A modified synthesis of iodoazidoaryl prazosin

被引：42

作者：

Andrus, MB ^{[1
]}

Mettath, SN ^{[1
]}

Song, C ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 23期

关键词：

D O I：

10.1021/jo026217o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The antihypertension agent iodoazidoaryl prazosin (IAAP) has been made using a convergent route involving addition of an acylated piperazine 7 to 2-chloroquinazoline 5. IAAP has been shown to function as a multidrug resistance (MDR) reversal agent and bind to P-glycoprotein, a transmembrane transport protein. A study is also reported involving palladium-catalyzed substitution with amine heterocycles. With N,N-bis(2,6-diisopropyl)dihydroimidazolium chloride (10) as the ligand (2 mol %) for palladium(II) acetate (2 mol %) in THF at room temperature, morpholine added to 5 in 81% yield.

引用

页码：8284 / 8286

页数：3

共 39 条

[1] SYNTHESIS AND IDENTIFICATION OF MAJOR METABOLITES OF PRAZOSIN FORMED IN DOG AND RAT [J].

ALTHUIS, TH ;

HESS, HJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (01) :146-149

[2] Biochemical, cellular, and pharmacological aspects of the multidrug transporter [J].

Ambudkar, SV ;

Dey, S ;

Hrycyna, CA ;

Ramachandra, M ;

Pastan, I ;

Gottesman, MM .

ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 1999, 39 :361-398

[3] Palladium-imidazolium carbene catalyzed Mizoroki-Heck coupling with aryl diazonium ions [J].

Andrus, MB ;

Song, C ;

Zhang, JQ .

ORGANIC LETTERS, 2002, 4 (12) :2079-2082

[4] Palladium-imidazolium carbene catalyzed aryl, vinyl, and alkyl Suzuki-Miyaura cross coupling [J].

Andrus, MB ;

Song, C .

ORGANIC LETTERS, 2001, 3 (23) :3761-3764

[5] The synthesis and evaluation of a solution phase indexed combinatorial library of non-natural polyenes for reversal of p-glycoprotein mediated multidrug resistance [J].

Andrus, MB ;

Turner, TM ;

Sauna, ZE ;

Ambudkar, SV .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :4973-4983

[6] Synthesis and analysis of polyethylene glycol linked P-glycoprotein-specific homodimers based on (-)-stipiamide [J].

Andrus, MB ;

Turner, TM ;

Updegraff, EP ;

Sauna, ZE ;

Ambudkar, SV .

TETRAHEDRON LETTERS, 2001, 42 (23) :3819-3822

[7] The synthesis and evaluation of a solution-phase indexed combinatorial library of non-natural polyenes for multidrug resistance reversal [J].

Andrus, MB ;

Turner, TM ;

Asgari, D ;

Li, WK .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :2978-2979

[8] Total synthesis of stipiamide and designed polyenes as new agents for the reversal of multidrug resistance [J].

Andrus, MB ;

Lepore, SD ;

Turner, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12159-12169

[9] RETRACTED: Structure of MsbA from E-coli:: A homolog of the multidrug resistance ATP binding cassette (ABC) transporters (Retracted Article. See vol 314, pg 1875, 2006) [J].

Chang, G ;

Roth, CB .

SCIENCE, 2001, 293 (5536) :1793-1800

[10]

CHAUFFERT B, 1986, CANCER RES, V46, P825

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