Synthesis of anticancer β-lactams:: mechanism of action

被引：143

作者：

Banik, BK ^{[1
]}

Becker, FF ^{[1
]}

Banik, I ^{[1
]}

机构：

[1] Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Unit 89, Houston, TX 77030 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2004年 / 12卷 / 10期

关键词：

beta-lactams; anticancer agents; cell cycle; apoptosis;

D O I：

10.1016/j.bmc.2004.03.033

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：

Synthesis of the trans 1-N-chrysenyl and 1-N-phenanthrenyl 3-acetoxy-4-phenyl-2-azetidinones has been achieved. Microwave-assisted reaction has proved useful in the synthesis of these compounds. Cell growth inhibition study has indicated selective anticancer activity against two leukemia and colon carcinoma cell lines. A mechanistic correlation of their anticancer activity has been described. Striking G(2) blockade that is clearly distinct in cell cycle analysis and demonstrated only in sensitive cell lines has been observed. They, do not induce apoptosis in sensitive or resistant lines. They also do not inhibit topoisomerases. Ames test has shown they are nonmutagenic. (C) 2004 Published by Elsevier Ltd.

引用

页码：2523 / 2528

页数：6

共 77 条

[1]

Beta-lactams derived from the reaction of phenanthridines and 11H-dibenzo[b,e]azepin-11-one with phenylvaleryl chloride.: Synthesis of fused analogs of the cholesterol absorption inhibitor Sch 48461. [J].

Afonso, A ;

Rosenblum, SB ;

Puar, MS ;

McPhail, AT .

TETRAHEDRON LETTERS, 1998, 39 (41) :7431-7434

[2]

A convenient trans-stereoselective synthesis of phenanthridine derived 2-azetidinones using the Staudinger ketene-imine cycloaddition [J].

Alcaide, B ;

Rodríguez-Vicente, A .

TETRAHEDRON LETTERS, 1999, 40 (10) :2005-2006

[3]

METHODS FOR DETECTING CARCINOGENS AND MUTAGENS WITH SALMONELLA-MAMMALIAN-MICROSOME MUTAGENICITY TEST [J].

AMES, BN ;

MCCANN, J ;

YAMASAKI, E .

MUTATION RESEARCH, 1975, 31 (06) :347-363

[4]

Conformationally constrained anesthetic steroids that modulate GABAA receptors [J].

Anderson, A ;

Boyd, AC ;

Clark, JK ;

Fielding, L ;

Gemmell, DK ;

Hamilton, NM ;

Maidment, MS ;

May, V ;

McGuire, R ;

McPhail, P ;

Sansbury, FH ;

Sundaram, H ;

Taylor, R .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (22) :4118-4125

[5]

ANIK BK, 1997, HETEROCYCLES, P405

[6]

Origins of the stereodivergent outcome in the Staudinger reaction between acyl chlorides and imines [J].

Arrieta, A ;

Lecea, B ;

Cossío, FP .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) :5869-5876

[7]

2-[(ARYLMETHYL)AMINO]-2-METHYL-1,3-PROPANEDIOL DNA INTERCALATORS - AN EXAMINATION OF THE EFFECTS OF AROMATIC RING VARIATION ON ANTITUMOR-ACTIVITY AND DNA-BINDING [J].

BAIR, KW ;

ANDREWS, CW ;

TUTTLE, RL ;

KNICK, VC ;

CORY, M ;

MCKEE, DD .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (07) :1983-1990

[8]

STUDIES ON LACTAMS .96. STEREOSPECIFIC GLYCOSYLATION VIA FERRIER REARRANGEMENT FOR OPTICAL RESOLUTION [J].

BANIK, BK ;

MANHAS, MS ;

BOSE, AK .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4714-4716

[9]

Banik BK, 2004, HETEROCYCLES, V63, P283

[10]

Banik BK, 2003, HETEROCYCLES, V61, P97

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