Construction, characterization, and antimicrobial evaluation of the novel heteroannulated chromeno[2′′,3′′:6′,5′]pyrido[2′,3′‐d] [1,3] thiazolo[3,2‐a]pyrimidines

Abstract

The reaction of chromone‐3‐carbonitrile with thiobarbituric acid afforded 2‐thioxochromeno[3′,2′:5,6]pyrido[2,3‐d]pyrimidine‐4,6(1H,3H)‐dione, which utilized as a building block for construction of a novel heteroannulated compounds containing chromenopyridothiazolopyrimidine moiety. Reactions of the starting compound with a variety of bielectrophilic reagents namely; chloroacetonitrile, bromomalononitrile, 3‐chloropentanedione, ethyl 2‐chloro‐3‐oxobutanoate, phenacyl bromide, chloroacetic acid, dibromoethane, and oxalyl chloride afforded the first known chromenopyridothiazolopyrimidines. Cyclization of the starting compound with 2,3‐dichloroquinoxaline gave the linear hepta‐annulated chromenopyridopyrimidothiazoloquinoxaline. In addition, chromenopyridopyrimido thiazolopyrimidines were efficiently synthesized. The antimicrobial activity was evaluated for the prepared compounds and some of them seemed notable activity against the tested microorganisms. Analytical and spectral data confirmed the structures of the new products.

Synthesis, anticancer activity and molecular docking of new quinolines, quinazolines and 1,2,4-triazoles with pyrido[2,3-d] pyrimidines

“…A literature survey revealed that pyrido [2,3- d ] pyrimidine derivatives have important potential in pharmaceutical and medicinal chemistry due to their diverse range of biological activity, including anti-viral properties [ 1 ], antioxidant [ [2] , [3] , [4] , [5] ], antimicrobial [ [6] , [7] , [8] ], anti-inflammatory [ [9] , [10] , [11] ], antitubercular [ 12 ], it is also used as an inhibitor of some enzymes such as dihydrofolate reductase inhibition [ 13 , 14 ], glucosidase inhibition [ 15 , 16 ], a threonine tyrosine kinase (TTK) inhibition [ 17 ] and adenosine kinase inhibition [ 18 ]. The pyrimidine moiety has excellent chemical, physical and biological properties, especially when it is combined with heterocyclic compounds, for example: Thieno [2,3-d] pyrimidine is a compound that possesses antioxidant, anticancer, and antitumor properties [ [19] , [20] , [21] , [22] , [23] ].…”

Synthesis, design, and antimicrobial activity of pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidinones based on quinoline derivatives

“…Most heterocyclic compounds possess many biological and pharmacological activities which are including pyrido[2,3‐ d ]pyrimidine derivatives and which inter in the structure of many drugs because they have many biological and pharmacological activities such as antimicrobial [1–3], antioxidant [4–7], antitubercular [8], antiviral [9], anti‐inflammatory [10–12], effective glucosidase inhibitor [13, 14], adenosine kinase inhibitor [15], a dihydrofolate reductase inhibitor [16, 17], and a threonine tyrosine kinase (TTK) inhibitor [18]. In addition, pyrido[2,3‐ d ][1,2,4]triazolo[4,3‐ a ]pyrimidin‐5‐ones are pharmacological scaffold that represent a wide range of biological activities such as analgesic, anti‐inflammatory, anti‐oxidant, and anti‐microbial [19], anti‐HCV, anti‐SSPE, antimicrobial, antioxidant, and antitumor activities [20], peroxynitrite inhibitory activity, anti‐HCV and antioxidant [21], antitumor activity, anti‐HCV [22].…”

Novel Pyrimidine Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Molecular Modeling Studies

“…Pyrido [2,3-d]pyrimidine is a privileged heterocyclic scaffold in drug design. Pyrido [2,3-d]pyrimidine ring systems have several biological and pharmacological activities, such as being analgesic, anti-inflammatory [14][15][16][17], anticancer [18], antitubercular [19], antimicrobial [20][21][22], a threonine tyrosine kinase (TT) inhibitor [23], an adenosine kinase inhibitor [24], a dihydrofolate reductase inhibitor [25,26], antiviral [27] and antioxidant [28][29][30].…”