COMPOUNDS INTERACTING WITH TUBULIN .1. SYNTHESIS OF ORTHO-ORTHO' SUBSTITUTED PHENYLPYRROLES WITH FREE OR RESTRICTED ROTATION

被引：0

作者：

ALAZARD, JP ^{[1
]}

BOYE, O ^{[1
]}

GILLET, B ^{[1
]}

GUENARD, D ^{[1
]}

BELOEIL, JC ^{[1
]}

THAL, C ^{[1
]}

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

来源：

BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE | 1993年 / 130卷 / 06期

关键词：

TUBULIN; PHENYLPYRROLE; ATROPISOMERS; CHIRAL SHIFT REAGENTS;

D O I：

暂无

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis of ortho-ortho' substituted phenylpyrroles that are susceptible to isomerization of the biaryl type (atropisomerism) was performed using a Michael addition of isocyanoacetates with nitrostyrenes. Atropisomerism in phenylpyrroles 14 and 15 was studied by means of H-1 NMR spectroscopy using chiral lanthanide shift reagents (LSR*). In the case of chiral phenylpyrrole 21, an evaluation of the interconversion parameters between diastereomers (k, DELTAG(T)*) was attempted.

引用

页码：779 / 787

页数：9

共 31 条

[1] SYNTHESIS OF TRICYCLIC PHENYLPYRROLE LACTAMS, NEW MODELS OF ANTITUBULIN AGENTS [J].

ALAZARD, JP ;

MILLETPAILLUSSON, C ;

BOYE, O ;

GUENARD, D ;

CHIARONI, A ;

RICHE, C ;

THAL, C .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (12) :725-728

[2] NUCLEAR MAGNETIC RESONANCE METHODS FOR DETERMINING CHEMICAL-EXCHANGE RATES [J].

ALLERHAN.A ;

GUTOWSKY, HS ;

JONAS, J ;

MEINZER, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (14) :3185-&

[3]

[Anonymous], 1977, WILEY ONLINE LIB

[4] A SYNTHESIS OF VITAMIN-A FROM CYCLOHEXANONE [J].

ATTENBURROW, J ;

CAMERON, AFB ;

CHAPMAN, JH ;

EVANS, RM ;

HEMS, BA ;

JANSEN, ABA ;

WALKER, T .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (MAR) :1094-1111

[5] PREPARATION OF N,O-AMINALS AS SYNTHETIC EQUIVALENTS OF H2C=NAR AND (H2C=NHAR)+ IONS - NEUTRAL-PROMOTED AND ACID-PROMOTED TRANSFORMATIONS [J].

BARLUENGA, J ;

BAYON, AM ;

CAMPOS, P ;

ASENSIO, G ;

GONZALEZNUNEZ, E ;

MOLINA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1631-1636

[6]

BARTON DHR, 1990, TETRAHEDRON, V46, P7587

[7]

BASSINDALE A, 1984, 3 DIMENSION ORGANIC, P77

[8]

BOYE O, 1988, THESIS U PARIS 11

[9] COLCHICINE AND ITS ANALOGS - RECENT FINDINGS [J].

BROSSI, A ;

YEH, HJC ;

CHRZANOWSKA, M ;

WOLFF, J ;

HAMEL, E ;

LIN, CM ;

QUIN, F ;

SUFFNESS, M ;

SILVERTON, J .

MEDICINAL RESEARCH REVIEWS, 1988, 8 (01) :77-94

[10]

BUDESINSKY Z, 1976, COLLECT CZECH CHEM C, V41, P3405

← 1 2 3 4 →