메뉴 건너뛰기




Volumn 46, Issue 3, 2003, Pages 417-426

Substituted pyrrol-1-ylacetic acids that combine aldose reductase enzyme inhibitory activity and ability to prevent the nonenzymatic irreversible modification of proteins from monosaccharides

Author keywords

[No Author keywords available]

Indexed keywords

(2 BENZOYLPYRROL 1 YL)ACETIC ACID; (3 BENZOYLPYRROL 1 YL)ACETIC ACID; [2,4 BIS(4 METHOXYBENZOYL)PYRROL 1 YL]ACETIC ACID; ACETIC ACID DERIVATIVE; ALDEHYDE REDUCTASE; EPALRESTAT; FIDARESTAT; MONOSACCHARIDE; PYRROLE DERIVATIVE; SERUM ALBUMIN; TOLRESTAT; TROLOX C; UNCLASSIFIED DRUG; ZOPOLRESTAT;

EID: 0037472690     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0209477     Document Type: Article
Times cited : (70)

References (74)
  • 1
    • 0031752685 scopus 로고    scopus 로고
    • Global burden of diabetes, 1995-2025: Prevalence, numeric estimates, and projections
    • (a) King, H.; Aubert, R. E.; Herman, W. H. Global Burden of Diabetes, 1995-2025: Prevalence, Numeric Estimates, and Projections. Diabetes Care 1998, 21, 1414-1431.
    • (1998) Diabetes Care , vol.21 , pp. 1414-1431
    • King, H.1    Aubert, R.E.2    Herman, W.H.3
  • 2
    • 0012881325 scopus 로고    scopus 로고
    • Avandia-from molecule to market for type 2 diabetes
    • Apr 7-11, 2002, Orlando, FL; American Chemical Society: Washington, DC; 132-MEDI
    • (b) Haigh, D.; Avandia-From Molecule to Market for Type 2 Diabetes. Abstracts of Papers; 223rd National Meeting of the American Chemical Society, Apr 7-11, 2002, Orlando, FL; American Chemical Society: Washington, DC, 2002; 132-MEDI.
    • (2002) Abstracts of Papers; 223rd National Meeting of the American Chemical Society , vol.132
    • Haigh, D.1
  • 3
    • 0032959371 scopus 로고    scopus 로고
    • Diabetes complications and their potential prevention: Aldose reductase inhibition and other approaches
    • Costantino, L.; Rastelli, G.; Vianello, P.; Cignarella, G.; Barlocco, D. Diabetes Complications and their Potential Prevention: Aldose Reductase Inhibition and other Approaches. Med. Res. Rev. 1999, 19, 3-23.
    • (1999) Med. Res. Rev. , vol.19 , pp. 3-23
    • Costantino, L.1    Rastelli, G.2    Vianello, P.3    Cignarella, G.4    Barlocco, D.5
  • 5
    • 4244176975 scopus 로고    scopus 로고
    • Strategies to reduce the burden of diabetic complications
    • (b) Parving, H. H. Strategies to Reduce the Burden of Diabetic Complications. Diabetologia 1997, 40, B9-B10.
    • (1997) Diabetologia , vol.40
    • Parving, H.H.1
  • 6
    • 0027370108 scopus 로고
    • The effect of intensive treatment of diabetes on the development and progression of long-term complications in insulin-dependent diabetes mellitus
    • The Diabetes Control and Complications Trial Research Group. The Effect of Intensive Treatment of Diabetes on the Development and Progression of Long-Term Complications in Insulin-Dependent Diabetes Mellitus. N. Engl. J. Med. 1993, 329, 977-986.
    • (1993) N. Engl. J. Med. , vol.329 , pp. 977-986
  • 7
    • 0029147687 scopus 로고
    • Intensive insulin therapy prevents the progression of diabetic microvascular complications in japanese patients with non-insuline-dependent diabetes mellitus: A randomized prospective 6-year study
    • (a) Okhubo, Y.; Kishikawa, H.; Araki, E.; Miyata, T.; Isami, S.; Motoyoshi, S.; Kojima, Y.; Furugoshi, N.; Shichiri, M. Intensive Insulin Therapy Prevents the Progression of Diabetic Microvascular Complications in Japanese Patients with Non-Insuline-Dependent Diabetes Mellitus: A Randomized Prospective 6-Year Study. Diabetes Res. Clin. Pract. 1995, 28, 103-117.
    • (1995) Diabetes Res. Clin. Pract. , vol.28 , pp. 103-117
    • Okhubo, Y.1    Kishikawa, H.2    Araki, E.3    Miyata, T.4    Isami, S.5    Motoyoshi, S.6    Kojima, Y.7    Furugoshi, N.8    Shichiri, M.9
  • 8
    • 0031964835 scopus 로고    scopus 로고
    • Implications of the diabetes control and complications trial
    • (b) American Diabetes Association. Implications of the Diabetes Control and Complications Trial. Diabetes Care 1998, 21, S88-90.
    • (1998) Diabetes Care , vol.21
  • 9
    • 0035814620 scopus 로고    scopus 로고
    • "Normal" blood glucose and coronary risk
    • Barrett-Connor, E.; Wingard, D. L. "Normal" Blood Glucose and Coronary Risk. Br. Med. J. 2001, 322, 5-6.
    • (2001) Br. Med. J. , vol.322 , pp. 5-6
    • Barrett-Connor, E.1    Wingard, D.L.2
  • 10
    • 0033393881 scopus 로고    scopus 로고
    • The aldose reductase pathway and nonenzymatic glycation in the pathogenesis of diabetic neuropathy: A critical review for the end of the 20th century
    • Carrington, A. L.; Litchfield, J. E. The Aldose Reductase Pathway and Nonenzymatic Glycation in the Pathogenesis of Diabetic Neuropathy: A Critical Review for the End of the 20th Century. Diabetes Rev. 1999, 7, 275-299.
    • (1999) Diabetes Rev. , vol.7 , pp. 275-299
    • Carrington, A.L.1    Litchfield, J.E.2
  • 11
    • 0023202006 scopus 로고
    • Insulin and atheroma - An update
    • Stout, R. W. Insulin and Atheroma-An Update. Lancet 1987, 1 (Iss. 8541), 1077-1079.
    • (1987) Lancet , vol.1 , Issue.ISS. 8541 , pp. 1077-1079
    • Stout, R.W.1
  • 12
    • 0032971837 scopus 로고    scopus 로고
    • Advanced glycosylated end products and hyperglycemia in the pathogenesis of diabetic complications
    • Friedman, E. A. Advanced Glycosylated End Products and Hyperglycemia in the Pathogenesis of Diabetic Complications. Diabetes Care, 1999, 22 (Suppl. 2), B65-71.
    • (1999) Diabetes Care , vol.22 , Issue.SUPPL. 2
    • Friedman, E.A.1
  • 13
    • 0032693720 scopus 로고    scopus 로고
    • Aldose reductase inhibitors: Therapeutic implications for diabetic complications
    • Oates, P. J.; Mylari, B. L. Aldose Reductase Inhibitors: Therapeutic Implications for Diabetic Complications. Expert Opin. Investig. Drugs 1999, 8, 2095-2119.
    • (1999) Expert Opin. Investig. Drugs , vol.8 , pp. 2095-2119
    • Oates, P.J.1    Mylari, B.L.2
  • 14
    • 0027934146 scopus 로고
    • Aldose reductase inhibitors and their potential for the treatment of diabetic complications
    • (a) Tomlinson, D. R.; Stevens, E. J.; Diemel, L. T. Aldose Reductase Inhibitors and their Potential for the Treatment of Diabetic Complications. Trends Pharmacol. Sci. 1994, 15, 293-297.
    • (1994) Trends Pharmacol. Sci. , vol.15 , pp. 293-297
    • Tomlinson, D.R.1    Stevens, E.J.2    Diemel, L.T.3
  • 15
    • 0031920049 scopus 로고    scopus 로고
    • Aldose reductase in glucose toxicity: A potential target for the prevention of diabetic complications
    • (b) Nishimura, C. Aldose Reductase in Glucose Toxicity: A Potential Target for the Prevention of Diabetic Complications. Pharmacol. Rev. 1998, 50, 21-33.
    • (1998) Pharmacol. Rev. , vol.50 , pp. 21-33
    • Nishimura, C.1
  • 16
    • 0027515572 scopus 로고
    • Mechanisms for D-glucose inhibition ofmyo-inositol influx into rats lens
    • (c) Mistry, K. P.; Beyer-Mears, A.; Diecke, F. P. J. Mechanisms for D-Glucose Inhibition ofmyo-Inositol Influx into Rats Lens. Diabetes 1993, 42, 1737-1744.
    • (1993) Diabetes , vol.42 , pp. 1737-1744
    • Mistry, K.P.1    Beyer-Mears, A.2    Diecke, F.P.J.3
  • 17
    • 0027285425 scopus 로고
    • Osmotically-induced nerve taurine depletion and the compatible osmolyte hypothesis in experimental diabetic neuropathy in the rat
    • (d) Stevens, M. J.; Lattimer, S. A.; Kamijo, M.; Van Huysen, C.; Sima, A. A. F.; Greene, D. A. Osmotically-Induced Nerve Taurine Depletion and the Compatible Osmolyte Hypothesis in Experimental Diabetic Neuropathy in the Rat. Diabetologia 1993, 36, 608-614.
    • (1993) Diabetologia , vol.36 , pp. 608-614
    • Stevens, M.J.1    Lattimer, S.A.2    Kamijo, M.3    Van Huysen, C.4    Sima, A.A.F.5    Greene, D.A.6
  • 19
    • 0032421502 scopus 로고    scopus 로고
    • Specific detections of the early process of the glycation reactions by fructose and glucose in diabetic rat lens
    • Kawasaki, Y.; Fujii, J.; Miyazawa, N.; Hoshi, A.; Okado, A.; Tano, Y.; Taniguchi, N. Specific Detections of the Early Process of the Glycation Reactions By Fructose and Glucose in Diabetic Rat Lens. FEBS Lett. 1998, 441, 116-120.
    • (1998) FEBS Lett. , vol.441 , pp. 116-120
    • Kawasaki, Y.1    Fujii, J.2    Miyazawa, N.3    Hoshi, A.4    Okado, A.5    Tano, Y.6    Taniguchi, N.7
  • 20
    • 0025853670 scopus 로고
    • Protein glycation and oxidative stress in diabetes mellitus and aging
    • (a) Wolff, S. P.; Jiang, Z. Y.; Hunt, J. V. Protein Glycation and Oxidative Stress in Diabetes Mellitus and Aging. Free Radic. Biol. Med. 1991, 10, 339-352.
    • (1991) Free Radic. Biol. Med. , vol.10 , pp. 339-352
    • Wolff, S.P.1    Jiang, Z.Y.2    Hunt, J.V.3
  • 21
    • 0028917712 scopus 로고
    • Significance of fructose-induced protein oxidation and formation of advanced glycation end product
    • (b) Takagi, Y.; Kashiwagi, A.; Tanaka, Y.; Asahina, T.; Kikkawa, R.; Shigeta, Y. Significance of Fructose-Induced Protein Oxidation and Formation of Advanced Glycation End Product. J. Diabetes Complicat. 1995, 9, 87-91.
    • (1995) J. Diabetes Complicat. , vol.9 , pp. 87-91
    • Takagi, Y.1    Kashiwagi, A.2    Tanaka, Y.3    Asahina, T.4    Kikkawa, R.5    Shigeta, Y.6
  • 22
    • 0030280345 scopus 로고    scopus 로고
    • Effects of oxygen and transition metals on the advanced maillard reaction of proteins with glucose
    • (c) Hayase, F.; Shibuya, T.; Sato, J.; Yamamoto, M. Effects of Oxygen and Transition Metals on the Advanced Maillard Reaction of Proteins with Glucose. Biosci. Biotech. Biochem. 1996, 60, 1820-1825.
    • (1996) Biosci. Biotech. Biochem. , vol.60 , pp. 1820-1825
    • Hayase, F.1    Shibuya, T.2    Sato, J.3    Yamamoto, M.4
  • 23
    • 0025930287 scopus 로고
    • Oxidative glycation and free radical production: A causal mechanism of diabetic complications
    • (a) Hunt, J. V.; Wolff, S. P. Oxidative Glycation and Free Radical Production: A Causal Mechanism of Diabetic Complications. Free Rad. Res. Commun. 1991, 12-13, 115-123.
    • (1991) Free Rad. Res. Commun. , vol.12-13 , pp. 115-123
    • Hunt, J.V.1    Wolff, S.P.2
  • 26
    • 0023770113 scopus 로고
    • Free radicals and diabetes
    • Oberley, L. W. Free Radicals and Diabetes. Free Radic. Biol. Med. 1988, 5, 113-124.
    • (1988) Free Radic. Biol. Med. , vol.5 , pp. 113-124
    • Oberley, L.W.1
  • 28
    • 77956756013 scopus 로고
    • To market, to market - 1992
    • Bristol, J. A., Ed.; Academic Press Inc.: San Diego
    • Strupczewski, J. D.; Ellis, D. B. To Market, To Market-1992. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed.; Academic Press Inc.: San Diego, 1993; vol. 28; p 330.
    • (1993) Annual Reports in Medicinal Chemistry , vol.28 , pp. 330
    • Strupczewski, J.D.1    Ellis, D.B.2
  • 30
    • 0035062863 scopus 로고    scopus 로고
    • Glucose-induced hyperproliferation of cultured rat aortic smooth muscle cells through polyol pathway hyperactivity
    • (b) Nakamura, J.; Kasuya, Y.; Hamad, Y.; Nakshima, E.; Naruse, K.; Yasuda, Y.; Kato, K.; Hotta, N. Glucose-Induced Hyperproliferation of Cultured Rat Aortic Smooth Muscle Cells through Polyol Pathway Hyperactivity. Diabetologia 2001, 44, 480-487.
    • (2001) Diabetologia , vol.44 , pp. 480-487
    • Nakamura, J.1    Kasuya, Y.2    Hamad, Y.3    Nakshima, E.4    Naruse, K.5    Yasuda, Y.6    Kato, K.7    Hotta, N.8
  • 31
    • 0035969875 scopus 로고    scopus 로고
    • The role of aldose reductase in sugar cataract formation: Aldose reductase plays a key role in lens epithelial cell death (apoptosis)
    • (c) Murata, M.; Ohta, N.; Sakurai, S.; Alam, S.; Tsai, J. Y.; Kador, P. F.; Sato, S. The Role of Aldose Reductase in Sugar Cataract Formation: Aldose Reductase Plays a Key Role in Lens Epithelial Cell Death (Apoptosis). Chem.-Biol. Interact. 2001, 130 (1-3 Special Issue S1), 617-625.
    • (2001) Chem.-Biol. Interact. , vol.130 , Issue.1-3 SPEC. ISSUE S1 , pp. 617-625
    • Murata, M.1    Ohta, N.2    Sakurai, S.3    Alam, S.4    Tsai, J.Y.5    Kador, P.F.6    Sato, S.7
  • 32
    • 0033803537 scopus 로고    scopus 로고
    • Epalrestat, an aldose reductase inhibitor, reduces the levels of n-epsilon-(carboxymethyl)lysine protein adducts and their precursors in erythrocytes from diabetic patients
    • (a) Hamada, Y.; Nakamura, J.; Naruse, K.; Komori, T.; Kato, K.; Kasuya, Y.; Nagai, R.; Horiuchi, S.; Hotta, N. Epalrestat, an Aldose Reductase Inhibitor, Reduces the Levels of N-Epsilon-(Carboxymethyl)Lysine Protein Adducts and their Precursors in Erythrocytes from Diabetic Patients. Diabetes Care 2000, 23, 1539-1544.
    • (2000) Diabetes Care , vol.23 , pp. 1539-1544
    • Hamada, Y.1    Nakamura, J.2    Naruse, K.3    Komori, T.4    Kato, K.5    Kasuya, Y.6    Nagai, R.7    Horiuchi, S.8    Hotta, N.9
  • 33
    • 0035378314 scopus 로고    scopus 로고
    • Aldose reductase inhibition ameliorates pupillary light reflex and f-wave latency in patients with mild diabetic neuropathy
    • (b) Nakayama, M.; Nakamura, J.; Hamada, J.; Chaya, S.; Mizubayashi, R.; Yasuda, Y.; Kamiya, K.; Koh, N.; Hotta, N. Aldose Reductase Inhibition Ameliorates Pupillary Light Reflex and F-Wave Latency in Patients with Mild Diabetic Neuropathy. Diabetes Care 2001, 24, 1093-1098.
    • (2001) Diabetes Care , vol.24 , pp. 1093-1098
    • Nakayama, M.1    Nakamura, J.2    Hamada, J.3    Chaya, S.4    Mizubayashi, R.5    Yasuda, Y.6    Kamiya, K.7    Koh, N.8    Hotta, N.9
  • 34
    • 0001991447 scopus 로고    scopus 로고
    • Aldose reductase inhibitor zopolrestat improves systolic function in diabetics
    • (c) Johnson, B. F.; Law, G.; Nesto, R.; Pfeifer, M.; Slater, W.; Vinic, A.; Wackers, F.; Young, L. Aldose Reductase Inhibitor Zopolrestat Improves Systolic Function in Diabetics. Diabetes, 1999, 48 (Iss. S1), 574.
    • (1999) Diabetes , vol.48 , Issue.ISS. S1 , pp. 574
    • Johnson, B.F.1    Law, G.2    Nesto, R.3    Pfeifer, M.4    Slater, W.5    Vinic, A.6    Wackers, F.7    Young, L.8
  • 35
    • 0003045851 scopus 로고    scopus 로고
    • Effects of fidarestat, an aldose reductase inhibitor, on diabetic peripheral neuropathy. A 52-week placebo-controlled double-blind-study
    • (d) Hotta, N.; Ishii, J.; Sakamoto, N. Effects of Fidarestat, an Aldose Reductase Inhibitor, on Diabetic Peripheral Neuropathy. A 52-Week Placebo-Controlled Double-Blind-Study. Diabetes 2000, 49 (Iss. S1), 142.
    • (2000) Diabetes , vol.49 , Issue.ISS. S1 , pp. 142
    • Hotta, N.1    Ishii, J.2    Sakamoto, N.3
  • 36
    • 0027929990 scopus 로고
    • Alpha-lipoate can protect against glycation of serum albumin, but not low-density lipoprotein
    • (a) Kawabata, T.; Packer, L. Alpha-Lipoate Can Protect Against Glycation of Serum Albumin, but not Low-Density Lipoprotein. Biochem. Biophys. Res. Commun. 1994, 203, 99-104.
    • (1994) Biochem. Biophys. Res. Commun. , vol.203 , pp. 99-104
    • Kawabata, T.1    Packer, L.2
  • 37
    • 0033213529 scopus 로고    scopus 로고
    • Oxidative modification of serum albumin in an experimental glycation model of diabetes mellitus in vitro: Effect of the pyridoindole antioxidant stobadine
    • (b) Stefek, M.; Krizanova, L.; Trnkova, Z. Oxidative Modification of Serum Albumin in an Experimental Glycation Model of Diabetes Mellitus In Vitro: Effect of the Pyridoindole Antioxidant Stobadine. Life Sci. 1999, 65, 1995-1997.
    • (1999) Life Sci. , vol.65 , pp. 1995-1997
    • Stefek, M.1    Krizanova, L.2    Trnkova, Z.3
  • 38
    • 0030446569 scopus 로고    scopus 로고
    • Inhibition of protein glycation and advanced glycation end products by ascorbic acid and other nutrients
    • Vinson, J. A.; Howard, T. B., III. Inhibition of Protein Glycation and Advanced Glycation End Products by Ascorbic Acid and other Nutrients. J. Nutr. Biochem. 1996, 7, 659-663.
    • (1996) J. Nutr. Biochem. , vol.7 , pp. 659-663
    • Vinson, J.A.1    Howard T.B. III2
  • 39
    • 0026575313 scopus 로고
    • Mechanistic studies of advanced glycation end product inhibition by aminoguanidine
    • Edelstein, D.; Brownlee, M. Mechanistic Studies of Advanced Glycation End Product Inhibition by Aminoguanidine. Diabetes 1992, 41, 26-29.
    • (1992) Diabetes , vol.41 , pp. 26-29
    • Edelstein, D.1    Brownlee, M.2
  • 40
    • 0033848991 scopus 로고    scopus 로고
    • Mechanism of the inhibitory effect of OPB-9195 [(±)-2-Isopropylidenehydrazono-4-oxo-thiazolidin-5-ylacetanilide] on advanced glycation end-product and advanced lipoxidation end-product formation
    • Miyata, T.; Ueda, Y.; Asahi, K.; Izuhara, Y.; Inagi, R.; Saito, A.; Destrihou, C. V.; Kurokawa, K. Mechanism of the Inhibitory Effect of OPB-9195 [(±)-2-Isopropylidenehydrazono-4-oxo-thiazolidin-5-ylacetanilide] on Advanced Glycation End-Product and Advanced Lipoxidation End-Product Formation. J. Am. Soc. Nephrol. 2000, 11, 1719-1725.
    • (2000) J. Am. Soc. Nephrol. , vol.11 , pp. 1719-1725
    • Miyata, T.1    Ueda, Y.2    Asahi, K.3    Izuhara, Y.4    Inagi, R.5    Saito, A.6    Destrihou, C.V.7    Kurokawa, K.8
  • 41
    • 0031922790 scopus 로고    scopus 로고
    • The glucose/insulin system and vitamin C: Implications in insulin-dependent diabetes mellitus
    • (a) Cunningham, J. J. The Glucose/Insulin System and Vitamin C: Implications in Insulin-Dependent Diabetes Mellitus. J. Am. Coll. Nutr. 1998, 17, 105-108.
    • (1998) J. Am. Coll. Nutr. , vol.17 , pp. 105-108
    • Cunningham, J.J.1
  • 42
    • 0031723579 scopus 로고    scopus 로고
    • Reversal of defective nerve conduction with vitamin E supplementation in type 2 diabetes-a preliminary study
    • (b) Tutuncu, N. B.; Bayraktar, M.; Varli, K. Reversal of Defective Nerve Conduction with Vitamin E Supplementation in Type 2 Diabetes-A Preliminary Study. Diabetes Care 1998, 21, 1915-1918.
    • (1998) Diabetes Care , vol.21 , pp. 1915-1918
    • Tutuncu, N.B.1    Bayraktar, M.2    Varli, K.3
  • 43
    • 0012782568 scopus 로고    scopus 로고
    • Decrease of TGF-Beta and type-IV collagen production in diabetic nephropathy by a novel AGE inhibitor OPB-9195
    • (a) Tsuchida, K.; Nakamura, S.; Fujii, W.; Atsumi, T.; Kawata, T.; Makita, Z.; Koike, T. Decrease of TGF-Beta and Type-IV Collagen Production in Diabetic Nephropathy by a Novel AGE Inhibitor OPB-9195. Diabetes 1998, 47 (Iss. S1), 503.
    • (1998) Diabetes , vol.47 , Issue.ISS. S1 , pp. 503
    • Tsuchida, K.1    Nakamura, S.2    Fujii, W.3    Atsumi, T.4    Kawata, T.5    Makita, Z.6    Koike, T.7
  • 44
    • 0035135246 scopus 로고    scopus 로고
    • Advanced glycation end-products: A Review
    • (b) Singh, R.; Barden, A.; Mori, T.; Beilin, L. Advanced Glycation End-Products: a Review. Diabetologia 2001, 44, 129-146.
    • (2001) Diabetologia , vol.44 , pp. 129-146
    • Singh, R.1    Barden, A.2    Mori, T.3    Beilin, L.4
  • 45
    • 0029560789 scopus 로고
    • Isomeric benzoylpyrroleacetic acids: Some structural aspects for aldose reductase inhibitory and antiinflammatory activities
    • Demopoulos, V. J.; Rekka, E. Isomeric Benzoylpyrroleacetic Acids: Some Structural Aspects for Aldose Reductase Inhibitory and Antiinflammatory Activities. J. Pharm. Sci. 1995, 84, 79-82.
    • (1995) J. Pharm. Sci , vol.84 , pp. 79-82
    • Demopoulos, V.J.1    Rekka, E.2
  • 46
    • 0034618541 scopus 로고    scopus 로고
    • Privileged molecules for protein binding identified from NMR-based screening
    • Hajduk, P. J.; Bures, M.; Praestgaard, J.; Fesik, S. W. Privileged Molecules for Protein Binding Identified from NMR-Based Screening. J. Med. Chem. 2000, 43, 3443-3447.
    • (2000) J. Med. Chem. , vol.43 , pp. 3443-3447
    • Hajduk, P.J.1    Bures, M.2    Praestgaard, J.3    Fesik, S.W.4
  • 48
    • 0012826069 scopus 로고
    • Free radicals in drug research
    • Testa, B., Ed.; Academic Press Limited: London
    • Roberfroid, M. B.; Viehe, H. G.; Remacle, J. Free Radicals in Drug Research. In Advances in Drug Research; Testa, B., Ed.; Academic Press Limited: London, 1987; vol. 16; pp 15-19.
    • (1987) Advances in Drug Research , vol.16 , pp. 15-19
    • Roberfroid, M.B.1    Viehe, H.G.2    Remacle, J.3
  • 49
    • 0032432679 scopus 로고    scopus 로고
    • A study of the friedel-crafts acylation of 1-benzenesulfonyl-1H-pyrrole in the preparation of 3-aroylpyrroles
    • (a) Nicolaou, I.; Demopoulos, V. J. A Study of the Friedel-Crafts Acylation of 1-Benzenesulfonyl-1H-pyrrole in the Preparation of 3-Aroylpyrroles. J. Heterocycl. Chem. 1998, 35, 1345-1348.
    • (1998) J. Heterocycl. Chem. , vol.35 , pp. 1345-1348
    • Nicolaou, I.1    Demopoulos, V.J.2
  • 50
    • 0001672256 scopus 로고
    • Synthesis of alkylpyrroles by the sodium borohydride reduction of acylpyrroles
    • (b) Greenhouse, R.; Ramrez, C.; Muchowski, J. M. Synthesis of Alkylpyrroles by the Sodium Borohydride Reduction of Acylpyrroles. J. Org. Chem. 1985, 50, 2961-2965.
    • (1985) J. Org. Chem. , vol.50 , pp. 2961-2965
    • Greenhouse, R.1    Ramrez, C.2    Muchowski, J.M.3
  • 51
    • 0022378015 scopus 로고
    • A convenient synthesis of 3-acylindoles via friedel-crafts acylation of 1-(phenylsulfonyl)indole. A new route to pyridocarbazole-5,11-quinones and ellipticine
    • (c) Ketcha, D. M.; Gribble, G. W. A Convenient Synthesis of 3-Acylindoles via Friedel-Crafts Acylation of 1-(Phenylsulfonyl)indole. A New Route to Pyridocarbazole-5,11-quinones and Ellipticine. J. Org. Chem. 1985, 50, 5451-5457.
    • (1985) J. Org. Chem. , vol.50 , pp. 5451-5457
    • Ketcha, D.M.1    Gribble, G.W.2
  • 53
    • 0001431527 scopus 로고
    • An efficient synthesis of new phenylpyrrolizine and phenylpyrrolopyrazine derivatives
    • Tembo, O. N.; Dallemagne, P.; Rault, S.; Robba, M. An Efficient Synthesis of New Phenylpyrrolizine and Phenylpyrrolopyrazine Derivatives. Heterocycles 1993, 36, 2129-2137.
    • (1993) Heterocycles , vol.36 , pp. 2129-2137
    • Tembo, O.N.1    Dallemagne, P.2    Rault, S.3    Robba, M.4
  • 54
    • 0028904895 scopus 로고
    • A facile synthesis of N-substituted pyrroles
    • Leysen, F. Y.; Ottenheijm, H. C. J. A Facile Synthesis of N-Substituted Pyrroles. Synth. Commun. 1995, 25, 1857-1861.
    • (1995) Synth. Commun. , vol.25 , pp. 1857-1861
    • Leysen, F.Y.1    Ottenheijm, H.C.J.2
  • 55
    • 0001550348 scopus 로고
    • Synthesis of pyrroloquinoline and pyrrolonaphthiridine by an intramolecular cyclisation reaction
    • Cardinaud, I.; Gueiffier, A.; Debouzy, J-C.; Milhared, J-C.; Chapat, J-P. Synthesis of Pyrroloquinoline and Pyrrolonaphthiridine by an Intramolecular Cyclisation Reaction. Heterocycles 1993, 36, 2513-2522.
    • (1993) Heterocycles , vol.36 , pp. 2513-2522
    • Cardinaud, I.1    Gueiffier, A.2    Debouzy, J.-C.3    Milhared, J.-C.4    Chapat, J.-P.5
  • 56
    • 0001276207 scopus 로고
    • 1,4-Dichloro-1,4-dimethoxybutane as a mild reagent for the conversion of primary amines to pyrroles. Synthesis of a pyrrole compound from tobacco
    • Chan, T. H.; Lee, S. D. 1,4-Dichloro-1,4-dimethoxybutane as a Mild Reagent for the Conversion of Primary Amines to Pyrroles. Synthesis of a Pyrrole Compound from Tobacco. J. Org. Chem. 1983, 48, 3059-3061.
    • (1983) J. Org. Chem. , vol.48 , pp. 3059-3061
    • Chan, T.H.1    Lee, S.D.2
  • 57
    • 0022993916 scopus 로고
    • Analgetic and antiinflammatory 7-aroylbenzofuran-5-ylacetic acids and 7-aroyl-benzothiophene-5-ylacetic acids
    • (a) Dunn, J. P.; Ackerman, N. A.; Tomolonis, A. J. Analgetic and Antiinflammatory 7-Aroylbenzofuran-5-ylacetic Acids and 7-Aroyl-benzothiophene-5-ylacetic Acids. J. Med. Chem. 1986, 29, 2326-2329.
    • (1986) J. Med. Chem. , vol.29 , pp. 2326-2329
    • Dunn, J.P.1    Ackerman, N.A.2    Tomolonis, A.J.3
  • 58
    • 0036023122 scopus 로고    scopus 로고
    • Pyrrolylbenzothiazole derivatives as aldose reductase inhibitors
    • (b) Zaher, N; Nicolaou, I; Demopoulos, V. J. Pyrrolylbenzothiazole Derivatives as Aldose Reductase Inhibitors. J. Enzyme Inhib. Med. Chem. 2002, 17, 131-135.
    • (2002) J. Enzyme Inhib. Med. Chem. , vol.17 , pp. 131-135
    • Zaher, N.1    Nicolaou, I.2    Demopoulos, V.J.3
  • 59
    • 37049072156 scopus 로고
    • General methods for synthesizing 2,4-diacylpyrroles and their precursors containing one or two masked acyl groups
    • Cadamuro, S.; Degani, I.; Dagnera, S.; Fachi, R.; Gatti. A.; Piscopo. L. General Methods for Synthesizing 2,4-Diacylpyrroles and their Precursors Containing One or Two Masked Acyl Groups. J. Chem. Soc., Perkin Trans. 1 1993, 273-283.
    • (1993) J. Chem. Soc., Perkin Trans. 1 , pp. 273-283
    • Cadamuro, S.1    Degani, I.2    Dagnera, S.3    Fachi, R.4    Gatti, A.5    Piscopo, L.6
  • 61
    • 4244004176 scopus 로고
    • Bell, Malcolm Rie (Sterling Drug Inc.) Ger. Offen. 1908541 (Cl. C 07d, A 61k), 18 Sep 1969, US Appl. Feb 1968; 1-(Carboxyalkyl)indoles
    • Bell, Malcolm Rie (Sterling Drug Inc.) Ger. Offen. 1908541 (Cl. C 07d, A 61k), 18 Sep 1969, US Appl. Feb 1968; 1-(Carboxyalkyl)indoles. Chem. Abstr. 1970, 72, 66807m.
    • (1970) Chem. Abstr. , vol.72
  • 62
    • 0013494728 scopus 로고
    • Demethylation of aryl methyl ethers by boron tribromide
    • McOmie, J. F.; Watts, M. L.; West, D. E. Demethylation of Aryl Methyl Ethers by Boron Tribromide. Tetrahedron 1968, 24, 2289-2292.
    • (1968) Tetrahedron , vol.24 , pp. 2289-2292
    • McOmie, J.F.1    Watts, M.L.2    West, D.E.3
  • 63
    • 0003686469 scopus 로고
    • Synthetic methods and reactions. Transformations with chlorotrimethylsilane/sodium iodide, a convenient in situ iodotrimethylsilane reagent
    • Olah, G. A.; Narany, S. C.; Gupta, B. J. B.; Mulhotra, R. Synthetic Methods and Reactions. Transformations with Chlorotrimethylsilane/Sodium Iodide, a Convenient in situ Iodotrimethylsilane Reagent. J. Org. Chem. 1979, 44, 1247-1251.
    • (1979) J. Org. Chem. , vol.44 , pp. 1247-1251
    • Olah, G.A.1    Narany, S.C.2    Gupta, B.J.B.3    Mulhotra, R.4
  • 64
    • 0036318249 scopus 로고    scopus 로고
    • Synthesis of [5-(4-Pyrrol-1-yl-benzoyl)-1H-pyrrol-2-yl)]-acetic acid and in vitro study of its inhibitory activity on aldose reductase enzyme and on protein glycation
    • Anagnostou, C.; Nicolaou, I.; Demopoulos, V. J. Synthesis of [5-(4-Pyrrol-1-yl-benzoyl)-1H-pyrrol-2-yl)]-acetic Acid and In Vitro Study of its Inhibitory Activity on Aldose Reductase Enzyme and on Protein Glycation. Pharmazie 2002, 57, 535-537.
    • (2002) Pharmazie , vol.57 , pp. 535-537
    • Anagnostou, C.1    Nicolaou, I.2    Demopoulos, V.J.3
  • 65
    • 0028839089 scopus 로고
    • Presence of a closely-related subgroup in the aldo-ketoreductase family of the mouse
    • Gui, T.; Tanimoto, T.; Kokai, Y.; Nishimura, C. Presence of a Closely-Related Subgroup in the Aldo-Ketoreductase Family of the Mouse. Eur. J. Biochem. 1995, 227, 448-453.
    • (1995) Eur. J. Biochem. , vol.227 , pp. 448-453
    • Gui, T.1    Tanimoto, T.2    Kokai, Y.3    Nishimura, C.4
  • 66
    • 0033679222 scopus 로고    scopus 로고
    • Aldose reductase does catalyse the reduction of glyceraldehyde through a stoichiometric oxidation of nadph
    • Del Corso, A.; Costantino, L; Rastelli, G.; Buono, F.; Mura, U. Aldose Reductase does Catalyse the Reduction of Glyceraldehyde through a Stoichiometric Oxidation of NADPH. Exp. Eye Res. 2000, 71, 515-521.
    • (2000) Exp. Eye Res. , vol.71 , pp. 515-521
    • Del Corso, A.1    Costantino, L.2    Rastelli, G.3    Buono, F.4    Mura, U.5
  • 67
    • 0021323690 scopus 로고
    • N-[[5-(Trifluoromethyl)-6-methoxy-1-naphthalenyl]-N-methylglycine (tolrestat), a potent, orally active aldose reductase inhibitor
    • (a) Sestanj, K.; Bellini, F.; Fung, S.; Abraham, N.; Treasurywala, A.; Humber, L.; Simard-Duquesne, N.; Dvornik, D. N-[[5-(Trifluoromethyl)-6-methoxy-1-naphthalenyl]-N-methylglycine (Tolrestat), a Potent, Orally Active Aldose Reductase Inhibitor. J. Med. Chem. 1984, 27, 255-256.
    • (1984) J. Med. Chem. , vol.27 , pp. 255-256
    • Sestanj, K.1    Bellini, F.2    Fung, S.3    Abraham, N.4    Treasurywala, A.5    Humber, L.6    Simard-Duquesne, N.7    Dvornik, D.8
  • 69
    • 0025967888 scopus 로고
    • Novel potent aldose reductase inhibitors: 3,4-Dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl] methyl]-1-phthalazineacetic acid (Zopolrestat) and congeners
    • (c) Mylari, B. L.; Larson, E. R.; Beyer, T. A.; Zembrowski, W. J.; Aldinger, C. E.; Dee, M. F.; Siegel. T. W.; Singleton. D. H. Novel Potent Aldose Reductase Inhibitors: 3,4-Dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl] methyl]-1-phthalazineacetic Acid (Zopolrestat) and Congeners. J. Med. Chem. 1991, 34, 108-122.
    • (1991) J. Med. Chem. , vol.34 , pp. 108-122
    • Mylari, B.L.1    Larson, E.R.2    Beyer, T.A.3    Zembrowski, W.J.4    Aldinger, C.E.5    Dee, M.F.6    Siegel, T.W.7    Singleton, D.H.8
  • 70
    • 0033920645 scopus 로고    scopus 로고
    • A potent aldose reductase inhibitor, (2S,4S)-6-Fluoro-2′,5′-dioxospiro[chroman-4, 4′-imidazolidine]-2-carboxamide (Fidarestat): Its absolute configuraton and interactions with the aldose reductase by x-ray crystallography
    • (d) Oka, M.; Matsumoto, Y.; Sugiyama, S.; Tsuruta. N.; Matsushima. M. A Potent Aldose Reductase Inhibitor, (2S,4S)-6-Fluoro-2′,5′-dioxospiro[chroman-4,4′- imidazolidine]-2-carboxamide (Fidarestat): Its Absolute Configuraton and Interactions with the Aldose Reductase by X-ray Crystallography. J. Med. Chem. 2000, 43, 2479-2483.
    • (2000) J. Med. Chem. , vol.43 , pp. 2479-2483
    • Oka, M.1    Matsumoto, Y.2    Sugiyama, S.3    Tsuruta, N.4    Matsushima, M.5
  • 71
    • 0012818501 scopus 로고    scopus 로고
    • Daylight Chemical Information Systems Inc.
    • ClogP Version 4.72, Daylight Chemical Information Systems Inc., (http://www.daylight.com/).
    • ClogP Version 4.72
  • 73
    • 4344622126 scopus 로고    scopus 로고
    • Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612
    • SPARTAN SGI Version 5.1.3 OpenGL, Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612.
    • SPARTAN SGI Version 5.1.3 OpenGL
  • 74
    • 0035899174 scopus 로고    scopus 로고
    • Toward the design of chemical libraries for mass screening biased against mutagenic compounds
    • Llorens, O.; Perez, J. J. Toward the Design of Chemical Libraries for Mass Screening Biased against Mutagenic Compounds. J. Med. Chem. 2001, 44, 2793-2804.
    • (2001) J. Med. Chem. , vol.44 , pp. 2793-2804
    • Llorens, O.1    Perez, J.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.