Antitumour polycyclic acridines. : Part 9. : Synthesis of 7H-pyrido[4,3,2-kl]acridines with basic side chains

被引：7

作者：

Ellis, MJ ^{[1
]}

Stevens, MFG ^{[1
]}

机构：

[1] Univ Nottingham, Sch Pharmaceut Sci, Canc Res Labs, Nottingham NG7 2RD, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / Royal Society of Chemistry卷 / 23期

关键词：

D O I：

10.1039/b106324n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[3 + 2] Cycloaddition of 3-(dialkylamino)-1-triphenylphosphoranylidenepropan-2-ones and 9-azidoacridine affords 9-[5-(dialkylaminomethyl)-1H-1,2,3-triazol-1-yl] acridines. Graebe-Ullmann thermolysis of the triazoles has been guided by differential scanning calorimetry to predict the optimum temperature for nitrogen extrusion. Boiling diphenyl ether (bp 259 degreesC) is a suitable solvent to convert the triazolylacridines to 2-(dialkylaminomethyl)-7H-pyrido[4,3,2-kl]acridines.

引用

页码：3174 / 3179

页数：6

共 20 条

[11] Creation of human tumour cells with defined genetic elements [J].

Hahn, WC ;

Counter, CM ;

Lundberg, AS ;

Beijersbergen, RL ;

Brooks, MW ;

Weinberg, RA .

NATURE, 1999, 400 (6743) :464-468

[12]

HEALD RA, IN PRESS J MED CHEM

[13] PREPARATION OF CHLOROMETHYL VINYL KETONES [J].

HUDSON, RF ;

CHOPARD, PA .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (09) :2446-&

[14] Antitumour polycyclic acridines.: Part 5.: Synthesis of 7H-pyrido[4,3,2-kl]acridines with exploitable functionality in the pyridine ring [J].

Julino, M ;

Stevens, MFG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (10) :1677-1684

[15] SPECIFIC ASSOCIATION OF HUMAN TELOMERASE ACTIVITY WITH IMMORTAL CELLS AND CANCER [J].

KIM, NW ;

PIATYSZEK, MA ;

PROWSE, KR ;

HARLEY, CB ;

WEST, MD ;

HO, PLC ;

COVIELLO, GM ;

WRIGHT, WE ;

WEINRICH, SL ;

SHAY, JW .

SCIENCE, 1994, 266 (5193) :2011-2015

[16] CYCLO-OCTA[DEF]CARBAZOLE, A NEW HETEROCYCLIC PARATROPIC RING-SYSTEM [J].

MITCHELL, G ;

REES, CW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (02) :403-412

[17]

Monks A, 1997, ANTI-CANCER DRUG DES, V12, P533

[18]

Neidle S, 1999, ANTI-CANCER DRUG DES, V14, P341

[19] Antitumor polycyclic acridines. 7. Synthesis and biological properties of DNA affinic tetra- and pentacyclic acridines [J].

Stanslas, J ;

Hagan, DJ ;

Ellis, MJ ;

Turner, C ;

Carmichael, J ;

Ward, W ;

Hammonds, TR ;

Stevens, MFG .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (08) :1563-1572

[20]

STEVENS MFG, 2001, P AM ASSOC CANC RES, V42, P4465

← 1 2 →