Synthesis and cytotoxicity of pyrido[4,3-b]carbazole alkaloids against HCT-116 and HL-60 cells

被引：12

作者：

Itoh, Tomoki ^{[1
]}

Hatae, Noriyuki ^{[1
]}

Nishiyama, Takashi ^{[2
,3
]}

Choshi, Tominari ^{[2
,3
]}

Hibino, Satoshi ^{[2
,3
]}

Yoshimura, Teruki ^{[1
]}

Ishikura, Minoru ^{[1
]}

机构：

[1] Hlth Sci Univ Hokkaido, Sch Pharmaceut Sci, Ishikari, Hokkaido 0610293, Japan

[2] Fukuyama Univ, Grad Sch Pharm & Pharmaceut Sci, Fukuyama, Hiroshima 7290292, Japan

[3] Fukuyama Univ, Fac Pharm & Pharmaceut Sci, Fukuyama, Hiroshima 7290292, Japan

来源：

MEDICINAL CHEMISTRY RESEARCH | 2018年 / 27卷 / 02期

关键词：

Pyrido[4,3-b]carbazole alkaloids; Cytotoxicity; HCT-116; cell; HL-60; ELLIPTICINE DERIVATIVES; INTERCALATIVE BINDING; ANTICANCER AGENTS; ANTITUMOR AGENTS; DNA; OLIVACINE; APOPTOSIS; ANALOGS; SERIES;

D O I：

10.1007/s00044-017-2068-6

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Ellipticine, olivacine, and their five reduced natural variants were synthesized via a palladium-catalyzed tandem cyclization/cross-coupling reaction as the key step. In addition, a previously unknown conformer of janetine was obtained through conformational inversion of the D ring in janetine. Because there are few synthetic approaches for reduced natural variants, little is known about the biological activities of these compounds. Six synthetic natural alkaloids and five of their derivatives were evaluated for their antiproliferative activity against HCT-116 and HL-60 cells. The activities of variants with the D-reduced ring or without the C(11)-Me group were lower than those of ellipticine. The conformer of guatambuine showed higher activities than guatambuine.

引用

页码：412 / 419

页数：8

共 50 条

[31] Apoptosis of HL-60 leukemia cells induced by carbazole alkaloids isolated from Murraya euchrestifolia
Chihiro Ito
Masataka Itoigawa
Keisuke Nakao
Tomiyasu Murata
Norio Kaneda
Hiroshi Furukawa
Journal of Natural Medicines, 2012, 66 : 357 - 361
[32] SYNTHESIS OF TUMOUR-INHIBITORY ALKALOIDS ELLIPTICINE 9-METHOXYELLIPTICINE AND RELATED PYRIDO[4,3-B]CARBAZOLES
DALTON, LK
DEMERAC, S
ELMES, BC
LODER, JW
SWAN, JM
TEITEI, T
AUSTRALIAN JOURNAL OF CHEMISTRY, 1967, 20 (12) : 2715 - &
[33] A novel entry to pyrido[4,3-b]carbazoles:: An efficient synthesis of ellipticine
Ishikura, M
Hino, A
Yaginuma, T
Agata, I
Katagiri, N
TETRAHEDRON, 2000, 56 (02) : 193 - 207
[34] SYNTHESIS OF NEW l-PHENYL-6H-PYRIDO[4,3-b]CARBAZOLE DERIVATIVES WITH POTENTIAL CYTOSTATIC ACTIVITY
Tylinska, Beata
Jasztold-Howorko, Ryszard
Mastalarz, Henryk
Szczaurska-Nowak, Katarzyna
Materek, Paulina
Wietrzyk, Joanna
ACTA POLONIAE PHARMACEUTICA, 2011, 68 (01): : 31 - 37
[35] The cytotoxicity of eutigosides fromEurya emarginata against HL-60 promyelocytic leukemia cells
Soo Yeong Park
Hong Chul Yang
Ji Young Moon
Nam Ho Lee
Se Jae Kim
Ji Hoon Kang
Young Ki Lee
Deok Bae Park
Eun Sook Yoo
Hee Kyoung Kang
Archives of Pharmacal Research, 2005, 28 : 1047 - 1052
[36] An in vitro cytotoxicity study on PANI/ZnO nanocomposites against HCT-116 cancer cells using MTT assay
Sudhadevi, D.
Jayamurugan, P.
Srinivas, G.
Suresh, B.
Gupta, Abha
Rajeshkumar, Raman
Mohd, Ubaidullah
Al-Kahtani, Abdullah A.
Kumar, Ashok
POLYMERS & POLYMER COMPOSITES, 2024, 32
[37] THE CHEMISTRY OF THE PYRIDO[4,3-B]CARBAZOLES .15. THE SYNTHESIS OF UNSYMMETRICALLY 1,4-DISUBSTITUTED CARBAZOLES AND THEIR USE IN THE SYNTHESIS OF 6H-PYRIDO[4,3-B]CARBAZOLES
HOGAN, I
JENKINS, PD
SAINSBURY, M
TETRAHEDRON, 1990, 46 (08) : 2943 - 2964
[38] A FACILE ENTRY INTO RING-D FUNCTIONALIZED 6H-PYRIDO[4,3-B]CARBAZOLE
SALIFOU, A
JOHNSON, ME
NAGARATHNAM, D
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 206 : 118 - MEDI
[39] SYNTHETIC APPROACHES TO ELLIPTICINES AND OTHER DERIVATIVES AND ANALOGS OF 6H-PYRIDO[4,3-B]CARBAZOLE
HEWLINS, MJE
OLIVEIRACAMPOS, AM
SHANNON, PVR
SYNTHESIS-STUTTGART, 1984, (04): : 289 - 302
[40] SYNTHESIS OF 3-ARYL-5H-PYRIDO[4,3-B]INDOLES
MOHANAKRISHNAN, AK
SRINIVASAN, PC
SYNTHETIC COMMUNICATIONS, 1995, 25 (16) : 2415 - 2424

← 1 2 3 4 5 →