Title:
AMINO-SUBSTITUTED CHROMENOQUINOLINE TYPE FLUORESCENT MARKER, AND PREPARATION AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2023/092814
Kind Code:
A1
Abstract:
An amino-substituted chromenoquinoline type fluorescent marker, and a preparation method therefor and the use thereof. The fluorescent marker is prepared by means of subjecting an amino group of an aromatic amine compound and two aldehyde coumarins containing chlorine at the ortho-positions to a one-step cyclization reaction, has an excellent fluorescence emission performance, and also has a good light stability in different organic solvents, effectively solves the problem of the poor light stability of cyanine dyes, and can mark different organelles at a cellular level. By means of introducing a nitrogen heterocyclic ring, the biocompatibility of the compound is improved, and a good foundation is laid for biological application thereof. The reaction raw materials are cheap and easily available, the steps for synthesizing the marker are simple and easy to operate, the production cost can be effectively reduced while the performance of the marker is not reduced, and a certain commercial value is obtained.
More Like This:
Inventors:
GE JIANFENG (CN)
ZHU MINGSEN (CN)
YU QING (CN)
SUN RU (CN)
ZHU MINGSEN (CN)
YU QING (CN)
SUN RU (CN)
Application Number:
PCT/CN2021/143133
Publication Date:
June 01, 2023
Filing Date:
December 30, 2021
Export Citation:
Assignee:
UNIV SOOCHOW (CN)
International Classes:
C07D491/052; C07D491/22; C09K11/06; G01N21/64
Foreign References:
| CN112778258A | 2021-05-11 | |||
| CN111440143A | 2020-07-24 |
Other References:
HUANG WEIMIN, LIN WEIYING, GUAN XIAOYU: "Development of ratiometric fluorescent pH sensors based on chromenoquinoline derivatives with tunable pKa values for bioimaging", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 55, no. 1, 1 January 2014 (2014-01-01), Amsterdam , NL , pages 116 - 119, XP093068329, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2013.10.130
SANTOSH KUMARI; S. M. ABDUL SHAKOOR; DATTA MARKAD; SANJAY K. MANDAL; RAJEEV SAKHUJA: "NH4OAc‐Promoted Cascade Approach towards Aberrant Synthesis of Chromene‐Fused Quinolinones", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2019, no. 4, 17 December 2018 (2018-12-17), DE , pages 705 - 714, XP072121306, ISSN: 1434-193X, DOI: 10.1002/ejoc.201801292
JOSHI S.: "Synthesis, solvatochromism and electric dipole moment study of coumarin-fused quinoline: experimental and quantum chemical computational investigations", EUR. PHYS. J. D, vol. 75, no. 5, 11 May 2021 (2021-05-11), XP037483651, DOI: 10.1140/epjd/s10053-021-00169-6
SHARGHI HASHEM, KHALIFEH REZA, RASHIDI ZAHRA: "Synthesis of chromeno[3,4- $${\varvec{b}}$$ b ]quinoline derivatives by heterogeneous [Cu(II)BHPPDAH] catalyst without being immobilized on any support under mild conditions using PEG 300 as green solvent", MOLECULAR DIVERSITY, SPRINGER INTERNATIONAL PUBLISHING, CHAM, vol. 17, no. 4, 1 November 2013 (2013-11-01), Cham, pages 721 - 730, XP093068327, ISSN: 1381-1991, DOI: 10.1007/s11030-013-9468-4
HEBER, D.: "Reaktionen an Heterocyclen mit 2-Acyl-2-propenon-Teilstruktur, 6. Mitt. Zur Synthese von 6-Oxo-6H-[1]benzopyrano[4,3-b]chinolinen", ARCHIV DER PHARMAZIE, WILEY VERLAG, WEINHEIM, vol. 320, no. 7, 31 December 1987 (1987-12-31), Weinheim , pages 595 - 599, XP009546556, ISSN: 0365-6233, DOI: 10.1002/ardp.19873200705
SANTOSH KUMARI; S. M. ABDUL SHAKOOR; DATTA MARKAD; SANJAY K. MANDAL; RAJEEV SAKHUJA: "NH4OAc‐Promoted Cascade Approach towards Aberrant Synthesis of Chromene‐Fused Quinolinones", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2019, no. 4, 17 December 2018 (2018-12-17), DE , pages 705 - 714, XP072121306, ISSN: 1434-193X, DOI: 10.1002/ejoc.201801292
JOSHI S.: "Synthesis, solvatochromism and electric dipole moment study of coumarin-fused quinoline: experimental and quantum chemical computational investigations", EUR. PHYS. J. D, vol. 75, no. 5, 11 May 2021 (2021-05-11), XP037483651, DOI: 10.1140/epjd/s10053-021-00169-6
SHARGHI HASHEM, KHALIFEH REZA, RASHIDI ZAHRA: "Synthesis of chromeno[3,4- $${\varvec{b}}$$ b ]quinoline derivatives by heterogeneous [Cu(II)BHPPDAH] catalyst without being immobilized on any support under mild conditions using PEG 300 as green solvent", MOLECULAR DIVERSITY, SPRINGER INTERNATIONAL PUBLISHING, CHAM, vol. 17, no. 4, 1 November 2013 (2013-11-01), Cham, pages 721 - 730, XP093068327, ISSN: 1381-1991, DOI: 10.1007/s11030-013-9468-4
HEBER, D.: "Reaktionen an Heterocyclen mit 2-Acyl-2-propenon-Teilstruktur, 6. Mitt. Zur Synthese von 6-Oxo-6H-[1]benzopyrano[4,3-b]chinolinen", ARCHIV DER PHARMAZIE, WILEY VERLAG, WEINHEIM, vol. 320, no. 7, 31 December 1987 (1987-12-31), Weinheim , pages 595 - 599, XP009546556, ISSN: 0365-6233, DOI: 10.1002/ardp.19873200705
Attorney, Agent or Firm:
CENTRAL SOUTH WELL INTELLECTUAL PROPERTY OFFICE (CN)
Download PDF: