中文
Announcement
More
Progress in Chemistry 2010, Vol. 22 Issue (09): 1760-1766 Previous Articles   Next Articles

• Review •

Synthesis of Chiral Drugs by Titanium-catalyzed Enantioselective Sulfoxidation

Gao Shan  Zeng Qingle**  Tang Hongyan   Liu Yang  Dong Junyu  Zhang Binbin   

  1. (College of Materials and Chemistry&Chemical Engineering, Chengdu University of Technology, Chengdu 610059, China)
  • Received: Revised: Online: Published:
  • Contact: Zeng Qingle E-mail:qinglezeng@hotmail.com
PDF ( 2258 ) Cited
Export

EndNote

Ris

BibTeX

Chiral sulfoxides have a wide range of applications, one of which is used as chiral drugs. The sulfoxides used as chiral drugs mostly contain a structure with amino groups or nitrogen-containing heterocycles. The enantioselective oxidation of their sulfide precursors, titanium catalyst systems can achieve good results compared with other catalyst systems. This paper briefly introduces the progress of titanium-catalyzed enantioselective sulfide oxidation at first; these catalyst systems include titanium/tartarate, titanium/BINOL and other diols, titanium/salen, and other titanium catalyst systems. Then this paper further describes the research advance of synthesis of various chiral sulfoxide medicines catalyzed by titanium in detail. These chiral sulfoxide drugs were mainly used as proton pump inhibitors, anti-inflammatory drugs, anti-cancer drugs, antibiotics, platelet adhesion inhibitors, antipsychotic drugs, lipid regulators, potassium channel openers, neurokinin inhibitors, etc.

Contents
1 Introduction
2 Introduction of titanium-catalyzed sulfide oxidation
2.1 Titanium/DET catalyst system
2.2 Titanium/BINOL and other diols catalyst system
2.3 Titanium/salen catalyst system
2.4 Other Titanium-catalyst systems
3 Titanium-catalyzed enantioselective sulfoxidation in the synthesis of chiral drugs
3.1 Proton pump inhibitors
3.2 Anti-inflammatory drugs
3.3 Anti-cancer drugs
3.4 Antibiotics
3.5 Platelet adhesion inhibitors
3.6 Antipsychotic drugs
3.7 Lipid regulators
3.8 Potassium channel openers
3.9 Neurokinin inhibitors
4. Conclusion and outlook

CLC Number: 

[1 ] Carreno M C. Chem. Rev. ,1995,95: 1717—1760
[2 ] Fernandez I,Khiar N. Chem. Rev. ,2003,103: 3651—3705
[3 ] Legros J,Dehli J R,Bolm C. Adv. Synth. Catal. ,2005,347:
19—31
[4 ] 黄秋亚(Huang Q Y) ,朱槿( Zhu J) ,邓金根( Deng J G) . 有
机化学( Chinese J. Org. Chem. ) ,2005,25(5) : 496—506
[5 ] 曾庆乐( Zeng Q L) . 化学进展( Prog. Chem. ) ,2007,19(5) :
745—750
[6 ] Weng W,Wang Q H,Yao B X,Zeng Q L. J. Chromatogr. A,
2004,1042: 81—87
[7 ] Weng W, Zeng Q L, Yao B X, Wang Q, Li S.
Chromatographia,2005,61: 561—566
[8 ] Zeng Q L,Wang H Q,Wang T J,Cai Y,Weng W,Zhao Y.
Adv. Synth. Catal. ,2005,347(15) : 1933—1936
[9 ] Drago C,Caggiano L,Jackson R F W. Angew. Chem. Int.
Ed. ,2005,44: 7221—7223
[10] Katsuki T,Sharpless K B. J. Am. Chem. Soc. ,1980,102
(18) : 5974—5976
[11] Pitchen P,Deshmykh M N,Dunach E,Kagan H B. J. Am.
Chem. Soc. ,1984,106: 8188—8193
[12] Bortolini O, di Furia F, Licini G, Modena G, Rossi M.
Tetrahedron Lett. ,1986,27(51) : 6257—6260
[13] Brunel J M,Kagan H B. Synlett,1996,404—406
[14] Komatsu N, Hashizume M, Sugita T, Uemura S. J. Org.
Chem. ,1993,58(17) : 4529—4533
[15] Komatau N, Hashizume M, Sugita T, Uemura S. J. Org.Chem. ,1993,58: 7624—7626
[16] Wang X,Wang X,Guo H,Wang Z,Ding K L. Chem. Eur.
J. ,2005,11: 4078—4088
[17] 袁小亚(Yuan X Y) ,王晓天(Wang X T) . 华中师范大学学
报( J. Cent. China Norm. Univ. ) ,2008,42(2) : 228—231
[18] Sun J,Yang M,Dai Z,Zhu C,Hu H W. Synthesis,2008,16:
2513—2518
[19] Zeng Q L,Wang H Q,Weng W,Lin W,Gao Y,Huang X,
Zhao Y. New J. Chem. ,2005,29(9) : 1125—1127
[20] Zeng Q L,Chen W Z,Zhao Y F. Int. J. Mass Spectr. ,2007,
262 (1 /2) : 161—167
[21] Zeng Q L,Wang H Q,Liu Z R,Li B G,Zhao Y F. Amino
Acids,2007,33(3) : 537—541
[22] Zeng Q L,Liu H,Cui X,Mi A,Jiang Y,Li X,Choi M C K,
Chan A S C. Tetrahedron: Asymm. ,2002,13(2) : 115—117
[23] Zeng Q L,Liu H,Mi A,Jiang Y,Li X,Choi M C K,Chan A
S C. Tetrahedron,2002,58: 8799—8803
[24] 曾庆乐( Zeng Q L) ,宓爱巧(Mi A Q) ,蒋耀忠( Jiang Y Z) .
化学进展( Prog. Chem. ) ,2004,16(4) : 603—612
[25] Zeng Q L,Liu Z,Li B,Wang F. Amino Acids,2004,27:
183—186
[26] Zeng Q L,Tang H Y,Zhang S,Liu J C. Chinese J. Chem. ,
2008,26(8) : 1435—1439
[27] Colombo A,Marturano G,Pasini A. Gazz. Chem. Ital. ,1986,
116(1) : 35—40
[28] Sasaki C,Nakajima K,Kojima M,Fujita J. Bull. Chem. Soc.
Jpn. ,1991,64(4) : 1318—1324
[29] Saito B,Katsuki T. Tetrahedron Lett. ,2001,42: 3873—3876
[30] 彭云贵( Peng Y G) ,冯小明( Feng X M) ,崔欣( Cui X) ,蒋
耀忠( Jiang Y Z ) . 高等学校化学学报( Chem. J. Chinese
Univ. ) ,2001,32(8) : 1326—1331
[31] Delamare M,Belot S,Caille J C,Martinet F,Kagan H B,
Henryon V. Tetrahedron Lett. ,2009,50: 1702—1704
[32] Lindberg P,Brandstrom A,Wallmark B,Mattsson H,Rikner L,
Hoffmann K J. Med. Res Rev. ,1990,10(1) : 1—54
[33] Cotton H,Elebring T,Larsson M,Li L,Sorensen H,von Unge
S. Tetrahedron Asymm. ,2000,11(18) : 3819—3825
[34] Bolm C,Bienewald F. Angew. Chem. Int. Ed. ,1996,34:
2640—2642
[35] Yamashita S,Ebina K. WO2004074285 A1,2004
[36] Maguire A R,Papot S,Ford A,Touhey S,O'Connor R,Clynes
M. Synlett,2001,41—44
[37] Naso F,Cardellicchio C,Affortunato F, et al. Tetrahedron:
Asymmetry,2006,17: 3226—3229
[38] 李娜( Li N) ,张利平( Zhang L P) ,刘京生( Liu J S) . 河北医
药(Hebei Med. J. ) ,2003,25(9) : 685—686
[39] Hutton C A,White J M. Tetrahedron Lett. ,1997,38 ( 9 ) :
1643—1646
[40] Moseley J D,Moss W O,Welham M J. Org. Process Res.
Dev. ,2001,5(5) : 491—497
[41] Hwang D R,Helquist P,Shekhani M S. J. Org. Chem. ,1985,
50(8) : 1264—1271
[42] Nakajima N,Enomoto T,Matsuura N,Ubukata M. Bioorg.
Med. Chem. Lett. ,1998,23(8) : 3331—3334
[43] Nishi T,Uno T,Shu Y,Tamura K,Okada M. WO9426732,
1994
[44] Matsugi M, Fukuda N, Muguruma Y, Yamaguchi T,
Minamikawa J,Otsuka S. Tetrahedron,2001,57: 2739—2744
[45] Hogan P J,Hopes P A,Moss W O,Robinson G E,Patel I.
Org. Process Res. Dev. ,2002,6(3) : 225—229
[46] Pitchen P,Collins A N,Sheldrake G N,Crosby J. Chirality in
Industry II: Developments in the Commercial Manufacture and
Applications of Optically Active Compounds. New York: John
Wiley & Sons,1997. 381—390
[47] Pitchen P,France C J,McFarlane I M,Newton C G,Thompson
D M. Tetrahedron Lett. ,1994,35(3) : 485—488
[48] Legros J,Dehli J R,Bolm C. Adv. Synth. Catal. ,2005,347
(1) : 19—31
[49] Bernstein P R,Aharony D,Albert J S,Andisik D,Barthlow H
G,Bialecki R,Davenport T,Dedinas R F,Dembofsky B T,
Koether G,Kosmider B J,Kirkland K,Ohnmacht C J,Potts W,
Rumsey W L,Shen L H,Shenvi A,Sherwood S,Stollman D,
Russell K. Bioorg. Med. Chem. Lett. ,2001,11(20) : 2769—
2773
[50] Albert J S,Aharony D,Andisik D,Barthlow H,Bernstein P R,
Bialecki R A,Dedinas R,Dembofsky B T,Hill D,Kirkland K,
Koether G M,Kosmider B J,Ohnmacht C,Palmer W,Potts W,
Rumsey W,Shen L H,Shenvi A,Sherwood S,Warwick P J,
Russell K. J. Med. Chem. ,2002,45(18) : 3972—3983

[1] Lujie Song, Youping Wu, Jianping Deng. Enantioselective Release of Chiral Drugs [J]. Progress in Chemistry, 2021, 33(9): 1550-1559.
[2] Dongya Bai, Junyao He, Bin Ouyang, Jin Huang, Pu Wang. Biocatalytic Asymmetric Synthesis of Chiral Aryl Alcohols [J]. Progress in Chemistry, 2017, 29(5): 491-501.
[3] Zeng Qingle**. Synthesis of Chiral Sulfoxides [J]. Progress in Chemistry, 2007, 19(05): 745-750.
[4] Chen Yijun* Wu Xuri. Biocatalysis in Drug Discovery and Development [J]. Progress in Chemistry, 2007, 19(012): 1947-1954.
[5] Zhang Chun,Zheng yansong**,Mei Fuming,Li Guangxing. Recognition of Bioactive Molecules by Calixarenes [J]. Progress in Chemistry, 2004, 16(06): 934-.
[6] Li Shukun,Bai Donglu*. Application of Chiral Sulfoxides in Asymmetric Synthes is [J]. Progress in Chemistry, 2001, 13(05): 351-.