Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones

被引：7

作者：

Bianchi, DA

Sutich, EG

Kaufman, TS

机构：

[1] Univ Nacl Rosario, Inst Quim Organ Sintesis, CONICET, UNR,Fac Ciencias Bioquim & Farmaceut, Rosario, Argentina

[2] Univ Nacl Rosario, Fac Ciencias Bioquim & Farmaceut, Dept Microbiol, Rosario, Argentina

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 03期

关键词：

D O I：

10.1016/j.bmcl.2003.11.015

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The elaboration and biological activity of 15, containing the proposed pharmacophore for the antibiotic activity of the pyranonaphthoquinones, are reported. The synthetic strategy involved acid-catalyzed lactonization of mandelate 17 for isochroman ring formation, in combination with a Wittig-oxa-Michael functionalization of isochroman-3-ol derivative 20, a lactonization involving configurational inversion of a benzylic alcohol and a final AgO oxidation. Compound 15 showed activity against Staphylococcus aureus and Bacillus subtilis with MIC of 64 and 32 mug/mL, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：757 / 760

页数：4

共 40 条

[11] General synthesis of alpha-acetoxy ethers from esters by DIBALH reduction and acetylation [J].

Dahanukar, VH ;

Rychnovsky, SD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8317-8320

[12] THE STEREOSELECTIVE SYNTHESIS OF ACYCLIC AND EXOCYCLIC TRISUBSTITUTED OLEFINS VIA A HYDROXYL-DIRECTED WITTIG REACTION [J].

GARNER, P ;

RAMAKANTH, S .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2629-2631

[13] THE STEREOSELECTIVE FORMATION OF NAPHTHO[1,2-C]PYRANS, ANGULAR ANALOGS OF THE APHIN-DERIVED GLUCOSIDE-B, BY AN INTRAMOLECULAR VERSION OF THE MUKAIYAMA REACTION OF 4-NAPHTHYLDIOXOLANES [J].

GILES, RGF ;

GREEN, IR ;

KNIGHT, LS ;

SON, VRL ;

YORKE, SC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (07) :865-873

[14] Synthesis of isochroman-3-ylacetates and isochromane-γ-lactones through rearrangement of aryldioxolanylacetates [J].

Giles, RGF ;

Rickards, RW ;

Senanayake, BD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (23) :3949-3956

[15] A NEW ISOCHROMANEQUINONE ANTIBIOTIC, SCH 38519, WITH A NOVEL SUGAR LINKAGE [J].

HEGDE, VR ;

KING, AH ;

PATEL, MG ;

PUAR, MS ;

MCPHAIL, AT .

TETRAHEDRON LETTERS, 1987, 28 (39) :4485-4488

[16] TOTAL SYNTHESIS OF (+/-)-NANAOMYCIN A AND (+/-)-FRENOLICIN [J].

ICHIHARA, A ;

UBUKATA, M ;

OIKAWA, H ;

MURAKAMI, K ;

SAKAMURA, S .

TETRAHEDRON LETTERS, 1980, 21 (46) :4469-4472

[17] PRODUCTION OF DEOXYFRENOLICIN AND A NEW ANTIBIOTIC, FRENOLICIN-B BY STREPTOMYCES-ROSEOFULVUS STRAIN AM-3867 [J].

IWAI, Y ;

KORA, A ;

TAKAHASHI, Y ;

HAYASHI, T ;

AWAYA, J ;

MASUMA, R ;

OIWA, R ;

OMURA, S .

JOURNAL OF ANTIBIOTICS, 1978, 31 (10) :959-965

[18]

IWAI Y, 1978, J ANTIBIOT, V31, P359

[19]

KAESKEMA H, 1976, J ANTIBIOT, V29, P704

[20]

KARWOWSKI JP, 1978, J ANITIBIOT, V41, P1205

← 1 2 3 4 →