Synthesis and cytotoxicity evaluation of substituted pyridazino[4,5-b]phenazine-5,12-diones and tri/tetra-azabenzofluorene-5,6-diones

Hyun Jung Lee; Jin Sung Kim; Myung Eun Suh; Hyen Joo Park; Sang Kook Lee; Hee Kyung Rhee; Hwa Jung Kim; Eun Kyung Seo; Choonmi Kim; Chong Ock Lee; Hea Young Park Choo

doi:10.1016/j.ejmech.2006.09.007

Synthesis and cytotoxicity evaluation of substituted pyridazino[4,5-b]phenazine-5,12-diones and tri/tetra-azabenzofluorene-5,6-diones

Hyun Jung Lee
, Jin Sung Kim
, Myung Eun Suh
, Hyen Joo Park
, Sang Kook Lee
, Hee Kyung Rhee
, Hwa Jung Kim
, Eun Kyung Seo
, Choonmi Kim
, Chong Ock Lee
, Hea Young Park Choo

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

26 Scopus citations

Abstract

The substituted pyridazino[4,5-b]phenazine-5,12-diones and tri/tetra-azabenzo[a]fluorene-5,6-diones were synthesized from 6,7-dichlorophthalazine-5,8-dione and 6,7-dichloroquinoline-5,8-dione, respectively. The cytotoxic activities of the prepared compounds were evaluated by an SRB (Sulforhodamine B) assay against the following human cancer cell lines: A549 (lung), SK-OV-3 (ovarian), SK-MEL-2 (melanoma), XF 498 (CNS), and HCT 15 (colon). Almost all synthesized pyridazino[4,5-b]phenazine-5,12-diones (7a-j) presented higher cytotoxicity than that of doxorubicin (IC₅₀ = 0.097-0.225 μM) against the cancer cell lines. In particular, the cytotoxicity of compounds 7f (R₁ = Et) and 7h (R₁, R₂ = Me) against all human cancer cell lines examined was about 10 times higher than that of doxorubicin. However, the cytotoxicities of several synthesized azabenzo[a]fluorene-5,6-diones (12a, 12c, 12d, 12e, and 12g) against the cancer cell lines in vitro were comparable to those of doxorubicin.

Original language	English
Pages (from-to)	168-174
Number of pages	7
Journal	European Journal of Medicinal Chemistry
Volume	42
Issue number	2
DOIs	https://doi.org/10.1016/j.ejmech.2006.09.007
State	Published - Feb 2007

Bibliographical note

Funding Information:
This work was supported by a Korea Research Foundation Grant (KRF-2003-E00004).

Keywords

Azabenzo[a]fluorene-5,6-diones
Cytotoxicity
Pyridazino[4,5-b]phenazine-5,12-diones

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Lee, H. J., Kim, J. S., Suh, M. E., Park, H. J., Lee, S. K., Rhee, H. K., Kim, H. J., Seo, E. K., Kim, C., Lee, C. O., & Park Choo, H. Y. (2007). Synthesis and cytotoxicity evaluation of substituted pyridazino[4,5-b]phenazine-5,12-diones and tri/tetra-azabenzofluorene-5,6-diones. European Journal of Medicinal Chemistry, 42(2), 168-174. https://doi.org/10.1016/j.ejmech.2006.09.007

@article{aa5b75276db942218ea321d03072bf41,

title = "Synthesis and cytotoxicity evaluation of substituted pyridazino[4,5-b]phenazine-5,12-diones and tri/tetra-azabenzofluorene-5,6-diones",

abstract = "The substituted pyridazino[4,5-b]phenazine-5,12-diones and tri/tetra-azabenzo[a]fluorene-5,6-diones were synthesized from 6,7-dichlorophthalazine-5,8-dione and 6,7-dichloroquinoline-5,8-dione, respectively. The cytotoxic activities of the prepared compounds were evaluated by an SRB (Sulforhodamine B) assay against the following human cancer cell lines: A549 (lung), SK-OV-3 (ovarian), SK-MEL-2 (melanoma), XF 498 (CNS), and HCT 15 (colon). Almost all synthesized pyridazino[4,5-b]phenazine-5,12-diones (7a-j) presented higher cytotoxicity than that of doxorubicin (IC50 = 0.097-0.225 μM) against the cancer cell lines. In particular, the cytotoxicity of compounds 7f (R1 = Et) and 7h (R1, R2 = Me) against all human cancer cell lines examined was about 10 times higher than that of doxorubicin. However, the cytotoxicities of several synthesized azabenzo[a]fluorene-5,6-diones (12a, 12c, 12d, 12e, and 12g) against the cancer cell lines in vitro were comparable to those of doxorubicin.",

keywords = "Azabenzo[a]fluorene-5,6-diones, Cytotoxicity, Pyridazino[4,5-b]phenazine-5,12-diones",

author = "Lee, \{Hyun Jung\} and Kim, \{Jin Sung\} and Suh, \{Myung Eun\} and Park, \{Hyen Joo\} and Lee, \{Sang Kook\} and Rhee, \{Hee Kyung\} and Kim, \{Hwa Jung\} and Seo, \{Eun Kyung\} and Choonmi Kim and Lee, \{Chong Ock\} and \{Park Choo\}, \{Hea Young\}",

note = "Funding Information: This work was supported by a Korea Research Foundation Grant (KRF-2003-E00004).",

year = "2007",

month = feb,

doi = "10.1016/j.ejmech.2006.09.007",

language = "English",

volume = "42",

pages = "168--174",

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T1 - Synthesis and cytotoxicity evaluation of substituted pyridazino[4,5-b]phenazine-5,12-diones and tri/tetra-azabenzofluorene-5,6-diones

AU - Lee, Hyun Jung

AU - Kim, Jin Sung

AU - Suh, Myung Eun

AU - Park, Hyen Joo

AU - Lee, Sang Kook

AU - Rhee, Hee Kyung

AU - Kim, Hwa Jung

AU - Seo, Eun Kyung

AU - Kim, Choonmi

AU - Lee, Chong Ock

AU - Park Choo, Hea Young

N1 - Funding Information: This work was supported by a Korea Research Foundation Grant (KRF-2003-E00004).

PY - 2007/2

Y1 - 2007/2

N2 - The substituted pyridazino[4,5-b]phenazine-5,12-diones and tri/tetra-azabenzo[a]fluorene-5,6-diones were synthesized from 6,7-dichlorophthalazine-5,8-dione and 6,7-dichloroquinoline-5,8-dione, respectively. The cytotoxic activities of the prepared compounds were evaluated by an SRB (Sulforhodamine B) assay against the following human cancer cell lines: A549 (lung), SK-OV-3 (ovarian), SK-MEL-2 (melanoma), XF 498 (CNS), and HCT 15 (colon). Almost all synthesized pyridazino[4,5-b]phenazine-5,12-diones (7a-j) presented higher cytotoxicity than that of doxorubicin (IC50 = 0.097-0.225 μM) against the cancer cell lines. In particular, the cytotoxicity of compounds 7f (R1 = Et) and 7h (R1, R2 = Me) against all human cancer cell lines examined was about 10 times higher than that of doxorubicin. However, the cytotoxicities of several synthesized azabenzo[a]fluorene-5,6-diones (12a, 12c, 12d, 12e, and 12g) against the cancer cell lines in vitro were comparable to those of doxorubicin.

AB - The substituted pyridazino[4,5-b]phenazine-5,12-diones and tri/tetra-azabenzo[a]fluorene-5,6-diones were synthesized from 6,7-dichlorophthalazine-5,8-dione and 6,7-dichloroquinoline-5,8-dione, respectively. The cytotoxic activities of the prepared compounds were evaluated by an SRB (Sulforhodamine B) assay against the following human cancer cell lines: A549 (lung), SK-OV-3 (ovarian), SK-MEL-2 (melanoma), XF 498 (CNS), and HCT 15 (colon). Almost all synthesized pyridazino[4,5-b]phenazine-5,12-diones (7a-j) presented higher cytotoxicity than that of doxorubicin (IC50 = 0.097-0.225 μM) against the cancer cell lines. In particular, the cytotoxicity of compounds 7f (R1 = Et) and 7h (R1, R2 = Me) against all human cancer cell lines examined was about 10 times higher than that of doxorubicin. However, the cytotoxicities of several synthesized azabenzo[a]fluorene-5,6-diones (12a, 12c, 12d, 12e, and 12g) against the cancer cell lines in vitro were comparable to those of doxorubicin.

KW - Azabenzo[a]fluorene-5,6-diones

KW - Cytotoxicity

KW - Pyridazino[4,5-b]phenazine-5,12-diones

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DO - 10.1016/j.ejmech.2006.09.007

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SN - 0223-5234

VL - 42

SP - 168

EP - 174

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 2

ER -

Synthesis and cytotoxicity evaluation of substituted pyridazino[4,5-b]phenazine-5,12-diones and tri/tetra-azabenzofluorene-5,6-diones

Abstract

Bibliographical note

Keywords

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