Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2025 Feb 17:21:358-368.
doi: 10.3762/bjoc.21.26. eCollection 2025.

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

Yurii A Sayapin  1 , Eugeny A Gusakov  2 , Inna O Tupaeva  2 , Alexander D Dubonosov  1 , Igor V Dorogan  2 , Valery V Tkachev  3 , Anna S Goncharova  4 , Gennady V Shilov  3 , Natalia S Kuznetsova  4 , Svetlana Y Filippova  4 , Tatyana A Krasnikova  2 , Yanis A Boumber  5   6 , Alexey Y Maksimov  4 , Sergey M Aldoshin  3 , Vladimir I Minkin  2
Affiliations

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

Yurii A Sayapin et al. Beilstein J Org Chem. .

Abstract

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.

Keywords: 1,3-tropolones; X-ray diffraction; cytotoxic activity; fluorescence; o-chloranil; quantum chemical DFT calculations.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Synthesis of 2-hetaryl-substituted 1,3-tropolones 1.
Scheme 2
Scheme 2
Synthesis of 1,3-tropolones 7a,b and 8a,b. Reagents and conditions: method A: dioxane, reflux; method B: AcOH, 40–50 °C.
Figure 1
Figure 1
Structural characteristics of (NH) and (OH) tautomeric forms of compounds 7 and 8 in the gas phase according to PBE0/6-311+G(d,p) calculations. Bond lengths are given in Ångstrom.
Figure 2
Figure 2
Scheme of HMBC correlations of compound 7a in DMSO-d6.
Figure 3
Figure 3
Molecular structure of 2-(3,3-dimethyl-3H-benzo[g]indolin-2-yl)-5,6,7-trichloro-1,3-tropolone (7b).
Figure 4
Figure 4
Result of matching structures of 7b (solid lines) and 2-(3,3-dimethylindolin-2-yl)-5,6,7-trichloro-1,3-tropolone (dashed lines) at the positions of N(1), C(2), and C(9) atoms.
Figure 5
Figure 5
Absorption and emission spectra of compound 8b in acetonitrile before (1,1’) (c 2.5 × 10−5 mol L–1) and after the addition of CN− (2,2’) and F− (3,3’) ions (c 5.0 × 10−5 mol L−1).
Scheme 3
Scheme 3
Possible binding mode of 7 and 8 with CN− and F−.
Figure 6
Figure 6
Dose–response curves for H1299 and A431 cells treated with compound 7a for 24 h. *Significant difference compared to control samples, p < 0.05.
See this image and copyright information in PMC

References

    1. Minkin V I, Aldoshin S M, Komissarov V N, Dorogan I V, Sayapin Y A, Tkachev V V, Starikov A G. Russ Chem Bull. 2006;55:2032–2055. doi: 10.1007/s11172-006-0547-x. - DOI
    1. Sayapin Y A, Komissarov V N, Bang D N, Dorogan I V, Minkin V I, Tkachev V V, Shilov G V, Aldoshin S M, Charushin V N. Mendeleev Commun. 2008;18(4):180–182. doi: 10.1016/j.mencom.2008.07.002. - DOI
    1. Sayapin Y A, Gusakov E A, Kolodina A A, Komissarov V N, Dorogan I V, Tkachev V V, Shilov G V, Nosova E V, Aldoshin S M, Charushin V N, et al. Russ Chem Bull. 2014;63:1364–1372. doi: 10.1007/s11172-014-0604-9. - DOI
    1. Sayapin Y A, Gusakov E A, Dorogan I V, Tupaeva I O, Teimurazov M G, Fursova N K, Ovchinnikov K V, Minkin V I. Russ J Bioorg Chem. 2016;42:224–228. doi: 10.1134/s1068162016020114. - DOI
    1. Sayapin Y A, Tupaeva I O, Kolodina A A, Gusakov E A, Komissarov V N, Dorogan I V, Makarova N I, Metelitsa A V, Tkachev V V, Aldoshin S M, et al. Beilstein J Org Chem. 2015;11:2179–2188. doi: 10.3762/bjoc.11.236. - DOI - PMC - PubMed

LinkOut - more resources