Chem. J. Chinese Universities ›› 2014, Vol. 35 ›› Issue (6): 1204.doi: 10.7503/cjcu20131033
• Organic Chemistry • Previous Articles Next Articles
NIU Chao1,2, LI Gen1, 1, Haji-Akber AISA1,*()
Received:
2013-10-23
Online:
2014-06-10
Published:
2013-11-25
Contact:
Haji-Akber AISA
E-mail:haji@ms.xjb.ac.cn
Supported by:
CLC Number:
TrendMD:
NIU Chao, LI Gen, , Haji-Akber AISA. Synthesis and Activity on Tyrosinase of Novel Chalcone Derivatives†[J]. Chem. J. Chinese Universities, 2014, 35(6): 1204.
Compound | R | R' | Substrate | EC50/(μmol·L-1) |
---|---|---|---|---|
4a | H | Bz | L-Tyrosine | 180.6 |
4b | CH3 | Bz | L-Tyrosine | 39.2 |
4c | OCH3 | Bz | L-Tyrosine | 67.3 |
4d | Cl | Bz | L-Tyrosine | 21.1 |
4e | CH3 | Ac | L-Tyrosine | >286 |
4f | Cl | Ac | L-Tyrosine | 167 |
4g | H | Ts | L-Tyrosine | 104.3 |
4h | Cl | Ts | L-Tyrosine | 25.8 |
5a | H | H | L-Tyrosine | >286 |
5b | CH3 | H | L-Tyrosine | 87.7 |
5c | OCH3 | H | L-Tyrosine | 123.3 |
5d | Cl | H | L-Tyrosine | 30.6 |
7a | H | Bz | L-Tyrosine | 141 |
7b | CH3 | Bz | L-Tyrosine | 17.1 |
7c | OCH3 | Bz | L-Tyrosine | 55.3 |
7d | Cl | Bz | L-Tyrosine | 9.6 |
8-MOP* | L-Tyrosine | 14.8 |
Table 1 Activator effect on tyrosinase of compounds
Compound | R | R' | Substrate | EC50/(μmol·L-1) |
---|---|---|---|---|
4a | H | Bz | L-Tyrosine | 180.6 |
4b | CH3 | Bz | L-Tyrosine | 39.2 |
4c | OCH3 | Bz | L-Tyrosine | 67.3 |
4d | Cl | Bz | L-Tyrosine | 21.1 |
4e | CH3 | Ac | L-Tyrosine | >286 |
4f | Cl | Ac | L-Tyrosine | 167 |
4g | H | Ts | L-Tyrosine | 104.3 |
4h | Cl | Ts | L-Tyrosine | 25.8 |
5a | H | H | L-Tyrosine | >286 |
5b | CH3 | H | L-Tyrosine | 87.7 |
5c | OCH3 | H | L-Tyrosine | 123.3 |
5d | Cl | H | L-Tyrosine | 30.6 |
7a | H | Bz | L-Tyrosine | 141 |
7b | CH3 | Bz | L-Tyrosine | 17.1 |
7c | OCH3 | Bz | L-Tyrosine | 55.3 |
7d | Cl | Bz | L-Tyrosine | 9.6 |
8-MOP* | L-Tyrosine | 14.8 |
[1] | Hu X. Y., Chen B. N., Wang L., Chen F. H., Chem. Res. Chinese Universities, 2012, 28(5), 862—865 |
[2] | Khan K. M., Maharvi G. M., Khan M. T. H., Shaikh A. J., Perveen S., Begum S., Choudhary M. I., Bioorg. Med. Chem., 2006, 14, 344—351 |
[3] | Nerya O., Musa R., Khatib S., Tamir S., Vaya J., Phytochemistry, 2004, 65, 1389—1395 |
[4] | Fenoll L. G., Rodriguez-Lopez J. N., Varon R., Garcia-Ruiz P. A., Garcia-Canovas F., Tudela J., Biol. Chem., 2000, 381(4), 313—320 |
[5] | Yao L., Li Q., Shang J., J. XinJiang Medical Univ., 2010, 33(10), 1191—1193 |
(姚莉, 李茜, 尚靖.新疆医科大学学报, 2010,33(10), 1191—1193 ) | |
[6] | Deng R. C., Zhou Y., Zhang J. G., Xu J. G., Shang J., Yu L. H., Wang D. P., Amino Acids & Biotic Resources, 2002, 24(1), 31—32 |
(邓瑞春, 周勇, 章金刚, 徐建国, 尚靖, 于鲁海, 王东平.氨基酸和生物资源, 2002,24(1), 31—32) | |
[7] | Sun L., Shang J., Li H. J., Wu L. J., Modern Chinese Medicine, 2006, 8(11), 10—12 |
(孙力, 尚靖, 李红健, 吴立军.中国现代中药, 2006,8(11), 10—12) | |
[8] | Liu T. H., Foreign Medical Sciences, 2004, 26(2), 103—104 |
(刘铜华.国外医学中医中药分册, 2004,26(2), 103—104) | |
[9] | Shang J., Xu J. G., Yu L. H., Sun L., Li H. J., Application of Butin and Its Derivatives in Preparing Drugs of Pigment Metabolism Disease, CP 1778294A, 2004-11-23 |
(尚靖, 徐建国, 于鲁海, 孙力, 李红健. 紫铆素及其衍生物在制备色素代谢疾病药物的用途, CP 1778294A, 2004-11-23) | |
[10] | Yan M., Huo S. X., Gao L., Peng X. M., Preparation and Application of Flavonoid Components in Ver-nohia Anthelmintica L, CP 102526153A, 2012-02-27 |
(闫明, 霍仕霞, 高莉, 彭晓明. 驱虫斑鸠菊黄酮组分及其制备方法和用途, CP 102526153A, 2012-02-27) | |
[11] | Khatib S., Nerya O., Musa R., Shmuel M., Tamir S., Vaya J., Bioorg. Med. Chem., 2005, 13, 433—441 |
[12] | Thanigaimalai P., Lee K.C., Sharma V. K., Rao E. V., Roh E., Kim Y., Jung S. H., Bioorg. Med. Chem. Lett., 2011, 21, 1922—1925 |
[13] | Jun N., Gao H., Jun K., Bioorg. Med. Chem., 2007, 15, 2396—2402 |
[14] | Zhang X. D., Hu X., Hou A. J., Wang H. Y., Biol. Pharm. Bull., 2009, 32(1), 86—90 |
[15] | Nixha A. R., Arslan M., Atalay Y., Gencer N., Ergun A., Arslan O., J. Enzyme. Inhib. Med. Chem., 2013, 28(4), 808—815 |
[16] | Sonmez F., Sevmezler S., Atahan A., Ceylan M., Demir D., Gencer N., Arslan O., Kucukislamoglu M., Bioorg. Med. Chem. Lett., 2011, 21, 7479—7482 |
[17] | Rao Y. K., Fang S. H., Tzeng Y. M., Bioorg. Med. Chem., 2009, 17, 7909—7914 |
[18] | Bandgar B. P., Patil S. A., Korbad B. L., Nile S. H., Khobragade C. N., Eur. J. Med. Chem., 2010, 45, 2629—2633 |
[19] | Chtourou M., Abdelhédi R., Frikha M. H., Trabelsi M., Ultrasonics Sonochemistry, 2010, 17, 246—249 |
[20] | Luis F. F., Boletim da Escola de Farmacia, Universidade de Coimbra, Edicao Cienpngica, 1980, 28, 49—52 |
[21] | Narender T., Reddy K. P., Tetrahedron Lett., 2007, 48, 3177—3180 |
[22] | Dimmock J. R., Jha A., Zello G. A., Allen T. M., Santos C. L., Balzarini J., de Clercq E., Manavathu E. K., Stables J. P., Pharmazie, 2003, 58(4), 227—232 |
[23] | Wu J. Z., Li J. L., Cai Y. P., Pan Y., Ye F. Q., Zhang Y. L., Zhao Y. J., Yang S. L., Li X. K., Liang G., J. Med. Chem., 2011, 54, 8110—8123 |
[24] | Keyes R. F., Gu Y. G., Sham H. L., Novel Acetyl-coa Carboxylase(ACC) Inhibitors and Their Use in Diabetes, Obesity and Metabolic Syndrome UP 20070219258A1, 2007-09-20 |
[25] | Zhao J. Y., Aisa H. A., Chin. J. Org. Chem., 2012, 32, 333—337 |
(赵江瑜, 阿吉艾克拜尔·艾萨. 有机化学, 2012, 32, 333—337) | |
[26] | Gu W. L., Ma Y. N., Wang C. L., Food Science and Technology, 2010, 35(7), 48—51 |
(顾玮蕾, 马跃能, 王春丽.食品科技, 2010,35(7), 48—51) | |
[27] | Ye X. Z., Gong S. Z., Liao G. J., Lin J. P., Zeng J. Y., China Surfactant Detergent & Cosmetics, 2010, 40(2), 98—100 |
(叶孝兆, 龚盛昭, 廖国俊, 林金沛, 曾金燕.日用化学工业, 2010,40(2), 98—100) | |
[28] | Pathak M. A., Fitzpatrick T. B., J. Photochem. Photobiol. B: Biol., 1992, 14(1/2), 3—22 |
[29] | Lener A. B., Denton C. R., Fitzpatrick T. B., J. Invest. Dermatol., 1953, 20, 299—314 |
[30] | Parrish J. A., Fitzpatrick T. B., Tannembaum L., Pathak M. A., N. Eng. J. Med., 1974, 291(23), 1207—1211 |
[31] | van Weelden H., Young E., van der Leun J. C., Br. J. Dermatol., 1980, 103(1), 1—9 |
[32] | Morison W. L., Photodermatol. Photoimmunol. Photomed., 2004, 20, 315—320 |
[33] | Hong N. J., Choi S. K., Koock S. U., Bull. Korean Chem. Soc., 1989, 10(1), 19—22 |
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