2-SUBSTITUTED 2-AMINOETHANOL - MINIMUM ESSENTIAL STRUCTURE FOR IMMUNOSUPPRESSIVE ACTIVITY OF ISP-I (MYRIOCIN)

被引:24
作者
FUJITA, T
HIROSE, R
HAMAMICHI, N
KITAO, Y
SASAKI, S
YONETA, M
CHIBA, K
机构
[1] TAITO CO LTD,RES LAB,NAGATA KU,KOBE,HYOGO 653,JAPAN
[2] KYOTO UNIV,FAC PHARMACEUT SCI,SAKYO KU,KYOTO 60601,JAPAN
[3] YOSHITOMI PHARMACEUT IND LTD,RES LABS,IRUMA,SAITAMA 358,JAPAN
关键词
D O I
10.1016/0960-894X(95)00304-C
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
2-Substituted 2-aminoethanol was shown to be the minimum essential structure for the immunosuppressive activity of ISP-I (myriocin, thermozymocidin) by simplification of 2-substituted 2-amino-1,3-propanediol, which was generated by modification of ISP-I. Among the series, 2-amino-4-(4-octylphenyl)butanol hydrochloride displayed comparably potent activity to 2-amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol hydrochloride, FTY720.
引用
收藏
页码:1857 / 1860
页数:4
相关论文
共 16 条
  • [1] DESIGN, SYNTHESIS, AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF 2-SUBSTITUTED-2-AMINO-1,3-PROPANEDIOLS - DISCOVERY OF A NOVEL IMMUNOSUPPRESSANT, FTY720
    ADACHI, K
    KOHARA, T
    NAKAO, N
    ARITA, M
    CHIBA, K
    MISHINA, T
    SASAKI, S
    FUJITA, T
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (08) : 853 - 856
  • [2] ISOLATION AND STRUCTURE DETERMINATION OF A NEW ANTIFUNGAL ALPHA-HYDROXYMHTHYL-ALPHA-AMINO ACID
    ARAGOZZINI, F
    CRAVERI, R
    SCOLASTICO, C
    RINDONE, B
    MANACHINI, PL
    [J]. TETRAHEDRON, 1972, 28 (21) : 5493 - +
  • [3] ELUCIDATION OF STRUCTURE AND STEREOCHEMISTRY OF MYRIOCIN - NOVEL ANTIFUNGAL ANTIBIOTIC
    BAGLI, JF
    KLUEPFEL, D
    STJACQUE.M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (07) : 1253 - 1260
  • [4] TOTAL SYNTHESIS OF (+)-THERMOZYMOCIDIN (MYRIOCIN) FROM D-FRUCTOSE
    BANFI, L
    BERETTA, MG
    COLOMBO, L
    GENNARI, C
    SCOLASTICO, C
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (09) : 488 - 490
  • [5] BANFI L, 1983, J CHEM SOC P1, P1614
  • [6] SIMPLE COMPOUNDS, 2-ALKYL-2-AMINO-1,3-PROPANEDIOLS HAVE POTENT IMMUNOSUPPRESSIVE ACTIVITY
    FUJITA, T
    YONETA, M
    HIROSE, R
    SASAKI, S
    INOUE, K
    KIUCHI, M
    HIRASE, S
    ADACHI, K
    ARITA, M
    CHIBA, K
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (08) : 847 - 852
  • [7] FUNGAL METABOLITES .11. A POTENT IMMUNOSUPPRESSIVE ACTIVITY FOUND IN ISARIA-SINCLAIRII METABOLITE
    FUJITA, T
    INOUE, K
    YAMAMOTO, S
    IKUMOTO, T
    SASAKI, S
    TOYAMA, R
    CHIBA, K
    HOSHINO, Y
    OKUMOTO, T
    [J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (02) : 208 - 215
  • [8] FUNGAL METABOLITES .12. POTENT IMMUNOSUPPRESSANT, 14-DEOXOMYRIOCIN, (2S,3R,4R)-(E)-2-AMINO-3,4-DIHYDROXY-2-HYDROXYMETHYLEICOS-6-ENOIC ACID AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF MYRIOCIN DERIVATIVES
    FUJITA, T
    INOUE, K
    YAMAMOTO, S
    IKUMOTO, T
    SASAKI, S
    TOYAMA, R
    YONETA, M
    CHIBA, K
    HOSHINO, Y
    OKUMOTO, T
    [J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (02) : 216 - 224
  • [9] FUJITA T, 1990, 17TH IUPAC INT S CHE, P68
  • [10] MYRIOCIN, A NEW ANTIFUNGAL ANTIBIOTIC FROM MYRIOCOCCUM-ALBOMYCES
    KLUEPFEL, D
    VEZINA, C
    SEHGAL, SN
    KUDELSKI, A
    CHAREST, MP
    BAGLI, J
    [J]. JOURNAL OF ANTIBIOTICS, 1972, 25 (02) : 109 - +