WO2016044636A3 - Method for producing benzazoloquinolium (bqs) salts and using the biological activity of the composition - Google Patents

Method for producing benzazoloquinolium (bqs) salts and using the biological activity of the composition Download PDF

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Publication number
WO2016044636A3
WO2016044636A3 PCT/US2015/050769 US2015050769W WO2016044636A3 WO 2016044636 A3 WO2016044636 A3 WO 2016044636A3 US 2015050769 W US2015050769 W US 2015050769W WO 2016044636 A3 WO2016044636 A3 WO 2016044636A3
Authority
WO
WIPO (PCT)
Prior art keywords
bqs
salts
substituent
benzazoloquinolium
producing
Prior art date
Application number
PCT/US2015/050769
Other languages
French (fr)
Other versions
WO2016044636A2 (en
Inventor
Osvaldo Cox
Beatriz Zayas
Original Assignee
Sistema Universitario Ana G. Mendez, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sistema Universitario Ana G. Mendez, Inc. filed Critical Sistema Universitario Ana G. Mendez, Inc.
Publication of WO2016044636A2 publication Critical patent/WO2016044636A2/en
Publication of WO2016044636A3 publication Critical patent/WO2016044636A3/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine

Abstract

Disclosed is the synthesis procedure for benzazolo[3,2-a]quinolinium chloride salts and the inclusion of chloro-substituent, amino-substituent, and nitro-substituent resulting in several compounds. The compounds are further used as markers due to their fluorescent properties including in hypoxic environments. This disclosure further describes anti-cancer screening of two BQS, namely, 7-benzyl-3-aminobenzimidazo[3,2-a]quinolinium chloride (ABQ-48: NSC D-763307) and the corresponding 7-benzyl-3-nitrobenzimidazo[3,2-a]quinolinium chloride (NBQ 48: NSC D-763303).
PCT/US2015/050769 2014-09-17 2015-09-17 Method for producing benzazoloquinolium (bqs) salts and using the biological activity of the composition WO2016044636A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201462051875P 2014-09-17 2014-09-17
US62/051,875 2014-09-17
US201562121157P 2015-02-26 2015-02-26
US62/121,157 2015-02-26

Publications (2)

Publication Number Publication Date
WO2016044636A2 WO2016044636A2 (en) 2016-03-24
WO2016044636A3 true WO2016044636A3 (en) 2016-05-06

Family

ID=55534011

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2015/050769 WO2016044636A2 (en) 2014-09-17 2015-09-17 Method for producing benzazoloquinolium (bqs) salts and using the biological activity of the composition

Country Status (1)

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WO (1) WO2016044636A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108947911B (en) * 2018-07-03 2022-02-22 中山大学 Benzimidazole compound with anti-hepatitis B virus activity and antibacterial activity and synthesis method and application thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100256378A1 (en) * 2009-04-01 2010-10-07 Beatriz Zayas Fluorescent cellular markers
US9085574B2 (en) * 2009-04-01 2015-07-21 Beatriz Zayas Method for producing benzazoloquinolium (BQs) salts, using the composition as cellular markers, and using the biological activity of the composition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100256378A1 (en) * 2009-04-01 2010-10-07 Beatriz Zayas Fluorescent cellular markers
US9085574B2 (en) * 2009-04-01 2015-07-21 Beatriz Zayas Method for producing benzazoloquinolium (BQs) salts, using the composition as cellular markers, and using the biological activity of the composition

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
RIOS-RODRIGUEZ ET AL.: "Toxicity screening, apoptosis hallmark events and nitro reduction of novel quinolinium salts (BQS) on lymphoma cells", 5 April 2014 (2014-04-05), Retrieved from the Internet <URL:Proceedingsofthe105thAnnualMeetingoftheAmericanAssociationforCancerResearch.> *
VIVAS-MEJIA ET AL.: "Inhibition of human topoisomerase II by anti-neoplastic benzazolo[3,2-a]quinolinium chlorides", MOLECULAR AND CELLULAR BIOCHEMISTRY, vol. 178, no. Issue 1, January 1998 (1998-01-01), pages 203 - 212 *

Also Published As

Publication number Publication date
WO2016044636A2 (en) 2016-03-24

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