Synthesis and antifungal activity of some new pyrido[2,3-d]pyrimidines

Abstract

KEYWORDSSome new pyrido [2,3-d]pyrimidine derivatives (3a-c) were synthesized from 2-amino-5-cyano-6-methoxy-4-(4-methoxyphenyl)pyridine-3-carboxamide.7-methoxy-5-(4-methoxy phenyl)-4-oxo-2-phenyl-3,4-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (3b) and 7-methoxy-5-(4-methoxyphenyl)-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (3c) are used in synthesizing 7a,b, then 8a,b. 7-methoxy-5-(4-methoxyphenyl)-2-methyl-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (3a) and 4-hydrazinyl-7-methoxy-5-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine-6-carbonitrile (8b) were condensed with different carbonyl compounds to produce compounds 4, 5, 6 and 9, 10, 11, 12. 3-Methoxy-1-(4-methoxyphenyl)-6-phenyl-7-hydropyridino[2,3-d]1,2,3,4-tetrazolo[1,5-e]pyrimidine-2-carbonitrile (13) was synthesized from 8a or 7a. Condensation of 8b with acetophenone to yield 14, which on further reaction gave 15 then 16. 4-Hydrazinyl-7-methoxy-5-(4-methoxyphenyl)-2-phenylpyrido[2,3-d]pyrimidine-6-carbonitrile (8a) also condensed with 4-amino antipyrine giving 17 then 18. Structures of these compounds have been deduced upon the basis of elemental analysis and spectral data. Significant antifungal activities were observed for some of the synthesized compounds.

Efficient synthesis and molecular docking of novel antibacterial pyrimidines and their related fused heterocyclic derivatives

“…[1][2][3][4][5][6][7][8][9][10][11][12][13] In addition, pyrido [2,3-d]pyrimidines exhibit antimicrobial, antifungal, and anti-inflammatory activities, [14][15][16] while thieno [2,3-d]pyrimidines exhibit antiproliferative and anti-inflammatory activities. Pyrimidines and their related fused heterocyclic derivatives possess antibacterial, antifungal, antiviral, anti-influenza, antioxidant, anti-inflammatory, antimalarial, antiproliferative, and antitumor activities.…”

One pot multi‐component synthesis of functionalized spiropyridine and pyrido[2,3‐d]pyrimidine scaffolds and their potent in‐vitro anti‐inflammatory and anti‐oxidant investigations

“…Among the heterocyclic compounds, pyridine and their analogues are the most prevalent structural units due to their wide spectrum of applications (Song, Huang, Yi, & Zhang, ), in natural products (Michael, ), pharmaceutical (Baumann & Baxendale, ; Vitaku, Smith, & Njardarson, ), agrochemical (Guan, Liu, Sun, & Xie, ) and material science (Desimoni, Faita, & Quadrelli, ; Gillissen et al., ). Many of the fused pyridine compounds have been proven as valuable candidates possessing anti‐bacterial (Elagamey, Sattar, El‐Taweel, & Said, ), anti‐fungal (Hanafy, ), anti‐microbial (Paresh & Yogesh, ), anti‐oxidant (Farghaly, Abass, Abdalla, & Mahgoub, ; Flefel et al., ), anti‐cancer (Bladt, Frisvad, Knudsen, & Larsen, ; Naresh Kumar et al., ), anti‐psychotic (Swain et al., ), anti‐inflammatory (Hend, At‐Allah, A‐Rahman, & El‐Gazza, ; Piero & Lucio, ), anti‐leishmanial (Samai, Nandi, Chowdhury, & Singh, ), anti‐viral (Tai et al., ), anti‐hypersensitive (Smith et al., ), anti‐convulsants (Kaminski, Obniska, Zagorska, & Maciag, ), anti‐malarial (Davoll, Clarke, & Elslage, ), potassium channel openers (Gadwood et al., ), anti‐diabetic (Sarges, Bordner, Dominy, Peterson, & Whipple, ) and anti‐tumour activities (Mohamed & Giuseppe, ). A few of previously reported bio‐active fused compounds ( A–D ) were represented in Figure .…”

Utility of 2-thioxo-pyrido[2,3-d]pyrimidinone in synthesis of pyridopyrimido[2,1-b][1,3,5]-thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones as antimicrobial agents

“…Pyridopyrimidines and their intertwined heterocyclic ring frameworks are of current interest [ 1 – 4 ]. Pyrido[2,3- d ]pyrimidines are annulated uracil which, have gotten significant consideration over the last years because of their extensive variety of biological and pharmacological activities, such as anticancer [ 5 – 9 ], antimicrobial [ 10 , 11 ], antiviral [ 12 , 13 ], anti-inflammatory agents [ 14 ] antifolate [ 15 , 16 ], PDE IV inhibitors [ 17 ], and Inhibitors for hepatitis B virus [ 18 ]. Also, pyridopyrimidine moiety was considered as the best-known tyrosine kinase inhibitor for the treatment of endless myelogenous leukemia and medication resistance rises by enhancement of the improvement of a transformation [ 19 ].…”