Synthesis, antitumor and DNA photocleaving activities of novel naphthalene carboxamides: Effects of different thio-heterocyclic rings and aminoalkyl side chains

Zhigang Li; Qing Yang; Xuhong Qian

doi:10.1016/j.tet.2005.06.097

Synthesis, antitumor and DNA photocleaving activities of novel naphthalene carboxamides: Effects of different thio-heterocyclic rings and aminoalkyl side chains

Zhigang Li
, Qing Yang
, Xuhong Qian^*

^*Corresponding author for this work

Dalian University of Technology
East China University of Science and Technology

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

Two kinds of thio-heterocyclic fused naphthalene carboxamides, 3a-b, 4a-b, were designed, synthesized and quantitatively evaluated as efficient antitumor and DNA photocleaving agents. Compound 3a or 3b, having the thiophene ring, intercalated into DNA more strongly than compound 4a or 4b, having the thioxanthene ring. Compound 4a or 4b, photocleaved DNA more efficiently than 3a or 3b via superoxide anion. Compound 4a was the strongest inhibitor for P388 (murine leukemia cell), while 3a was the most cytotoxic one against A549 (human lung cancer cell). Each new compound showed stronger DNA photocleaving activity than corresponding naphthalimide.

Original language	English
Pages (from-to)	8711-8717
Number of pages	7
Journal	Tetrahedron
Volume	61
Issue number	36
DOIs	https://doi.org/10.1016/j.tet.2005.06.097
State	Published - 5 Sep 2005
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Antitumor
DNA photocleavage
Intercalating

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10.1016/j.tet.2005.06.097

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title = "Synthesis, antitumor and DNA photocleaving activities of novel naphthalene carboxamides: Effects of different thio-heterocyclic rings and aminoalkyl side chains",

abstract = "Two kinds of thio-heterocyclic fused naphthalene carboxamides, 3a-b, 4a-b, were designed, synthesized and quantitatively evaluated as efficient antitumor and DNA photocleaving agents. Compound 3a or 3b, having the thiophene ring, intercalated into DNA more strongly than compound 4a or 4b, having the thioxanthene ring. Compound 4a or 4b, photocleaved DNA more efficiently than 3a or 3b via superoxide anion. Compound 4a was the strongest inhibitor for P388 (murine leukemia cell), while 3a was the most cytotoxic one against A549 (human lung cancer cell). Each new compound showed stronger DNA photocleaving activity than corresponding naphthalimide.",

keywords = "Antitumor, DNA photocleavage, Intercalating",

author = "Zhigang Li and Qing Yang and Xuhong Qian",

year = "2005",

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doi = "10.1016/j.tet.2005.06.097",

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TY - JOUR

T1 - Synthesis, antitumor and DNA photocleaving activities of novel naphthalene carboxamides

T2 - Effects of different thio-heterocyclic rings and aminoalkyl side chains

AU - Li, Zhigang

AU - Yang, Qing

AU - Qian, Xuhong

PY - 2005/9/5

Y1 - 2005/9/5

N2 - Two kinds of thio-heterocyclic fused naphthalene carboxamides, 3a-b, 4a-b, were designed, synthesized and quantitatively evaluated as efficient antitumor and DNA photocleaving agents. Compound 3a or 3b, having the thiophene ring, intercalated into DNA more strongly than compound 4a or 4b, having the thioxanthene ring. Compound 4a or 4b, photocleaved DNA more efficiently than 3a or 3b via superoxide anion. Compound 4a was the strongest inhibitor for P388 (murine leukemia cell), while 3a was the most cytotoxic one against A549 (human lung cancer cell). Each new compound showed stronger DNA photocleaving activity than corresponding naphthalimide.

AB - Two kinds of thio-heterocyclic fused naphthalene carboxamides, 3a-b, 4a-b, were designed, synthesized and quantitatively evaluated as efficient antitumor and DNA photocleaving agents. Compound 3a or 3b, having the thiophene ring, intercalated into DNA more strongly than compound 4a or 4b, having the thioxanthene ring. Compound 4a or 4b, photocleaved DNA more efficiently than 3a or 3b via superoxide anion. Compound 4a was the strongest inhibitor for P388 (murine leukemia cell), while 3a was the most cytotoxic one against A549 (human lung cancer cell). Each new compound showed stronger DNA photocleaving activity than corresponding naphthalimide.

KW - Antitumor

KW - DNA photocleavage

KW - Intercalating

UR - https://www.scopus.com/pages/publications/23444439628

U2 - 10.1016/j.tet.2005.06.097

DO - 10.1016/j.tet.2005.06.097

M3 - 文章

AN - SCOPUS:23444439628

SN - 0040-4020

VL - 61

SP - 8711

EP - 8717

JO - Tetrahedron

JF - Tetrahedron

IS - 36

ER -

Synthesis, antitumor and DNA photocleaving activities of novel naphthalene carboxamides: Effects of different thio-heterocyclic rings and aminoalkyl side chains

Abstract

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Keywords

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