메뉴 건너뛰기




Volumn 349, Issue 1, 2006, Pages 39-49

Synthesis, discovery and mechanism of 2,6-dimethoxy-N-(4-methoxyphenyl)benzamide as potent depigmenting agent in the skin

Author keywords

Biaryl amide; Depigment agent; Dopachrome tautomerase; Melanin; Skin

Indexed keywords

2,6 DIMETHOXY N (4 METHOXYPHENYL)BENZAMIDE; 5,6 DIHYDROXYINDOLE 2 CARBOXYLIC ACID; ANILINE; BENZAMIDE DERIVATIVE; BENZOIC ACID; DEPIGMENTING AGENT; DOPACHROME TAUTOMERASE; MELAN A; MELANIN; MONOPHENOL MONOOXYGENASE; UNCLASSIFIED DRUG;

EID: 33748447149     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2006.07.206     Document Type: Article
Times cited : (23)

References (38)
  • 1
    • 0041335218 scopus 로고    scopus 로고
    • Melanogenesis and melanoma
    • Riley P. Melanogenesis and melanoma. Pigment Cell Res. 16 (2003) 548-552
    • (2003) Pigment Cell Res. , vol.16 , pp. 548-552
    • Riley, P.1
  • 3
    • 0035999729 scopus 로고    scopus 로고
    • Comparative biochemistry of eumelanogenesis and the protective roles of phenoloxidase and melanin in insects
    • Sugumaran M. Comparative biochemistry of eumelanogenesis and the protective roles of phenoloxidase and melanin in insects. Pigment Cell Res. 15 (2002) 2-9
    • (2002) Pigment Cell Res. , vol.15 , pp. 2-9
    • Sugumaran, M.1
  • 4
    • 0027233399 scopus 로고
    • Role of tyrosinase as the determinant of pigmentation in cultured human melanocytes
    • Iozumi K., Hoganson G.E., Pemella R., Everett M.A., and Fuller B.B. Role of tyrosinase as the determinant of pigmentation in cultured human melanocytes. J. Invest. Dermatol. 100 (1993) 806-811
    • (1993) J. Invest. Dermatol. , vol.100 , pp. 806-811
    • Iozumi, K.1    Hoganson, G.E.2    Pemella, R.3    Everett, M.A.4    Fuller, B.B.5
  • 8
    • 0034798327 scopus 로고    scopus 로고
    • Variation in melanin content and composition in type V and VI photoexposed and photoprotected human skin: the dominant role of DHI
    • Alaluf S., Heath A., Carter N., Atkins D., Mahalingam H., Barrett K., Kolb R., and Smitt N. Variation in melanin content and composition in type V and VI photoexposed and photoprotected human skin: the dominant role of DHI. Pigment Cell Res. 14 (2001) 337-347
    • (2001) Pigment Cell Res. , vol.14 , pp. 337-347
    • Alaluf, S.1    Heath, A.2    Carter, N.3    Atkins, D.4    Mahalingam, H.5    Barrett, K.6    Kolb, R.7    Smitt, N.8
  • 9
    • 0038577971 scopus 로고
    • Function and skin depigmental activity of crude drugs
    • Ikeda T., and Tsutsumi T. Function and skin depigmental activity of crude drugs. J. Fragrance 6 (1990) 59-66
    • (1990) J. Fragrance , vol.6 , pp. 59-66
    • Ikeda, T.1    Tsutsumi, T.2
  • 10
    • 0037013315 scopus 로고    scopus 로고
    • Oxyresveratrol and hydrostilbene compounds: inhibitory effect on tyrosinase and mechanism of action
    • Kim Y.M., Yun J., Lee C.K., Lee H., Min K.R., and Kim Y.S. Oxyresveratrol and hydrostilbene compounds: inhibitory effect on tyrosinase and mechanism of action. J. Biol. Chem. 277 (2002) 16340-16344
    • (2002) J. Biol. Chem. , vol.277 , pp. 16340-16344
    • Kim, Y.M.1    Yun, J.2    Lee, C.K.3    Lee, H.4    Min, K.R.5    Kim, Y.S.6
  • 12
    • 0036549924 scopus 로고    scopus 로고
    • (4-Methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a nitrogen analog of stilbene as a potent inhibitor of melanin production
    • Choi S.Y., Kim S., Kim H., Suk K., Hwang J.S., Lee B.G., Kim A., and Kim S.Y. (4-Methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a nitrogen analog of stilbene as a potent inhibitor of melanin production. Chem. Pharm. Bull. 50 (2002) 450-452
    • (2002) Chem. Pharm. Bull. , vol.50 , pp. 450-452
    • Choi, S.Y.1    Kim, S.2    Kim, H.3    Suk, K.4    Hwang, J.S.5    Lee, B.G.6    Kim, A.7    Kim, S.Y.8
  • 13
    • 0031053263 scopus 로고    scopus 로고
    • Simple synthesis of 5-substituted resorcinols
    • Alonso E., Ramon D., and Yus M. Simple synthesis of 5-substituted resorcinols. J. Org. Chem. 62 (1997) 417-421
    • (1997) J. Org. Chem. , vol.62 , pp. 417-421
    • Alonso, E.1    Ramon, D.2    Yus, M.3
  • 14
    • 0032514987 scopus 로고    scopus 로고
    • Synthesis of higher oxidized metabolites of dibenz[a,j] anthracene implicated in the mechanism of carcinogenesis
    • Zang J., and Doi W. Synthesis of higher oxidized metabolites of dibenz[a,j] anthracene implicated in the mechanism of carcinogenesis. J. Org. Chem. 63 (1998) 8125-8132
    • (1998) J. Org. Chem. , vol.63 , pp. 8125-8132
    • Zang, J.1    Doi, W.2
  • 15
    • 0033578694 scopus 로고    scopus 로고
    • Convergent solution-phase combinatorial synthesis with multiplication of diversity though rigid biaryl and diarylacetylene couplings
    • Borger D., Jiang W., and Goldberg J. Convergent solution-phase combinatorial synthesis with multiplication of diversity though rigid biaryl and diarylacetylene couplings. J. Org. Chem. 64 (1999) 7094-7100
    • (1999) J. Org. Chem. , vol.64 , pp. 7094-7100
    • Borger, D.1    Jiang, W.2    Goldberg, J.3
  • 16
    • 1642493656 scopus 로고    scopus 로고
    • Benzylamide derivative compound attenuates the ultraviolet B-induced hyperpigmentation in the brownish guinea pig skin
    • Choi S.Y., Kim S., Hwang J.S., Lee B.G., Kim H., and Kim S.Y. Benzylamide derivative compound attenuates the ultraviolet B-induced hyperpigmentation in the brownish guinea pig skin. Biochem. Pharmacol. 67 (2004) 707-715
    • (2004) Biochem. Pharmacol. , vol.67 , pp. 707-715
    • Choi, S.Y.1    Kim, S.2    Hwang, J.S.3    Lee, B.G.4    Kim, H.5    Kim, S.Y.6
  • 17
    • 0024461524 scopus 로고
    • Dietary supplementation with n-6 essential fatty acids in atopic eczema
    • Wright S. Dietary supplementation with n-6 essential fatty acids in atopic eczema. J. Dermatol. Treat. 1 (1990) 47-49
    • (1990) J. Dermatol. Treat. , vol.1 , pp. 47-49
    • Wright, S.1
  • 18
    • 0021796067 scopus 로고
    • Regulation of melanin synthesis of B16 mouse melanoma cells by 1 alpha, 2,5-dihydroxyvitamin D3 and retinoic acid
    • Hosoi J., Abe E., Suda T., and Kuroki T. Regulation of melanin synthesis of B16 mouse melanoma cells by 1 alpha, 2,5-dihydroxyvitamin D3 and retinoic acid. Cancer Res. 45 (1985) 1474-1478
    • (1985) Cancer Res. , vol.45 , pp. 1474-1478
    • Hosoi, J.1    Abe, E.2    Suda, T.3    Kuroki, T.4
  • 19
    • 0032804137 scopus 로고    scopus 로고
    • Inhibition of l-tyrosine-induced micronuclei production by phenylthiourea in human melanoma cells
    • Poma A., Bianchini S., and Miranoa M. Inhibition of l-tyrosine-induced micronuclei production by phenylthiourea in human melanoma cells. Mutat. Res. 446 (1999) 143-148
    • (1999) Mutat. Res. , vol.446 , pp. 143-148
    • Poma, A.1    Bianchini, S.2    Miranoa, M.3
  • 21
    • 0034047660 scopus 로고    scopus 로고
    • Downregulation of tyrosinase activity in human melanocyte cell culture by yohimbine
    • Fuller B.B., Drake M.A., Spaulding D.T., and Chaudhry F. Downregulation of tyrosinase activity in human melanocyte cell culture by yohimbine. J. Invest. Dermatol. 114 (2000) 268-276
    • (2000) J. Invest. Dermatol. , vol.114 , pp. 268-276
    • Fuller, B.B.1    Drake, M.A.2    Spaulding, D.T.3    Chaudhry, F.4
  • 22
    • 1642509686 scopus 로고
    • The effect of fatty acids on tyrosinase activity
    • Seiji M. (Ed), University of Tokyo Press, Tokyo
    • Shono S., and Toda K. The effect of fatty acids on tyrosinase activity. In: Seiji M. (Ed). Pigment Cell (1981), University of Tokyo Press, Tokyo 263-268
    • (1981) Pigment Cell , pp. 263-268
    • Shono, S.1    Toda, K.2
  • 23
    • 0031711547 scopus 로고    scopus 로고
    • Linoleic acid and α-linoleic acid lightens ultraviolet-induced hyperpigmentation of the skin
    • Hideya A., Atsuko R., Akira H., Masahiro O., and Masamitsu I. Linoleic acid and α-linoleic acid lightens ultraviolet-induced hyperpigmentation of the skin. Arch. Dermatol. Res. 290 (1998) 375-381
    • (1998) Arch. Dermatol. Res. , vol.290 , pp. 375-381
    • Hideya, A.1    Atsuko, R.2    Akira, H.3    Masahiro, O.4    Masamitsu, I.5
  • 24
    • 0022536094 scopus 로고
    • Differential analysis of experimental hypermelanogenesis induced by UVB, PUVA and allegic dermatitis using a brownish guinea pig model
    • Imokawa G., Kawai M., Mishima Y., and Motegi I. Differential analysis of experimental hypermelanogenesis induced by UVB, PUVA and allegic dermatitis using a brownish guinea pig model. Arch. Dermatol. Res. 278 (1986) 352-362
    • (1986) Arch. Dermatol. Res. , vol.278 , pp. 352-362
    • Imokawa, G.1    Kawai, M.2    Mishima, Y.3    Motegi, I.4
  • 25
    • 0031705436 scopus 로고    scopus 로고
    • The sodium hydroxide erosion assay: a revision of alkali resistance test
    • Ludger K., Albert M.K., and Tracy S. The sodium hydroxide erosion assay: a revision of alkali resistance test. Arch. Dermatol. Res. 290 (1998) 382-387
    • (1998) Arch. Dermatol. Res. , vol.290 , pp. 382-387
    • Ludger, K.1    Albert, M.K.2    Tracy, S.3
  • 27
    • 0034602334 scopus 로고    scopus 로고
    • A pinacol rearrangement/oxidation synthetic route to hydroxyphenstatin
    • Pettit G., Lippert III W.J., and Herald D. A pinacol rearrangement/oxidation synthetic route to hydroxyphenstatin. J. Org. Chem. 65 (2000) 7438-7444
    • (2000) J. Org. Chem. , vol.65 , pp. 7438-7444
    • Pettit, G.1    Lippert III, W.J.2    Herald, D.3
  • 28
    • 0029066847 scopus 로고
    • Antineoplastic agents 291. Isolation and synthesis of combretastatin A-4, A-5 and A-6
    • Pettit G., Singh S., Boyd M., Hamel E., Pettit R., Schmidt J., and Hogan F. Antineoplastic agents 291. Isolation and synthesis of combretastatin A-4, A-5 and A-6. J. Med. Chem. 38 (1995) 1666-1672
    • (1995) J. Med. Chem. , vol.38 , pp. 1666-1672
    • Pettit, G.1    Singh, S.2    Boyd, M.3    Hamel, E.4    Pettit, R.5    Schmidt, J.6    Hogan, F.7
  • 29
    • 0033533645 scopus 로고    scopus 로고
    • Synthesis and cytotoxic activities of a new benzo[c] phenanthridine alkaloid, 7-hydroxynitidine, and some 9-oxygenated benzo[cphenanthridine derivatives
    • Nakanishi T., and Suzuki M. Synthesis and cytotoxic activities of a new benzo[c] phenanthridine alkaloid, 7-hydroxynitidine, and some 9-oxygenated benzo[cphenanthridine derivatives. Org. Lett. 1 7 (1999) 985-988
    • (1999) Org. Lett. , vol.1 , Issue.7 , pp. 985-988
    • Nakanishi, T.1    Suzuki, M.2
  • 31
    • 0023145290 scopus 로고
    • A line of non-tumorigenic mouse melanocytes, syngeneic with the B16 melanoma and requiring a tumour promoter for growth
    • Bennett D., Cooper P., and Hart I. A line of non-tumorigenic mouse melanocytes, syngeneic with the B16 melanoma and requiring a tumour promoter for growth. Int. J. Cancer 39 (1987) 414-418
    • (1987) Int. J. Cancer , vol.39 , pp. 414-418
    • Bennett, D.1    Cooper, P.2    Hart, I.3
  • 33
    • 0036293855 scopus 로고    scopus 로고
    • Functional expression and characterization of aceds aegypi dopachrome conversion enzyme
    • Fang J., Han Q., Johnson J.K., Christensen B.M., and Li J. Functional expression and characterization of aceds aegypi dopachrome conversion enzyme. Biochem. Biophys. Res. Commun. 290 (2002) 287-293
    • (2002) Biochem. Biophys. Res. Commun. , vol.290 , pp. 287-293
    • Fang, J.1    Han, Q.2    Johnson, J.K.3    Christensen, B.M.4    Li, J.5
  • 34
    • 0026661225 scopus 로고
    • α-MSH and other melanogenic activators mediate opposite effects on tyrosinase and dopachrome tautomerase in B16/F10 mouse melanoma cells
    • Martinez J., Solano F., Garcia J., Jara J., and Lozano J. α-MSH and other melanogenic activators mediate opposite effects on tyrosinase and dopachrome tautomerase in B16/F10 mouse melanoma cells. J. Invest. Dermatol. 99 (1992) 435-439
    • (1992) J. Invest. Dermatol. , vol.99 , pp. 435-439
    • Martinez, J.1    Solano, F.2    Garcia, J.3    Jara, J.4    Lozano, J.5
  • 35
    • 0021905120 scopus 로고
    • Decreased dopachrome oxidoreductase activity in yellow mice
    • Barber J.I., Townsend D., Olds D.P., and King R.A. Decreased dopachrome oxidoreductase activity in yellow mice. J. Hered. 76 (1985) 59-60
    • (1985) J. Hered. , vol.76 , pp. 59-60
    • Barber, J.I.1    Townsend, D.2    Olds, D.P.3    King, R.A.4
  • 37
    • 0035091825 scopus 로고    scopus 로고
    • Interaction of major coat color gene functions in mice as studied by chemical analysis of eumelanin and pheomelanin
    • Lamoreux M.L., Wakamatsu K., and Ito S. Interaction of major coat color gene functions in mice as studied by chemical analysis of eumelanin and pheomelanin. Pigment Cell Res. 14 (2001) 23-31
    • (2001) Pigment Cell Res. , vol.14 , pp. 23-31
    • Lamoreux, M.L.1    Wakamatsu, K.2    Ito, S.3
  • 38
    • 0026446976 scopus 로고
    • TRP-2/DT, a new early melanoblast marker, shows that steel growth factor (C-kit ligand) is a survival factor
    • Steel K.P., Davidson D.R., and Jackson I.J. TRP-2/DT, a new early melanoblast marker, shows that steel growth factor (C-kit ligand) is a survival factor. Development 115 (1992) 1111-1119
    • (1992) Development , vol.115 , pp. 1111-1119
    • Steel, K.P.1    Davidson, D.R.2    Jackson, I.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.