Direct diazo-transfer reaction on β-lactam:: Synthesis and preliminary biological activities of 6-triazolylpenicillanic acids

被引：19

作者：

Chen, Po C. ^{[1
]}

Wharton, Rebekah E. ^{[1
]}

Patel, Pratiq A. ^{[1
]}

Oyelere, Adegboyega K. ^{[1
]}

机构：

[1] Georgia Inst Technol, Parker H Petit Inst Bioengn & Biosci, Sch Chem & Biochem, Atlanta, GA 30332 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2007年 / 15卷 / 23期

关键词：

beta-lactam; antibiotic; diazo-transfer; penicillin; Huisgen cycloaddition; 6-triazolylpenicillanic acids; click chemistry; terminal alkynes; azide;

D O I：

10.1016/j.bmc.2007.08.035

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 [生物化学与分子生物学]; 081704 [应用化学];

摘要：

In this study we report the first example of a direct diazo-transfer reaction on readily available 6-aminopenicillanates to give 6-azidopenicillanates in high yield. Subsequent Cu(I)-catalyzed Huisgen cycloaddition between these 6-azidopenicillanates and assorted terminal alkynes facilely furnished 6-triazolylpenicillanic acids. Preliminary biological screening indicates that these triazolylpenicillanic acids possess low to moderate antibacterial activities. (C) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：7288 / 7300

页数：13

相关论文

共 64 条

[1]

Metal catalyzed diazo transfer for the synthesis of azides from amines [J].

Alper, PB ;

Hung, SC ;

Wong, CH .

TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032

[2]

2-AMINO ALCOHOLS FROM ALPHA-AMINO-ACIDS - SINGLE-STEP MILD PROCEDURE [J].

ANHOURY, ML ;

ARICKX, M ;

CROOY, P ;

DENEYS, R ;

ELIAERS, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (02) :191-192

[3]

STUDIES RELATED TO PENICILLINS AND CEPHALOSPORINS .5. NEW RELAY SYNTHESIS OF PENICILLIN [J].

BACHI, MD ;

BREIMAN, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (01) :11-13

[4]

Inhibitors of metallo-β-lactamase generated from β-lactam antibiotics [J].

Badarau, A ;

Llinás, A ;

Laws, AP ;

Damblon, C ;

Page, MI .

BIOCHEMISTRY, 2005, 44 (24) :8578-8589

[5]

TOTAL SYNTHESES OF PENICILLANIC ACID S,S-DIOXIDE AND 6-AMINOPENICILLANIC ACID USING (BENZYLOXY)NITROMETHANE [J].

BARRETT, AGM ;

SAKADARAT, S .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17) :5110-5117

[6]

C2-symmetric macrocyclic carbohydrate/amino acid hybrids through copper(I)-catalyzed formation of 1,2,3-triazoles [J].

Billing, JF ;

Nilsson, UJ .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12) :4847-4850

[7]

1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics [J].

Bock, Victoria D. ;

Speijer, Dave ;

Hiemstra, Henk ;

van Maarseveen, Jan H. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (06) :971-975

[8]

1,2,3-triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors [J].

Brik, A ;

Alexandratos, J ;

Lin, YC ;

Elder, JH ;

Olson, AJ ;

Wlodawer, A ;

Goodsell, DS ;

Wong, CH .

CHEMBIOCHEM, 2005, 6 (07) :1167-+

[9]

Taking inventory: antibacterial agents currently at or beyond Phase 1 [J].

Bush, K ;

Macielag, M ;

Weidner-Wells, M .

CURRENT OPINION IN MICROBIOLOGY, 2004, 7 (05) :466-476

[10]

The discovery and development of modified penicillin- and cephalosporin-derived β-lactamase inhibitors [J].

Buynak, JD .

CURRENT MEDICINAL CHEMISTRY, 2004, 11 (14) :1951-1964

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