Synthesis and biological evaluation of 2,2-disubstituted 2-aminoethanols: Analogues of FTY720

被引：60

作者：

Kiuchi, M

Adachi, K

Kohara, T

Teshima, K

Masubuchi, Y

Mishina, T

Fujita, T

机构：

[1] Yoshitomi Pharmaceut Ind Ltd, Res Labs, Iruma, Saitama 358, Japan

[2] Setsunan Univ, Fac Pharmaceut Sci, Hirakata, Osaka 57301, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1998年 / 8卷 / 01期

关键词：

D O I：

10.1016/S0960-894X(97)10188-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Desymmerization of symmetric FTY720 by substitution of different alkyl groups for one of the prochiral hydroxymethyl groups was performed. The size of the alkyl groups and the absolute configuration at quaternary carbon were important on immunosuppressive activity. (C) 1997 Elsevier Science Ltd. All rights reserved.

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页码：101 / 106

页数：6

相关论文

共 18 条

[1] DESIGN, SYNTHESIS, AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF 2-SUBSTITUTED-2-AMINO-1,3-PROPANEDIOLS - DISCOVERY OF A NOVEL IMMUNOSUPPRESSANT, FTY720 [J].

ADACHI, K ;

KOHARA, T ;

NAKAO, N ;

ARITA, M ;

CHIBA, K ;

MISHINA, T ;

SASAKI, S ;

FUJITA, T .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (08) :853-856

[2] ISOLATION AND STRUCTURE DETERMINATION OF A NEW ANTIFUNGAL ALPHA-HYDROXYMHTHYL-ALPHA-AMINO ACID [J].

ARAGOZZINI, F ;

CRAVERI, R ;

SCOLASTICO, C ;

RINDONE, B ;

MANACHINI, PL .

TETRAHEDRON, 1972, 28 (21) :5493-+

[3] ELUCIDATION OF STRUCTURE AND STEREOCHEMISTRY OF MYRIOCIN - NOVEL ANTIFUNGAL ANTIBIOTIC [J].

BAGLI, JF ;

KLUEPFEL, D ;

STJACQUE.M .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (07) :1253-1260

[4] TOTAL SYNTHESIS OF (+)-THERMOZYMOCIDIN (MYRIOCIN) FROM D-FRUCTOSE [J].

BANFI, L ;

BERETTA, MG ;

COLOMBO, L ;

GENNARI, C ;

SCOLASTICO, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (09) :488-490

[5]

BANFI L, 1983, J CHEM SOC P1, P1614

[6]

Chiba K, 1996, TRANSPLANT P, V28, P1056

[7] Potent immunosuppressants, 2-alkyl-2-aminopropane-1,3-diols [J].

Fujita, T ;

Hirose, R ;

Yoneta, M ;

Sasaki, S ;

Inoue, K ;

Kiuchi, M ;

Hirase, S ;

Chiba, K ;

Sakamoto, H ;

Arita, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (22) :4451-4459

[8] SIMPLE COMPOUNDS, 2-ALKYL-2-AMINO-1,3-PROPANEDIOLS HAVE POTENT IMMUNOSUPPRESSIVE ACTIVITY [J].

FUJITA, T ;

YONETA, M ;

HIROSE, R ;

SASAKI, S ;

INOUE, K ;

KIUCHI, M ;

HIRASE, S ;

ADACHI, K ;

ARITA, M ;

CHIBA, K .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (08) :847-852

[9] 2-SUBSTITUTED 2-AMINOETHANOL - MINIMUM ESSENTIAL STRUCTURE FOR IMMUNOSUPPRESSIVE ACTIVITY OF ISP-I (MYRIOCIN) [J].

FUJITA, T ;

HIROSE, R ;

HAMAMICHI, N ;

KITAO, Y ;

SASAKI, S ;

YONETA, M ;

CHIBA, K .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (16) :1857-1860

[10] FUNGAL METABOLITES .11. A POTENT IMMUNOSUPPRESSIVE ACTIVITY FOUND IN ISARIA-SINCLAIRII METABOLITE [J].

FUJITA, T ;

INOUE, K ;

YAMAMOTO, S ;

IKUMOTO, T ;

SASAKI, S ;

TOYAMA, R ;

CHIBA, K ;

HOSHINO, Y ;

OKUMOTO, T .

JOURNAL OF ANTIBIOTICS, 1994, 47 (02) :208-215