Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones

被引：0

作者：

Sayapin, Yurii A. ^{[1
]}

Gusakov, Eugeny A. ^{[2
]}

Tupaeva, Inna O. ^{[2
]}

Dubonosov, Alexander D. ^{[1
]}

V. Dorogan, Igor ^{[2
]}

Tkachev, Valery V. ^{[3
]}

Goncharova, Anna S. ^{[4
]}

Shilov, Gennady V. ^{[3
]}

Kuznetsova, Natalia S. ^{[4
]}

Filippova, Svetlana Y. ^{[4
]}

Krasnikova, Tatyana A. ^{[2
]}

Boumber, Yanis A. ^{[5
,6
]}

Maksimov, Alexey Y. ^{[4
]}

Aldoshin, Sergey M. ^{[3
]}

Minkin, Vladimir I. ^{[2
]}

机构：

[1] Russian Acad Sci, Fed Res Ctr Southern Sci Ctr, Southern Sci Ctr, Rostov Na Donu 344006, Russia

[2] Southern Fed Univ, Inst Phys & Organ Chem, Rostov Na Donu 344090, Russia

[3] Russian Acad Sci, Fed Res Ctr Problems Chem Phys & Med Chem, Chernogolovka 142432, Russia

[4] Natl Med Res Ctr Oncol, Chernogolovka 344037, Russia

[5] Kazan Volga Reg Fed Univ, Inst Fundamental Med & Biol, Kazan 420008, Russia

[6] Univ Alabama Birmingham, ONeil Comprehens Canc Ctr, Heersink Sch Med, Dept Med, Birmingham, AL 35233 USA

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 21卷

关键词：

cytotoxic activity; fluorescence; o-chloranil; quantum chemical DFT calculations; 1,3-tropolones; X-ray diffraction; INTRAMOLECULAR PROTON-TRANSFER; 2-METHYLQUINOLINES; CONDENSATION; RECOGNITION; DERIVATIVES; INDOLES;

D O I：

10.3762/bjoc.21.26

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The acid-catalyzed reaction of benzo[e(g)] derivatives of 2,3,3-trimethylindolenines with o-chloranil leads to new 2-(benzo[e(g)]indolin-2-yl)-5,6,7-trichloro-1,3-tropolones and 2-(benzo[e(g)]indolin-2-yl)-4,5,6,7-tetrachloro-1,3-tropolones. Based on the results of PBE0/6-311+G(d,p) calculations, the structural and energetic characteristics of the tautomeric forms of the obtained 1,3-tropolones were determined. The structure of 2-(3,3-dimethyl-3H-benzo[g]indolin-2-yl)-5,6,7-trichloro-1,3-tropolone was determined by X-ray diffraction analysis. The compounds obtained are capable of switching emission at 420-440 nm and 476-530 nm upon successive exposure to CN- and Hg2+ ions in an acetonitrile solution. 2-(1,1-Dimethyl-1H-benzo[e]indolin-2- yl)-5,6,7-trichloro-1,3-tropolone exhibited high in vitro cytotoxic activity against A431 skin cancer and H1299 lung cancer cell lines.

引用

页码：358 / 368

页数：11

共 40 条

[1] Toward reliable density functional methods without adjustable parameters: The PBE0 model [J].

Adamo, C ;

Barone, V .

JOURNAL OF CHEMICAL PHYSICS, 1999, 110 (13) :6158-6170

[2] Catalytic Functionalization of Indoles in a New Dimension [J].

Bandini, Marco ;

Eichholzer, Astrid .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644

[3] Substituted titanocenes induce caspase-dependent apoptosis in human epidermoid carcinoma cells in vitro and exhibit antitumour activity in vivo [J].

Bannon, J. H. ;

Fichtner, I. ;

O'Neill, A. ;

Pampillon, C. ;

Sweeney, N. J. ;

Strohfeldt, K. ;

Watson, R. W. ;

Tacke, M. ;

Mc Gee, M. M. .

BRITISH JOURNAL OF CANCER, 2007, 97 (09) :1234-1241

[4] A new definition of cavities for the computation of solvation free energies by the polarizable continuum model [J].

Barone, V ;

Cossi, M ;

Tomasi, J .

JOURNAL OF CHEMICAL PHYSICS, 1997, 107 (08) :3210-3221

[5] A CONVENIENT SYNTHESIS OF 3-HYDROXYTROPONE [J].

BECKER, AM ;

RICKARDS, RW .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1983, 15 (04) :239-242

[6] A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics [J].

Cances, E ;

Mennucci, B ;

Tomasi, J .

JOURNAL OF CHEMICAL PHYSICS, 1997, 107 (08) :3032-3041

[7] A GENERAL SYNTHESIS OF TROPONOID SYSTEM BASED ON SOLVOLYSIS OF 1,4-DIHYDROBENZYL TOSYLATES [J].

CHAPMAN, OL ;

FITTON, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (01) :41-&

[8] Synthesis of Furo[2,3-f]dibenzotropones via Intramolecular Wittig Reaction of Alkylidene Dibenzo-β-tropolones [J].

Chien, Po-Chung ;

Chen, Yi-Ru ;

Chen, You-Jie ;

Chang, Ching-Fen ;

Marri, Gangababu ;

Lin, Wenwei .

ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (03) :420-425

[9]

Frisch M. J., 2016, Gaussian 09W

[10] Design, synthesis and biological evaluation of 2-quinolyl-1,3-tropolone derivatives as new anti-cancer agents [J].

Gusakov, Evgeniy A. ;

Topchu, Iuliia A. ;

Mazitova, Aleksandra M. ;

Dorogan, Igor, V ;

Bulatov, Emil R. ;

Serebriiskii, Ilya G. ;

Abramova, Zinaida, I ;

Tupaeva, Inna O. ;

Demidov, Oleg P. ;

Duong Ngoc Toan ;

Tran Dai Lam ;

Duong Nghia Bang ;

Boumber, Yanis A. ;

Sayapin, Yurii A. ;

Minkin, Vladimir, I .

RSC ADVANCES, 2021, 11 (08) :4555-4571

← 1 2 3 4 →