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A 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 is provided. The compounds are further used as markers due to their fluorescent properties including in hypoxic environments. Furthermore, 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) are provided.

Titel:	Method for producing benzazoloquinolium (BQs) salts and using the biological activity of the composition
Link:	View record in USPTO Patent Applications (Volltext)
Veröffentlichung:	2024
Medientyp:	Patent
Sonstiges:	Nachgewiesen in: USPTO Patent Applications Sprachen: English Document Number: 20240066023 Publication Date: February 29, 2024 Appl. No: 18/380245 Application Filed: October 16, 2023 Assignees: Sistema Universitario Ana G. Mendez, Inc. (San Juan, PR, US) Claim: 1. A synthesis procedure for a benzazolo[3,2-a]quinolinium chloride salt of formula [chemical expression included] wherein R1 is 3-NO2; R2 is selected from a group consisting of hydrogen and OCH3; R3 is OCH3; R4 is OCH3; and R5 is hydrogen, when R2 is OCH3, and OCH3, when R2 is hydrogen; comprising the steps of: a. reacting a first mixture comprising o-phenylenediamine and ethyl acetate to obtain a 2-aminoacetanilide; b. reacting a second mixture comprising a 2-aminoacetanilide and a benzaldehyde of formula [chemical expression included] to obtain a [(benzylideneamino)phenyl]acetanilide of formula [chemical expression included] c. reacting a third mixture comprising said [(benzylideneamino)phenyl]acetanilide and sodium borohydride to obtain a [(benzylamino)phenyl]acetamide of formula [chemical expression included] d. reacting a fourth mixture comprising said [(benzylamino)phenyl]acetamide and a Bronsted acid to obtain a benzimidazole of formula [chemical expression included] e. condensing a fifth mixture comprising said benzimidazole and 2-chloro-5-nitrobenzaldehyde to obtain a 1-(Trimethoxybenzyl)-2-(2-chloro-5-nitrostyryl)benzimidazolole of formula [chemical expression included] f. and irradiating a sixth mixture comprising said 1-(Trimethoxybenzyl)-2-(2-chloro-5-nitrostyryl)benzimidazolole at 350 nm. Claim: 2. A synthesis procedure for a benzazolo[3,2-a]quinolinium chloride salt of formula [chemical expression included] wherein R1 is 3-NH2; R2 is selected from a group consisting of hydrogen and OCH3; R3 is OCH3; R4 is OCH3; and R5 is hydrogen, when R2 is OCH3, and OCH3, when R2 is hydrogen; comprising the steps of: a. reacting a first mixture comprising o-phenylenediamine and ethyl acetate to obtain a 2-aminoacetanilide; b. reacting a second mixture comprising a 2-aminoacetanilide and a benzaldehyde of formula [chemical expression included] to obtain a [(benzylideneamino)phenyl]acetanilide of formula [chemical expression included] c. reacting a third mixture comprising said [(benzylideneamino)phenyl]acetanilide and sodium borohydride to obtain a [(benzylamino)phenyl]acetamide of formula [chemical expression included] d. reacting a fourth mixture comprising said [(benzylamino)phenyl]acetamide and a Bronsted acid to obtain a benzimidazole of formula [chemical expression included] e. condensing a fifth mixture comprising said benzimidazole and 2-chloro-5-nitrobenzaldehyde to obtain a 1-(Trimethoxybenzyl)-2-(2-chloro-5-nitrostyryl)benzimidazolole of formula [chemical expression included] wherein R1′ is 3-NO2 f. reducing the 3-NO2 to 3-NH2 to obtain a 1-(Trimethoxybenzyl)-2-(2-chloro-5-aminostyryl)benzimidazolole of formula [chemical expression included] wherein R1 is 3-NH2, and g. irradiating a sixth mixture comprising said 1-(Trimethoxybenzyl)-2-(2-chloro-5-aminostyryl)benzimidazolole at 350 nm. Current International Class: 61; 61

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Method for producing benzazoloquinolium (BQs) salts and using the biological activity of the composition