soc. 1960, 82, 5731.
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    • Angeli's salt is cytotoxic at low millimolar concentrations: Wink, D. A. Arch. Biochem. Biophys. 1998, 351, 66.
    • Angeli's salt is cytotoxic at low millimolar concentrations: Wink, D. A. Arch. Biochem. Biophys. 1998, 351, 66.
  • 17
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    • Piloty's acids have shown to be selective inhibitors of human mitochondrial aldehyde dehydrogenase and potent vasodilators. See:, Packer, L, Ed, Academic Press: New York
    • (b) Piloty's acids have shown to be selective inhibitors of human mitochondrial aldehyde dehydrogenase and potent vasodilators. See: King, S. B.; Nagasawa, H. T. Chemical approaches toward generation of nitroxyl (HNO), in Methods in Enzymology; Packer, L., Ed.; Academic Press: New York, 1998, 211-220.
    • (1998) Chemical approaches toward generation of nitroxyl (HNO), in Methods in Enzymology , pp. 211-220
    • King, S.B.1    Nagasawa, H.T.2
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    • and references cited therein
    • Miranda, K. M. Coord. Chem. Rev. 2005, 249, 433; and references cited therein.
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    • Recently, Toscano et al. have demonstrated that a series of aromatic and nonaromatic N-hydroxysulfonamide derivatives release nitroxyl at a controlled rate under physiological conditions: Toscano, J. P, Brookfield, F. A, Cohen, A. D, Courtney, S. M, Frost, L. M, Kalish, V. J. US Patent, 20070299107A1, 2007
    • Recently, Toscano et al. have demonstrated that a series of aromatic and nonaromatic N-hydroxysulfonamide derivatives release nitroxyl at a controlled rate under physiological conditions: Toscano, J. P.; Brookfield, F. A.; Cohen, A. D.; Courtney, S. M.; Frost, L. M.; Kalish, V. J. US Patent, 20070299107A1, 2007.
  • 32
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    • During the recrystallization of benzenesulfohydroxamic acid previously prepared via a classical sulfonylation procedure Engel et al, ref. 14b) have isolated and characterized several side products such as, for example: PhSO 3, H3NNHSO2Ph and PhSH accounted for the reduction of PhSO2Cl by NH2OH
    • 2OH).
  • 35
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    • Although sulfonyl chlorides are widely used for N-sulfonylation of amines, their drawbacks are the instability and the too strong reactivity: Kim, H.-K, Park, Y.-D, Lee, M.-H, Chung, H.-A, Kweon, D.-H, Cho, S.-D, Yoon, Y.-J. Bull. Korean Chem. Soc. 2003, 24, 1655
    • Although sulfonyl chlorides are widely used for N-sulfonylation of amines, their drawbacks are the instability and the too strong reactivity: Kim, H.-K.; Park, Y.-D.; Lee, M.-H.; Chung, H.-A.; Kweon, D.-H.; Cho, S.-D.; Yoon, Y.-J. Bull. Korean Chem. Soc. 2003, 24, 1655.
  • 36
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    • Low molecular weight aliphatic sulfohydroxamic acids are the most important compounds for their tendency to generate HNO under physiological condition at about pH 7, see Scheme 1
    • Low molecular weight aliphatic sulfohydroxamic acids are the most important compounds for their tendency to generate HNO under physiological condition (at about pH 7, see Scheme 1).
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    • Among these metal-mediated reactions, magnesium oxide has received considerable interest because of its novel surface catalytic properties: Kim, D.-H.; Rho, H.-S.; Youb, J. W.; Lee, J. C. Tetrahedron Lett. 2002, 43, 277.
    • Among these metal-mediated reactions, magnesium oxide has received considerable interest because of its novel surface catalytic properties: Kim, D.-H.; Rho, H.-S.; Youb, J. W.; Lee, J. C. Tetrahedron Lett. 2002, 43, 277.
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    • Babu et al. have demonstrated the advantages obtained by the use of magnesium oxide in the synthesis of N-Fmoc-protected amino acid hydroxamates: Vasanthakumar, G .-R.; Babu, V. V. S. Tetrahedron Lett. 2003, 44, 4099.
    • Babu et al. have demonstrated the advantages obtained by the use of magnesium oxide in the synthesis of N-Fmoc-protected amino acid hydroxamates: Vasanthakumar, G .-R.; Babu, V. V. S. Tetrahedron Lett. 2003, 44, 4099.
  • 57
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    • 13C NMR and mass spectroscopy.
    • 13C NMR and mass spectroscopy.
  • 58
    • 68949179170 scopus 로고    scopus 로고
    • General Procedure for the Sulfonylation of Hydroxylamine in the Presence of MgO; N-Hydroxy-2-methylbenzenesulfonamide (2b, Hydroxylamine hydrochloride (0.72 g, 10 mmol) in MeOH-H2O (3:2, 5 mL) was treated with MgO (0.34 g, 8.6 mmol, then a solution of o-toluenesulfonyl chloride (1a; 0.8 g, 4.3 mmol) in THF (30 mL, and MgO (0.17 g, 4.3 mmol) were added. The reaction was vigorously stirred at r.t. until the sulfonyl chloride had completely disappeared (TLC: EtOAc-hexane, 1:1; 2 h, Then, the mixture was filtered first through a pad of Celite, and then on a short plug of silica gel. The clear filtrate was dried over MgSO 4 and evaporated to dryness to give the resulting N-hydroxysulfonamide 2b (0.59 g, 74, as a crystalline white solid (96% purity, mp 178-180°C. 1H NMR (CDCl3, δ, 7.93 (d, J, 8.0 Hz, 1 H, 7.75 (br s, 1 H, 7.42 (t, J, 7.3 Hz, 1 H, 7.27 t, J
    • 5S: C, 41.20; H, 4.75; N, 6.01. Found: C, 41.31; H, 4.70; N, 6.12. N-Hydroxythiophene-2- sulfonamide (2f): According to the procedure previously described for 2b, the sulfohydroxamic acid 2f was isolated as a waxy solid in 96% yield (97% purity).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.