3-Amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno [2,3-d ]pyrimidine: An Effecient Key Precursor for Novel Synthesis of Some Interesting Triazines and Triazepines as Potential Anti-Tumor Agents

Abstract

A number of interesting heterocycles were prepared through interaction of the intermediate 3-amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno-[2,3-d]pyrimidine (1) and reagents such as hydrazonyl halides 2 to furnish triazine derivatives 4a–l. Reaction of 1 with phenacyl bromide afforded compound 5. Moreover, the title compound 1 was subjected to condensation with active methylene compounds (ethyl acetoacetate and ethyl benzoylacetate) to give triazipinones 8a,b. The condensation with aromatic aldehydes afforded either the triazole derivatives 10a–d or Schiff base 11. In addition, the behaviour of compound 1 towards activated unsaturated compounds namely dimethyl acetylene dicarboxylate and ethoxymethylenemalonitrile was studied and it was found to furnish the triazine 13 and triazepine derivative 15, respectively. Combination of title compound 1 with chlorinated active methylene compounds delivered the triazine derivatives 18a–c. Reaction of 1 with chloroacetonitrile furnished compound 20. The structures of the products were elucidated based on their microanalyses and spectroscopic data. Finally, the antitumor activity of the new compounds 4a and 8a against human breast cell MCF-7 line and liver carcinoma cell line HepG2 were recorded.

Synthesis and Preliminary In‐Vitro Cytotoxic Evaluation of Some Novel bis‐Heterocycles Incorporating Thienothiophene

“…In addition, substituted thienothiophenes have been used as building blocks in the synthesis of polycondensed systems, which include sulfur analogues of electronic devices, due to their many fundamental advantages over their inorganic counterparts in achieving low-cost, large area and mechanically flexible electronics [13][14][15][16]. Encouraged by all these findings and in continuation of our previous work aimed to the synthesis of a variety of heterocyclic systems for biological and pharmacological evaluation [17][18][19][20][21][22][23][24][25][26], we report herein a convenient route to several new thienothiophene-based bis-heterocyclic compounds of expected interesting biological activity, via the reaction of bis-2-bromoacetylthieno [2,3-b]thiophene derivative with several heterocyclic amines and thioles.…”

Synthesis and biological evaluation of novel fused triazolo[4,3-$a$] pyrimidinones

“…A novel series of fused [1,2,4]triazolo [1,5-a]pyrimidines were synthesized by different methods and evaluated for their in vitro antibacterial, antifungal, and anticancer activities. From the screening results, it can be seen that compounds 8f and 15f showed excellent activity against gram-positive bacteria and compound 15d showed potent activity against gram-negative bacteria.…”

Synthesis, reactions, and antimicrobial activity of some novel pyrazolo[3,4‐d]pyrimidine, pyrazolo[4,3‐e][1,2,4]triazolo[1,5‐c]pyrimidine, and pyrazolo[4,3‐e][1,2,4]triazolo[3,4‐c]pyrimidine derivatives

“…1, 55.5, 103.8, 116.0, 119.8, 123.6, 126.3, 128.9, 129.6, 129.9, 130.5, 131.2, 131.7, 135.3, 140.4, 141.3, 145.8, 149.9, 150.9, 157.8; MS (EI, 70 eV) m/z (%): 448 (M + , 100). Found: C,69.54;H,4.55;N,18.79. 30;H,3.78;Cl,7.83;N,18.56. Calcd.…”