11-Oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid, an orally active antiallergy agent

Schwender, Charles F.; Sunday, B. R.; Herzig, David

doi:10.1021/jm00187a026

Cited by 33 publications

(15 citation statements)

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“…More specifically, pyridoquinazolones exhibit strong tuberculostatic activity. Since both the linear3 and angular4 fused isomers have unique pharmacological and/or biological activity, synthetic methodologies which can provide these two isomers in a convenient and efficient manner are highly desired.…”

Section: Model Synthesis Of Pyridoquinazolones: Optimization Of the Rmentioning

confidence: 99%

“…Although many attractive procedures have been developed for rapid access to quinazolinones,2a,b, 3, 5 the related synthesis of pyridoquinazolones is still very limited. So far, known procedures require a high temperature (210 °C), multistep synthesis, or specific ortho ‐halogen‐substituted benzoyl derivatives as the substrates 6.…”

Section: Model Synthesis Of Pyridoquinazolones: Optimization Of the Rmentioning

confidence: 99%

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Base‐Controlled Selectivity in the Synthesis of Linear and Angular Fused Quinazolinones by a Palladium‐Catalyzed Carbonylation/Nucleophilic Aromatic Substitution Sequence

et al. 2014

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A new approach for the facile synthesis of fused quinazolinone scaffolds through a palladium-catalyzed carbonylative coupling followed by an intramolecular nucleophilic aromatic substitution is described. The base serves as the key modulator: Whereas DBU gives rise to the linear isomers, Et 3 N promotes the preferential formation of angular products. Interestingly, a light-induced 4+4 reaction of the product was also observed.

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Section: Model Synthesis Of Pyridoquinazolones: Optimization Of the Rmentioning

confidence: 99%

Section: Model Synthesis Of Pyridoquinazolones: Optimization Of the Rmentioning

confidence: 99%

Base‐Controlled Selectivity in the Synthesis of Linear and Angular Fused Quinazolinones by a Palladium‐Catalyzed Carbonylation/Nucleophilic Aromatic Substitution Sequence

et al. 2014

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“…For example, compounds A and B as shown in Scheme 1 were proved to have efficient antitumor activities. 1,2 Poly cyclic nitrogen-containing heterocycles were also commonly applied in anticonvulsant, 3−5 anti-inflammatory, 6 antiallergy, 7,8 antimicrobial, 9 cardiotonic, 10 and cell imaging 11,12 research. Scaffold of 11 H -pyrido[2,1- b ]quinazolin-11-one H was found in many natural products 13 (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Ru(II)/Ir(III)-Catalyzed C–H Bond Activation/Annulation of Cyclic Amides with 1,3-Diketone-2-diazo Compounds: Facile Access to 8H-Isoquinolino[1,2-b]quinazolin-8-ones and Phthalazino[2,3-a]cinnoline-8,13-diones

Cai

Zhang

et al. 2018

ACS Omega

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Efficient access to 8 H -isoquinolino[1,2- b ]quinazolin-8-ones and phthalazino[2,3- a ]cinnoline-8,13-diones through cyclic amide-directed Ru(II)/Ir(III)-catalyzed C–H bond activation, has been developed. Consecutive C–H bond activation, carbene insertion, and condensation annulation processes were realized, affording 8 H -isoquinolino[1,2- b ]quinazolin-8-one and phthalazino[2,3- a ]cinnoline-8,13-dione derivatives in good-to-excellent yields under mild conditions, with H 2 O and N 2 being generated as the only byproducts.

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“…1, 3-Diaza-heterocycles like pyrimidine and quinazoline derivatives, quinazolinones in particular, have been identified as potential drug molecules against various types of diseases. Innumerable quinazolinone alkaloids isolated from plants, animals, and microorganisms shows different types of pharmacological activities 9-15 . towards the syntheses of various types of analogs, and this led to the identification of novel quinazolinone derivatives showing a wide variety of activities like antiallergic, 21 anticonvulsant, [22][23][24] sedative-hypnotic, 25 antihypertensive 26 and also anticancer 27,28 , etc.…”

Section: Introductionmentioning

confidence: 99%

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2014

IJPSR

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A series of new Baylis-Hillman derived cinnamyl substituted quinazolinone derivatives have been synthesized by the condensation reaction between Baylis-Hillman bromides and quinazolinones in a simple and efficient manner in less reaction time with high yields. Methyl quinazolinone yields two isomers of Baylis-Hillman derived 3-N-cinnamyl substituted quinazoline-4-one derivatives and 4-O-cinnamyl substituted quinazoline derivatives, and the structures were confirmed by X-ray crystallography. All the newly synthesized compounds were characterized by their spectral data and evaluated their antibacterial and antifungal activity. The compounds (3a, 4a) without any substitution at the aryl group exhibited good antibacterial activity especially on S. epidermidis (gram positive), Replacement of hydrogen atom of the aryl group by CF 3 (3c, 4c) or by fluorine (3g) exhibited significant antibacterial activity on both grampositive (S. epidermidis) and gram-negative (K. pneumonia) organisms compared to other compounds. All the compounds exhibited interesting antifungal activity on C. albicans microorganism exclusively and inactive on the remaining organisms. Compound 3a and 4f exhibited good antifungal activity compared to the other compounds.

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11-Oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid, an orally active antiallergy agent

Cited by 33 publications

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Base‐Controlled Selectivity in the Synthesis of Linear and Angular Fused Quinazolinones by a Palladium‐Catalyzed Carbonylation/Nucleophilic Aromatic Substitution Sequence

Base‐Controlled Selectivity in the Synthesis of Linear and Angular Fused Quinazolinones by a Palladium‐Catalyzed Carbonylation/Nucleophilic Aromatic Substitution Sequence

Ru(II)/Ir(III)-Catalyzed C–H Bond Activation/Annulation of Cyclic Amides with 1,3-Diketone-2-diazo Compounds: Facile Access to 8H-Isoquinolino[1,2-b]quinazolin-8-ones and Phthalazino[2,3-a]cinnoline-8,13-diones

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