Acridine derivatives. <b>V</b>. Synthesis and P388 antitumor activity of the novel 9‐anilino‐2,3‐ethylenedioxyacridines

Kimura, Michio; Okabayashi, Ichizo; Kato, Akira

doi:10.1002/jhet.5570300446

Cited by 13 publications

(8 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It significantly simplifies the formation of aryl- [12] and azaaryl-substituted 9-AAs with EW groups, which are not accessible by using the standard "reverse" approach, which calls for nucleophilic substitution of the deactivated aminopyridines or aminopyrimidines with 9-chloroacridines. [12,13] An additional advantage of the one-pot S N Ar reaction with 9-AAs is the commercial availability of appropriately substituted 2-pyridyl and 2-pyrimidinyl halide reagents. We also attempted the preparation of dicarboxyl compounds 1f-h by treating 9-AA with 3-fluorophthalic, 4-bromoisophthalic and 2-bromoterephthalic acids 3f-h, respectively (Scheme 2).…”

Section: Synthesis Of 9-(azaarylamino)acridine Derivatives 1a-e By Usmentioning

confidence: 99%

One‐Pot Synthesis of Novel Antiproliferative 9‐Aminoacridines

et al. 2011

View full text Add to dashboard Cite

show abstract

Section: Synthesis Of 9-(azaarylamino)acridine Derivatives 1a-e By Usmentioning

confidence: 99%

One‐Pot Synthesis of Novel Antiproliferative 9‐Aminoacridines

et al. 2011

View full text Add to dashboard Cite

show abstract

“…Acridine derivatives (Nasim & Brychcy, 1979;Thull & Testa, 1994;Má ndi et al, 1994), well known as therapeutic agents, are important because of their range of applications in the dye and pharmaceutical industries. Certain acridinedione derivatives exhibit good inhibition against the pathogen vibro isolate-I (Josephrajan et al, 2005), display anti-cancer (Sondhi et al, 2004;Sugaya et al, 1994;Kimura et al, 1993) and antitumour (Talacki et al, 1974) activity and act as K-channel openers (Li et al, 1996).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 10-benzyl-9-(3-ethoxy-4-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione

Babu¹,

Sughanya²,

Dhandapani³

et al. 2020

Acta Cryst E

View full text Add to dashboard Cite

In the fused ring system of the title compound, C32H37NO4, the central dihydropyridine ring adopts a flattened boat conformation, the mean and maximum deviations of the dihydropyridine ring being 0.1429 (2) and 0.2621 (2) Å, respectively. The two cyclohexenone rings adopt envelope conformations with the tetrasubstituted C atoms as flap atoms. The benzene and phenyl rings form dihedral angles of 85.81 (2) and 88.90 (2)°, respectively, with the mean plane of the dihydropyridine ring. In the crystal, molecules are linked via an O—H...O hydrogen bond, forming a helical chain along the b-axis direction. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (65.2%), O...H/H...O (18.8%) and C...H/H...C (13.9%) contacts. Quantum chemical calculations for the frontier molecular orbitals were undertake to determine the chemical reactivity of the title compound.

show abstract

“…Acridines fused with an ethylenedioxy group at the 2-and 3-positions of the acridine ring showed the same potency of antitumor activities as m-AMSA in the P-388 antitumor test [96,97] (Table 5).…”

mentioning

confidence: 94%

Synthesis and Biological Activity of New Class of Dioxygenated Anticancer Agents

Pujol¹,

Romero²,

Sánchez

2005

CMCACA

View full text Add to dashboard Cite

This paper describes extensive research on the activity of more of 100 cytotoxic compounds containing an oxygenated ring in their structure and isolated from natural plants or prepared by semisynthesis or synthesis from available intermediates. Anticancer drugs have been classified according to the chemical structure of the natural products that are considered to lead the series. The origin and mechanism of action involved in each case have been considered. This new family of natural, semisynthetic and synthetic products includes compounds with interesting antitumor activity such as podophyllotoxin derivatives, NK-611 (15), TOP-53 (16), NPF (24) and Tafluposide (28); camptothecin analogs such as 45 with a considerable cytotoxicity against beta-cell chronic lymphocytic leukemia (CLL), and 52 (new piperazinyl-CPT analog). New dioxygenated ellipticine analogs showed more activity and stability than the natural pattern when the structure incorporated a lactone function instead of the pyridine ring. In the acridine series the new tetracyclic derivatives 75 and 76 containing ethylenedioxy groups at the 2- and 3-positions of the acridine system exhibited the same activity as m-AMSA in vivo against murine P-388 leukemia. Other isolated compounds containing a dioxygenated ring in their structure such as 100 and 101 showed antitumor activities related to kinase inhibition, and are attractive candidates for development of new synthetic antitumor agents.

show abstract

Acridine derivatives. V. Synthesis and P388 antitumor activity of the novel 9‐anilino‐2,3‐ethylenedioxyacridines

Cited by 13 publications

References 21 publications

One‐Pot Synthesis of Novel Antiproliferative 9‐Aminoacridines

One‐Pot Synthesis of Novel Antiproliferative 9‐Aminoacridines

Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 10-benzyl-9-(3-ethoxy-4-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione

Synthesis and Biological Activity of New Class of Dioxygenated Anticancer Agents

Contact Info

Product

Resources

About